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Nestled in the serene Prospect Bay community, this charming ranch-style home offers a perfect blend of comfort and convenience. Roof is only 3-4 years old. HVAC 2024-2025 . Hardie Plank Siding and Soffits were installed only a couple of years ago, with Aztec PVC Trim and new gutters and gutter guards, make this pretty much a maintenance free home. With three bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining. The heart of the home features a well-appointed kitchen equipped (redone in 2021) with Viking appliances, including a double wall oven, gas cooktop, and a Bosch dishwasher, making meal preparation a delight. Step into the inviting living area, where a cozy fireplace beckons for quiet evenings or gatherings with loved ones in the Sunroom or relax in the separate Living Room. The thoughtful layout ensures that every corner of this home feels warm and welcoming. The attached garage provides ample space for vehicles and storage. Outside, the community amenities are truly exceptional. Dive into the refreshing outdoor pool, challenge friends on the tennis courts, or enjoy leisurely strolls around the beautifully maintained grounds. For golf enthusiasts, a golf course membership is available, offering endless opportunities for recreation. With a generous one-acre lot and access to navigable waters, this property is perfect for those who appreciate nature and outdoor activities. Experience the tranquility of living in a community that prioritizes leisure and lifestyle. This home is not just a place to live; it's a place to thrive.

344 Prospect Bay Dr W, Grasonville

Listing courtesy of Rosendale Realty. Contact:

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

$663,089

An incredible opportunity in the sold out community of Perry’s Retreat just hit the market! Situated on one of the largest premium lots in the back of the neighborhood (not on one of the main roads), this is also one of the largest models offered, giving you the space, layout, and upgrades everyone loves. This impressive home features 5 spacious bedrooms, 3 full baths, including a main-level in-law suite, plus a main level office, perfect for multigenerational living, guests, or working from home. Upstairs, you’ll also find a large bonus room offering flexible space for a media room, playroom, or additional lounge area. The expansive primary suite is a true retreat with a large walk-in shower and dual closets. And the gourmet kitchen… absolutely GORGEOUS! Beautiful finishes, thoughtful design, and plenty of space to gather make it the heart of the home and ideal for entertaining. Everything still feels almost brand new, there is truly nothing to do but move in and enjoy.

5 Beds ⋅ 3 Baths

An incredible opportunity in the sold out community of Perry’s Retreat just hit the market! Situated on one of the largest premium lots in the back of the neighborhood (not on one of the main roads), this is also one of the largest models offered, giving you the space, layout, and upgrades everyone loves. This impressive home features 5 spacious bedrooms, 3 full baths, including a main-level in-law suite, plus a main level office, perfect for multigenerational living, guests, or working from home. Upstairs, you’ll also find a large bonus room offering flexible space for a media room, playroom, or additional lounge area. The expansive primary suite is a true retreat with a large walk-in shower and dual closets. And the gourmet kitchen… absolutely GORGEOUS! Beautiful finishes, thoughtful design, and plenty of space to gather make it the heart of the home and ideal for entertaining. Everything still feels almost brand new, there is truly nothing to do but move in and enjoy.

109 Walters Way, Grasonville

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

Selling Office: Redfin Corp.

$799,990

The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern living. This home includes 4 bedrooms, 3 baths, and a 2-car garage, with flexible spaces designed to adapt to everyday needs. Notable highlights include a dedicated home office and a welcoming shiplap-accented fireplace that anchors the main living area. Luxury vinyl plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, Bedroom 2, the owner’s suite, and the HovHall, while tile finishes enhance all full baths and the laundry room. Plush carpet adds comfort to the loft, second floor, and Bedrooms 3 and 4. The kitchen is thoughtfully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all paired with quartz countertops that continue into the owner’s bath. The owner’s bath is designed for comfort with a shower featuring a built-in seat, handheld shower wand, and double sinks. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

4 Beds ⋅ 3 Baths

The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern living. This home includes 4 bedrooms, 3 baths, and a 2-car garage, with flexible spaces designed to adapt to everyday needs. Notable highlights include a dedicated home office and a welcoming shiplap-accented fireplace that anchors the main living area. Luxury vinyl plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, Bedroom 2, the owner’s suite, and the HovHall, while tile finishes enhance all full baths and the laundry room. Plush carpet adds comfort to the loft, second floor, and Bedrooms 3 and 4. The kitchen is thoughtfully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all paired with quartz countertops that continue into the owner’s bath. The owner’s bath is designed for comfort with a shower featuring a built-in seat, handheld shower wand, and double sinks. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

259 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: The KW Collective.

$685,000

Open house CANCELLED due to multiple offers. First time on the market, this exceptional waterfront property on Crab Alley Bay offers stunning views, one-level living, and endless potential. The home currently includes two bedrooms, with the possibility of creating a third bedroom with a new design. Spacious rooms, a large kitchen, and a sunroom filled with sliding glass doors showcase the home’s beautiful bayfront setting. Important improvements have already been made, including a new roof in 2024, a recently serviced water treatment system, and a boiler in great working order. Outside, the property is well-equipped with a pier, bulkhead, and rip rap, plus a large attached garage and bonus space between the house and garage. Ideally located near shopping and everyday conveniences, this home is a wonderful opportunity for waterfront living in sought-after Marling Farms, where residents enjoy four community beaches, boat launches, kayak launches, and playgrounds. Property is being sold strictly as-is and will require updating.

Open house CANCELLED due to multiple offers. First time on the market, this exceptional waterfront property on Crab Alley Bay offers stunning views, one-level living, and endless potential. The home currently includes two bedrooms, with the possibility of creating a third bedroom with a new design. Spacious rooms, a large kitchen, and a sunroom filled with sliding glass doors showcase the home’s beautiful bayfront setting. Important improvements have already been made, including a new roof in 2024, a recently serviced water treatment system, and a boiler in great working order. Outside, the property is well-equipped with a pier, bulkhead, and rip rap, plus a large attached garage and bonus space between the house and garage. Ideally located near shopping and everyday conveniences, this home is a wonderful opportunity for waterfront living in sought-after Marling Farms, where residents enjoy four community beaches, boat launches, kayak launches, and playgrounds. Property is being sold strictly as-is and will require updating.

1700 Saint Marys Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

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

$399,900

Welcome to 1824 Price Station Rd—a 3 bedroom, 2 full bath home offering space, updates, and versatility in a highly convenient location. Situated on a generous homesite in Church Hill and surrounded by scenic farmland, this property enjoys a truly bucolic setting while remaining just minutes from Rt. 301 for an easy commute. Inside, the home features updated flooring throughout, along with a newer kitchen and baths that blend modern finishes with everyday practicality. The spacious eat-in kitchen serves as the heart of the home, complete with a slider door providing access to a spacious deck overlooking the level, private backyard setting—perfect for everyday living and entertaining. A spacious sitting area provides the ideal place for relaxing or hosting guests. The layout flows comfortably with abundant natural light enhancing the interior spaces. The primary suite includes a large private bath, offering a comfortable and private retreat. Step outside to enjoy the peaceful surroundings, where the meticulously landscaped grounds and mature plantings frame the backyard and provide a sense of privacy. The expansive driveway offers a large parking area at the home, along with an additional oversized parking area in front of the detached building—ideal for accommodating multiple vehicles, boats, RVs, and more. A standout feature of the property is the oversized detached building, complete with two spacious bays and a dedicated workshop area. This versatile structure is insulated, heated, and includes plumbing—perfect for hobbyists, contractors, or anyone in need of additional workspace or storage. Offering the perfect balance of rural charm, functionality, and commuter convenience, this property is a rare opportunity to enjoy country living with room to spread out. Mortgage savings may be available for buyers of this listing.

