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Welcome to Pine Cove. A small peaceful enclave of homes that sits oh so close to the Chester River and the Deep Landing Boat Launch. Surrounded by working farms and pastoral views this beautifully maintained home is just 9 years young. Boasting an open concept layout with soaring cathedral ceilings in the main living areas, a gourmet kitchen with granite counters, stainless-steel appliances, and hardwood floors throughout, you will fall in love with this idyllic rural retreat. One level living is the key to comfort and ease. Two bedrooms and a full bath on one side of the house and a gorgeous Owners suite on the other side with a generous walk-in closet and Spa like bath with stand-up shower and a soaking tub. A double vanity ensures room for all your needs. Laundry and mechanicals are just off the hallway by the owner's suite and garage access is just off the main foyer. Storage shelving in the double size garage will stay with the home and there is an additional storage shed in the back yard. The back yard is fully fenced with a pretty vinyl fence just the right size for small pets. You will also find garden beds and bird feeder poles. The rear of the house boasts a custom deck for your entertaining pleasure. Many perennials and lovely landscaping bring the front and back yards to life and attracts birds and pollinators alike. It's a short walk down to the local Boat ramp and the river for your summer activities. Come and see how this beautiful turnkey home can be yours!

720 Deep Landing Rd, Chestertown

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Benson & Mangold, LLC.

$3,150,000

With approximately 2,650 feet of private waterfront along Southeast Creek and sweeping views toward the Chester River, this exceptional 13.2-acre estate in the desirable Kennersley Farm community offers the rare combination of protected water, expansive acreage, and extraordinary privacy — complemented by a beautifully crafted main residence and detached carriage house. Originally constructed as a builder’s personal residence, this coastal farmhouse showcases exceptional craftsmanship and enduring quality throughout. The main home offers eight bedrooms and six-and-a-half baths, including three private ensuites thoughtfully positioned for comfort and privacy. A detached stone carriage house provides two additional bedrooms, a full kitchen, and bath above a side-loading two-car garage with conditioned workshop and storage space — ideal for extended guests, multigenerational living, or private accommodations. Inside, timeless architectural details define the interiors: wide hewn pine hardwood flooring, substantial eight-inch base trim, solid wood doors, raised panel wainscoting, and four fireplaces that add warmth and character throughout. The waterside great room serves as a striking focal point, featuring a coffered ceiling, a dramatic stone fireplace with a custom mantel designed by Vicco VonVoss, built-in media cabinetry, and breathtaking water views. A central gourmet kitchen anchors the home and flows seamlessly into expansive gathering spaces, including a remarkable three-sided waterfront game room with pool table that conveys — designed for year-round entertaining. The main-level ensuite with adjoining sunroom opens to a private side deck, creating an ideal space for quiet mornings or evening retreats. Upstairs, the primary suite offers built-in bookcases, a fireplace, generous walk-in closets, a jetted tub, and plumbing for a future steam shower. An additional expansive ensuite on the second level provides exceptional privacy and includes a separate sitting area large enough for a sofa — perfect for guests seeking their own retreat. Additional bedrooms on the upper level provide ample space to relax and unwind. Dual laundry rooms on both the main and upper levels enhance everyday convenience, while a finished attic suite with sitting area and half bath offers additional flexibility. The unfinished walk-up basement with exterior access presents an opportunity for future customization. Outdoor living rivals that of a private resort. A waterside saltwater pool with a 10-foot diving well and diving rock is surrounded by an expansive paver patio, while a 12-foot-deep wraparound porch, tiered covered porch, upper balcony, and stone fire pit provide multiple vantage points to enjoy sunset views over the water. Custom exterior lighting enhances the architecture and landscaping in the evening, while a private, alarm-secured driveway ensures a refined sense of arrival and seclusion. The private dock has electric service run to it and water access, along with two boat slips and two jet ski lifts, providing direct access to Southeast Creek and beyond. A natural shoreline, kayak launch, mature trees, and resident bald eagles enhance the serenity of the setting. Just minutes from Kennersley Point Marina and within easy boating distance to Chestertown, Rock Hall, and Annapolis, this estate offers both tranquility and accessibility. The residence is also being offered fully furnished, presenting a rare turnkey waterfront opportunity. Defined by the elements that matter most — substantial water frontage, protected deep water, acreage, privacy, quality construction, and turnkey furnishings — this is a legacy offering for refined waterfront living on Maryland’s Eastern Shore.

8 Beds ⋅ 7 Baths

With approximately 2,650 feet of private waterfront along Southeast Creek and sweeping views toward the Chester River, this exceptional 13.2-acre estate in the desirable Kennersley Farm community offers the rare combination of protected water, expansive acreage, and extraordinary privacy — complemented by a beautifully crafted main residence and detached carriage house. Originally constructed as a builder’s personal residence, this coastal farmhouse showcases exceptional craftsmanship and enduring quality throughout. The main home offers eight bedrooms and six-and-a-half baths, including three private ensuites thoughtfully positioned for comfort and privacy. A detached stone carriage house provides two additional bedrooms, a full kitchen, and bath above a side-loading two-car garage with conditioned workshop and storage space — ideal for extended guests, multigenerational living, or private accommodations. Inside, timeless architectural details define the interiors: wide hewn pine hardwood flooring, substantial eight-inch base trim, solid wood doors, raised panel wainscoting, and four fireplaces that add warmth and character throughout. The waterside great room serves as a striking focal point, featuring a coffered ceiling, a dramatic stone fireplace with a custom mantel designed by Vicco VonVoss, built-in media cabinetry, and breathtaking water views. A central gourmet kitchen anchors the home and flows seamlessly into expansive gathering spaces, including a remarkable three-sided waterfront game room with pool table that conveys — designed for year-round entertaining. The main-level ensuite with adjoining sunroom opens to a private side deck, creating an ideal space for quiet mornings or evening retreats. Upstairs, the primary suite offers built-in bookcases, a fireplace, generous walk-in closets, a jetted tub, and plumbing for a future steam shower. An additional expansive ensuite on the second level provides exceptional privacy and includes a separate sitting area large enough for a sofa — perfect for guests seeking their own retreat. Additional bedrooms on the upper level provide ample space to relax and unwind. Dual laundry rooms on both the main and upper levels enhance everyday convenience, while a finished attic suite with sitting area and half bath offers additional flexibility. The unfinished walk-up basement with exterior access presents an opportunity for future customization. Outdoor living rivals that of a private resort. A waterside saltwater pool with a 10-foot diving well and diving rock is surrounded by an expansive paver patio, while a 12-foot-deep wraparound porch, tiered covered porch, upper balcony, and stone fire pit provide multiple vantage points to enjoy sunset views over the water. Custom exterior lighting enhances the architecture and landscaping in the evening, while a private, alarm-secured driveway ensures a refined sense of arrival and seclusion. The private dock has electric service run to it and water access, along with two boat slips and two jet ski lifts, providing direct access to Southeast Creek and beyond. A natural shoreline, kayak launch, mature trees, and resident bald eagles enhance the serenity of the setting. Just minutes from Kennersley Point Marina and within easy boating distance to Chestertown, Rock Hall, and Annapolis, this estate offers both tranquility and accessibility. The residence is also being offered fully furnished, presenting a rare turnkey waterfront opportunity. Defined by the elements that matter most — substantial water frontage, protected deep water, acreage, privacy, quality construction, and turnkey furnishings — this is a legacy offering for refined waterfront living on Maryland’s Eastern Shore.

148 Vernick Ln, Church Hill

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: BHHS Fox & Roach - Hockessin.

$485,000

Come fall in love with this beautiful home in the sought after 55+ community of Symphony Village with tons of amenities & activities. Enjoy having solar with super low $118 a month electric bills! Wonderful location yet close to hospitals, doctors, shopping, restaurants, beaches, parks, boat ramps & more. Gorgeous custom 3BR, 2BA rancher with stunning hardwood floors and lots of upgrades. New roof only 3 years old! Original owner has taken meticulous care of his home. 9' ceilings, huge kitchen with corian counters, pantry, gas fireplace, relaxing back patio, sky basement with finished room for an office and storage area. Great location within the community as it is situated on the outside edge and over looks woods in the front so very peaceful. ONE YEAR HOME WARRANTY given at settlement for peace of mind. Owner is having house repainted next week as a bonus! Come get this wonderful home before its gone!! Check out the inside and outside virtual tours in this listing.

