Movewithsamantha.com Search Results

317 Virginia Rd, Stevensville

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

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

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3 bedrooms and 2.5 baths, along with a 2-car garage and a newly paved blacktop driveway. Inside, enjoy a bright, functional layout with brand-new carpet throughout the entire upstairs, giving the home a fresh, move-in-ready feel. Additional updates include a new roof, offering peace of mind for years to come. The spacious living areas flow seamlessly, making it ideal for both everyday living and entertaining. Step outside to a large backyard with plenty of space to relax and enjoy. The property includes a children’s play area and a vegetable garden, perfect for outdoor fun and homegrown produce. Highlights: 3 Bedrooms | 2.5 Bathrooms 1,784 Sq Ft | Built in 2004 2-Car Garage New Roof New Carpet Upstairs Blacktop Driveway Large Backyard Children’s Play Area Vegetable Garden Conveniently located just minutes from downtown Chestertown, Washington College, local shops, dining, and the waterfront, this home offers the perfect balance of peaceful living and accessibility. Schedule your showing today—this move-in-ready home won’t last long! Professional pictures coming 5/7 .

3 Beds ⋅ 3 Baths

Beautiful, Well-Maintained 3BR/2.5BA Home with Upgrades – 215 Fairview Drive Owner pride shines inside and out in this exceptional home located in the charming town of Chestertown, nestled in Queen Anne's County. Built in 2004 and offering 1,784 sq ft of living space, this property blends comfort, functionality, and thoughtful updates—perfect for today’s lifestyle. This inviting home features 3 bedrooms and 2.5 baths, along with a 2-car garage and a newly paved blacktop driveway. Inside, enjoy a bright, functional layout with brand-new carpet throughout the entire upstairs, giving the home a fresh, move-in-ready feel. Additional updates include a new roof, offering peace of mind for years to come. The spacious living areas flow seamlessly, making it ideal for both everyday living and entertaining. Step outside to a large backyard with plenty of space to relax and enjoy. The property includes a children’s play area and a vegetable garden, perfect for outdoor fun and homegrown produce. Highlights: 3 Bedrooms | 2.5 Bathrooms 1,784 Sq Ft | Built in 2004 2-Car Garage New Roof New Carpet Upstairs Blacktop Driveway Large Backyard Children’s Play Area Vegetable Garden Conveniently located just minutes from downtown Chestertown, Washington College, local shops, dining, and the waterfront, this home offers the perfect balance of peaceful living and accessibility. Schedule your showing today—this move-in-ready home won’t last long! Professional pictures coming 5/7 .

215 Fairview Dr, Chestertown

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

Selling Office: Berkshire Hathaway Homeservice Homesale Realty.

$465,000

Highly motivated Seller! Prince improvement of $485,000- Welcome to 324 Kidwell Avenue! Looks can be deceiving! This home is much larger than it appears! Offering 3,146 sq. ft. of living space, this beautifully maintained ranch-style home with a fully finished walkout basement combines space, comfort, and charm in the heart of historic Centreville. Inside, you’ll find hardwood and ceramic tile flooring throughout, a warm country-style kitchen, a separate dining area, and a spacious family room perfect for entertaining. The primary suite features a relaxing soaking tub and separate stall shower, creating the perfect place to unwind. Two fireplaces add warmth and character, making the home feel cozy year-round.The main-level laundry room adds convenience, while the finished walkout basement offers flexible space for a recreation room, home office, gym, or guest area. Step outside to a peaceful backyard surrounded by mature trees, providing privacy and tranquil views. The front porch offers a perfect vantage point to enjoy Centreville’s beloved annual parades, bringing the charm of this historic town right to your doorstep.If you’re looking for more space than expected, small-town charm, and a move-in ready home, this one is a must-see. Homes like this in Centreville don’t last long—schedule your showing today!

4 Beds ⋅ 3 Baths

Highly motivated Seller! Prince improvement of $485,000- Welcome to 324 Kidwell Avenue! Looks can be deceiving! This home is much larger than it appears! Offering 3,146 sq. ft. of living space, this beautifully maintained ranch-style home with a fully finished walkout basement combines space, comfort, and charm in the heart of historic Centreville. Inside, you’ll find hardwood and ceramic tile flooring throughout, a warm country-style kitchen, a separate dining area, and a spacious family room perfect for entertaining. The primary suite features a relaxing soaking tub and separate stall shower, creating the perfect place to unwind. Two fireplaces add warmth and character, making the home feel cozy year-round.The main-level laundry room adds convenience, while the finished walkout basement offers flexible space for a recreation room, home office, gym, or guest area. Step outside to a peaceful backyard surrounded by mature trees, providing privacy and tranquil views. The front porch offers a perfect vantage point to enjoy Centreville’s beloved annual parades, bringing the charm of this historic town right to your doorstep.If you’re looking for more space than expected, small-town charm, and a move-in ready home, this one is a must-see. Homes like this in Centreville don’t last long—schedule your showing today!

324 Kidwell Ave, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

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

$390,000

If you have been looking for a meticulously maintained and restored house in the center of historic Centreville, look no further. Tucked away on a quiet side street, 104 Windsor is the ultimate example of fine craftsmanship and pride of ownership. From the lush perennial flower gardens surrounding the house, to the careful and thoughtful restorations performed over decades of ownership, no detail has been overlooked. This classic farmhouse with a white picket fence offers original charm with modern upgrades. The millwork and original windows, many with the original glass, have been meticulously restored. The home's improvements include the incorporation of the original slate from the roof of the Centreville Courthouse, laid in the entryway, installation of new storm windows to improve energy efficiency for the original, restored, windows, a new roof, as well as the recent addition of a full bathroom and mudroom off of the kitchen. The house also has ductwork already installed, for easy installation of a central air conditioning system. For the hobby enthusiast, take your pick of workspaces in the basement, boat shed and rear accessory building. If you have been looking for a property where an ADU could be added, look no further as the outbuilding currently used as a workshop and for storage is the perfect size for tiny home living.

3 Beds ⋅ 2 Baths

If you have been looking for a meticulously maintained and restored house in the center of historic Centreville, look no further. Tucked away on a quiet side street, 104 Windsor is the ultimate example of fine craftsmanship and pride of ownership. From the lush perennial flower gardens surrounding the house, to the careful and thoughtful restorations performed over decades of ownership, no detail has been overlooked. This classic farmhouse with a white picket fence offers original charm with modern upgrades. The millwork and original windows, many with the original glass, have been meticulously restored. The home's improvements include the incorporation of the original slate from the roof of the Centreville Courthouse, laid in the entryway, installation of new storm windows to improve energy efficiency for the original, restored, windows, a new roof, as well as the recent addition of a full bathroom and mudroom off of the kitchen. The house also has ductwork already installed, for easy installation of a central air conditioning system. For the hobby enthusiast, take your pick of workspaces in the basement, boat shed and rear accessory building. If you have been looking for a property where an ADU could be added, look no further as the outbuilding currently used as a workshop and for storage is the perfect size for tiny home living.

104 Windsor Ave, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: Benson & Mangold, LLC.

$1,198,526

Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

3 Beds ⋅ 3 Baths

Finley Creek Estates, an exclusive new community nestled in between Centreville and historic Chestertown situated on 1 plus acre lots. This luxurious estate like home is to be built by Red oak Properties, LLC, one of the Eastern Shore Premier builders. One lot remains with this builder. Call for additional details.

Lot 4 Finley Creek, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Douglas Realty LLC.