Welcome to 1824 Price Station Rd—a 3 bedroom, 2 full bath home offering space, updates, and versatility in a highly convenient location. Situated on a generous homesite in Church Hill and surrounded by scenic farmland, this property enjoys a truly bucolic setting while remaining just minutes from Rt. 301 for an easy commute. Inside, the home features updated flooring throughout, along with a newer kitchen and baths that blend modern finishes with everyday practicality. The spacious eat-in kitchen serves as the heart of the home, complete with a slider door providing access to a spacious deck overlooking the level, private backyard setting—perfect for everyday living and entertaining. A spacious sitting area provides the ideal place for relaxing or hosting guests. The layout flows comfortably with abundant natural light enhancing the interior spaces. The primary suite includes a large private bath, offering a comfortable and private retreat. Step outside to enjoy the peaceful surroundings, where the meticulously landscaped grounds and mature plantings frame the backyard and provide a sense of privacy. The expansive driveway offers a large parking area at the home, along with an additional oversized parking area in front of the detached building—ideal for accommodating multiple vehicles, boats, RVs, and more. A standout feature of the property is the oversized detached building, complete with two spacious bays and a dedicated workshop area. This versatile structure is insulated, heated, and includes plumbing—perfect for hobbyists, contractors, or anyone in need of additional workspace or storage. Offering the perfect balance of rural charm, functionality, and commuter convenience, this property is a rare opportunity to enjoy country living with room to spread out. Mortgage savings may be available for buyers of this listing.

1824 Price Station Rd, Church Hill

Listing courtesy of Redfin Corp. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$615,000

Nestled in the serene community of Perry's Retreat, this exquisite ranch-style home, built in 2023, offers a perfect blend of modern luxury and Eastern Shore charm. This highly desirable two-story rancher offers 3 bedrooms and 3 full bathrooms, with the convenience of main-level living. The first floor features 2 bedrooms and 2 full baths, including a spacious primary suite designed for comfort and privacy. A dedicated office provides the flexibility for a home workspace or can easily function as an additional bedroom. The open-concept layout is filled with natural light and designed for both everyday living and effortless entertaining. Upstairs, you’ll find a versatile loft space, which is perfect for a second living area, media room, or guest retreat, along with an additional bedroom and full bathroom, creating the ideal setup for visitors or multigenerational living. Step outside to your own private backyard oasis. Enjoy the screened-in patio for relaxing evenings, an open-air patio for entertaining, and a hot tub that brings a true resort-style feel right to your home. The property also features an irrigation system to keep your lawn lush and low-maintenance year-round. Loaded with modern upgrades, this home also features a Level 2 EV charger and a hookup for a whole-house generator, offering both convenience and peace of mind.

3 Beds ⋅ 3 Baths

Nestled in the serene community of Perry's Retreat, this exquisite ranch-style home, built in 2023, offers a perfect blend of modern luxury and Eastern Shore charm. This highly desirable two-story rancher offers 3 bedrooms and 3 full bathrooms, with the convenience of main-level living. The first floor features 2 bedrooms and 2 full baths, including a spacious primary suite designed for comfort and privacy. A dedicated office provides the flexibility for a home workspace or can easily function as an additional bedroom. The open-concept layout is filled with natural light and designed for both everyday living and effortless entertaining. Upstairs, you’ll find a versatile loft space, which is perfect for a second living area, media room, or guest retreat, along with an additional bedroom and full bathroom, creating the ideal setup for visitors or multigenerational living. Step outside to your own private backyard oasis. Enjoy the screened-in patio for relaxing evenings, an open-air patio for entertaining, and a hot tub that brings a true resort-style feel right to your home. The property also features an irrigation system to keep your lawn lush and low-maintenance year-round. Loaded with modern upgrades, this home also features a Level 2 EV charger and a hookup for a whole-house generator, offering both convenience and peace of mind.

129 Perrys Retreat Blvd, Grasonville

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Corner House Realty.

$385,000

Adorable rancher on Kent Island in the community of Harbor View! Featuring 4 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit. The living room has a cozy fireplace with wood stove insert. The primary bedroom has a private bath with tile and stand up shower. Updates include both bathrooms, updated windows, roof 2020. Close to Route 50 for easy access to the beaches or the Bay Bridge, trails, medical, restaurants, and shopping.

4 Beds ⋅ 2 Baths

Adorable rancher on Kent Island in the community of Harbor View! Featuring 4 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit. The living room has a cozy fireplace with wood stove insert. The primary bedroom has a private bath with tile and stand up shower. Updates include both bathrooms, updated windows, roof 2020. Close to Route 50 for easy access to the beaches or the Bay Bridge, trails, medical, restaurants, and shopping.

1803 Chester Dr, Chester

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: EXP Realty, LLC.

602 Main St, Church Hill

Listing courtesy of LPT Realty, LLC. Contact:

Charming and thoughtfully updated rancher in the heart of Grasonville! This adorable home features an open-concept living and dining area with vaulted ceilings, creating a bright and airy feel throughout. The updated kitchen offers granite countertops, stainless steel appliances, and overlooks a spacious, fully fenced backyard—perfect for entertaining, pets, or relaxing evenings outdoors. Enjoy easy one-level living with two generously sized bedrooms, a full bath, and an additional half bath conveniently located off the kitchen. Home offers a full Reverse Osmosis system. Ideally situated close to shopping, dining, and major commuter routes (less than 15 minutes to the Bay Bridge), this home also offers a lifestyle bonus—walkable access to Cabin Creek Public Landing, perfect for fishing, kayaking, or paddleboarding. A wonderful opportunity for comfortable living in a great location!

$365,000

Charming and thoughtfully updated rancher in the heart of Grasonville! This adorable home features an open-concept living and dining area with vaulted ceilings, creating a bright and airy feel throughout. The updated kitchen offers granite countertops, stainless steel appliances, and overlooks a spacious, fully fenced backyard—perfect for entertaining, pets, or relaxing evenings outdoors. Enjoy easy one-level living with two generously sized bedrooms, a full bath, and an additional half bath conveniently located off the kitchen. Home offers a full Reverse Osmosis system. Ideally situated close to shopping, dining, and major commuter routes (less than 15 minutes to the Bay Bridge), this home also offers a lifestyle bonus—walkable access to Cabin Creek Public Landing, perfect for fishing, kayaking, or paddleboarding. A wonderful opportunity for comfortable living in a great location!

604 Perrys Corner Rd, Grasonville

Listing courtesy of Compass. Contact:

Selling Office: Hyatt & Company Real Estate, LLC.

$625,000

Tranquil Country Retreat on 19 Acres Escape to the serenity of country living with this beau􀆟fully situated home, perfect for nature lovers seeking peace, privacy, and scenic surroundings. A picturesque tree-lined driveway welcomes you to this charming residence, complete with durable vinyl siding and a spacious three-car garage. Home Features: 5 bedrooms and 2 full bathrooms Efficient 2-zone heating and air conditioning for year-round comfort Cozy pellet stove capable of heating the entire home Large kitchen equipped with dishwasher, stove, and refrigerator Bright three-season room offering stunning panoramic views of the property Outdoor & Land Highlights: Expansive 19+ acre property teeming with wildlife, including deer, turkeys, and a variety of bird Peaceful, private setting ideal for relaxation or outdoor actvities Private 400 +- ft deep well Existing private sewage system with drainage field This property combines comfort, functionality, and natural beauty—an exceptional opportunity to enjoy a quiet rural lifestyle .