Come fall in love with this beautiful home in the sought after 55+ community of Symphony Village with tons of amenities & activities. Enjoy having solar with super low $118 a month electric bills! Wonderful location yet close to hospitals, doctors, shopping, restaurants, beaches, parks, boat ramps & more. Gorgeous custom 3BR, 2BA rancher with stunning hardwood floors and lots of upgrades. New roof only 3 years old! Original owner has taken meticulous care of his home. 9' ceilings, huge kitchen with corian counters, pantry, gas fireplace, relaxing back patio, sky basement with finished room for an office and storage area. Great location within the community as it is situated on the outside edge and over looks woods in the front so very peaceful. ONE YEAR HOME WARRANTY given at settlement for peace of mind. Owner is having house repainted next week as a bonus! Come get this wonderful home before its gone!! Check out the inside and outside virtual tours in this listing.

225 Opera Ct, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: Non Subscribing Office.

$75,000

Investor, special, major rehab, Has enclosed front porch and enclosed back porch.

2 Beds ⋅ 1 Baths

Investor, special, major rehab, Has enclosed front porch and enclosed back porch.

1500 Roe Ingleside Rd, Ingleside

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Keller Williams Flagship.

$679,000

Welcome to this beautifully maintained home in Ellendale on Kent Island, ideally situated on a premium corner lot with peaceful pond views and a spacious, fenced backyard. Offering four bedrooms and two and a half bathrooms, this home combines thoughtful upgrades, comfortable living spaces, and scenic surroundings, all in one of the most conveniently located communities on the Eastern Shore. As you enter, you are greeted by high ceilings and a dedicated office just off the entryway that provides the perfect work-from-home space with views of the pond. The living room is filled with natural light and features a cozy propane fireplace along with built-in surround sound for your home theatre, creating a warm and inviting gathering space. The kitchen offers refinished cabinetry, a pantry, and abundant storage, flowing seamlessly into the dining area and sunroom that overlook the backyard—ideal for everyday living and entertaining. Interior access to the two-car garage is located off the kitchen, as well as a door to the approximately four-foot-tall conditioned crawlspace with plenty of space for additional storage. Upstairs, the oversized primary suite enjoys tranquil views of the pond and trees beyond and includes multiple closets and a spacious en-suite bathroom with double sinks and a tiled shower. Three additional bedrooms and a full bathroom complete the upper level. This home also features hardwood flooring throughout much of the main level, a sunroom addition with a breakfast nook, French glass doors in the office, an upgraded staircase banister, and dual-zone climate control. Recent improvements include a new HVAC system (2023), solar panels, a whole-home generator, a deck, a new sliding glass door with built-in blinds, refinished kitchen cabinets, updated appliances including a dishwasher (2023) and washer and dryer (2025), and new living room carpet. Ellendale is one of the most sought-after communities on Kent Island, offering a clubhouse, community pool, playground, pier perfect for launching kayaks and canoes into Thompson Creek, community social events, and more, all conveniently located at the first exit off Route 50 and the Chesapeake Bay Bridge. Just minutes to local shopping and dining options and offering a quick commute to Annapolis, Baltimore, Washington, DC, St. Michaels, Easton, and beyond. Schedule your tour today to learn all about what Ellendale and the Kent Island lifestyle have to offer!

Welcome to this beautifully maintained home in Ellendale on Kent Island, ideally situated on a premium corner lot with peaceful pond views and a spacious, fenced backyard. Offering four bedrooms and two and a half bathrooms, this home combines thoughtful upgrades, comfortable living spaces, and scenic surroundings, all in one of the most conveniently located communities on the Eastern Shore. As you enter, you are greeted by high ceilings and a dedicated office just off the entryway that provides the perfect work-from-home space with views of the pond. The living room is filled with natural light and features a cozy propane fireplace along with built-in surround sound for your home theatre, creating a warm and inviting gathering space. The kitchen offers refinished cabinetry, a pantry, and abundant storage, flowing seamlessly into the dining area and sunroom that overlook the backyard—ideal for everyday living and entertaining. Interior access to the two-car garage is located off the kitchen, as well as a door to the approximately four-foot-tall conditioned crawlspace with plenty of space for additional storage. Upstairs, the oversized primary suite enjoys tranquil views of the pond and trees beyond and includes multiple closets and a spacious en-suite bathroom with double sinks and a tiled shower. Three additional bedrooms and a full bathroom complete the upper level. This home also features hardwood flooring throughout much of the main level, a sunroom addition with a breakfast nook, French glass doors in the office, an upgraded staircase banister, and dual-zone climate control. Recent improvements include a new HVAC system (2023), solar panels, a whole-home generator, a deck, a new sliding glass door with built-in blinds, refinished kitchen cabinets, updated appliances including a dishwasher (2023) and washer and dryer (2025), and new living room carpet. Ellendale is one of the most sought-after communities on Kent Island, offering a clubhouse, community pool, playground, pier perfect for launching kayaks and canoes into Thompson Creek, community social events, and more, all conveniently located at the first exit off Route 50 and the Chesapeake Bay Bridge. Just minutes to local shopping and dining options and offering a quick commute to Annapolis, Baltimore, Washington, DC, St. Michaels, Easton, and beyond. Schedule your tour today to learn all about what Ellendale and the Kent Island lifestyle have to offer!

402 Conor Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

$650,000

Welcome to 450 Web Foot Lane, a beautifully updated retreat on Kent Island that checks every box! This stunning 4-bedroom, 2.5-bath home has been thoughtfully updated and is truly move-in ready. The main level is designed for effortless living with a wonderfully open floor plan connecting the living room, sunroom, and kitchen. A cozy pellet stove anchors the living room with warmth and charm. The den tucked off the kitchen offers the perfect space for relaxing or entertaining, while a separate dining area provides an elegant setting for meals. A private study just off the main entrance is ideal for working from home or a quiet retreat. The outdoor living spaces are second to none. Enjoy summer days in your private pool, gather around the fire pit on cool evenings, and entertain with ease on the elegant paver stone patio. Everyday living is effortless with a dedicated laundry room featuring two washers and two dryers, a rare and practical luxury that busy families will love. Conveniently located just minutes from the Chesapeake Bay Bridge and close to Kent Island High School, with easy access to all the shopping, dining, and waterfront charm that Stevensville and Kent Island have to offer. This one won't last, schedule your showing today!

Welcome to 450 Web Foot Lane, a beautifully updated retreat on Kent Island that checks every box! This stunning 4-bedroom, 2.5-bath home has been thoughtfully updated and is truly move-in ready. The main level is designed for effortless living with a wonderfully open floor plan connecting the living room, sunroom, and kitchen. A cozy pellet stove anchors the living room with warmth and charm. The den tucked off the kitchen offers the perfect space for relaxing or entertaining, while a separate dining area provides an elegant setting for meals. A private study just off the main entrance is ideal for working from home or a quiet retreat. The outdoor living spaces are second to none. Enjoy summer days in your private pool, gather around the fire pit on cool evenings, and entertain with ease on the elegant paver stone patio. Everyday living is effortless with a dedicated laundry room featuring two washers and two dryers, a rare and practical luxury that busy families will love. Conveniently located just minutes from the Chesapeake Bay Bridge and close to Kent Island High School, with easy access to all the shopping, dining, and waterfront charm that Stevensville and Kent Island have to offer. This one won't last, schedule your showing today!

450 Web Foot Ln, Stevensville

Listing courtesy of RE/MAX United Real Estate. Contact:

This exceptional property checks all the boxes in real estate! Location, condition, and price! Nestled in the highly sought-after, amenity-rich community of Cloverfields right on Kent Island, it truly offers the complete package. 4BR, 2.5BA, and a spacious primary suite with a generously sized en-suite bath and a tremendous bonus room off primary that serves as a expansive walk in closet with the possibility of fully converting it into a dressing room or any other feature you need! The main level offers multiple living spaces, perfect for everyone. Enjoy a great size kitchen that opens seamlessly to the family and dining rooms, along with multiple sliders leading to an expansive deck and large backyard where the possibilities are endless. Grow a garden, add a pool, or expand the patio. It's YOUR HOME, do what you have been dreaming of!! Cloverfields is known for its exceptional amenities and low HOA fees...residents enjoy access to a community pool, beach, clubhouse, marina, playground, and even a swim team. All that PLUS the LOCATION - just minutes the Chesapeake Bay Bridge, historic Stevensville, waterfront dining, shopping, and more - YOUR HOME AWAITS!!