$477,500

Private home and driveway, do not "drive by" without appointment. Adorable Cape Cod located just a few miles outside the town of Centreville, nestled on a very private lot, of 1.6 acres backing to peaceful woods for ultimate serenity and seclusion. Behind the home lies acres and acres of protected land , offering lasting privacy and beautiful natural views. This charming 3 bedroom, 2 bath home offers the perfect blend of comfort and indoor/outdoor living, with inviting spaces designed for both relaxation and entertaining. Lovingly maintained by its original owners, the home exudes warmth, comfort and a deep tie-in to nature. Step outside to your own private retreat featuring multiple porches, perfect for morning coffee, evening gatherings, or simply unwinding in nature. A serene screened-in porch provides the ideal spot to enjoy the outdoors in comfort year-round. The seamless connection between indoor comfort and outdoor beauty makes this property truly special. This is a rare opportunity to own a peaceful escape with charm, privacy, and lifestyle all in one. Once you visit, you may never want to leave! Convenient location, off of 213 with easy access to 301/50 and an easy commute to Annapolis/Baltimore and DC.

3 Beds ⋅ 2 Baths

Private home and driveway, do not "drive by" without appointment. Adorable Cape Cod located just a few miles outside the town of Centreville, nestled on a very private lot, of 1.6 acres backing to peaceful woods for ultimate serenity and seclusion. Behind the home lies acres and acres of protected land , offering lasting privacy and beautiful natural views. This charming 3 bedroom, 2 bath home offers the perfect blend of comfort and indoor/outdoor living, with inviting spaces designed for both relaxation and entertaining. Lovingly maintained by its original owners, the home exudes warmth, comfort and a deep tie-in to nature. Step outside to your own private retreat featuring multiple porches, perfect for morning coffee, evening gatherings, or simply unwinding in nature. A serene screened-in porch provides the ideal spot to enjoy the outdoors in comfort year-round. The seamless connection between indoor comfort and outdoor beauty makes this property truly special. This is a rare opportunity to own a peaceful escape with charm, privacy, and lifestyle all in one. Once you visit, you may never want to leave! Convenient location, off of 213 with easy access to 301/50 and an easy commute to Annapolis/Baltimore and DC.

141 Cat Pause Ln, Centreville

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Doug Ashley Realtors, LLC.

$690,000

117 Overlook (1.15 Acres) is ideally located in Queenstown, Maryland—just 30 minutes to Annapolis and only 15 minutes to Easton—offering both convenience and a peaceful setting. This spacious home features 2,672 square feet of finished living space above, along with the basement area of 1270 sf/ 400 sf finished, providing ample opportunity for customization or future expansion. The property includes 5 bedrooms, with two serving as primary suites. One of the main-level bedrooms can also function as a private in-law suite, offering flexibility for multi-generational living or guest accommodations. Throughout the home, you’ll find custom molding, granite counter tops, hardwood flooring, custom build-in, ceramic tile, and two wood-burning fireplaces, adding warmth and character. A two-car attached garage provides added convenience. The roof is only 2.5 yrs young. The large barn at the rear of the property is a standout feature, offering a workshop, office space, and second-floor storage that could easily be transformed into a studio. Electricity is already in place, enhancing its functionality. The barn also provides ample space for RV or large boat storage, along with room for lawn equipment and more.

5 Beds ⋅ 4 Baths

117 Overlook (1.15 Acres) is ideally located in Queenstown, Maryland—just 30 minutes to Annapolis and only 15 minutes to Easton—offering both convenience and a peaceful setting. This spacious home features 2,672 square feet of finished living space above, along with the basement area of 1270 sf/ 400 sf finished, providing ample opportunity for customization or future expansion. The property includes 5 bedrooms, with two serving as primary suites. One of the main-level bedrooms can also function as a private in-law suite, offering flexibility for multi-generational living or guest accommodations. Throughout the home, you’ll find custom molding, granite counter tops, hardwood flooring, custom build-in, ceramic tile, and two wood-burning fireplaces, adding warmth and character. A two-car attached garage provides added convenience. The roof is only 2.5 yrs young. The large barn at the rear of the property is a standout feature, offering a workshop, office space, and second-floor storage that could easily be transformed into a studio. Electricity is already in place, enhancing its functionality. The barn also provides ample space for RV or large boat storage, along with room for lawn equipment and more.

117 Overlook Dr, Queenstown

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

Selling Office: Taylor Properties.

$817,000

Welcome to 751 Ruthsburg Rd. in Centreville, Maryland—a truly one-of-a-kind farmette offering over 6 acres of privacy, rolling hills, and a picturesque pond, all just minutes from town. Beautifully renovated throughout, this expansive 7-bedroom, 3.5-bath home blends modern updates with timeless character and space to grow. From the moment you step inside, you’ll appreciate the generous living areas designed for both everyday comfort and effortless entertaining. At the heart of the home is a stunning, fully updated kitchen featuring a walk-in pantry and a seamless flow into the dining room. Here, vaulted ceilings and dramatic floor-to-ceiling windows flood the space with natural light while framing peaceful views of the surrounding landscape—creating a setting that truly connects indoor living with the beauty of nature. The first floor also offers a thoughtfully designed mudroom and laundry area complete with custom built-in cubbies—perfect for an active or growing household. Additionally, you’ll find a versatile and private in-law suite or main-level primary suite, featuring high ceilings that enhance the sense of space, along with its own kitchenette, spacious living room, large bedroom, and a beautifully appointed full bathroom. Upstairs, the second level includes four well-sized bedrooms with ample closet space and a fully updated bathroom. The third floor adds even more flexibility, offering a generously sized primary bedroom, an additional bedroom, and a half bath, along with unfinished space already prepped for a future full bathroom—giving you the opportunity to expand even further. Outside, the property is just as impressive. With over 6 acres of serene land, a private pond, and gently rolling terrain, this farmette offers endless possibilities—whether you’re looking for a peaceful retreat, hobby farm, or space to spread out and enjoy. An expansive garage provides abundant room for vehicles, equipment, or additional storage. Properties like this are rare—offering privacy, acreage, modern updates, and close proximity to all the shopping, dining, and conveniences of Centreville. Talkie fiber optic internet is the current internet provider and a line for Atlantic broadband has been run which is also an internet option. Schedule your private showing today and experience everything this exceptional property has to offer.

7 Beds ⋅ 4 Baths

Welcome to 751 Ruthsburg Rd. in Centreville, Maryland—a truly one-of-a-kind farmette offering over 6 acres of privacy, rolling hills, and a picturesque pond, all just minutes from town. Beautifully renovated throughout, this expansive 7-bedroom, 3.5-bath home blends modern updates with timeless character and space to grow. From the moment you step inside, you’ll appreciate the generous living areas designed for both everyday comfort and effortless entertaining. At the heart of the home is a stunning, fully updated kitchen featuring a walk-in pantry and a seamless flow into the dining room. Here, vaulted ceilings and dramatic floor-to-ceiling windows flood the space with natural light while framing peaceful views of the surrounding landscape—creating a setting that truly connects indoor living with the beauty of nature. The first floor also offers a thoughtfully designed mudroom and laundry area complete with custom built-in cubbies—perfect for an active or growing household. Additionally, you’ll find a versatile and private in-law suite or main-level primary suite, featuring high ceilings that enhance the sense of space, along with its own kitchenette, spacious living room, large bedroom, and a beautifully appointed full bathroom. Upstairs, the second level includes four well-sized bedrooms with ample closet space and a fully updated bathroom. The third floor adds even more flexibility, offering a generously sized primary bedroom, an additional bedroom, and a half bath, along with unfinished space already prepped for a future full bathroom—giving you the opportunity to expand even further. Outside, the property is just as impressive. With over 6 acres of serene land, a private pond, and gently rolling terrain, this farmette offers endless possibilities—whether you’re looking for a peaceful retreat, hobby farm, or space to spread out and enjoy. An expansive garage provides abundant room for vehicles, equipment, or additional storage. Properties like this are rare—offering privacy, acreage, modern updates, and close proximity to all the shopping, dining, and conveniences of Centreville. Talkie fiber optic internet is the current internet provider and a line for Atlantic broadband has been run which is also an internet option. Schedule your private showing today and experience everything this exceptional property has to offer.