5 Beds

Tranquil Country Retreat on 19 Acres Escape to the serenity of country living with this beau􀆟fully situated home, perfect for nature lovers seeking peace, privacy, and scenic surroundings. A picturesque tree-lined driveway welcomes you to this charming residence, complete with durable vinyl siding and a spacious three-car garage. Home Features: 5 bedrooms and 2 full bathrooms Efficient 2-zone heating and air conditioning for year-round comfort Cozy pellet stove capable of heating the entire home Large kitchen equipped with dishwasher, stove, and refrigerator Bright three-season room offering stunning panoramic views of the property Outdoor & Land Highlights: Expansive 19+ acre property teeming with wildlife, including deer, turkeys, and a variety of bird Peaceful, private setting ideal for relaxation or outdoor actvities Private 400 +- ft deep well Existing private sewage system with drainage field This property combines comfort, functionality, and natural beauty—an exceptional opportunity to enjoy a quiet rural lifestyle .

1301 Bridgetown Rd, Henderson

Listing courtesy of Beach Real Estate Inc. Contact:

Welcome to this beautifully remodeled Colonial set on a spacious, level half-acre lot in the sought-after Queen Anne school district. Offering 2,114 finished square feet across two levels, this home blends timeless character with modern upgrades throughout. Enjoy convenient in-town living with the ability to walk to nearby shops, restaurants, and local amenities. Completely renovated in 2025, the home features a durable metal roof, new HVAC system, fresh paint, updated lighting, and fully renovated bathrooms. The stunning kitchen showcases brand-new white shaker cabinets, quartz countertops, a stylish backsplash, and all-new appliances including a dishwasher and stove. The convenient kitchen and dining combination layout creates a functional space for both everyday living and entertaining. The family/living room is located just off the kitchen and dining area, creating an easy and open flow for gatherings. An entry-level laundry room is also located just off the kitchen for added convenience. The spacious entry-level primary bedroom offers flexible living options. Throughout the home, you'll find all new flooring, including laminate plank in the living areas and bedrooms, along with custom tile in both bathrooms. The primary bathroom features a luxurious soaking tub, quartz vanity countertop, and a beautifully finished tile shower. Outdoor highlights include a welcoming front porch, a newly installed 6-foot white vinyl fence, designated play area, and a newly paved driveway providing parking for three to four vehicles, along with additional off-street parking. Located on a charming street of well-kept homes, this property offers both comfort and convenience. Conveniently located just a short drive from historic Chestertown and historic Centreville, offering additional shopping, dining, and waterfront attractions.

$362,500

Welcome to this beautifully remodeled Colonial set on a spacious, level half-acre lot in the sought-after Queen Anne school district. Offering 2,114 finished square feet across two levels, this home blends timeless character with modern upgrades throughout. Enjoy convenient in-town living with the ability to walk to nearby shops, restaurants, and local amenities. Completely renovated in 2025, the home features a durable metal roof, new HVAC system, fresh paint, updated lighting, and fully renovated bathrooms. The stunning kitchen showcases brand-new white shaker cabinets, quartz countertops, a stylish backsplash, and all-new appliances including a dishwasher and stove. The convenient kitchen and dining combination layout creates a functional space for both everyday living and entertaining. The family/living room is located just off the kitchen and dining area, creating an easy and open flow for gatherings. An entry-level laundry room is also located just off the kitchen for added convenience. The spacious entry-level primary bedroom offers flexible living options. Throughout the home, you'll find all new flooring, including laminate plank in the living areas and bedrooms, along with custom tile in both bathrooms. The primary bathroom features a luxurious soaking tub, quartz vanity countertop, and a beautifully finished tile shower. Outdoor highlights include a welcoming front porch, a newly installed 6-foot white vinyl fence, designated play area, and a newly paved driveway providing parking for three to four vehicles, along with additional off-street parking. Located on a charming street of well-kept homes, this property offers both comfort and convenience. Conveniently located just a short drive from historic Chestertown and historic Centreville, offering additional shopping, dining, and waterfront attractions.

115 Cemetery Ln, Church Hill

Listing courtesy of Redfin Corp. Contact:

Selling Office: Benson & Mangold, LLC.

$965,000

A Waterfront Retreat on the Chester River! Wake up to glowing Sunrises, unwind to painted Sunsets and savor the Peaceful rhythm of life on the Waters of the Chester River. This beautifully renovated Home offers 75 feet of waterfront and a rare lot‑and‑a‑half setting comfortably outside the flood zone, giving you both serenity and security. Inside, the Home feels bright and welcoming from the moment you step in! With 4 Bedrooms, including a spacious primary en‑suite, and newly renovated Bathrooms, every space has been thoughtfully Updated for comfort and ease. The heart of the Home is the stunning Chef’s Kitchen, where a Large Quartz island invites gathering and conversation with Picturesque Views of the Water! A Wolf gas Cooktop, Brizo Vegetable Sink, Wolf Steam Convection Wall Oven, Bosch Microwave Drawer, Ceramic Farm Sink, Stainless Steel Appliances, Spice Drawer and leathered Granite countertops make cooking a true joy! Custom (Friel Lumber) Walnut Cabinetry with soft close and pull-out drawers along with Hardwood floors add timeless charm throughout. Downstairs, the cozy Family Room becomes the perfect gathering spot with its Wood‑burning stove, custom Wainscoting and a Quartz ledge that frames the Water Views like Artwork. Additional highlights include Custom Closets, Recessed Lighting, Ceiling Fans and a spacious Laundry Room. Updated white Vinyl Board-and-Batten Siding with cylinder lighting create a mesmerizing view as you come home by boat or walking back to the house from a night on the Pier! New high‑end black "Marvin" Casement windows fill the home with natural light, while a New Trane HVAC System keeps everything comfortable year‑round. Step outside and you’ll find a wraparound Teak Deck overlooking the Water, an ideal place for morning coffee, evening wine and enjoying all of those Crab Feasts! The yard is a Gardener’s delight, with mature Cherry Blossoms, a Fig Tree, a White Peach Tree, raised Garden Beds and Grapevines draped over an Italian‑inspired Arbor. Three outdoor Sheds and a Dock Box provide plenty of storage for tools, gardening and waterfront gear. The 130' Pier with L-Deck is ready for your adventures, complete with Copper capped Pilings, High Speed Boat Lift, Jet Ski/SUP/small boat Lift, Swim Ladder and Lighting Stations with water and electricity! Whether you love Crabbing, Fishing, Boating, or simply watching the River drift by, this property brings Waterfront Living to Life! Osprey, Blue Heron, Green Heron, Bald Eagles, Purple Martins, Dolphins, Buffleheads, Mallards, Rockfish, Blue Crabs and many more Wildlife will keep you entertained throughout the Seasons! The Chester River Beach Community adds to the charm with events like a 4th of July Parade, Chili cook‑off, Easter Egg Hunt, Santa visits, Holiday Lights contest, Halloween festivities and Movie nights in the Park! You’re also just a short Boat ride to the Narrows for Waterfront Dining, Rock Hall for your crab feasts and St. Michaels for all the shopping and Maritime fun! Take a quick bike ride, walk or run to the Kent Island Cross Trail and an easy drive to local Restaurants, Boutiques, Parks, Beaches and Marinas. A turnkey Waterfront haven with deep water, sweeping panoramic views and thoughtful upgrades throughout... this is the Waterfront Lifestyle you’ve been Dreaming of!