$580,000

This exceptional property checks all the boxes in real estate! Location, condition, and price! Nestled in the highly sought-after, amenity-rich community of Cloverfields right on Kent Island, it truly offers the complete package. 4BR, 2.5BA, and a spacious primary suite with a generously sized en-suite bath and a tremendous bonus room off primary that serves as a expansive walk in closet with the possibility of fully converting it into a dressing room or any other feature you need! The main level offers multiple living spaces, perfect for everyone. Enjoy a great size kitchen that opens seamlessly to the family and dining rooms, along with multiple sliders leading to an expansive deck and large backyard where the possibilities are endless. Grow a garden, add a pool, or expand the patio. It's YOUR HOME, do what you have been dreaming of!! Cloverfields is known for its exceptional amenities and low HOA fees...residents enjoy access to a community pool, beach, clubhouse, marina, playground, and even a swim team. All that PLUS the LOCATION - just minutes the Chesapeake Bay Bridge, historic Stevensville, waterfront dining, shopping, and more - YOUR HOME AWAITS!!

705 Davol Rd, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Coldwell Banker Realty.

$800,000

New Construction in Willow Branch Community - Only 5 Lots Left! Build your dream home with Mike's Custom Homes in the sought after Willow Branch Community in Centreville, MD! Choose from three stunning models or bring your own custom floor plan to create the perfect home tailored to your needs. Nestled in a serene setting with spacious lots, high-quality craftmanship, and modern finishes, these homes offer the best of the Eastern Shore living. Don't miss this opportunity to build in a prime location with easy access to local amenities, schools and major routes. Secure your lot today - contact us for more details! **Photos are of a previously sold model and may feature options that are upgrades. *Additional lot premium fees will apply.

New Construction in Willow Branch Community - Only 5 Lots Left! Build your dream home with Mike's Custom Homes in the sought after Willow Branch Community in Centreville, MD! Choose from three stunning models or bring your own custom floor plan to create the perfect home tailored to your needs. Nestled in a serene setting with spacious lots, high-quality craftmanship, and modern finishes, these homes offer the best of the Eastern Shore living. Don't miss this opportunity to build in a prime location with easy access to local amenities, schools and major routes. Secure your lot today - contact us for more details! **Photos are of a previously sold model and may feature options that are upgrades. *Additional lot premium fees will apply.

107 Thicket Ct, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Samson Properties.

$632,500

Beautifully appointed Modern Farmhouse! Massive kitchen with quartz countertops, farm-style sink, stainless appliances, huge island with plenty of seating as well as additional dining space. Open Family Room, Dining Area, and Kitchen layout. Separate living space on the 2nd floor for a more private hang out area or home office. Powder room is tucked away from the main living area on the first floor for privacy as is the separate laundry room. The composite deck with vinyl rails allows for a seamless transition from the indoor living space to the outdoors. LVP flooring runs throughout the entire first floor as well as the spacious master suite and bathrooms. Master suite has a sumptuous walk in closet with some killer waterviews as does the master bedroom. Sit on the front porch, enjoy your coffee, and enjoy the transquility of the Chesapeake Bay. Some of the best sunsets you'll ever see can be had as you pull into your driveway after day's work. Or walk down to the water's edge and cast your line into the bay as the sun sets. Front picture shows grass and landscaping that does not exist. Sod and landscaping can be installed for additional cost. Lawn has been seeded and strawed. Public sewer. Private well. Home is nearly complete! Cleaners scheduled for next week! Call today for more details!

Beautifully appointed Modern Farmhouse! Massive kitchen with quartz countertops, farm-style sink, stainless appliances, huge island with plenty of seating as well as additional dining space. Open Family Room, Dining Area, and Kitchen layout. Separate living space on the 2nd floor for a more private hang out area or home office. Powder room is tucked away from the main living area on the first floor for privacy as is the separate laundry room. The composite deck with vinyl rails allows for a seamless transition from the indoor living space to the outdoors. LVP flooring runs throughout the entire first floor as well as the spacious master suite and bathrooms. Master suite has a sumptuous walk in closet with some killer waterviews as does the master bedroom. Sit on the front porch, enjoy your coffee, and enjoy the transquility of the Chesapeake Bay. Some of the best sunsets you'll ever see can be had as you pull into your driveway after day's work. Or walk down to the water's edge and cast your line into the bay as the sun sets. Front picture shows grass and landscaping that does not exist. Sod and landscaping can be installed for additional cost. Lawn has been seeded and strawed. Public sewer. Private well. Home is nearly complete! Cleaners scheduled for next week! Call today for more details!

102 Lagorce Dr, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Home Towne Real Estate.

$365,000

Romancoke on the Bay - This wonderful rancher is located on .83 of an acre to give you additional outdoor living space. The 3-bedroom, 2 bath home has been recently painted, new carpet and lighting fixtures. The oversized two car garage is a nice feature as well. It is in move in ready condition. Close to the water will a slight view from the home. Call today for your showing appointment.

Romancoke on the Bay - This wonderful rancher is located on .83 of an acre to give you additional outdoor living space. The 3-bedroom, 2 bath home has been recently painted, new carpet and lighting fixtures. The oversized two car garage is a nice feature as well. It is in move in ready condition. Close to the water will a slight view from the home. Call today for your showing appointment.

211 Long Point Rd, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$550,000

Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views overlooking Castle Harbor Marina, the home features multiple decks, updated finishes, and, if you choose Castle Harbor Marina, easy access to your boat slip, only steps away. With approximately 2,100 square feet on three finished levels, highlights include a gourmet kitchen with granite counters, a center island with prep sink, gas cooking, double ovens, an expanded great room with fireplace and hardwood floors, a spacious primary suite with a deck and sitting area, and a versatile top level with a great room, living area that has plenty of room for bunk beds and more. Water views again from your picture window. Community amenities include a clubhouse, pool, tennis courts, and volleyball courts.

3 Beds ⋅ 4 Baths

Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views overlooking Castle Harbor Marina, the home features multiple decks, updated finishes, and, if you choose Castle Harbor Marina, easy access to your boat slip, only steps away. With approximately 2,100 square feet on three finished levels, highlights include a gourmet kitchen with granite counters, a center island with prep sink, gas cooking, double ovens, an expanded great room with fireplace and hardwood floors, a spacious primary suite with a deck and sitting area, and a versatile top level with a great room, living area that has plenty of room for bunk beds and more. Water views again from your picture window. Community amenities include a clubhouse, pool, tennis courts, and volleyball courts.

200 Schooner Way, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: RE/MAX Leading Edge.

$450,000

Welcome to 118 Stewart Lane in Grasonville — a beautifully maintained 3-bedroom, 2.5-bath home with a 1-car garage, ideally situated on a quiet cul-de-sac. This move-in ready home offers a charming front porch, spacious fenced yard, and numerous updates that make everyday living both comfortable and convenient. Inside, you'll find luxury vinyl plank flooring, brand-new carpet on the stairs and in the primary bedroom, fresh paint in the stairwell and upstairs hallway, and a functional layout designed for modern living. The kitchen features granite countertops, stainless steel appliances, and a new dishwasher, while the primary bath offers a double sink vanity and the half bath has been tastefully updated. Recent improvements provide peace of mind, including a crawl space encapsulation by Master Kleen in 2023, new sump pump and French drain system in 2026, tankless hot water heater (2021), added attic insulation following a 2025 energy audit, new garage door and openers (2025), paved driveway (2025), new well tank and pump (2022), water softener and filtration system (2021), and washer and dryer (2023). The HVAC has been regularly maintained for continued efficiency. Conveniently located just minutes from everything Kent Island has to offer, including shopping, restaurants, marinas, and easy access to Route 50 for an easy commute.