751 Ruthsburg Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: EXP Realty, LLC.

$630,000

Amazing new price ——-RECENT APPRAISAL IN HAND -buyers may walk into instant equity opportunity.- Priced below recent appraised value. Rare opportunity to own a versatile property featuring over 4,600 sq ft of finished space, geothermal HVAC, and a 30x48 pole barn Welcome to 242 Hayden Road in Centreville — a property that offers the space, flexibility, and functionality today’s buyers are searching for. With over 4,600 sq ft of total living space, this home is designed to adapt to your lifestyle. The main level features 4 bedrooms and 2.5 baths, including a spacious primary suite with a beautifully updated spa-style shower. The kitchen is well-equipped with stainless steel appliances, abundant cabinetry, and a bright breakfast nook that flows into the inviting family room, where a wood stove creates a warm and comfortable gathering space. Main-level laundry adds everyday convenience. The fully finished lower level is a standout feature, offering a full bath and second kitchen—ideal for multi-generational living, extended guests, private quarters, or flexible use as a recreation or work-from-home space. Energy-efficient geothermal heating and cooling provide long-term savings and year-round comfort. A massive attic offers exceptional storage and potential for future expansion. Outside, the property continues to impress with a partially fenced rear yard and a large insulated pole barn with electric—perfect for a workshop, car enthusiast, contractor, or home-based business. With no HOA, you have the freedom to truly make this property your own. Located just minutes from historic downtown Centreville and approximately 20 minutes to the Bay Bridge, this home delivers the ideal combination of space, versatility, and convenience—all in one exceptional setting.

4 Beds ⋅ 4 Baths

Amazing new price ——-RECENT APPRAISAL IN HAND -buyers may walk into instant equity opportunity.- Priced below recent appraised value. Rare opportunity to own a versatile property featuring over 4,600 sq ft of finished space, geothermal HVAC, and a 30x48 pole barn Welcome to 242 Hayden Road in Centreville — a property that offers the space, flexibility, and functionality today’s buyers are searching for. With over 4,600 sq ft of total living space, this home is designed to adapt to your lifestyle. The main level features 4 bedrooms and 2.5 baths, including a spacious primary suite with a beautifully updated spa-style shower. The kitchen is well-equipped with stainless steel appliances, abundant cabinetry, and a bright breakfast nook that flows into the inviting family room, where a wood stove creates a warm and comfortable gathering space. Main-level laundry adds everyday convenience. The fully finished lower level is a standout feature, offering a full bath and second kitchen—ideal for multi-generational living, extended guests, private quarters, or flexible use as a recreation or work-from-home space. Energy-efficient geothermal heating and cooling provide long-term savings and year-round comfort. A massive attic offers exceptional storage and potential for future expansion. Outside, the property continues to impress with a partially fenced rear yard and a large insulated pole barn with electric—perfect for a workshop, car enthusiast, contractor, or home-based business. With no HOA, you have the freedom to truly make this property your own. Located just minutes from historic downtown Centreville and approximately 20 minutes to the Bay Bridge, this home delivers the ideal combination of space, versatility, and convenience—all in one exceptional setting.

242 Hayden Rd, Centreville

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

Selling Office: Taylor Properties.

$599,900

Introducing 106 Charles St in Sudlersville, MD — a fully renovated, turn-key property offering a rare opportunity for Assisted Living, Transitional Housing, or Specialty Care operations. Formerly licensed and now newly approved by the Town of Sudlersville for a 16-bed Assisted Living Facility, this building is ready for launch by a first-time operator, an expanding provider, or a real estate investor seeking strong cash flow. This expansive facility includes 12 bedrooms, 3 full baths, 2 half baths, and is fully equipped with fire suppression (sprinkler) and fire alarm systems for safety and compliance. A commercial kitchen, large recreation/activity room, and multiple communal spaces create an ideal resident experience. A key highlight is the separate 2-bedroom apartment with its own kitchen and bathroom—perfect for an on-site caregiver, staff suite, or premium private living area. Additional features include, Large rear deck for outdoor enjoyment, Full basement for storage, Parking for 8 vehicles, Recently completed site plan (available upon request). Comparable facilities in the region are renting for $10,000–$12,000/month, creating an excellent value proposition whether you choose to operate the facility yourself or lease it to an operator. A rare, ready-to-go opportunity in a growing market—schedule your private tour today! Buyer responsible for verifying use and obtaining the required U&O permit.

106 Charles St, Sudlersville

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Douglas Realty LLC.

$685,000

Welcome to 335 Anna Carol Dr, a stunning home nestled in the highly sought-after Ellendale community in the town of Stevensville on Kent Island. Built in 2022, this 5-bedroom, 3.5-bathroom “Wright” model by Baldwin Homes offers the perfect blend of contemporary design and the relaxed Eastern Shore lifestyle. With over 3,500 square feet of finished living space across three levels, this home is designed for flexibility. Step inside to find an open, airy floor plan bathed in natural light, featuring luxury vinyl plank flooring and elegant recessed lighting. Just off of the entryway, you’ll find a convenient half bath and access to the garage. At the heart of the home on the main level, the gourmet kitchen is a chef’s dream, boasting a massive center island for gathering, sleek quartz countertops, stainless steel appliances, and a large pantry. The seamless flow to the attached dining space includes access to the rear deck overlooking the private fenced backyard, perfect for al fresco dining on those warm Eastern shore evenings. The grand living room, highlighted by a cozy gas fireplace and integrated surround sound, is perfect for movie nights or entertaining friends and family. The upper level features a luxurious primary suite with ample closet space and en-suite with a spa-like soaking tub and walk-in shower. Additionally, 3 spacious bedrooms with desirable closet space, a second full bathroom and a convenient laundry room complete the upper level. The expansive finished basement adds significant value, providing a daylight-filled retreat for a home gym, theater, or guest suite including a fifth bedroom and a third full bathroom. This level also includes a dedicated utility room and ample storage. Take advantage of the resort like amenities Ellendale has to offer. Launch your canoe or kayak from the community pier into Thompson Creek, or enjoy the outdoor pool all season long with your neighbors. The community also features a clubhouse, boat storage, playground and scenic walking/jogging paths. Situated just minutes from the Chesapeake Bay Bridge, this home offers a unique opportunity to enjoy peaceful Eastern Shore living, while being conveniently located to commuter routes, dining, shopping, parks, trails, golfing, farmers markets, and public fishing piers. Your Eastern Shore escape awaits. Schedule your tour today!

5 Beds ⋅ 4 Baths

Welcome to 335 Anna Carol Dr, a stunning home nestled in the highly sought-after Ellendale community in the town of Stevensville on Kent Island. Built in 2022, this 5-bedroom, 3.5-bathroom “Wright” model by Baldwin Homes offers the perfect blend of contemporary design and the relaxed Eastern Shore lifestyle. With over 3,500 square feet of finished living space across three levels, this home is designed for flexibility. Step inside to find an open, airy floor plan bathed in natural light, featuring luxury vinyl plank flooring and elegant recessed lighting. Just off of the entryway, you’ll find a convenient half bath and access to the garage. At the heart of the home on the main level, the gourmet kitchen is a chef’s dream, boasting a massive center island for gathering, sleek quartz countertops, stainless steel appliances, and a large pantry. The seamless flow to the attached dining space includes access to the rear deck overlooking the private fenced backyard, perfect for al fresco dining on those warm Eastern shore evenings. The grand living room, highlighted by a cozy gas fireplace and integrated surround sound, is perfect for movie nights or entertaining friends and family. The upper level features a luxurious primary suite with ample closet space and en-suite with a spa-like soaking tub and walk-in shower. Additionally, 3 spacious bedrooms with desirable closet space, a second full bathroom and a convenient laundry room complete the upper level. The expansive finished basement adds significant value, providing a daylight-filled retreat for a home gym, theater, or guest suite including a fifth bedroom and a third full bathroom. This level also includes a dedicated utility room and ample storage. Take advantage of the resort like amenities Ellendale has to offer. Launch your canoe or kayak from the community pier into Thompson Creek, or enjoy the outdoor pool all season long with your neighbors. The community also features a clubhouse, boat storage, playground and scenic walking/jogging paths. Situated just minutes from the Chesapeake Bay Bridge, this home offers a unique opportunity to enjoy peaceful Eastern Shore living, while being conveniently located to commuter routes, dining, shopping, parks, trails, golfing, farmers markets, and public fishing piers. Your Eastern Shore escape awaits. Schedule your tour today!