4 Beds ⋅ 2 Baths

A Waterfront Retreat on the Chester River! Wake up to glowing Sunrises, unwind to painted Sunsets and savor the Peaceful rhythm of life on the Waters of the Chester River. This beautifully renovated Home offers 75 feet of waterfront and a rare lot‑and‑a‑half setting comfortably outside the flood zone, giving you both serenity and security. Inside, the Home feels bright and welcoming from the moment you step in! With 4 Bedrooms, including a spacious primary en‑suite, and newly renovated Bathrooms, every space has been thoughtfully Updated for comfort and ease. The heart of the Home is the stunning Chef’s Kitchen, where a Large Quartz island invites gathering and conversation with Picturesque Views of the Water! A Wolf gas Cooktop, Brizo Vegetable Sink, Wolf Steam Convection Wall Oven, Bosch Microwave Drawer, Ceramic Farm Sink, Stainless Steel Appliances, Spice Drawer and leathered Granite countertops make cooking a true joy! Custom (Friel Lumber) Walnut Cabinetry with soft close and pull-out drawers along with Hardwood floors add timeless charm throughout. Downstairs, the cozy Family Room becomes the perfect gathering spot with its Wood‑burning stove, custom Wainscoting and a Quartz ledge that frames the Water Views like Artwork. Additional highlights include Custom Closets, Recessed Lighting, Ceiling Fans and a spacious Laundry Room. Updated white Vinyl Board-and-Batten Siding with cylinder lighting create a mesmerizing view as you come home by boat or walking back to the house from a night on the Pier! New high‑end black "Marvin" Casement windows fill the home with natural light, while a New Trane HVAC System keeps everything comfortable year‑round. Step outside and you’ll find a wraparound Teak Deck overlooking the Water, an ideal place for morning coffee, evening wine and enjoying all of those Crab Feasts! The yard is a Gardener’s delight, with mature Cherry Blossoms, a Fig Tree, a White Peach Tree, raised Garden Beds and Grapevines draped over an Italian‑inspired Arbor. Three outdoor Sheds and a Dock Box provide plenty of storage for tools, gardening and waterfront gear. The 130' Pier with L-Deck is ready for your adventures, complete with Copper capped Pilings, High Speed Boat Lift, Jet Ski/SUP/small boat Lift, Swim Ladder and Lighting Stations with water and electricity! Whether you love Crabbing, Fishing, Boating, or simply watching the River drift by, this property brings Waterfront Living to Life! Osprey, Blue Heron, Green Heron, Bald Eagles, Purple Martins, Dolphins, Buffleheads, Mallards, Rockfish, Blue Crabs and many more Wildlife will keep you entertained throughout the Seasons! The Chester River Beach Community adds to the charm with events like a 4th of July Parade, Chili cook‑off, Easter Egg Hunt, Santa visits, Holiday Lights contest, Halloween festivities and Movie nights in the Park! You’re also just a short Boat ride to the Narrows for Waterfront Dining, Rock Hall for your crab feasts and St. Michaels for all the shopping and Maritime fun! Take a quick bike ride, walk or run to the Kent Island Cross Trail and an easy drive to local Restaurants, Boutiques, Parks, Beaches and Marinas. A turnkey Waterfront haven with deep water, sweeping panoramic views and thoughtful upgrades throughout... this is the Waterfront Lifestyle you’ve been Dreaming of!

816 Chester River Dr, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: RE/MAX Realty Group.

$955,000

Nestled on 1.32 peaceful acres along scenic Little Greenwood Creek, this waterfront residence offers a sense of calm from the moment you arrive. Surrounded by nature and gently bordered by water, this home blends comfort with effortless living. Step inside to rich hardwood floors that flow throughout, setting a warm and inviting tone. The living room, designed with custom ceiling and gas fireplace, feels both elegant and welcoming—an ideal setting for relaxed evenings and lingering conversations. From here, the home unfolds seamlessly into a sunlit kitchen and family room, where expansive windows bring the outdoors in. Designed for both everyday living and entertaining, this bright and spacious kitchen features a five-burner gas stove, Granite counter tops, a pantry, and a breakfast bar that subtly defines the adjoining family area. Crown molding and chair railing grace the separate dining room providing an elegant backdrop for gatherings and special occasions. The versatile main-level office offers flexibility to suit your needs—whether as a productive workspace, cozy den, or guest bedroom. The addition of a new full bath with a walk-in shower enhances both its convenience and functionality. Upstairs, the gracious primary serves as a private retreat that is complemented by an equally gracious primary bath featuring a soaking tub, walk-in shower, double vanities, and a generous walk-in closet. Outdoor living is equally enticing. A Trex deck and screened porch create inviting spaces to relax or entertain while enjoying the peaceful nature views. And just beyond the lawn, a private pier awaits—perfect for quiet mornings on the water, spontaneous kayak adventures, or evenings spent watching the sky change colors. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant—this remarkable property captures the very best of Chesapeake living in a serene, nature filled setting.

4 Beds ⋅ 4 Baths

Nestled on 1.32 peaceful acres along scenic Little Greenwood Creek, this waterfront residence offers a sense of calm from the moment you arrive. Surrounded by nature and gently bordered by water, this home blends comfort with effortless living. Step inside to rich hardwood floors that flow throughout, setting a warm and inviting tone. The living room, designed with custom ceiling and gas fireplace, feels both elegant and welcoming—an ideal setting for relaxed evenings and lingering conversations. From here, the home unfolds seamlessly into a sunlit kitchen and family room, where expansive windows bring the outdoors in. Designed for both everyday living and entertaining, this bright and spacious kitchen features a five-burner gas stove, Granite counter tops, a pantry, and a breakfast bar that subtly defines the adjoining family area. Crown molding and chair railing grace the separate dining room providing an elegant backdrop for gatherings and special occasions. The versatile main-level office offers flexibility to suit your needs—whether as a productive workspace, cozy den, or guest bedroom. The addition of a new full bath with a walk-in shower enhances both its convenience and functionality. Upstairs, the gracious primary serves as a private retreat that is complemented by an equally gracious primary bath featuring a soaking tub, walk-in shower, double vanities, and a generous walk-in closet. Outdoor living is equally enticing. A Trex deck and screened porch create inviting spaces to relax or entertain while enjoying the peaceful nature views. And just beyond the lawn, a private pier awaits—perfect for quiet mornings on the water, spontaneous kayak adventures, or evenings spent watching the sky change colors. Located in the waterfront community of Prospect Bay, offering resort-style amenities—including golf, a swimming pool, boat ramp, tennis courts and a clubhouse with restaurant—this remarkable property captures the very best of Chesapeake living in a serene, nature filled setting.

26 Greenwood Shls, Grasonville

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

**BACK ON THE MARKET** Buyer got cold feet due to permit issues that arose during inspections - unbeknownst to the seller until that point. Sellers have taken care of everything with the county and the house is as wonderful as ever! Welcome to the heart of Kent Island, nestled in the highly sought-after Marling Farms community—where space, comfort, and water-privileged living come together beautifully. This charming home sits on a huge, fully fenced yard with an in-ground pool featuring a new liner installed in 2024, making it the ultimate backyard for entertaining, relaxing, or keeping the kids busy all summer long. The large pool house adds flexibility and storage, complete with a subpanel upgraded in 2020, along with the home’s main electrical panel upgrade the same year. Inside, you’ll find a brand-new luxury kitchen installed in 2022, designed for both everyday living and hosting. The home offers three generously sized bedrooms and two full bathrooms, including a beautifully updated family bathroom completed in 2025. Additional major updates include a new roof in 2020, providing peace of mind for years to come. Equally important—but often overlooked—the crawl space has been thoughtfully improved, featuring a French drain installed in 2023, PVC underlayment added in 2024, and a brand-new sump pump installed in 2025, helping protect the home from moisture and enhancing long-term durability. A two-car garage, plenty of storage space, and undeniable curb appeal round out the package. Add in the gorgeous setting and water-privileged opportunities that Marling Farms is known for, and you’ve got a home that checks every box for island living. This is Kent Island living done right—updated, well-maintained, and ready to enjoy.