Welcome to 118 Stewart Lane in Grasonville — a beautifully maintained 3-bedroom, 2.5-bath home with a 1-car garage, ideally situated on a quiet cul-de-sac. This move-in ready home offers a charming front porch, spacious fenced yard, and numerous updates that make everyday living both comfortable and convenient. Inside, you'll find luxury vinyl plank flooring, brand-new carpet on the stairs and in the primary bedroom, fresh paint in the stairwell and upstairs hallway, and a functional layout designed for modern living. The kitchen features granite countertops, stainless steel appliances, and a new dishwasher, while the primary bath offers a double sink vanity and the half bath has been tastefully updated. Recent improvements provide peace of mind, including a crawl space encapsulation by Master Kleen in 2023, new sump pump and French drain system in 2026, tankless hot water heater (2021), added attic insulation following a 2025 energy audit, new garage door and openers (2025), paved driveway (2025), new well tank and pump (2022), water softener and filtration system (2021), and washer and dryer (2023). The HVAC has been regularly maintained for continued efficiency. Conveniently located just minutes from everything Kent Island has to offer, including shopping, restaurants, marinas, and easy access to Route 50 for an easy commute.

118 Stewart Ln, Grasonville

Listing courtesy of Samson Properties. Contact:

Selling Office: Compass.

$299,900

Property is a combination of an Estate Sale (being sold As-Is) and a pre-approved short sale. 3Bd/2ba rancher on approximately .4 acres. Well and septic. Livrm, dinrm, famrm w/electric fireplace and kitchen. Off of the kitchen there is an enclosed room, concrete patio, and an additional screened-in patio. Backyard is partially fenced and has an in-ground pool (drained and in as-is condition) Convenient to Rte 50, Bay Bridge, and Annapolis. PR requests property be on the market for 7 days before reviewing any offer(s). PR and Asset Manager prefer using Gemini Title.

Property is a combination of an Estate Sale (being sold As-Is) and a pre-approved short sale. 3Bd/2ba rancher on approximately .4 acres. Well and septic. Livrm, dinrm, famrm w/electric fireplace and kitchen. Off of the kitchen there is an enclosed room, concrete patio, and an additional screened-in patio. Backyard is partially fenced and has an in-ground pool (drained and in as-is condition) Convenient to Rte 50, Bay Bridge, and Annapolis. PR requests property be on the market for 7 days before reviewing any offer(s). PR and Asset Manager prefer using Gemini Title.

1914 Anchorage Dr, Chester

Listing courtesy of Century 21 Downtown. Contact:

Selling Office: Rosendale Realty.

$575,000

Welcome to Bay Bridge Cove! This highly desired, 55+ luxury, waterfront community is known for its gorgeous setting, beautifully maintained grounds, exceptional amenities, and a true easy, low-maintenance lifestyle. This thoughtfully designed and updated 2BR/2BA villa offers a warm, inviting layout with bonus living space that truly sets it apart. Inside, hardwood flooring and an open floor plan create a seamless flow throughout the main living areas. The beautifully updated kitchen features quartz countertops, crisp cabinetry, and a spacious center island, opening to a large living room/dining room combo space anchored by a stunning gas fireplace - ideal for both everyday living and entertaining. At the rear of the home, a bright and sunny bonus room (den, office, reading room?) extends the living space and leads to a custom screened-in porch—perfect for enjoying the outdoors in comfort, whether it’s for morning coffee or a quiet evening respite. The elegant primary suite offers a comfortable retreat with two walk-in closets and an updated bath featuring a tiled shower. A second bedroom and full hall bath with a tub/shower combination provide flexibility for guests or a home office. The two-car garage is a must-have! This home offers an abundance of storage on the main level, along with a unique lower-level storage space that spans nearly the full footprint of the home. Bay Bridge Cove residents enjoy a vibrant lifestyle with a clubhouse, outdoor pool, tennis court, fitness center, stylish indoor gathering spaces, and beautifully maintained common grounds, plus lawn care, snow removal, and exterior maintenance for each villa! Conveniently located on Kent Island, with easy access to Annapolis, BWI, Washington, D.C., and more. Come enjoy this elevated blend of comfort, convenience, and community. Bay Bridge Cove can’t wait to welcome you home!

2 Beds ⋅ 2 Baths

Welcome to Bay Bridge Cove! This highly desired, 55+ luxury, waterfront community is known for its gorgeous setting, beautifully maintained grounds, exceptional amenities, and a true easy, low-maintenance lifestyle. This thoughtfully designed and updated 2BR/2BA villa offers a warm, inviting layout with bonus living space that truly sets it apart. Inside, hardwood flooring and an open floor plan create a seamless flow throughout the main living areas. The beautifully updated kitchen features quartz countertops, crisp cabinetry, and a spacious center island, opening to a large living room/dining room combo space anchored by a stunning gas fireplace - ideal for both everyday living and entertaining. At the rear of the home, a bright and sunny bonus room (den, office, reading room?) extends the living space and leads to a custom screened-in porch—perfect for enjoying the outdoors in comfort, whether it’s for morning coffee or a quiet evening respite. The elegant primary suite offers a comfortable retreat with two walk-in closets and an updated bath featuring a tiled shower. A second bedroom and full hall bath with a tub/shower combination provide flexibility for guests or a home office. The two-car garage is a must-have! This home offers an abundance of storage on the main level, along with a unique lower-level storage space that spans nearly the full footprint of the home. Bay Bridge Cove residents enjoy a vibrant lifestyle with a clubhouse, outdoor pool, tennis court, fitness center, stylish indoor gathering spaces, and beautifully maintained common grounds, plus lawn care, snow removal, and exterior maintenance for each villa! Conveniently located on Kent Island, with easy access to Annapolis, BWI, Washington, D.C., and more. Come enjoy this elevated blend of comfort, convenience, and community. Bay Bridge Cove can’t wait to welcome you home!

932 Moorings Cir, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Taylor Properties.

$665,600

**OPEN HOUSE SATURDAY MAY 16th from 10am to 12pm** CHESTER RIVER WATER VIEWS! Enjoy Beautiful Water Views of the scenic Chester River from this bright and inviting Home designed for comfortable everyday living and effortless entertaining. Offering a total of 2.5 Baths, a Primary En-suite and two large additional Bedrooms complete with new carpet. This thoughtfully designed Custom Home spans three finished Levels, including a Huge Bonus room to use an Office space ideal for working from home, as a 4th Bedroom or a recreation/game room! The main level features gleaming Hardwood Floors, Ceramic Tile, fresh Paint throughout and a Gas Fireplace anchoring the light-filled Living Room. The Eat-In Kitchen shines with newer stainless-steel appliances, Corian countertops and a Bay Window which allows abundant natural light. A wet bar in the formal Dining Room is the perfect place for entertaining and family gatherings. Outdoor living is just as impressive with a welcoming wrap-around front porch to enjoy your morning coffee as you gaze at the water and a screened rear porch overlooking the spacious back yard where you can enjoy a drink to wind down the day! A newly paved driveway and attached two-car garage provide ample parking. Take a short stroll to the community landing where you’ll find a fishing and crabbing Pier, Boat ramp, Beaches, Kayak & SUP Rack, Tot Lot and a Pavilion... everything you need to enjoy the very best of Eastern Shore waterfront living! A rare opportunity to combine water views, community amenities and generous living space in one EXCEPTIONAL Property! Located just minutes from the Kent Island Cross Trail, local Marinas, Waterfront Dining and Boutique shopping! 959 Chester River Drive is ready to WELCOME YOU HOME!

**OPEN HOUSE SATURDAY MAY 16th from 10am to 12pm** CHESTER RIVER WATER VIEWS! Enjoy Beautiful Water Views of the scenic Chester River from this bright and inviting Home designed for comfortable everyday living and effortless entertaining. Offering a total of 2.5 Baths, a Primary En-suite and two large additional Bedrooms complete with new carpet. This thoughtfully designed Custom Home spans three finished Levels, including a Huge Bonus room to use an Office space ideal for working from home, as a 4th Bedroom or a recreation/game room! The main level features gleaming Hardwood Floors, Ceramic Tile, fresh Paint throughout and a Gas Fireplace anchoring the light-filled Living Room. The Eat-In Kitchen shines with newer stainless-steel appliances, Corian countertops and a Bay Window which allows abundant natural light. A wet bar in the formal Dining Room is the perfect place for entertaining and family gatherings. Outdoor living is just as impressive with a welcoming wrap-around front porch to enjoy your morning coffee as you gaze at the water and a screened rear porch overlooking the spacious back yard where you can enjoy a drink to wind down the day! A newly paved driveway and attached two-car garage provide ample parking. Take a short stroll to the community landing where you’ll find a fishing and crabbing Pier, Boat ramp, Beaches, Kayak & SUP Rack, Tot Lot and a Pavilion... everything you need to enjoy the very best of Eastern Shore waterfront living! A rare opportunity to combine water views, community amenities and generous living space in one EXCEPTIONAL Property! Located just minutes from the Kent Island Cross Trail, local Marinas, Waterfront Dining and Boutique shopping! 959 Chester River Drive is ready to WELCOME YOU HOME!