335 Anna Carol Dr, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: RE/MAX Executive.

$600,000

Welcome to Perry’s Retreat, an exquisite coastal-inspired community in the heart of Grasonville, where luxury living meets the charm of the Chesapeake Bay lifestyle. Built by Ryan Homes, this stunning Craftsman-style residence showcases exceptional curb appeal with a covered front entry, handsome stone accents, classic siding details, and a spacious two-car garage, creating a warm and timeless first impression. Inside, a spacious and welcoming foyer sets the tone for the home’s thoughtfully designed interior. Nearby, elegant French doors open to a versatile flex room, perfect as a private home office, formal dining room, or optional guest bedroom. Beautiful luxury vinyl plank flooring spans the main level, complemented by recessed lighting throughout the home and plush carpeting upstairs for added comfort. The thoughtfully designed open floor plan is anchored by an extraordinary great room and show-stopping chef’s kitchen that truly define the heart of the home. Designed with impeccable attention to detail, the gourmet kitchen features crisp white cabinetry beautifully contrasted by a striking navy center island, a stunning blue herringbone tile backsplash, and premium Wolf appliances including an induction cooktop and M Series double wall ovens. A custom coffee station with pull-out drawers and pocket doors offers both convenience and seamless style, while the floor-to-ceiling pantry with pull-out storage provides exceptional organization. The oversized island with breakfast bar seating and adjoining dining area flow effortlessly into the spacious family room, highlighted by a dramatic floor-to-ceiling board and batten accent wall with a 50” Dimplex linear electric fireplace. The main-level primary suite is a luxurious retreat featuring a coffered ceiling, expansive walk-in closet, and spa-inspired ensuite bath with dual vanities and a beautifully appointed walk-in shower. A second sunny main-level bedroom is conveniently served by a full hall bath with a tiled tub/shower combination. Upstairs, flexible loft space offers endless possibilities for a media room, family room, hobby space, or playroom. An additional bedroom featuring custom millwork headboard detailing capped off with a picture shelf, and a spacious walk-in closet provides both charm and functionality. A third full bath and a large storage room complete the upper level. Outdoor living is equally impressive. Step from the dining area onto the covered patio, ideal for relaxing evenings, entertaining, and cookouts overlooking the beautifully landscaped, fully fenced backyard. Stone garden beds, dual side gates, privacy vinyl fencing, and a 10x14 storage shed add both beauty and functionality to the outdoor space. Perry’s Retreat offers the charm of a quaint, thoughtfully designed neighborhood complete with sidewalks, classic lamppost lighting, beautifully maintained green spaces, and a neighborhood park with playgrounds that create a warm and inviting community atmosphere perfect for evening strolls, outdoor recreation, and connecting with neighbors. Perfectly situated in Grasonville, a picturesque Chesapeake Bay waterfront town known for its proximity to the Kent Narrows marinas, waterfront dining, boutique shopping, and coastal charm, Perry’s Retreat offers an unmatched lifestyle. Enjoy the peaceful beauty and Eastern Shore tranquility of a bucolic waterfront setting while being just a hop, skip, and a jump across the Bay Bridge to Annapolis in approximately 15 minutes, with convenient commuting access to both Washington, D.C. and Baltimore. This exceptional location truly offers the best of both worlds, an idyllic Eastern Shore lifestyle paired with effortless access to all the conveniences and opportunities of Maryland’s Western Shore.

3 Beds ⋅ 3 Baths

Welcome to Perry’s Retreat, an exquisite coastal-inspired community in the heart of Grasonville, where luxury living meets the charm of the Chesapeake Bay lifestyle. Built by Ryan Homes, this stunning Craftsman-style residence showcases exceptional curb appeal with a covered front entry, handsome stone accents, classic siding details, and a spacious two-car garage, creating a warm and timeless first impression. Inside, a spacious and welcoming foyer sets the tone for the home’s thoughtfully designed interior. Nearby, elegant French doors open to a versatile flex room, perfect as a private home office, formal dining room, or optional guest bedroom. Beautiful luxury vinyl plank flooring spans the main level, complemented by recessed lighting throughout the home and plush carpeting upstairs for added comfort. The thoughtfully designed open floor plan is anchored by an extraordinary great room and show-stopping chef’s kitchen that truly define the heart of the home. Designed with impeccable attention to detail, the gourmet kitchen features crisp white cabinetry beautifully contrasted by a striking navy center island, a stunning blue herringbone tile backsplash, and premium Wolf appliances including an induction cooktop and M Series double wall ovens. A custom coffee station with pull-out drawers and pocket doors offers both convenience and seamless style, while the floor-to-ceiling pantry with pull-out storage provides exceptional organization. The oversized island with breakfast bar seating and adjoining dining area flow effortlessly into the spacious family room, highlighted by a dramatic floor-to-ceiling board and batten accent wall with a 50” Dimplex linear electric fireplace. The main-level primary suite is a luxurious retreat featuring a coffered ceiling, expansive walk-in closet, and spa-inspired ensuite bath with dual vanities and a beautifully appointed walk-in shower. A second sunny main-level bedroom is conveniently served by a full hall bath with a tiled tub/shower combination. Upstairs, flexible loft space offers endless possibilities for a media room, family room, hobby space, or playroom. An additional bedroom featuring custom millwork headboard detailing capped off with a picture shelf, and a spacious walk-in closet provides both charm and functionality. A third full bath and a large storage room complete the upper level. Outdoor living is equally impressive. Step from the dining area onto the covered patio, ideal for relaxing evenings, entertaining, and cookouts overlooking the beautifully landscaped, fully fenced backyard. Stone garden beds, dual side gates, privacy vinyl fencing, and a 10x14 storage shed add both beauty and functionality to the outdoor space. Perry’s Retreat offers the charm of a quaint, thoughtfully designed neighborhood complete with sidewalks, classic lamppost lighting, beautifully maintained green spaces, and a neighborhood park with playgrounds that create a warm and inviting community atmosphere perfect for evening strolls, outdoor recreation, and connecting with neighbors. Perfectly situated in Grasonville, a picturesque Chesapeake Bay waterfront town known for its proximity to the Kent Narrows marinas, waterfront dining, boutique shopping, and coastal charm, Perry’s Retreat offers an unmatched lifestyle. Enjoy the peaceful beauty and Eastern Shore tranquility of a bucolic waterfront setting while being just a hop, skip, and a jump across the Bay Bridge to Annapolis in approximately 15 minutes, with convenient commuting access to both Washington, D.C. and Baltimore. This exceptional location truly offers the best of both worlds, an idyllic Eastern Shore lifestyle paired with effortless access to all the conveniences and opportunities of Maryland’s Western Shore.

115 Pathfinder Cir, Grasonville

Listing courtesy of Northrop Realty. Contact:

Selling Office: Coldwell Banker Realty.