$501,200

**BACK ON THE MARKET** Buyer got cold feet due to permit issues that arose during inspections - unbeknownst to the seller until that point. Sellers have taken care of everything with the county and the house is as wonderful as ever! Welcome to the heart of Kent Island, nestled in the highly sought-after Marling Farms community—where space, comfort, and water-privileged living come together beautifully. This charming home sits on a huge, fully fenced yard with an in-ground pool featuring a new liner installed in 2024, making it the ultimate backyard for entertaining, relaxing, or keeping the kids busy all summer long. The large pool house adds flexibility and storage, complete with a subpanel upgraded in 2020, along with the home’s main electrical panel upgrade the same year. Inside, you’ll find a brand-new luxury kitchen installed in 2022, designed for both everyday living and hosting. The home offers three generously sized bedrooms and two full bathrooms, including a beautifully updated family bathroom completed in 2025. Additional major updates include a new roof in 2020, providing peace of mind for years to come. Equally important—but often overlooked—the crawl space has been thoughtfully improved, featuring a French drain installed in 2023, PVC underlayment added in 2024, and a brand-new sump pump installed in 2025, helping protect the home from moisture and enhancing long-term durability. A two-car garage, plenty of storage space, and undeniable curb appeal round out the package. Add in the gorgeous setting and water-privileged opportunities that Marling Farms is known for, and you’ve got a home that checks every box for island living. This is Kent Island living done right—updated, well-maintained, and ready to enjoy.

1363 Calvert Rd, Chester

Listing courtesy of Revol Real Estate, LLC. Contact:

Selling Office: RE/MAX Executive.

$965,000

This stunning, truly one of a kind coastal-style home in Gibsons Grant offers a perfect blend of comfort and community. With a total of 4 spacious bedrooms and 3.5 baths (1 bed and bath is over garage), the open floor plan invites natural light, showcasing a modern kitchen with an island and a dining area and cozy living room. The main level primary suite features a luxurious bath and walk-in closet, ensuring it is truly a retreat. The upper level on the main house features two bedrooms, 1 full bath and a large family room and game room that leads to a covered balcony. Set on a generous corner lot of 0.22 acres, enjoy outdoor living on the balcony, covered porch, or patio, perfect for gatherings or quiet evenings. Three season room joins to FROG extending living area making FROG accessible without going outside. The community amenities include a refreshing outdoor pool, fitness center, pier, kayak rack and launch, playground and scenic jog/walk paths that connect to the Cross Island Trail, fostering an active lifestyle. Located near the Chester River, residents can appreciate the beauty of nature while being just minutes from local parks and top-rated schools. Experience the warmth of community living in a home that truly feels like a sanctuary. Take comfort knowing property had a thorough Pre Home Sale Inspection and is completely turnkey!

4 Beds ⋅ 4 Baths

This stunning, truly one of a kind coastal-style home in Gibsons Grant offers a perfect blend of comfort and community. With a total of 4 spacious bedrooms and 3.5 baths (1 bed and bath is over garage), the open floor plan invites natural light, showcasing a modern kitchen with an island and a dining area and cozy living room. The main level primary suite features a luxurious bath and walk-in closet, ensuring it is truly a retreat. The upper level on the main house features two bedrooms, 1 full bath and a large family room and game room that leads to a covered balcony. Set on a generous corner lot of 0.22 acres, enjoy outdoor living on the balcony, covered porch, or patio, perfect for gatherings or quiet evenings. Three season room joins to FROG extending living area making FROG accessible without going outside. The community amenities include a refreshing outdoor pool, fitness center, pier, kayak rack and launch, playground and scenic jog/walk paths that connect to the Cross Island Trail, fostering an active lifestyle. Located near the Chester River, residents can appreciate the beauty of nature while being just minutes from local parks and top-rated schools. Experience the warmth of community living in a home that truly feels like a sanctuary. Take comfort knowing property had a thorough Pre Home Sale Inspection and is completely turnkey!

102 Carriage Heath, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Rare opportunity to own a versatile parcel in the heart of Crumpton, just one block from the Chester River. This NC-20 zoned property offers a unique combination of flexibility and function, ideal for a variety of potential uses (buyer to verify). The lot is perk approved and includes an existing 3-car garage, providing immediate utility for storage, workshop space, or future plans. Located within close proximity to navigable water, this property offers the lifestyle appeal of the Eastern Shore with added convenience and accessibility. Whether you're looking to build, invest, or secure a property with multiple potential uses, this parcel delivers both present-day value and long-term opportunity. Additional property located across the street (115 2nd St) is also available for purchase separately or together.

$75,000

116 2nd St, Crumpton

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Chesapeake Real Estate Associates, LLC.

$960,000

Stevensville - This large homestead features 4,012 sq feet on .69 of an acre. The first floor features formal living and dining rooms, but an exceptional huge country kitchen for all of your entertaining needs. The first floor features a primary bedroom and of course the screen in porch and wrap around porch is a must have! Large rooms and spacious bedrooms upstairs as well as laundry on both levels. Extra storage space with two walking closets upstairs. Call today for your showing appointment.

5 Beds ⋅ 3 Baths

Stevensville - This large homestead features 4,012 sq feet on .69 of an acre. The first floor features formal living and dining rooms, but an exceptional huge country kitchen for all of your entertaining needs. The first floor features a primary bedroom and of course the screen in porch and wrap around porch is a must have! Large rooms and spacious bedrooms upstairs as well as laundry on both levels. Extra storage space with two walking closets upstairs. Call today for your showing appointment.

432 Love Point Rd, Stevensville

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

Stevensville - The Ye Olde Church house is listed for sale. This unique property is being sold with 2 additional lots. A total of 1.74 acres of prime location in downtown Stevensville. The property has been previously used as an antique store but has many other uses under the zoning of SHVC. This is opportunity knocking for your new business. The property is located in the enterprise zone, that will offer business discounts or credits when bringing your business to Stevensville. The property has just been surveyed and stacked with corner markers. Additional tax #1804057503 and 1804112385 convey with sale.

$985,000

426 Love Point Rd, Stevensville

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

OPEN HOUSE SATURDAY & SUNDAY, MARCH 21 & 22, 1–3 PM. SHOWINGS MAY BE SCHEDULED BEGINNING MARCH 20. Another fabulous new listing in sought-after Bay Bridge Cove! This upgraded and expanded Easton model sits on a premium lot in one of the community’s most desirable locations, backing to a pristine conservation area. Enter through the charming paver courtyard into a beautifully maintained home featuring an island kitchen with upgraded appliances, a spacious open dining area, a great room with a fireplace, and a gorgeous three-season room with peaceful wooded views. The main-level primary suite offers two walk-in closets and a beautifully finished bath, plus a second bedroom/den and full bath. Upstairs includes a loft, third bedroom, and full bath—ideal for guests. Bay Bridge Cove offers exceptional amenities, including an outdoor pool, tennis, pickleball, and bocce courts, a crab shack, a clubhouse with a fitness room, a library, meeting and party rooms, community herb and vegetable gardens, walking paths around three community ponds, and a dog park. Ideally located less than five minutes to the Bay Bridge with easy access to shopping, golf, public parks, walking trails, waterfront restaurants, Annapolis, BWI, Baltimore, DC, and several nationally recognized medical facilities. Home sweet home!