959 Chester River Dr, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

Brand New Construction – Nearing Completion! This beautifully crafted 3 bedroom, 2.5 bath home offers 1,344 sq ft of modern comfort, thoughtful design, and a location that makes everyday living easy. Step inside to a welcoming family room that flows seamlessly into the open-concept kitchen and dining area, creating a comfortable space for both relaxing and entertaining. The main level features durable LVP flooring throughout, extending into the full bathrooms upstairs for a clean, cohesive look. The kitchen is designed to impress with White soft-close cabinetry, Granite countertops, Stainless steel appliances, and a functional layout perfect for daily living. A washer and dryer are included for added convenience. Upstairs, the owner’s suite offers a walk-in closet and private en suite bath, while two additional bedrooms with ample closet space and a full hall bath round out the 2nd level. Enjoy a flat backyard backing to a wooded/forest retention area, offering a peaceful setting with room to create your ideal outdoor space. Located just moments from Rt. 50 for easy access and only steps from Hunter’s Seafood, you’ll love the convenience of fresh local seafood and nearby amenities right at your fingertips. Don’t miss this opportunity to own a brand new home with modern finishes in a highly convenient location! Professional Photos coming once home is completed...some current photos are virtually staged with AI.

$399,900

Brand New Construction – Nearing Completion! This beautifully crafted 3 bedroom, 2.5 bath home offers 1,344 sq ft of modern comfort, thoughtful design, and a location that makes everyday living easy. Step inside to a welcoming family room that flows seamlessly into the open-concept kitchen and dining area, creating a comfortable space for both relaxing and entertaining. The main level features durable LVP flooring throughout, extending into the full bathrooms upstairs for a clean, cohesive look. The kitchen is designed to impress with White soft-close cabinetry, Granite countertops, Stainless steel appliances, and a functional layout perfect for daily living. A washer and dryer are included for added convenience. Upstairs, the owner’s suite offers a walk-in closet and private en suite bath, while two additional bedrooms with ample closet space and a full hall bath round out the 2nd level. Enjoy a flat backyard backing to a wooded/forest retention area, offering a peaceful setting with room to create your ideal outdoor space. Located just moments from Rt. 50 for easy access and only steps from Hunter’s Seafood, you’ll love the convenience of fresh local seafood and nearby amenities right at your fingertips. Don’t miss this opportunity to own a brand new home with modern finishes in a highly convenient location! Professional Photos coming once home is completed...some current photos are virtually staged with AI.

4606 Main St, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Coveted Bay City has a new opening, and this lovingly maintained 3 Bedroom, 2.5 Bath Colonial w/ den- or opt. 4th Bedroom, near end of quiet cul-de-sac won't last!! Just minutes from Bay Bridge- Matapeake Schools- Move-in-ready w/ updated flooring, fresh paint, NEW Kitchen open to spacious family room, separate dining room & den make for easy everyday living- Attached one-car garage for ample storage- Welcoming front porch greets guests to a cheery home ready for her lucky new owners! Community amenities include: boat ramp, dock, playground, pavilion, fire pit & Bayfront park. Hurry- this beauty won't last! Check out THIS virtual tour- Kent Island living is calling!!

$529,000

Coveted Bay City has a new opening, and this lovingly maintained 3 Bedroom, 2.5 Bath Colonial w/ den- or opt. 4th Bedroom, near end of quiet cul-de-sac won't last!! Just minutes from Bay Bridge- Matapeake Schools- Move-in-ready w/ updated flooring, fresh paint, NEW Kitchen open to spacious family room, separate dining room & den make for easy everyday living- Attached one-car garage for ample storage- Welcoming front porch greets guests to a cheery home ready for her lucky new owners! Community amenities include: boat ramp, dock, playground, pavilion, fire pit & Bayfront park. Hurry- this beauty won't last! Check out THIS virtual tour- Kent Island living is calling!!

308 Wallman Way, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: 4th Colony Realty.

$592,000

Price improvement. Now listed under recent appraisal, offering immediate value. Flexible one-hour open house windows scheduled regularly for easy, convenient access. Don't miss the full property video for an enhanced look before stepping inside. Welcome to 102 Fair Brook Way, an exceptional 2012 colonial nestled on a premium corner lot in the highly sought-after North Brook community. Offering approximately 3,402 total square feet including the fully finished basement, this residence is privately positioned toward the rear of the neighborhood and showcases an ideal blend of sophistication, comfort, and refined living. This impressive home features 4 expansive bedrooms, 3.5 bathrooms, and a rare fully finished lower level complete with a full bath, theatre room, recreation space, and a versatile bonus area ideal for a private office or potential 5th bedroom—creating incredible flexibility for today’s lifestyle. Designed with both elegance and functionality in mind, the interior showcases rich hardwood flooring, custom trim work, a striking brick-faced fireplace, and a sun-drenched sunroom. The well-appointed kitchen opens seamlessly to the main living areas, creating an inviting space for both everyday living and upscale entertaining. Recent enhancements include fresh designer paint on the main level and new carpeting on the upper level, offering a truly turnkey experience. The spacious primary suite serves as a private retreat, featuring a tray ceiling, walk-in closet, and a luxurious en-suite bath complete with a soaking tub and walk-in shower. Bonus features - permanent Holiday lights and theater equipment included! Step outside to your private outdoor oasis situated on a fabulous, oversized corner lot, fully fenced and thoughtfully designed with an expansive paver patio and fire pit—perfect for entertaining or enjoying peaceful Eastern Shore evenings. Residents of North Brook enjoy access to community amenities including walking paths, scenic ponds, playground, soccer field, and pavilion. Ideally located near local dining, shopping, schools, and waterfront attractions with convenient access to Annapolis, Baltimore, Washington, D.C., and Delaware beaches. Homes of this caliber, square footage, and setting—especially with a finished basement and premium lot—are rarely available. Schedule your private showing today.

Price improvement. Now listed under recent appraisal, offering immediate value. Flexible one-hour open house windows scheduled regularly for easy, convenient access. Don't miss the full property video for an enhanced look before stepping inside. Welcome to 102 Fair Brook Way, an exceptional 2012 colonial nestled on a premium corner lot in the highly sought-after North Brook community. Offering approximately 3,402 total square feet including the fully finished basement, this residence is privately positioned toward the rear of the neighborhood and showcases an ideal blend of sophistication, comfort, and refined living. This impressive home features 4 expansive bedrooms, 3.5 bathrooms, and a rare fully finished lower level complete with a full bath, theatre room, recreation space, and a versatile bonus area ideal for a private office or potential 5th bedroom—creating incredible flexibility for today’s lifestyle. Designed with both elegance and functionality in mind, the interior showcases rich hardwood flooring, custom trim work, a striking brick-faced fireplace, and a sun-drenched sunroom. The well-appointed kitchen opens seamlessly to the main living areas, creating an inviting space for both everyday living and upscale entertaining. Recent enhancements include fresh designer paint on the main level and new carpeting on the upper level, offering a truly turnkey experience. The spacious primary suite serves as a private retreat, featuring a tray ceiling, walk-in closet, and a luxurious en-suite bath complete with a soaking tub and walk-in shower. Bonus features - permanent Holiday lights and theater equipment included! Step outside to your private outdoor oasis situated on a fabulous, oversized corner lot, fully fenced and thoughtfully designed with an expansive paver patio and fire pit—perfect for entertaining or enjoying peaceful Eastern Shore evenings. Residents of North Brook enjoy access to community amenities including walking paths, scenic ponds, playground, soccer field, and pavilion. Ideally located near local dining, shopping, schools, and waterfront attractions with convenient access to Annapolis, Baltimore, Washington, D.C., and Delaware beaches. Homes of this caliber, square footage, and setting—especially with a finished basement and premium lot—are rarely available. Schedule your private showing today.