$453,000

HOME IS STILL AVAILABLE TO SEE AND MAKE OFFERS!!! 72 Hour Kick Out Clause in Effect. Tucked away in the peaceful countryside on the Queen Anne’s County side of Chestertown, this charming one-level rancher offers the space, comfort, and tranquility you’ve been waiting for. Situated on a full acre and boasting over 2,000 sq. ft. of living space, this home is designed for easy, one-level living with room to truly spread out. Offering 3 large bedrooms and 2.5 bathrooms, plus the added convenience of two separate entrances into the home—perfect for flexibility, guests, or everyday functionality. The heart of the home is the expansive kitchen, loaded with counter space and ready for your personal touch and creative design. Just off the kitchen, the family room features soaring vaulted ceilings and a cozy fireplace, creating a warm and inviting space to gather or unwind. Step outside and you’ll fall in love with the lifestyle this property offers… a screened-in porch for peaceful mornings, a spacious deck for entertaining, and a private backyard surrounded by nature. If you’ve been searching for space, privacy, and a home that feels like a retreat, this is it.

3 Beds ⋅ 3 Baths

HOME IS STILL AVAILABLE TO SEE AND MAKE OFFERS!!! 72 Hour Kick Out Clause in Effect. Tucked away in the peaceful countryside on the Queen Anne’s County side of Chestertown, this charming one-level rancher offers the space, comfort, and tranquility you’ve been waiting for. Situated on a full acre and boasting over 2,000 sq. ft. of living space, this home is designed for easy, one-level living with room to truly spread out. Offering 3 large bedrooms and 2.5 bathrooms, plus the added convenience of two separate entrances into the home—perfect for flexibility, guests, or everyday functionality. The heart of the home is the expansive kitchen, loaded with counter space and ready for your personal touch and creative design. Just off the kitchen, the family room features soaring vaulted ceilings and a cozy fireplace, creating a warm and inviting space to gather or unwind. Step outside and you’ll fall in love with the lifestyle this property offers… a screened-in porch for peaceful mornings, a spacious deck for entertaining, and a private backyard surrounded by nature. If you’ve been searching for space, privacy, and a home that feels like a retreat, this is it.

704 Truslow Rd, Chestertown

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Coldwell Banker Chesapeake Real Estate Company.

$937,990

Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a quiet and productive workspace, while the screened patio extends the living area outdoors—perfect for relaxing or entertaining. Practical touches such as a utility sink add convenience to everyday living. The kitchen is designed for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz countertops are also featured in the primary bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, extra suite, primary suite, and loft. Tile flooring is featured in the full baths and laundry room, while carpet provides comfort in bedrooms 3, 4, and 5. The primary bath offers a spa-like retreat with a freestanding tub, a walk-in shower with seat and handheld shower wand, and a double-sink vanity. 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.

5 Beds ⋅ 5 Baths

Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a quiet and productive workspace, while the screened patio extends the living area outdoors—perfect for relaxing or entertaining. Practical touches such as a utility sink add convenience to everyday living. The kitchen is designed for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz countertops are also featured in the primary bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, extra suite, primary suite, and loft. Tile flooring is featured in the full baths and laundry room, while carpet provides comfort in bedrooms 3, 4, and 5. The primary bath offers a spa-like retreat with a freestanding tub, a walk-in shower with seat and handheld shower wand, and a double-sink vanity. 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.

121 Kinglet Ct, Chester

Listing courtesy of KOVO Realty. Contact:

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

$228,000

3 Beds ⋅ 2 Baths

221 Dutchess Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

Selling Office: Non Subscribing Office.

$450,000

Meticulously maintained by the original owners, this beautifully UPGRADED End-unit Townhome offers 3 finished levels totaling 2300sqft, a 2-car garage, and Rarely found DUAL Primary Suites—each featuring a spa-inspired bath with soaking tub, separate shower, ceramic tile floors & surrounds, and expansive walk-in closets. The versatile entry-level flex space provides an easy option for a private 3rd bedroom (written quote available), office or living room & features hardwood floors & a powder room. Venture up the Oak hardwood staircase to the Open-concept main level, showcasing gleaming hardwood floors in the Great room with corner fireplace that flows seamlessly into the Gourmet kitchen. Highlights include: 42” maple glazed cabinets with soft-close doors and drawers, under and over cabinet lighting, Granite countertops, Stainless steel appliances, Double wall ovens, Gas cooktop, 12x12 Ceramic Tile floors, Lighted pantry, Upgraded Trim package, plus a two-tier island with seating and a separate dining area. Step outside to the 12x20 Trex deck complete w/ propane line for your Grill & outdoor speakers making it perfect for entertaining on these upcoming Summer nights! The upper level features dual primary suites, including a front bedroom with vaulted ceiling and exceptional space throughout & Full size Laundry room w/ Front loading washer/dryer. Additional features include: Brand NEW Roof, central vacuum, whole-house audio throughout main living areas, bedrooms & deck, whole-house humidifier, ceiling fans, brushed nickel fixtures, utility sink rough-ins (laundry and garage), custom garage shelving, and kayak storage under the deck. Thoughtfully landscaped perennial gardens provide color year after year and is just another example of the love that was poured into designing this home! Enjoy an amenity-rich community with pool, clubhouse, and floating dock/pier with access to Thompson Creek. Ideally located just minutes to the Chesapeake Bay Bridge for an easy commute and convenient access on and off the Shore. Don’t forget to Check out the 3D iGuide Tour!

2 Beds ⋅ 4 Baths

Meticulously maintained by the original owners, this beautifully UPGRADED End-unit Townhome offers 3 finished levels totaling 2300sqft, a 2-car garage, and Rarely found DUAL Primary Suites—each featuring a spa-inspired bath with soaking tub, separate shower, ceramic tile floors & surrounds, and expansive walk-in closets. The versatile entry-level flex space provides an easy option for a private 3rd bedroom (written quote available), office or living room & features hardwood floors & a powder room. Venture up the Oak hardwood staircase to the Open-concept main level, showcasing gleaming hardwood floors in the Great room with corner fireplace that flows seamlessly into the Gourmet kitchen. Highlights include: 42” maple glazed cabinets with soft-close doors and drawers, under and over cabinet lighting, Granite countertops, Stainless steel appliances, Double wall ovens, Gas cooktop, 12x12 Ceramic Tile floors, Lighted pantry, Upgraded Trim package, plus a two-tier island with seating and a separate dining area. Step outside to the 12x20 Trex deck complete w/ propane line for your Grill & outdoor speakers making it perfect for entertaining on these upcoming Summer nights! The upper level features dual primary suites, including a front bedroom with vaulted ceiling and exceptional space throughout & Full size Laundry room w/ Front loading washer/dryer. Additional features include: Brand NEW Roof, central vacuum, whole-house audio throughout main living areas, bedrooms & deck, whole-house humidifier, ceiling fans, brushed nickel fixtures, utility sink rough-ins (laundry and garage), custom garage shelving, and kayak storage under the deck. Thoughtfully landscaped perennial gardens provide color year after year and is just another example of the love that was poured into designing this home! Enjoy an amenity-rich community with pool, clubhouse, and floating dock/pier with access to Thompson Creek. Ideally located just minutes to the Chesapeake Bay Bridge for an easy commute and convenient access on and off the Shore. Don’t forget to Check out the 3D iGuide Tour!

131 John Patrick Dr, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Kinetic Realty, Inc..

$150,000

Welcome to your new home site in historic Centreville. Great location in a country setting yet so close to everything. Walk to county parks. The owner is having this lot perced currently and should have an approval by the end of May. Soils and water table may allow for a basement on this lot. Contracts can be contingent on the perc approval. Not many lots like this left. Grab it before its gone!