$650,000

3 Beds ⋅ 3 Baths

OPEN HOUSE SATURDAY & SUNDAY, MARCH 21 & 22, 1–3 PM. SHOWINGS MAY BE SCHEDULED BEGINNING MARCH 20. Another fabulous new listing in sought-after Bay Bridge Cove! This upgraded and expanded Easton model sits on a premium lot in one of the community’s most desirable locations, backing to a pristine conservation area. Enter through the charming paver courtyard into a beautifully maintained home featuring an island kitchen with upgraded appliances, a spacious open dining area, a great room with a fireplace, and a gorgeous three-season room with peaceful wooded views. The main-level primary suite offers two walk-in closets and a beautifully finished bath, plus a second bedroom/den and full bath. Upstairs includes a loft, third bedroom, and full bath—ideal for guests. Bay Bridge Cove offers exceptional amenities, including an outdoor pool, tennis, pickleball, and bocce courts, a crab shack, a clubhouse with a fitness room, a library, meeting and party rooms, community herb and vegetable gardens, walking paths around three community ponds, and a dog park. Ideally located less than five minutes to the Bay Bridge with easy access to shopping, golf, public parks, walking trails, waterfront restaurants, Annapolis, BWI, Baltimore, DC, and several nationally recognized medical facilities. Home sweet home!

614 Moorings Cir, Stevensville

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

One of the largest lots in the community, fenced rear yard, area to expand, recent roof, siding and windows, updated bathroom, community beach, club house and boat ramp. Large family room with wood burning stove, brick fireplace n living room with pellet stove insert, propane and electric heat. Large gravel asphalt mixed driveway. New garage,

$445,000

One of the largest lots in the community, fenced rear yard, area to expand, recent roof, siding and windows, updated bathroom, community beach, club house and boat ramp. Large family room with wood burning stove, brick fireplace n living room with pellet stove insert, propane and electric heat. Large gravel asphalt mixed driveway. New garage,

209 Olive Branch Rd, Stevensville

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

Selling Office: RE/MAX One.

$3,200,000

Welcome to 3207 Bennett Point, a breathtaking Norman Jaffe–designed waterfront estate set on over 5 private acres along the widest stretch of the Wye River. Designed to maximize its setting, the home offers floor-to-ceiling glass, seamless indoor-outdoor living, and panoramic water views from nearly every room. The main residence showcases timeless craftsmanship with Tennessee Quarry FlagStone, rich hardwoods, and warm wood-clad ceilings and walls. Expansive living areas and a waterfront screened porch highlight the home’s indoor-outdoor flow, while a home office, elevator, and a gourmet kitchen that was renovated in 2017 with an oversized island, contemporary cabinetry, and premium finishes that add comfort and function. Upstairs, the primary suite offers a stunning wall of glass framing the river, a fireplace, dual walk-in closets, and a spa-inspired bath. The estate’s separate 4-bedroom, 4-bath guest house was taken down to the studs and completely reimagined in 2017. The renovation added two bedrooms and two bathrooms, a full kitchen, and a spacious living area all with sweeping water views. Providing luxurious accommodations for family and guests. Outdoors, the property delivers resort-style amenities at every turn: a 22’x44’ PebbleTec heated pool with pool house, a Bradford hot tub designed for year-round relaxation, and a 340’ pier with 8’ MLW, boat lift, davits, and deep-water access for boating, fishing, and swimming. Recent upgrades (2017) include kitchen and bath renovations, the guest house addition, elevator installation, whole-house generator for the main and guest house, new insulation, HVAC, electric service, lighting, and flooring- ensuring peace of mind for years to come. With expansive shoreline, mature landscaping, and sunset views over the Wye, this estate pairs architectural pedigree with resort-like amenities that is just minutes from the Chesapeake Bay Bridge. Experience the pinnacle of Eastern Shore living at 3207 Bennett Point.

5 Beds ⋅ 7 Baths

Welcome to 3207 Bennett Point, a breathtaking Norman Jaffe–designed waterfront estate set on over 5 private acres along the widest stretch of the Wye River. Designed to maximize its setting, the home offers floor-to-ceiling glass, seamless indoor-outdoor living, and panoramic water views from nearly every room. The main residence showcases timeless craftsmanship with Tennessee Quarry FlagStone, rich hardwoods, and warm wood-clad ceilings and walls. Expansive living areas and a waterfront screened porch highlight the home’s indoor-outdoor flow, while a home office, elevator, and a gourmet kitchen that was renovated in 2017 with an oversized island, contemporary cabinetry, and premium finishes that add comfort and function. Upstairs, the primary suite offers a stunning wall of glass framing the river, a fireplace, dual walk-in closets, and a spa-inspired bath. The estate’s separate 4-bedroom, 4-bath guest house was taken down to the studs and completely reimagined in 2017. The renovation added two bedrooms and two bathrooms, a full kitchen, and a spacious living area all with sweeping water views. Providing luxurious accommodations for family and guests. Outdoors, the property delivers resort-style amenities at every turn: a 22’x44’ PebbleTec heated pool with pool house, a Bradford hot tub designed for year-round relaxation, and a 340’ pier with 8’ MLW, boat lift, davits, and deep-water access for boating, fishing, and swimming. Recent upgrades (2017) include kitchen and bath renovations, the guest house addition, elevator installation, whole-house generator for the main and guest house, new insulation, HVAC, electric service, lighting, and flooring- ensuring peace of mind for years to come. With expansive shoreline, mature landscaping, and sunset views over the Wye, this estate pairs architectural pedigree with resort-like amenities that is just minutes from the Chesapeake Bay Bridge. Experience the pinnacle of Eastern Shore living at 3207 Bennett Point.

3207 Bennett Point Rd, Queenstown

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Select Land & Homes, LLC.

$450,000

Sellers Requesting All Offers be submitted no Later than 6pm Thursday April 9th Welcome to 324 Flat Iron Square Road — an exceptional, fully renovated 4-bedroom, 2-bath residence gracefully set on 1.97 private acres in northern Queen Anne’s County. Offering over 2,000 square feet of refined living space, this home seamlessly blends modern luxury with the tranquility of Maryland's Eastern Shore. Step inside to discover a thoughtfully curated interior featuring a designer kitchen complete with elegant quartz countertops, upgraded 42” cabinetry, and a sophisticated finish throughout. The main level showcases a seamless combination of luxury plank and rich hardwood flooring, complemented by beautifully updated bathrooms that elevate everyday living. No detail has been overlooked, with major capital improvements already in place — including a new roof, new windows, and updated HVAC — delivering both style and peace of mind. The home also offers an unfinished walk-out basement, presenting a rare opportunity to expand and customize additional living space to suit your lifestyle. Outdoors, the property transforms into a private retreat. Enjoy a fully stocked fish pond, perfect for relaxing or entertaining around the fire, along the charming grounds that invite endless possibilities. The acreage also offers excellent natural surroundings with wildlife presence, creating opportunities for outdoor enthusiasts, including deer activity on the property. Ideally located just minutes from Route 301, this property offers effortless accessibility while maintaining the quiet, sought-after Shore lifestyle.

4 Beds ⋅ 2 Baths

Sellers Requesting All Offers be submitted no Later than 6pm Thursday April 9th Welcome to 324 Flat Iron Square Road — an exceptional, fully renovated 4-bedroom, 2-bath residence gracefully set on 1.97 private acres in northern Queen Anne’s County. Offering over 2,000 square feet of refined living space, this home seamlessly blends modern luxury with the tranquility of Maryland's Eastern Shore. Step inside to discover a thoughtfully curated interior featuring a designer kitchen complete with elegant quartz countertops, upgraded 42” cabinetry, and a sophisticated finish throughout. The main level showcases a seamless combination of luxury plank and rich hardwood flooring, complemented by beautifully updated bathrooms that elevate everyday living. No detail has been overlooked, with major capital improvements already in place — including a new roof, new windows, and updated HVAC — delivering both style and peace of mind. The home also offers an unfinished walk-out basement, presenting a rare opportunity to expand and customize additional living space to suit your lifestyle. Outdoors, the property transforms into a private retreat. Enjoy a fully stocked fish pond, perfect for relaxing or entertaining around the fire, along the charming grounds that invite endless possibilities. The acreage also offers excellent natural surroundings with wildlife presence, creating opportunities for outdoor enthusiasts, including deer activity on the property. Ideally located just minutes from Route 301, this property offers effortless accessibility while maintaining the quiet, sought-after Shore lifestyle.