102 Fair Brook Way, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: EXP Realty, LLC.

$349,500

This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a spacious living room that flows seamlessly into the kitchen, complete with gorgeous granite countertops and newer stainless-steel appliances. The cozy primary bedroom is complete with a wood-burning fireplace ideal for relaxing evenings. Enjoy your morning coffee on the welcoming front porch just across the street from views of the Chester River, or host gatherings in the fenced-in backyard with space for play and gardening. You also have peace of mind with a newer HVAC system (2023) and solar panels for a more energy efficient home! Located towards the end of this peaceful street, you’re close to Chestertown’s historic charm, Washington College, a nearby boat ramp, and tax-free shopping just across the Delaware line and still located in Queen Anne's County!

This charming 3 bedroom, 2 bathroom home offers the perfect blend of comfort, convenience, and functionality that has major upgrades including Fresh Paint throughout, Renovated Primary Bath and New carpet. The bonus office room is an essential for remote work! The property also features a large 2-car garage/workshop, you’ll have plenty of room for vehicles, projects, or storage. Step inside to a spacious living room that flows seamlessly into the kitchen, complete with gorgeous granite countertops and newer stainless-steel appliances. The cozy primary bedroom is complete with a wood-burning fireplace ideal for relaxing evenings. Enjoy your morning coffee on the welcoming front porch just across the street from views of the Chester River, or host gatherings in the fenced-in backyard with space for play and gardening. You also have peace of mind with a newer HVAC system (2023) and solar panels for a more energy efficient home! Located towards the end of this peaceful street, you’re close to Chestertown’s historic charm, Washington College, a nearby boat ramp, and tax-free shopping just across the Delaware line and still located in Queen Anne's County!

126 Char Nor Manor Blvd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here -- just bring your ideas and your tools and make it shine again. Close to Chestertown while enjoying the benefits of Queen Anne's County living!

$175,000

3 Beds ⋅ 1 Baths

OPPORTUNITY KNOCKS!! This home is being sold as-is and is ready for someone with vision and plenty of elbow grease. Located in Queen Anne's County on Pear Tree Point Rd, the property sits on a generous 2.08-acre lot bordered by farmland on one side of the road, offering peaceful views, and room to breathe. With wood floors, a spacious living room and a living/dining area, the bones are here -- just bring your ideas and your tools and make it shine again. Close to Chestertown while enjoying the benefits of Queen Anne's County living!

113 Pear Tree Point Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$374,600

Welcome to this charming 3-bedroom, 1.5-bath Cape Cod, thoughtfully remodeled from top to bottom. Priced under appraised value, this home offers instant equity. With its traditional exterior, the interior has been beautifully updated and offers approximately 1,600 sq. ft. of comfortable living space. Major updates include a new roof and siding, luxury vinyl plank flooring, stainless steel appliances, and newly added central air conditioning. The newly updated kitchen opens to a welcoming main living area, centered around a beautiful fireplace that draws you in. Every detail has been carefully refreshed, creating a warm, move-in-ready home. The first-floor primary bedroom features a versatile sitting area, perfect for a nursery, office space, or just a cozy spot to curl up with a good book. Enjoy your morning coffee on the screened-in porch, entertain guests on the large deck, and relax in the fenced-in yard for privacy. For those who like to tinker or need extra space, there is a workshop in the backyard. Conveniently located just minutes from the Kent Narrows, this home provides easy access to shopping, hospitals, beaches, fishing, hunting, top restaurants, parks, boat landings, and marinas. Easy access to Route 50 and 301.

Welcome to this charming 3-bedroom, 1.5-bath Cape Cod, thoughtfully remodeled from top to bottom. Priced under appraised value, this home offers instant equity. With its traditional exterior, the interior has been beautifully updated and offers approximately 1,600 sq. ft. of comfortable living space. Major updates include a new roof and siding, luxury vinyl plank flooring, stainless steel appliances, and newly added central air conditioning. The newly updated kitchen opens to a welcoming main living area, centered around a beautiful fireplace that draws you in. Every detail has been carefully refreshed, creating a warm, move-in-ready home. The first-floor primary bedroom features a versatile sitting area, perfect for a nursery, office space, or just a cozy spot to curl up with a good book. Enjoy your morning coffee on the screened-in porch, entertain guests on the large deck, and relax in the fenced-in yard for privacy. For those who like to tinker or need extra space, there is a workshop in the backyard. Conveniently located just minutes from the Kent Narrows, this home provides easy access to shopping, hospitals, beaches, fishing, hunting, top restaurants, parks, boat landings, and marinas. Easy access to Route 50 and 301.

119 Watkins Rd, Grasonville

Listing courtesy of RE/MAX Advantage Realty. Contact:

Selling Office: Crown Homes Real Estate.

$799,500

Like-new luxury living in Four Seasons at Kent Island. Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to purchase furnishings—this home is truly turn-key and ready today. Enjoy peek-a-boo Chester River views and an unbeatable location so close to the clubhouse you can see it. Plus, the builder’s full warranty remains in place through August 2026 for added peace of mind. Residents enjoy Four Seasons’ resort-style amenities: waterfront clubhouse, indoor & outdoor pools, fitness center, pickleball & tennis, walking trails, and a vibrant social calendar. Effortless luxury, prime location, island living at its best.

Like-new luxury living in Four Seasons at Kent Island. Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to purchase furnishings—this home is truly turn-key and ready today. Enjoy peek-a-boo Chester River views and an unbeatable location so close to the clubhouse you can see it. Plus, the builder’s full warranty remains in place through August 2026 for added peace of mind. Residents enjoy Four Seasons’ resort-style amenities: waterfront clubhouse, indoor & outdoor pools, fitness center, pickleball & tennis, walking trails, and a vibrant social calendar. Effortless luxury, prime location, island living at its best.

528 Warbler Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Keller Williams Flagship.

$805,000

Welcome home to this beautifully custom-built home set on 2.5 acres, where thoughtful design and stylish upgrades come together for everyday comfort and easy living. The spacious first-floor primary suite offers the convenience you’ve been looking for, while a dedicated home office provides the perfect spot for working remotely, studying, or simply having a quiet flex space. At the heart of the home, the bright and inviting kitchen features upgraded appliances and flows seamlessly into the main living areas—ideal for entertaining or relaxed nights in. You’ll love the LVP flooring throughout and the abundance of upgrades that elevate every space. Step outside and unwind on the large covered back porch, a favorite place to enjoy morning coffee, evening sunsets, or gatherings with friends and family—surrounded by the privacy and open space that 2.5 acres provides. Upstairs, you’ll find two comfortable bedrooms connected by a convenient Jack-and-Jill bath, plus an additional room that can easily serve as a playroom, media room, hobby space, or extra bedroom—whatever fits your lifestyle. Above the garage, you’ll appreciate the unfinished storage space with an already framed-in doorway—perfect for extra storage now or ready to be finished into another room in the future. This one truly checks all the boxes: space, quality, upgrades, and that unmistakable “welcome home” feeling.

Welcome home to this beautifully custom-built home set on 2.5 acres, where thoughtful design and stylish upgrades come together for everyday comfort and easy living. The spacious first-floor primary suite offers the convenience you’ve been looking for, while a dedicated home office provides the perfect spot for working remotely, studying, or simply having a quiet flex space. At the heart of the home, the bright and inviting kitchen features upgraded appliances and flows seamlessly into the main living areas—ideal for entertaining or relaxed nights in. You’ll love the LVP flooring throughout and the abundance of upgrades that elevate every space. Step outside and unwind on the large covered back porch, a favorite place to enjoy morning coffee, evening sunsets, or gatherings with friends and family—surrounded by the privacy and open space that 2.5 acres provides. Upstairs, you’ll find two comfortable bedrooms connected by a convenient Jack-and-Jill bath, plus an additional room that can easily serve as a playroom, media room, hobby space, or extra bedroom—whatever fits your lifestyle. Above the garage, you’ll appreciate the unfinished storage space with an already framed-in doorway—perfect for extra storage now or ready to be finished into another room in the future. This one truly checks all the boxes: space, quality, upgrades, and that unmistakable “welcome home” feeling.

114 Piper Ct, Church Hill

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RLAH @properties.