266 White Marsh Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: Weese Properties, LLC.

$450,000

If you’ve had your eye on this home, now is your opportunity to make a move. Back on the market due to the buyer’s home sale contingency falling through—no fault of the seller. Priced below value and featuring a brand-new roof (completed 9/24/2025), this move-in ready home offers both value and peace of mind. Additional updates include a new well pump, HVAC system, stove, and refrigerator. For added confidence, a one-year home warranty is included. Offering approximately 1,900 sq ft of living space (buyer to verify), this 4-bedroom, 2-bath home provides the flexibility to fit a variety of lifestyles. Originally built in 1988 and thoughtfully expanded, it now includes a spacious family room with vaulted ceilings, perfect for everyday living and entertaining alike. Enjoy the outdoors from the welcoming front porch or one of the two decks, all surrounded by mature landscaping. The detached garage offers excellent storage and workspace, while the camper hook-up adds extra versatility for guests or those who love to travel. Located just one block from the water, with access to a community beach ideal for kayaking and paddleboarding, and in close proximity to the local marina and store—this home captures the essence of Eastern Shore living.

4 Beds ⋅ 2 Baths

If you’ve had your eye on this home, now is your opportunity to make a move. Back on the market due to the buyer’s home sale contingency falling through—no fault of the seller. Priced below value and featuring a brand-new roof (completed 9/24/2025), this move-in ready home offers both value and peace of mind. Additional updates include a new well pump, HVAC system, stove, and refrigerator. For added confidence, a one-year home warranty is included. Offering approximately 1,900 sq ft of living space (buyer to verify), this 4-bedroom, 2-bath home provides the flexibility to fit a variety of lifestyles. Originally built in 1988 and thoughtfully expanded, it now includes a spacious family room with vaulted ceilings, perfect for everyday living and entertaining alike. Enjoy the outdoors from the welcoming front porch or one of the two decks, all surrounded by mature landscaping. The detached garage offers excellent storage and workspace, while the camper hook-up adds extra versatility for guests or those who love to travel. Located just one block from the water, with access to a community beach ideal for kayaking and paddleboarding, and in close proximity to the local marina and store—this home captures the essence of Eastern Shore living.

116 Kent Point Rd, Stevensville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Intelligent Enterprises.

$414,500

Charming Renovated Home in the Heart of Centreville! Welcome to 220 Belvedere Avenue—cute as a button and completely renovated from top to bottom in 2019! This beautifully updated home blends modern comforts with timeless charm, offering move-in-ready convenience in a prime Centreville location. Step inside to find a bright and inviting interior with stylish finishes throughout. The thoughtfully designed layout features a convenient first-floor primary suite, providing comfort and flexibility for everyday living. Situated on a rare double lot, this property offers plenty of outdoor space to enjoy. Relax on the welcoming front porch, perfect for morning coffee or evening unwinding. The fenced backyard provides privacy and room for pets, play, or entertaining, while the detached garage adds extra storage and functionality. Whether you’re looking for your first home, downsizing, or seeking a turnkey property with character, this one checks all the boxes. Don’t miss your chance to own this charming, fully renovated gem in Centreville!

4 Beds ⋅ 2 Baths

Charming Renovated Home in the Heart of Centreville! Welcome to 220 Belvedere Avenue—cute as a button and completely renovated from top to bottom in 2019! This beautifully updated home blends modern comforts with timeless charm, offering move-in-ready convenience in a prime Centreville location. Step inside to find a bright and inviting interior with stylish finishes throughout. The thoughtfully designed layout features a convenient first-floor primary suite, providing comfort and flexibility for everyday living. Situated on a rare double lot, this property offers plenty of outdoor space to enjoy. Relax on the welcoming front porch, perfect for morning coffee or evening unwinding. The fenced backyard provides privacy and room for pets, play, or entertaining, while the detached garage adds extra storage and functionality. Whether you’re looking for your first home, downsizing, or seeking a turnkey property with character, this one checks all the boxes. Don’t miss your chance to own this charming, fully renovated gem in Centreville!

220 Belvedere Ave, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Selling Office: Rosendale Realty.

$551,000

Welcome to 412 Bay City Road — where modern upgrade meets relaxed coastal living. This 4-bedroom, 3-bath beauty offers 2,000+ sq ft of thoughtfully curated space, a detached 2-car garage, and the peek-a-boo views of the Chesapeake Bay to keep your heart fluttering. Spread out on two levels, four full bedrooms and multiple outdoor living spaces. The kitchen boasts granite countertops and high end Kitchen Aid appliances (2021). Totally renovated Spa-inspired bathrooms make even weekday routines feel luxe with oversized tubs and floor to ceiling tiles. Newer/upgraded flooring throughout balances durability + aesthetic. The lower level is an amazing bonus for living on Kent Island! You will love having a second living space with a wood stove that heats the whole home, the beautiful laundry room with sink, 4th bedroom and a/ full bath. This space could easily be converted into an in-law suite! The 5 year old deck is made for gatherings, lazy sundowners, and soaking up ambient coastal energy. The fenced in yard offer two secure spaces. This thoughtful layout balances community + quiet zones that feel like home. Parking will never be an issue. There is a detached 2 car garage with it's own electric panel, plus an extended driveway that can accommodate nearly 10 vehicles, boats, or even a RV! If you’re ready for a home that checks the boxes (style, function, location, and charm), plus all new electrical and doors - make sure to come see 412 Bay City Road before it's SOLD. Bay City is a waterfront community offering amenities including boat ramp, pavilion and playgrounds for just $150/year. Public Sewer and Water. Matapeake School District.

4 Beds ⋅ 3 Baths

Welcome to 412 Bay City Road — where modern upgrade meets relaxed coastal living. This 4-bedroom, 3-bath beauty offers 2,000+ sq ft of thoughtfully curated space, a detached 2-car garage, and the peek-a-boo views of the Chesapeake Bay to keep your heart fluttering. Spread out on two levels, four full bedrooms and multiple outdoor living spaces. The kitchen boasts granite countertops and high end Kitchen Aid appliances (2021). Totally renovated Spa-inspired bathrooms make even weekday routines feel luxe with oversized tubs and floor to ceiling tiles. Newer/upgraded flooring throughout balances durability + aesthetic. The lower level is an amazing bonus for living on Kent Island! You will love having a second living space with a wood stove that heats the whole home, the beautiful laundry room with sink, 4th bedroom and a/ full bath. This space could easily be converted into an in-law suite! The 5 year old deck is made for gatherings, lazy sundowners, and soaking up ambient coastal energy. The fenced in yard offer two secure spaces. This thoughtful layout balances community + quiet zones that feel like home. Parking will never be an issue. There is a detached 2 car garage with it's own electric panel, plus an extended driveway that can accommodate nearly 10 vehicles, boats, or even a RV! If you’re ready for a home that checks the boxes (style, function, location, and charm), plus all new electrical and doors - make sure to come see 412 Bay City Road before it's SOLD. Bay City is a waterfront community offering amenities including boat ramp, pavilion and playgrounds for just $150/year. Public Sewer and Water. Matapeake School District.

412 Bay City Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

Selling Office: RE/MAX Executive.

$1,600,000

STUNNING waterfront private oasis just minutes from the Bay Bridge, where coastal luxury meets effortless Chesapeake Bay living. Nearly 3100 sf, , this gorgeous retreat features four spacious bedrooms and three beautifully updated baths, designed for comfort, style & unforgettable gatherings. Main level bedroom & full bath offer flexibility! The heart of the home? A magazine-worthy coastal kitchen with new custom cabinetry, gleaming white quartz countertops, & shiny stainless steel appliances. Wide-plank white oak flooring that carries warmth and sophistication. Open, airy, and filled with natural light — every space feels intentional and elevated. Primary suite emulates the finest of hotels with cozy gas fireplace, catwalk to waterfront balcony, bonus room/office & STUNNING spa bath with sunken tub, walk-in-shower & vanity for two, heated floors & spacious closet for ample storage. Step outside to your own resort setting — with private in-ground pool, expansive entertaining areas, maintenance-free deck with cable rails for nautical feel. and a private pier with boat lift & two jet ski lifts - just three lots from direct Chesapeake Bay access. With 4' MLW, boating enthusiasts will appreciate effortless access to open water in minutes. This is more than a home — it’s a lifestyle, waterfront living re-defined. Opportunities like this don't float by twice- your boat belongs here!