324 Flat Iron Square Rd, Church Hill

Listing courtesy of Samson Properties. Contact:

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

$310,000

Welcome to easy, waterfront-inspired living in the heart of Chester! This beautifully maintained first-floor condo at 501 Teal Ct offers the perfect blend of comfort, style, and convenience—plus peaceful views of the community pond right from your backyard. Step inside to find gorgeous hardwood floors flowing throughout the main living space, anchored by a cozy propane fireplace—perfect for those crisp Shore evenings. The updated kitchen is a true standout, featuring stunning granite countertops, a designer backsplash, and stainless steel appliances, making it as functional as it is eye-catching. Enjoy your morning coffee or unwind at the end of the day with tranquil pond views—no stairs, no hassle, just easy living. Located in the sought-after Bayside community, residents enjoy access to a clubhouse, fitness center, and pool, plus direct proximity to the Cross Island Trail for walking, biking, and soaking in that Kent Island lifestyle. All of this just minutes to local dining, shopping, and the Chesapeake Bay Bridge—making commuting or a quick getaway a breeze. If you’ve been waiting for low-maintenance living with high-impact style… this is it.

5 Beds ⋅ 4 Baths

Welcome to easy, waterfront-inspired living in the heart of Chester! This beautifully maintained first-floor condo at 501 Teal Ct offers the perfect blend of comfort, style, and convenience—plus peaceful views of the community pond right from your backyard. Step inside to find gorgeous hardwood floors flowing throughout the main living space, anchored by a cozy propane fireplace—perfect for those crisp Shore evenings. The updated kitchen is a true standout, featuring stunning granite countertops, a designer backsplash, and stainless steel appliances, making it as functional as it is eye-catching. Enjoy your morning coffee or unwind at the end of the day with tranquil pond views—no stairs, no hassle, just easy living. Located in the sought-after Bayside community, residents enjoy access to a clubhouse, fitness center, and pool, plus direct proximity to the Cross Island Trail for walking, biking, and soaking in that Kent Island lifestyle. All of this just minutes to local dining, shopping, and the Chesapeake Bay Bridge—making commuting or a quick getaway a breeze. If you’ve been waiting for low-maintenance living with high-impact style… this is it.

501 Teal Ct, Chester

Listing courtesy of Samson Properties. Contact:

Selling Office: Realty Navigator.

$300,000

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Just in time for spring! This exquisitely renovated 2-bedroom, 2-bathroom home offers the ideal space to bring your dream lifestyle to life. This property is perfect for the weekend warrior, first time buyer or someone downsizing! Boasting an open-concept design, it features a spacious living room, dining area, and a modern kitchen complete with quartz countertops, stainless steel appliances, and stylish white shaker cabinets. Enjoy brand-new luxury vinyl plank flooring throughout, freshly painted interiors, and a newly constructed front porch deck. With its thoughtful details and inviting layout, this home has everything you need and more. https://homesale.plus/Listing/Details/8269880. Please schedule all showings online via Showing Time. Offers will be accepted through Tuesday, March 24, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Just in time for spring! This exquisitely renovated 2-bedroom, 2-bathroom home offers the ideal space to bring your dream lifestyle to life. This property is perfect for the weekend warrior, first time buyer or someone downsizing! Boasting an open-concept design, it features a spacious living room, dining area, and a modern kitchen complete with quartz countertops, stainless steel appliances, and stylish white shaker cabinets. Enjoy brand-new luxury vinyl plank flooring throughout, freshly painted interiors, and a newly constructed front porch deck. With its thoughtful details and inviting layout, this home has everything you need and more. https://homesale.plus/Listing/Details/8269880. Please schedule all showings online via Showing Time. Offers will be accepted through Tuesday, March 24, 2026 at 5:00 pm. AT SELLER'S DISCRETION, AN OFFER MAY BE ACCEPTED AT ANY TIME.

102 Bobbitt Ct, Stevensville

Listing courtesy of Keller Williams Legacy. Contact:

Selling Office: Douglas Realty LLC.

$285,000

INVESTORS!! THIS COULD BE YOUR NEXT PROJECT!! Estate Sale – Peaceful Tranquility on the Eastern Shore There’s something special about living near the water—the smell of the bay, the calm in the air, and the sound of birds all around you. This brick rancher in the desirable Marling Farms community is right in the center of it all. With views of Crab Alley Creek and located within the Chester River watershed, the setting offers the peaceful lifestyle so many seek on the Eastern Shore. While the home needs a little TLC, it’s graciously waiting for its next homeowner to bring their vision to life. The property is being sold AS-IS, and no repairs will be made—BUT- it’s the perfect opportunity to add your own special touches. The home does feature a newer roof.... update to suit your taste-- Highlights include a welcoming front porch, attached two-car garage, and a driveway that accommodates additional parking. Inside, you'll find a spacious living room with a fireplace (ambiance for a snow-fall) and walls of windows that allow natural light to pour in while showcasing the surrounding beauty. .. and a view of the Crab Alley Bay is just across the road-- The home also offers an entrance foyer, an eat-in kitchen, and a four-season sunroom overlooking open green space—perfect for relaxing or gathering with family and friends. Situated on a little over a half-acre lot, the backyard offers a blank canvas to create your own outdoor oasis. The home includes one full and one half bathroom, two bedrooms, and a versatile breezeway bonus room currently set up as a club room with a pool table. This flexible space could easily be converted into additional living space or a bedroom— There is also a laundry closet and ample storage throughout. Marling Farms is a water-oriented community surrounded by natural beauty, offering three beach areas with playgrounds and covered picnic spaces. You don’t have to be a crabber or fisherman—but those hobbies certainly fit right in here! Enjoy nature walks, fishing, or relaxing at the community waterfront. Located just minutes from waterfront restaurants, shopping, and everyday conveniences on Kent Island-- Its the home you’ve always wanted in a water community—You just have to get here

INVESTORS!! THIS COULD BE YOUR NEXT PROJECT!! Estate Sale – Peaceful Tranquility on the Eastern Shore There’s something special about living near the water—the smell of the bay, the calm in the air, and the sound of birds all around you. This brick rancher in the desirable Marling Farms community is right in the center of it all. With views of Crab Alley Creek and located within the Chester River watershed, the setting offers the peaceful lifestyle so many seek on the Eastern Shore. While the home needs a little TLC, it’s graciously waiting for its next homeowner to bring their vision to life. The property is being sold AS-IS, and no repairs will be made—BUT- it’s the perfect opportunity to add your own special touches. The home does feature a newer roof.... update to suit your taste-- Highlights include a welcoming front porch, attached two-car garage, and a driveway that accommodates additional parking. Inside, you'll find a spacious living room with a fireplace (ambiance for a snow-fall) and walls of windows that allow natural light to pour in while showcasing the surrounding beauty. .. and a view of the Crab Alley Bay is just across the road-- The home also offers an entrance foyer, an eat-in kitchen, and a four-season sunroom overlooking open green space—perfect for relaxing or gathering with family and friends. Situated on a little over a half-acre lot, the backyard offers a blank canvas to create your own outdoor oasis. The home includes one full and one half bathroom, two bedrooms, and a versatile breezeway bonus room currently set up as a club room with a pool table. This flexible space could easily be converted into additional living space or a bedroom— There is also a laundry closet and ample storage throughout. Marling Farms is a water-oriented community surrounded by natural beauty, offering three beach areas with playgrounds and covered picnic spaces. You don’t have to be a crabber or fisherman—but those hobbies certainly fit right in here! Enjoy nature walks, fishing, or relaxing at the community waterfront. Located just minutes from waterfront restaurants, shopping, and everyday conveniences on Kent Island-- Its the home you’ve always wanted in a water community—You just have to get here

1905 Bayside Dr, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: RE/MAX Leading Edge.

$326,000

Price improvement just in time for the spring market! Come see all of amazing amenities this water privileged community has! Enjoy the boating, pool, restaurants and Cross Island trail all within walking distance of this great home! Lovely 3 level townhome in the water oriented community of Bayside Marina offering 2/3 bedrooms and 3 full and one half baths. This multifunctional unit can be two bedrooms up and one down or use the downstairs room with a full bath as a tv or relaxing/entertaining area. Walk out to the patio and enjoy views of the community pond or walk to the pool, community clubhouse or gym. The current owners upgraded the kitchen in 2022 with quartz countertops, new lighting and new gas stove and refrigerator. The dishwasher is brand new/never used. The roof was replaced in 2023 and most of the unit has just been painted and professionally cleaned. Carefree living on the island. It doesn’t get any better than this!