$710,000

We are accepting backup offers and will allow showings. Perfectly situated on over an acre in a peaceful Centreville setting, this expansive custom-built home offers more than 4,000 square feet of beautifully designed living space across three finished levels, combining comfort, functionality, and exceptional value. The main level is ideal for both everyday living and entertaining, featuring a formal dining room and a gourmet kitchen with center island, dual wall ovens, induction cooktop, walk-in pantry, and sunlit breakfast nook. Just off the kitchen, the inviting family room includes a pellet stove, wet bar, and oversized sliding doors that open to a screened-in porch and spacious deck, creating seamless indoor-outdoor living. Upstairs, the oversized primary suite serves as a private retreat, complete with a propane fireplace, dual walk-in closets, and a spa-inspired bathroom featuring a jacuzzi soaking tub and rainfall shower. This level also includes two additional bedrooms, a large bonus room with pellet stove, a full bathroom, and a conveniently located laundry room. The third floor offers two additional versatile bedrooms and another full bathroom, perfect for guests, home offices, or hobby spaces. Outside, the property truly shines. Enjoy a fully fenced yard on over an acre, an oversized attached two-car garage, a detached two-car garage/workshop, storage shed, and a partial whole-house generator. With no HOA, you have the freedom to fully enjoy the property while still being just minutes from downtown Centreville, local shops and dining, Route 301, and only 13 miles from the Bay Bridge for an easy commute. A solar energy system is installed on the home, helping offset utility costs. This exceptional property offers size, privacy, and versatility rarely found at this price point in Centreville.

5 Beds ⋅ 4 Baths

We are accepting backup offers and will allow showings. Perfectly situated on over an acre in a peaceful Centreville setting, this expansive custom-built home offers more than 4,000 square feet of beautifully designed living space across three finished levels, combining comfort, functionality, and exceptional value. The main level is ideal for both everyday living and entertaining, featuring a formal dining room and a gourmet kitchen with center island, dual wall ovens, induction cooktop, walk-in pantry, and sunlit breakfast nook. Just off the kitchen, the inviting family room includes a pellet stove, wet bar, and oversized sliding doors that open to a screened-in porch and spacious deck, creating seamless indoor-outdoor living. Upstairs, the oversized primary suite serves as a private retreat, complete with a propane fireplace, dual walk-in closets, and a spa-inspired bathroom featuring a jacuzzi soaking tub and rainfall shower. This level also includes two additional bedrooms, a large bonus room with pellet stove, a full bathroom, and a conveniently located laundry room. The third floor offers two additional versatile bedrooms and another full bathroom, perfect for guests, home offices, or hobby spaces. Outside, the property truly shines. Enjoy a fully fenced yard on over an acre, an oversized attached two-car garage, a detached two-car garage/workshop, storage shed, and a partial whole-house generator. With no HOA, you have the freedom to fully enjoy the property while still being just minutes from downtown Centreville, local shops and dining, Route 301, and only 13 miles from the Bay Bridge for an easy commute. A solar energy system is installed on the home, helping offset utility costs. This exceptional property offers size, privacy, and versatility rarely found at this price point in Centreville.

112 Browning Ln, Centreville

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Taylor Properties.

$381,400

This is an Estate sale and selling all "as is." Seller in process of removing some items but some household contents will remain. Priced well for a quick sell! Property overall has been well taken care of. Andersen windows and thermal doors, hardwood floors in kitchen area, separate laundry room. The fenced rear yard has a detached screened gazebo and a shed. There is an outside entrance to a deck from the kitchen area. Three car garage and off street parking. Three blocks to the Chesapeake Bay and a Community members only small beach area. Close to several county boat ramps and park areas. A road maintenance fee is $40.00 per year and the sewer fee is $300.00 per quarter.

This is an Estate sale and selling all "as is." Seller in process of removing some items but some household contents will remain. Priced well for a quick sell! Property overall has been well taken care of. Andersen windows and thermal doors, hardwood floors in kitchen area, separate laundry room. The fenced rear yard has a detached screened gazebo and a shed. There is an outside entrance to a deck from the kitchen area. Three car garage and off street parking. Three blocks to the Chesapeake Bay and a Community members only small beach area. Close to several county boat ramps and park areas. A road maintenance fee is $40.00 per year and the sewer fee is $300.00 per quarter.

106 Utah Rd, Stevensville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

Selling Office: Coldwell Banker Realty.

$1,300,000

Expansive views stretch along Jackson Creek to the Chester River, creating a waterfront setting that is truly exceptional. For anyone who loves life on the water, this property offers a rare opportunity, complete with a sandy beach and impressive waterfront frontage. The outdoor amenities are designed for both relaxation and recreation, including a pier with boat lift and electric, a beach house cabana, pool, pergola, hardscape, and plenty of space for poolside entertaining. Natural light fills the home from sunrise over the Chester River throughout the day as the sun moves west. The main house is in excellent condition and offers multiple living spaces, including three sitting areas, a breakfast room, and a formal dining room. Beautiful finishes include hardwood floors, cherry kitchen cabinetry, stainless steel appliances, and a beverage bar. A stone fireplace adds warmth and ambiance to the open living areas. The home features five bedrooms, three full baths, and one-half bath, with hardwood flooring throughout both levels. A first-floor bedroom with a full bath provides flexibility for guests or multigenerational living. The primary suite is ideally positioned on the waterside and includes a private balcony. An indoor porch, outdoor porches, and a game room make this home especially well-suited for entertaining. Surrounded by mature trees, the property also offers a spacious yard with fencing already in place for children and pets.

5 Beds ⋅ 4 Baths

Expansive views stretch along Jackson Creek to the Chester River, creating a waterfront setting that is truly exceptional. For anyone who loves life on the water, this property offers a rare opportunity, complete with a sandy beach and impressive waterfront frontage. The outdoor amenities are designed for both relaxation and recreation, including a pier with boat lift and electric, a beach house cabana, pool, pergola, hardscape, and plenty of space for poolside entertaining. Natural light fills the home from sunrise over the Chester River throughout the day as the sun moves west. The main house is in excellent condition and offers multiple living spaces, including three sitting areas, a breakfast room, and a formal dining room. Beautiful finishes include hardwood floors, cherry kitchen cabinetry, stainless steel appliances, and a beverage bar. A stone fireplace adds warmth and ambiance to the open living areas. The home features five bedrooms, three full baths, and one-half bath, with hardwood flooring throughout both levels. A first-floor bedroom with a full bath provides flexibility for guests or multigenerational living. The primary suite is ideally positioned on the waterside and includes a private balcony. An indoor porch, outdoor porches, and a game room make this home especially well-suited for entertaining. Surrounded by mature trees, the property also offers a spacious yard with fencing already in place for children and pets.

110 Perrys Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

$860,000

Welcome to this beautifully upgraded home at the Enclave in Prospect Bay, the Eastern Shore’s premier golf course community, offering main-level living, thoughtful design, and premium finishes throughout. Perfectly situated on a premium lot, this home blends comfort, style, and functionality both inside and out. Located on a private lot next to the golf cart path with access to Prospect Bay’s 18-hole golf course, you are greeted by a welcoming covered front porch as you arrive. The main level features a spacious primary suite along with two additional bedrooms and two full baths, providing convenient single-level living. The primary suite showcases elegant tray ceilings and a luxurious ensuite bath with a frameless glass shower. Upstairs, a versatile loft with LVP flooring and surround sound offers flexible living space and includes a third full bath, giving it the potential to serve as an office, guest suite, or recreation room. The upgraded kitchen is a standout, featuring enhanced cabinetry, KitchenAid appliances, under-cabinet lighting, and a stand-alone ice machine, making it as functional as it is beautiful. The kitchen opens to the living room and a dining area overlooking the paver patio and the 11th hole of Prospect Bay’s golf course. Also located on this level is a spacious office with barn doors. With direct access to the garage, the conveniently located laundry room continues the upscale finishes with upgraded cabinetry and granite countertops. Designed with both style and entertaining in mind, the home features luxury vinyl plank flooring throughout the main living areas and primary bedroom, tray ceilings in the primary bedroom, dining room, kitchen, and living room, and crown molding in all main-level bedrooms and living spaces. Stylish board and batten molding and a custom wall mural in the main hallway and main-level office add distinctive character. Smart and modern touches include motorized blinds and a surround sound system in both the living room and loft. The two car garage is fully finished and thoughtfully upgraded, featuring complete interior painting, custom epoxy flooring, a bump-out for your golf car and built-in shelving for additional storage. Above the garage, extended pull-down stairs provide convenient access to additional storage space. Outdoor living is just as impressive, with a sealed and coated front porch and a paver patio with a gas-lit fire pit, perfect for relaxing evenings or entertaining guests. The community maintains the gardens and lawn, offering a true turn-key experience. Located within the exclusive Enclave at Prospect Bay, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this golf course-view property offers an unmatched lifestyle in one of Maryland’s most prestigious communities.