4 Beds ⋅ 3 Baths

STUNNING waterfront private oasis just minutes from the Bay Bridge, where coastal luxury meets effortless Chesapeake Bay living. Nearly 3100 sf, , this gorgeous retreat features four spacious bedrooms and three beautifully updated baths, designed for comfort, style & unforgettable gatherings. Main level bedroom & full bath offer flexibility! The heart of the home? A magazine-worthy coastal kitchen with new custom cabinetry, gleaming white quartz countertops, & shiny stainless steel appliances. Wide-plank white oak flooring that carries warmth and sophistication. Open, airy, and filled with natural light — every space feels intentional and elevated. Primary suite emulates the finest of hotels with cozy gas fireplace, catwalk to waterfront balcony, bonus room/office & STUNNING spa bath with sunken tub, walk-in-shower & vanity for two, heated floors & spacious closet for ample storage. Step outside to your own resort setting — with private in-ground pool, expansive entertaining areas, maintenance-free deck with cable rails for nautical feel. and a private pier with boat lift & two jet ski lifts - just three lots from direct Chesapeake Bay access. With 4' MLW, boating enthusiasts will appreciate effortless access to open water in minutes. This is more than a home — it’s a lifestyle, waterfront living re-defined. Opportunities like this don't float by twice- your boat belongs here!

802 Broadcreek Dr, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

$280,000

Eastern Shore charm in the heart of Grasonville! This adorable cottage offers easy one-level living and features a thoughtfully designed addition that creates an expansive gathering space perfect for entertaining family and friends. Accessibility is enhanced with a convenient ramp, making everyday living comfortable and practical. Numerous improvements have been completed over the years, including an energy-efficient mini-split heating and cooling system. Move-in ready and full of character, this home presents an excellent opportunity for buyers seeking affordability, convenience, and Eastern Shore living. Being sold as-is, with plenty of potential for a handy homeowner to add their own finishing touches and build additional equity.

2 Beds ⋅ 1 Baths

Eastern Shore charm in the heart of Grasonville! This adorable cottage offers easy one-level living and features a thoughtfully designed addition that creates an expansive gathering space perfect for entertaining family and friends. Accessibility is enhanced with a convenient ramp, making everyday living comfortable and practical. Numerous improvements have been completed over the years, including an energy-efficient mini-split heating and cooling system. Move-in ready and full of character, this home presents an excellent opportunity for buyers seeking affordability, convenience, and Eastern Shore living. Being sold as-is, with plenty of potential for a handy homeowner to add their own finishing touches and build additional equity.

4003 Main St, Grasonville

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

Selling Office: Keller Williams Realty.

$1,690,000

Positioned along the serene waters of Tanners Creek within the enclave of Cove Creek Club, this exceptional waterfront residence offers a rare opportunity to secure a premier setting while tailoring the interiors to your own vision. Major capital improvements have already been completed—including a new roof, upgraded HVAC system, and the addition of a private pool; providing a strong foundation for the next owner to elevate the home to their exact standards. From nearly every room, sweeping water views create a seamless connection to the surrounding landscape, with sunsets that define the daily experience. The home features a light-filled, open-concept layout designed for both comfortable living and effortless entertaining. The kitchen offers generous cabinetry, a spacious pantry, and a gas cooktop, flowing naturally into the main living and dining areas—all oriented to capture the waterfront backdrop. With four bedrooms and three full baths, there is ample space for family and guests, along with the flexibility to reimagine and enhance over time. Outdoors, the lifestyle is immediate. A private dock provides direct access to kayaking, paddle boarding, crabbing, and fishing just steps from your door, while the protected waters of the creek offer a peaceful, usable setting. For larger vessels, the community marina accommodates boats up to approximately 40 feet and offers water, electric, fuel, and pump-out services which delivers a level of convenience rarely found. The addition of the pool introduces a resort-style element, ideal for relaxing afternoons or entertaining against a waterfront backdrop. The setting, combined with the home’s footprint and improvements, creates a compelling opportunity for a buyer seeking both lifestyle and long-term value. Residents of Cove Creek Club enjoy access to an exceptional amenity package, including a USGA-rated golf course, private beach, marina with boat launch, clubhouse, tennis and basketball courts, and bocce. This is a rare chance to secure a waterfront property with strong fundamentals, significant recent upgrades, and the ability to create a truly custom coastal retreat in one of the Eastern Shore’s most desirable gated communities.

5 Beds ⋅ 3 Baths

Positioned along the serene waters of Tanners Creek within the enclave of Cove Creek Club, this exceptional waterfront residence offers a rare opportunity to secure a premier setting while tailoring the interiors to your own vision. Major capital improvements have already been completed—including a new roof, upgraded HVAC system, and the addition of a private pool; providing a strong foundation for the next owner to elevate the home to their exact standards. From nearly every room, sweeping water views create a seamless connection to the surrounding landscape, with sunsets that define the daily experience. The home features a light-filled, open-concept layout designed for both comfortable living and effortless entertaining. The kitchen offers generous cabinetry, a spacious pantry, and a gas cooktop, flowing naturally into the main living and dining areas—all oriented to capture the waterfront backdrop. With four bedrooms and three full baths, there is ample space for family and guests, along with the flexibility to reimagine and enhance over time. Outdoors, the lifestyle is immediate. A private dock provides direct access to kayaking, paddle boarding, crabbing, and fishing just steps from your door, while the protected waters of the creek offer a peaceful, usable setting. For larger vessels, the community marina accommodates boats up to approximately 40 feet and offers water, electric, fuel, and pump-out services which delivers a level of convenience rarely found. The addition of the pool introduces a resort-style element, ideal for relaxing afternoons or entertaining against a waterfront backdrop. The setting, combined with the home’s footprint and improvements, creates a compelling opportunity for a buyer seeking both lifestyle and long-term value. Residents of Cove Creek Club enjoy access to an exceptional amenity package, including a USGA-rated golf course, private beach, marina with boat launch, clubhouse, tennis and basketball courts, and bocce. This is a rare chance to secure a waterfront property with strong fundamentals, significant recent upgrades, and the ability to create a truly custom coastal retreat in one of the Eastern Shore’s most desirable gated communities.

132 Tanners Point Dr, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Washington Fine Properties, LLC.

$9,000

Rare opportunity to own 1.05-Acre Vacant Land in Chestertown, MD! Located at 206 Burchard Sawmill Rd. Surrounded by natural beauty and close to local amenities, this lot provides both privacy and convenience. Don’t miss out on this rare chance to own land in historic Chestertown! The property sell AS IS. Buyer will need to verify zoning and utilities.

206 Burchard Sawmill Rd, Chestertown

Listing courtesy of XRealty.NET LLC. Contact:

Selling Office: Patterson-Schwartz Real Estate.

$450,000

The desirable Cloverfields community! This spacious four-bedroom, three-bath split foyer home offers an open-concept living area with durable vinyl plank flooring throughout the living room, dining room, and kitchen—perfect for everyday living and entertaining. The upper level features three comfortable bedrooms, including a primary suite with a private bath. The lower level provides exceptional additional space, including a generously sized fourth bedroom, a large family room, full bath, laundry area, and a workshop—ideal for hobbies, storage, or flexible living needs. Step outside to enjoy a fenced yard and multiple decks, a shed, all set on the lot to add privacy. Residents of Cloverfields also enjoy fantastic community amenities, including a pool, picnic area, and boat launch. Stay tuned—this one is coming soon!

