Talbot County Public Schools Homes with Colonial Style

Beautifully maintained two-story Colonial in Matthewstown Run. Situated on a large lot that backs to a farm with a peaceful spring fed pond, offering privacy and picturesque views, plus room for a pool and all kinds of outdoor activities. There 4 bedrooms, 2½ updated bathrooms, and a beautifully renovated kitchen This is the model with the laundry room addition between kitchen and garage. with attached two-car garage. BONUS this home has a basement - 1/2 finished and 1/2 awesome storage. Plus all of the mechanicals, including tankless hotwater heater.. Roof, HVAC, appliances, all updated. Even the siding was replaced in 2011. There is not a lot original in this home. Seller would like October settlement, but will consider earlier for the right situation. These were the premium lots when the community was developed and the owners along that strip have made the layout very nice.

29803 Standish St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$1,625,000

3 Beds ⋅ 3 Baths

Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

32137 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,850,000

6 Beds ⋅ 6 Baths

This exceptional waterfront estate was thoughtfully designed and custom built by its current owner after years of meticulous research and planning, drawing architectural inspiration from the timeless elegance of Colonial Williamsburg. Constructed with an uncompromising commitment to quality and authenticity, this remarkable residence is a true showcase of enduring craftsmanship. Offering 6 bedrooms, 5 full baths, 1 half bath, and an impressive 7 fireplaces, the home is rich with period-inspired architectural details. From the Flemish Bond brickwork and cypress plank siding to the one-of-a-kind, 2.5-inch-thick solid cherry and mahogany entry door, every element was carefully selected to reflect both beauty and longevity. Exceptional custom woodwork is found throughout the home, complemented by stunning Brazilian Teak, Brazilian Cherry, and White Oak hardwood flooring. Adding to the home’s distinction are custom light fixtures crafted by Virginia MetalCrafters, among the final pieces ever produced by the renowned Virginia manufacturer. The chef’s kitchen was designed with both elegance and functionality in mind, featuring custom cherry cabinetry, dual sinks, dual dishwashers, dual Sub-Zero refrigerator and freezer units, and abundant workspace for entertaining or everyday living. The inviting living room showcases custom built-in cabinetry and a magnificent fireplace designed to accommodate both a traditional open hearth and a wood-burning stove. The spacious first-floor primary suite offers a private retreat complete with a luxurious en-suite bath featuring a jetted soaking tub, walk-in shower, and generous walk-in closet. Upstairs, five additional bedrooms enjoy abundant natural light, southern exposure, and beautiful water views. Nearly every principal living space throughout the home captures breathtaking southern-facing waterfront vistas, creating a seamless connection between the interior and its spectacular setting. Outdoor living is equally impressive. A gracious waterside patio with elegant bifurcated brick steps leads to the expansive 720-square-foot swimming pool, creating an ideal space for relaxing or entertaining. Beyond, the riprap-protected shoreline leads to a custom private dock with approximately 3 feet of water depth at mean low water (MLW), providing convenient access to the water. A rare offering on Maryland’s Eastern Shore, this extraordinary waterfront home blends historic architectural inspiration with modern comfort and exceptional craftsmanship. Designed and built to stand the test of time, it is a legacy property meant to be enjoyed for generations.

7250 Maxmore Creek Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$344,000

2 Beds ⋅ 3 Baths

This attractive end-unit townhouse is located in the desirable Easton Club community offering well-maintained, move-in ready living just minutes from historic downtown Easton. The home features a welcoming front porch that leads to the foyer and spacious kitchen, complete with granite counters, a pantry, breakfast bar, ample cabinet and counter space and appliances that are all less than two years old. The spacious living room offers flexible space for both living and dining and features two sliding glass doors leading to the rear deck overlooking ponds and a wooded setting. Upstairs, the primary suite features a large walk-in closet and spacious private bath, while the second bedroom also includes its own full bath and walk-in closet. Bedroom-level laundry adds everyday convenience. An attached outdoor storage shed provides ample space for tools, bikes, seasonal decor or any of your storage needs. A new roof was installed in June 2026 giving a buyer peace of mind for years to come. Residents of Easton Club enjoy a newly refinished in-ground pool, newly refinished tennis and pickleball courts and multiple ponds throughout the community, all just minutes from downtown Easton's charming boutiques, restaurants and local attractions. Downtown Oxford is approximately 10 minutes away where you can enjoy local waterfront dining, the beach at “The Strand” and so much more.