Welcome to this beautifully upgraded home at the Enclave in Prospect Bay, the Eastern Shore’s premier golf course community, offering main-level living, thoughtful design, and premium finishes throughout. Perfectly situated on a premium lot, this home blends comfort, style, and functionality both inside and out. Located on a private lot next to the golf cart path with access to Prospect Bay’s 18-hole golf course, you are greeted by a welcoming covered front porch as you arrive. The main level features a spacious primary suite along with two additional bedrooms and two full baths, providing convenient single-level living. The primary suite showcases elegant tray ceilings and a luxurious ensuite bath with a frameless glass shower. Upstairs, a versatile loft with LVP flooring and surround sound offers flexible living space and includes a third full bath, giving it the potential to serve as an office, guest suite, or recreation room. The upgraded kitchen is a standout, featuring enhanced cabinetry, KitchenAid appliances, under-cabinet lighting, and a stand-alone ice machine, making it as functional as it is beautiful. The kitchen opens to the living room and a dining area overlooking the paver patio and the 11th hole of Prospect Bay’s golf course. Also located on this level is a spacious office with barn doors. With direct access to the garage, the conveniently located laundry room continues the upscale finishes with upgraded cabinetry and granite countertops. Designed with both style and entertaining in mind, the home features luxury vinyl plank flooring throughout the main living areas and primary bedroom, tray ceilings in the primary bedroom, dining room, kitchen, and living room, and crown molding in all main-level bedrooms and living spaces. Stylish board and batten molding and a custom wall mural in the main hallway and main-level office add distinctive character. Smart and modern touches include motorized blinds and a surround sound system in both the living room and loft. The two car garage is fully finished and thoughtfully upgraded, featuring complete interior painting, custom epoxy flooring, a bump-out for your golf car and built-in shelving for additional storage. Above the garage, extended pull-down stairs provide convenient access to additional storage space. Outdoor living is just as impressive, with a sealed and coated front porch and a paver patio with a gas-lit fire pit, perfect for relaxing evenings or entertaining guests. The community maintains the gardens and lawn, offering a true turn-key experience. Located within the exclusive Enclave at Prospect Bay, residents enjoy access to a wealth of amenities including an 18-hole golf course with pro shop, driving range, tennis and pickleball courts, a members-only clubhouse with restaurant and bar, community pool, playground, private boat launch, and more. Whether you're seeking a full-time residence or a weekend escape, this golf course-view property offers an unmatched lifestyle in one of Maryland’s most prestigious communities.

167 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

$400,000

Brand New Construction – Move-In Ready Soon! This beautifully crafted 3 bedroom, 2.5 bath home offers 1,344 sq ft of modern comfort, thoughtful design, and a location that makes everyday living easy. Step inside to a welcoming family room that flows seamlessly into the open-concept kitchen and dining area, creating a comfortable space for both relaxing and entertaining. The main level features durable LVP flooring throughout, extending into the full bathrooms upstairs for a clean, cohesive look. The kitchen is designed to impress with White soft-close cabinetry, Granite countertops, Stainless steel appliances, and a functional layout perfect for daily living. A washer and dryer are included for added convenience. Upstairs, the owner’s suite offers a walk-in closet and private en suite bath, while two additional bedrooms with ample closet space and a full hall bath round out the 2nd level. Enjoy a flat backyard backing to a wooded/forest retention area, offering a peaceful setting with room to create your ideal outdoor space. Located just moments from Rt. 50 for easy access and only steps from Hunter’s Seafood, you’ll love the convenience of fresh local seafood and nearby amenities right at your fingertips. Don’t miss this opportunity to own a brand new home with modern finishes in a highly convenient location! Professional Photos coming once home is completed...some current photos are virtually staged with AI.

Brand New Construction – Move-In Ready Soon! This beautifully crafted 3 bedroom, 2.5 bath home offers 1,344 sq ft of modern comfort, thoughtful design, and a location that makes everyday living easy. Step inside to a welcoming family room that flows seamlessly into the open-concept kitchen and dining area, creating a comfortable space for both relaxing and entertaining. The main level features durable LVP flooring throughout, extending into the full bathrooms upstairs for a clean, cohesive look. The kitchen is designed to impress with White soft-close cabinetry, Granite countertops, Stainless steel appliances, and a functional layout perfect for daily living. A washer and dryer are included for added convenience. Upstairs, the owner’s suite offers a walk-in closet and private en suite bath, while two additional bedrooms with ample closet space and a full hall bath round out the 2nd level. Enjoy a flat backyard backing to a wooded/forest retention area, offering a peaceful setting with room to create your ideal outdoor space. Located just moments from Rt. 50 for easy access and only steps from Hunter’s Seafood, you’ll love the convenience of fresh local seafood and nearby amenities right at your fingertips. Don’t miss this opportunity to own a brand new home with modern finishes in a highly convenient location! Professional Photos coming once home is completed...some current photos are virtually staged with AI.

4604 Main St, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Real Broker, LLC - Annapolis.

$1,350,000

This stunning 4,500+ sq ft home with 5 bedrooms and 4.5 baths is set on a private 1.25-acre lot in the sought-after water-privileged Tower Gardens community—just minutes from the Bay Bridge. Ideal for generational living, the home features primary suites on both the first and second floors, offering flexibility for a variety of lifestyles. At the heart of the home, the gourmet kitchen boasts a massive island, custom cabinetry, a hidden walk-in pantry, and a Viking appliance package—all accented with designer finishes. The open-concept layout flows seamlessly into multiple living areas, anchored by indoor and outdoor fireplaces that create inviting spaces to gather year-round. The second-floor primary suite includes a private balcony, with expansive windows throughout filling the home with natural light. Thoughtful upgrades like a high-efficiency 2-stage HVAC, Anderson 400 series casement windows, Hardie siding, and a tankless water heater ensure lasting quality and comfort. Tower Gardens residents enjoy a private community beach and pier with sweeping sunset views over the Chesapeake Bay, plus a boat ramp just around the corner for easy access to the water. From this tranquil setting, you’re only minutes from Annapolis or St. Michaels and just 45 minutes to Washington, D.C. or BWI Airport.

5 Beds ⋅ 5 Baths

This stunning 4,500+ sq ft home with 5 bedrooms and 4.5 baths is set on a private 1.25-acre lot in the sought-after water-privileged Tower Gardens community—just minutes from the Bay Bridge. Ideal for generational living, the home features primary suites on both the first and second floors, offering flexibility for a variety of lifestyles. At the heart of the home, the gourmet kitchen boasts a massive island, custom cabinetry, a hidden walk-in pantry, and a Viking appliance package—all accented with designer finishes. The open-concept layout flows seamlessly into multiple living areas, anchored by indoor and outdoor fireplaces that create inviting spaces to gather year-round. The second-floor primary suite includes a private balcony, with expansive windows throughout filling the home with natural light. Thoughtful upgrades like a high-efficiency 2-stage HVAC, Anderson 400 series casement windows, Hardie siding, and a tankless water heater ensure lasting quality and comfort. Tower Gardens residents enjoy a private community beach and pier with sweeping sunset views over the Chesapeake Bay, plus a boat ramp just around the corner for easy access to the water. From this tranquil setting, you’re only minutes from Annapolis or St. Michaels and just 45 minutes to Washington, D.C. or BWI Airport.

208 Tower Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

$375,000

Start living the watermen dream! This charming home offers a thoughtfully designed layout with an open, airy flow and spacious rooms throughout. Situated on nearly one acre, you’ll enjoy both comfort and room to roam. The oversized living area is filled with natural sunlight streaming through the windows, creating a warm and inviting atmosphere. The first floor recently fresh coat of paint. Step outside to the private side deck — perfect for entertaining, hosting summer barbecues, or simply relaxing with friends and family. Featuring three bedrooms and 1.5 baths, this home includes a generously sized primary bedroom with vaulted ceilings and a walk-in closet. A storage shed provides extra space for tools and equipment, while the expansive yard offers endless possibilities for outdoor fun, gardening, or future enhancements. Bring your personal touches and make this home truly your own!