4 Beds ⋅ 3 Baths

The desirable Cloverfields community! This spacious four-bedroom, three-bath split foyer home offers an open-concept living area with durable vinyl plank flooring throughout the living room, dining room, and kitchen—perfect for everyday living and entertaining. The upper level features three comfortable bedrooms, including a primary suite with a private bath. The lower level provides exceptional additional space, including a generously sized fourth bedroom, a large family room, full bath, laundry area, and a workshop—ideal for hobbies, storage, or flexible living needs. Step outside to enjoy a fenced yard and multiple decks, a shed, all set on the lot to add privacy. Residents of Cloverfields also enjoy fantastic community amenities, including a pool, picnic area, and boat launch. Stay tuned—this one is coming soon!

708 Dixon Dr, Stevensville

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

Selling Office: RE/Max Experience.

$715,000

Beautiful home with over 3,000 sq ft of living space nestled on 1.83 peaceful acres! The main level welcomes you with a bright, open concept layout, hardwood flooring, and a spacious primary bedroom complete with a walk-in closet and en-suite bath featuring a soaking tub. Two additional bedrooms, a full bath with double sinks, and a dedicated laundry room round out the first floor beautifully. Head upstairs and discover a fully renovated upper level (2021) with three additional bedrooms, a cozy sitting room or home office, and a stunning full bath with a walk-in tile shower. A brand new HVAC system (2023) and encapsulated crawlspace add comfort and peace of mind throughout. Outside, the all-season porch and expansive concrete patio are perfect for relaxing or entertaining while soaking in the gorgeous country surroundings. The impressive 36x42 detached garage with a 12x24 lean-out is fully equipped with 50-amp and 30-amp RV hookups. This is the one you've been waiting for — come take a look!

6 Beds ⋅ 4 Baths

Beautiful home with over 3,000 sq ft of living space nestled on 1.83 peaceful acres! The main level welcomes you with a bright, open concept layout, hardwood flooring, and a spacious primary bedroom complete with a walk-in closet and en-suite bath featuring a soaking tub. Two additional bedrooms, a full bath with double sinks, and a dedicated laundry room round out the first floor beautifully. Head upstairs and discover a fully renovated upper level (2021) with three additional bedrooms, a cozy sitting room or home office, and a stunning full bath with a walk-in tile shower. A brand new HVAC system (2023) and encapsulated crawlspace add comfort and peace of mind throughout. Outside, the all-season porch and expansive concrete patio are perfect for relaxing or entertaining while soaking in the gorgeous country surroundings. The impressive 36x42 detached garage with a 12x24 lean-out is fully equipped with 50-amp and 30-amp RV hookups. This is the one you've been waiting for — come take a look!

615 Ell Downes Rd, Henderson

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RE/MAX Executive.

$387,499

Bright and modern home with an open layout and plenty of natural light. Features a fully updated kitchen with stainless steel appliances, white cabinetry, and subway tile backsplash. Highlights include new flooring, contemporary lighting, and a beautifully renovated bathroom. The exterior offers a large, level backyard with a private driveway and a spacious storage shed. Move-in ready and perfect for modern living.

3 Beds ⋅ 1 Baths

Bright and modern home with an open layout and plenty of natural light. Features a fully updated kitchen with stainless steel appliances, white cabinetry, and subway tile backsplash. Highlights include new flooring, contemporary lighting, and a beautifully renovated bathroom. The exterior offers a large, level backyard with a private driveway and a spacious storage shed. Move-in ready and perfect for modern living.

300 Talbot Rd, Stevensville

Listing courtesy of Real Estate Professionals, Inc.. Contact:

Selling Office: EXP Realty, LLC.

$600,000

This exceptional four‑unit property sits in the heart of Queenstown and makes a fantastic addition to any rental portfolio. The building features a well‑designed mix of units, including a one‑bedroom with an office, a three‑bedroom unit, and two spacious two‑bedroom units, along with a detached two‑car garage that adds valuable flexibility and potential for additional income. The property currently grosses $6,075 per month, with renewals bringing that figure closer to $6,300 per month starting in June. It is home to outstanding tenants who take pride in where they live, and there is always a strong pool of interested renters for these units, ensuring consistently low vacancy. The location is a major draw, with Queenstown Golf just moments away, the Queenstown Premium Outlets right nearby, and a welcoming community atmosphere that includes Food Truck Fridays at the start of each month, walkable access to the local park, a lively summer concert series, and plenty more to enjoy. This is a rare opportunity to own a stable, income‑producing property in a thriving and highly desirable town. Must See!

7112 Maryland Ave, Queenstown

Listing courtesy of Clark & Co Realty, LLC. Contact:

Selling Office: Unrepresented.

$258,000

Updated 2-Bedroom Condo with Garage in Water-Privileged Community – Immediate Occupancy! Don’t miss this beautifully renovated two-level condo featuring 2 bedrooms, 1.5 baths, and a one-car garage. Priced to sell! Thoughtfully updated over the past five years, this home offers newer carpet and luxury vinyl plank flooring, a remodeled kitchen and bathrooms, and a high-efficiency Bosch HVAC system. All major appliances—including kitchen appliances, oversized washer and dryer, and hot water heater—have been recently replaced. The main level features an open living room, galley-style kitchen, convenient half bath, and a versatile bonus room ideal for a dining area or home office. Sliding glass doors lead to a private rear deck with direct access to the parking area and spacious 21x10 garage. Upstairs, you’ll find two generously sized bedrooms and a full bath. Enjoy the benefits of a water-privileged community with access to a pool, pier, and boat docks. HOA fees cover fresh and wastewater, trash pickup, lawn care, shrub maintenance, roof and shingles, crawl space upkeep, exterior hose bib, pool, boat dock, fishing pier, and maintenance of common areas and entrance decking—providing low-maintenance living. Conveniently located for an easy commute to Rt. 50, Annapolis, and Easton, and within walking distance to restaurants and shopping.

2 Beds ⋅ 2 Baths

Updated 2-Bedroom Condo with Garage in Water-Privileged Community – Immediate Occupancy! Don’t miss this beautifully renovated two-level condo featuring 2 bedrooms, 1.5 baths, and a one-car garage. Priced to sell! Thoughtfully updated over the past five years, this home offers newer carpet and luxury vinyl plank flooring, a remodeled kitchen and bathrooms, and a high-efficiency Bosch HVAC system. All major appliances—including kitchen appliances, oversized washer and dryer, and hot water heater—have been recently replaced. The main level features an open living room, galley-style kitchen, convenient half bath, and a versatile bonus room ideal for a dining area or home office. Sliding glass doors lead to a private rear deck with direct access to the parking area and spacious 21x10 garage. Upstairs, you’ll find two generously sized bedrooms and a full bath. Enjoy the benefits of a water-privileged community with access to a pool, pier, and boat docks. HOA fees cover fresh and wastewater, trash pickup, lawn care, shrub maintenance, roof and shingles, crawl space upkeep, exterior hose bib, pool, boat dock, fishing pier, and maintenance of common areas and entrance decking—providing low-maintenance living. Conveniently located for an easy commute to Rt. 50, Annapolis, and Easton, and within walking distance to restaurants and shopping.

1 Compass Cir Unit 2, Stevensville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

Selling Office: Maverick Realty, LLC.

$10,000

Beautiful 1.81 acre wooded lot. No perc test, no contracts considered with perc test contingency. Long term investment opportunity.

101 Recovery Dr, Centreville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

Selling Office: Rosendale Realty.

How much is your home worth?

How much is your home worth?