28491 Pinehurst Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$437,000

3 Beds ⋅ 4 Baths

Enjoy the combination of privacy, convenience, and low-maintenance living in this beautifully updated townhome just minutes from downtown. Nestled against a peaceful wooded backdrop, this home offers a rare sense of seclusion with an exceptionally private balcony-style deck overlooking the trees. Inside, hardwood floors enhance the main level’s open-concept design, featuring a bright kitchen with stainless steel appliances, a dining area, and spacious living room. The upper level offers a private primary suite with a full bath, walk-in closet, and versatile loft space, along with two additional bedrooms and a full bath. The lower level provides even more space with a cozy family room, half bath, laundry area, and convenient garage access.

300 Dixon St Unit #505, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$1,095,000

3 Beds ⋅ 3 Baths

Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$250,000

4 Beds ⋅ 3 Baths

Welcome to 3759 Rumsey Drive, Trappe, MD, located in the “La Trappe Heights” community; within the town limits of Trappe and connected to public water and sewer. This spacious home offers 4 bedrooms and 2.5 bathrooms, making it an excellent opportunity for buyers looking to add their personal touches. Being sold strictly sold AS-IS! This property is being sold strictly AS IS. The seller will make no repairs or improvements. Buyers are encouraged to conduct any inspections they deem necessary for informational purposes. This is a great opportunity for investors, renovators, or buyers looking to build equity while enjoying the convenience of an in-town location. The main level features a comfortable spacious living area with a wood-burning fireplace, a formal dining area, along with a kitchen/dining combo area as well. A convenient half bath, and access to the rear deck, perfect for relaxing or entertaining. The home also includes an attached one-car garage for parking and additional storage. Upstairs, you'll find all four bedrooms. The primary suite includes a private bathroom with a walk-in shower, while the second full bathroom, located off the hallway, features a tub/shower combination to accommodate family and guests. Outside, enjoy a spacious rear yard complete with a storage shed for lawn equipment, tools, or seasonal items. Please note that the HVAC system provides heating and cooling to the first floor only that was installed six years ago. The hot water tank is two years old. With some TLC this home is truly a gem in the lovely town of Trappe, Maryland.

3759 Rumsey Dr, Trappe

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

$549,900

4 Beds ⋅ 3 Baths

Professional Photos coming soon. You’ll love this beautiful recently updated home with 4 bedrooms, 3 full baths in a sought after neighborhood. The home features a large family room with a gas fireplace, living room with wood burning fireplace, a formal dining room, first floor bedroom, master bath with walk in shower and double vanities. Downstairs is a large unfinished basement that could add 1,000 square feet to the living space. There's great storage with a 2 car garage with epoxy flooring and a block storage shed attached to the house. The home is energy efficient with forced air heat powered by the natural gas water heater. You’ll love relaxing outside in the private fenced-in backyard with a multi-level back deck. This well cared for home could be yours. Schedule your tour today!

29700 Lexington St, Easton

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

$5,995,000

8 Beds ⋅ 6 Baths

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$7,900,000

8 Beds ⋅ 6 Baths

"Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$5,995,000

8 Beds ⋅ 6 Baths

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 76+-acre waterfront estate has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

8612 Tilghman Island Rd, Wittman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344

$1,100,000

4 Beds ⋅ 5 Baths

Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with abundant natural light. The thoughtfully designed floor plan includes formal living and dining rooms, as well as inviting spaces for everyday living and entertainment. A private first-floor office offers flexibility to serve as a main-level bedroom if desired. Dual staircases provide convenient access to the second level. The gourmet kitchen features beautiful 42-inch cabinetry, Corian countertops, a center island, and a sunny breakfast room with a door leading to the backyard, making indoor-outdoor entertainment effortless. The spacious primary suite is a true retreat, highlighted by a coffered ceiling, a generous walk-in closet, and a luxurious en-suite bath. The second floor offers four bedrooms and three baths. The finished basement expands the living space with a full bathroom and endless possibilities for recreation, entertaining, or multi-generational living. Situated on a private lot backing to open space, the property extends beyond the wrought iron fenced around the gunite pool, into a serene stand of mature pine trees, creating a peaceful and picturesque setting. The professionally landscaped grounds feature lush flower beds with an irrigation system, extensive hardscaping surrounding the gunite pool, patio, and a wraparound porch on the front, catches all the curb appeal you want, paved driveway leading to the side-entry garage. Additional highlights include an epoxy-coated garage floor with an organized wall storage system, professional-grade landscaping, and exceptional pride of ownership throughout. This home shows like a new offering the quality and feel of new construction without the wait. Despite its remarkably quiet and private setting, the home is conveniently located just minutes from shopping, dining, community events, water access, major commuter routes, offering the perfect balance of tranquility and accessibility. So, if you are ready to design your new life style or have a second home, come see this beautiful home.

13446 Blackberry Ln, Wye Mills

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

Talbot County Public Schools Homes with Colonial Style

Newest Talbot County Public Schools Homes with Colonial Style