3 Beds ⋅ 4 Baths

Price improvement just in time for the spring market! Come see all of amazing amenities this water privileged community has! Enjoy the boating, pool, restaurants and Cross Island trail all within walking distance of this great home! Lovely 3 level townhome in the water oriented community of Bayside Marina offering 2/3 bedrooms and 3 full and one half baths. This multifunctional unit can be two bedrooms up and one down or use the downstairs room with a full bath as a tv or relaxing/entertaining area. Walk out to the patio and enjoy views of the community pond or walk to the pool, community clubhouse or gym. The current owners upgraded the kitchen in 2022 with quartz countertops, new lighting and new gas stove and refrigerator. The dishwasher is brand new/never used. The roof was replaced in 2023 and most of the unit has just been painted and professionally cleaned. Carefree living on the island. It doesn’t get any better than this!

204 Ringneck Ct, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

Selling Office: Redfin Corp.

$527,000

PRICE IMPROVEMENT-Welcome to 124 Overlook Drive nestled in the Overlook at Carmichael Community on a quiet non-thru street. This well-maintained Colonial-style spanning over 2,454 square feet is designed to cater to both relaxation and entertainment. Featuring an open floor plan with 3 Spacious Bedrooms and 2 and a Half Bathrooms. Step Inside to a Formal Living Room and Dining Room with newer luxury vinyl tile flooring spanning the entire first floor. The kitchen boasts ample cabinet space with counter seating and table space. The adjoining family room, complete with a cozy gas brick fireplace and mantel, invites you to unwind after a long day and don't forget the cozy updated Sunroom off the kitchen for extra living space with a Pellet Stove, new windows and new French doors leading to the rear yard. Head upstairs to the Primary Bedroom offering a spacious walk-in closet and an ensuite bath. 2 Additional Bedrooms are generously sized and a Full Hall Bathroom completing the second level. Enjoy the outdoors on the charming concrete patio with a picturesque view of the adjacent farmland, perfect for morning coffee or evening gatherings under the stars. When needed there is a 20’ Sun Setter Auto Awning. The exterior of the property is equally impressive, set on a sprawling 1.23-acre lot that adjoins open space, offering a sense of tranquility, privacy and invisible fence with landscaped grounds. Parking is a breeze with an oversized side-entry (newer insulated garage doors) that accommodates 2 Vehicles, work shop/extra storage along with an expansive driveway providing ample space for your Camper, Boat and Guests. Easy access to RT50 and RT301 and only 15 minutes to the Bay Bridge which is ideal for commuting. Close to area Waterfront Restaurants, Golf & More. Short drive to historic Annapolis and St. Michael’s. Only 90 minutes to the Atlantic Ocean. Schedule your private showing today and experience everything this outstanding home has to offer. This property is not just a house; it's a lifestyle waiting to be embraced. Quick settlement available. 1 Year Home Warranty included.

3 Beds ⋅ 3 Baths

PRICE IMPROVEMENT-Welcome to 124 Overlook Drive nestled in the Overlook at Carmichael Community on a quiet non-thru street. This well-maintained Colonial-style spanning over 2,454 square feet is designed to cater to both relaxation and entertainment. Featuring an open floor plan with 3 Spacious Bedrooms and 2 and a Half Bathrooms. Step Inside to a Formal Living Room and Dining Room with newer luxury vinyl tile flooring spanning the entire first floor. The kitchen boasts ample cabinet space with counter seating and table space. The adjoining family room, complete with a cozy gas brick fireplace and mantel, invites you to unwind after a long day and don't forget the cozy updated Sunroom off the kitchen for extra living space with a Pellet Stove, new windows and new French doors leading to the rear yard. Head upstairs to the Primary Bedroom offering a spacious walk-in closet and an ensuite bath. 2 Additional Bedrooms are generously sized and a Full Hall Bathroom completing the second level. Enjoy the outdoors on the charming concrete patio with a picturesque view of the adjacent farmland, perfect for morning coffee or evening gatherings under the stars. When needed there is a 20’ Sun Setter Auto Awning. The exterior of the property is equally impressive, set on a sprawling 1.23-acre lot that adjoins open space, offering a sense of tranquility, privacy and invisible fence with landscaped grounds. Parking is a breeze with an oversized side-entry (newer insulated garage doors) that accommodates 2 Vehicles, work shop/extra storage along with an expansive driveway providing ample space for your Camper, Boat and Guests. Easy access to RT50 and RT301 and only 15 minutes to the Bay Bridge which is ideal for commuting. Close to area Waterfront Restaurants, Golf & More. Short drive to historic Annapolis and St. Michael’s. Only 90 minutes to the Atlantic Ocean. Schedule your private showing today and experience everything this outstanding home has to offer. This property is not just a house; it's a lifestyle waiting to be embraced. Quick settlement available. 1 Year Home Warranty included.

124 Overlook Dr, Queenstown

Listing courtesy of Keller Williams Flagship. Contact:

Welcome to Storybook charm meets waterfront living at 212 Dutcher Rd in Queenstown… and this one is something truly special 🌊🏡 Nestled on a stunning 1.34-acre waterfront lot, this Cape Cod offers the kind of Eastern Shore lifestyle people dream about—complete with a updated private pier, electric boat lift, and even your own sandy beach. Days on the water, evenings by the shoreline… this is what it’s all about.The main home (2,425 sq ft.) features 4 bedrooms and 3 full baths, filled with warmth, character, and timeless design. And just when you think it couldn’t get better—there’s a separate 1 bedroom, 1 bath guest house, perfect for visitors, extended family, or a private retreat. With nearly 3,000 sq ft of total living space and located in the desirable Belle Point community (low HOA!), this property offers both privacy and connection—just minutes to the Bay Bridge, marinas, and everything the Shore has to offer.

$1,340,000

4 Beds ⋅ 4 Baths

Welcome to Storybook charm meets waterfront living at 212 Dutcher Rd in Queenstown… and this one is something truly special 🌊🏡 Nestled on a stunning 1.34-acre waterfront lot, this Cape Cod offers the kind of Eastern Shore lifestyle people dream about—complete with a updated private pier, electric boat lift, and even your own sandy beach. Days on the water, evenings by the shoreline… this is what it’s all about.The main home (2,425 sq ft.) features 4 bedrooms and 3 full baths, filled with warmth, character, and timeless design. And just when you think it couldn’t get better—there’s a separate 1 bedroom, 1 bath guest house, perfect for visitors, extended family, or a private retreat. With nearly 3,000 sq ft of total living space and located in the desirable Belle Point community (low HOA!), this property offers both privacy and connection—just minutes to the Bay Bridge, marinas, and everything the Shore has to offer.

212 Dutcher Rd, Queenstown

Listing courtesy of Samson Properties. Contact: