Talbot County Real Estate

Talbot County Real Estate

**Discover Talbot County, Maryland: A Hidden Gem on the Eastern Shore**

Nestled on the picturesque Eastern Shore of Maryland, Talbot County is a captivating blend of rich history, stunning natural beauty, and vibrant community life. Known for its charming waterfront towns, including Easton, St. Michaels, and Oxford, Talbot County offers a serene escape from the hustle and bustle of city life, making it an ideal destination for both residents and visitors alike.

With its lush landscapes and scenic waterways, Talbot County is a haven for outdoor enthusiasts. The region boasts miles of hiking and biking trails, tranquil parks, and pristine beaches along the Chesapeake Bay. Whether you're kayaking through the calm waters or enjoying a leisurely stroll along the historic streets, the natural beauty of Talbot County is sure to captivate your heart.

Rich in history, Talbot County is home to numerous historic sites and landmarks, including the elegant Victorian architecture of Easton and the charming maritime heritage of St. Michaels. The county also hosts various cultural events, art galleries, and local festivals that celebrate its vibrant community spirit, making it a wonderful place to connect with neighbors and make lasting memories.

For those seeking a lifestyle that balances tranquility with cultural richness, Talbot County is a perfect choice. With a range of real estate options from waterfront properties to quaint cottages, there’s something to suit every taste and budget. Experience the charm, beauty, and welcoming community of Talbot County—your new home awaits!

Newest Listings in Talbot County

2 Beds ⋅ 2 Baths

Welcome to the Spring Lake II, a beautifully designed home that pairs an open-concept layout with timeless Loft elements. Offering 2 bedrooms, 2 baths, and a 2-car garage, this home provides both elegance and everyday functionality. Just off the foyer, a formal dining room creates the perfect setting for hosting holidays and special gatherings. The spacious kitchen is both stunning and practical, featuring a large island and walk-in pantry to support effortless entertaining and daily living. The open and airy great room impresses with a vaulted ceiling, optional beams, and a sliding door leading to the covered patio, seamlessly blending indoor and outdoor living. A cozy fireplace with mantel and hearth adds warmth and character to the space, while the screened-in patio offers another inviting area to relax. The luxurious primary suite is a true retreat, highlighted by triple windows for abundant natural light and a gorgeous primary bath with a walk-in closet. 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.

29496 Mason Ln, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

1 Beds ⋅ 1 Baths

409 Railroad Ave, St Michaels

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

3 Beds ⋅ 4 Baths

Located in the desirable Cooke’s Hope community, 28706 Hope Circle offers approximately 4,172 square feet of finished living space, including three bedrooms and four bathrooms. The home combines classic Eastern Shore character with spacious living areas, thoughtful updates, and appealing indoor and outdoor amenities. The first floor features a private primary suite, complemented by a large first-floor laundry facility. The main-level family room includes a gas fireplace and provides a welcoming setting for relaxing or entertaining. Additional first-floor spaces include a separate formal dining room and a separate dedicated sitting/piano room, offering versatile areas for formal gatherings, quiet relaxation, or enjoying music. A wraparound porch adds curb appeal and provides multiple areas for enjoying the outdoors. The recently refreshed kitchen features new appliances and countertops, along with a dedicated kitchen dining area ideal for casual meals. A separate coffee and bar area provides additional storage and serving space, making it perfect for morning coffee, entertaining, or evening cocktails. The second floor includes two bedrooms, two bathrooms, a dedicated office area, and a second large family room. This flexible space is well suited for movie nights, watching sports, hosting guests, or creating a comfortable retreat for family and friends. Two dedicated second-floor storage areas provide convenient space for important household items. The backyard is a private oasis, featuring a heated pool, professionally landscaping, and a Hunter sprinkler system. The thoughtfully landscaped setting provides a peaceful and inviting environment for relaxing, entertaining, and enjoying the outdoors. Additional features include a new roof and a heated and cooled two-car garage with 9-foot-wide doors. The second floor of the garage provides an additional large finished storage area with potential for flexible use. The expansive garage offers ample room for vehicles, equipment, hobbies, seasonal items, or a workshop. The combination of generous interior spaces, abundant storage, updated features, and attractive outdoor amenities makes this home ideal for both everyday living and entertaining. Cooke’s Hope amenities include a community dock, canoe storage and launch, walking and exercise trails, tennis and pickleball courts, a private community mailroom, and a fitness center. Conveniently located near downtown Easton, the property offers a peaceful neighborhood setting with easy access to the area’s shops, restaurants, cultural attractions, and waterfront destinations.

28706 Hope Cir, Easton

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

3 Beds ⋅ 3 Baths

Welcome to Lakelands at Easton! This spacious home offers a versatile floor plan with the convenience of main-level living and plenty of room to spread out. The primary suite is located on the main level, along with a dedicated home office and laundry room. The gorgeous kitchen features abundant cabinetry, granite countertops, stainless steel appliances, a large pantry, and plenty of workspace, opening to a light-filled living room with high ceilings, beautiful windows, tons of natural light, and a cozy gas fireplace. Step outside to the patio and enjoy a backyard and side yard that back to mature trees, creating a peaceful setting with added privacy. The attached two-car garage provides everyday convenience, and the additional area alongside the home offers extra parking space—a great bonus for guests or additional vehicles. Upstairs, the possibilities continue with two additional bedrooms and a full bathroom, plus a large open loft area perfect for a TV room, sitting area, game room, playroom, or teen hangout. An impressive finished bonus room, estimated at approximately 400 square feet, adds even more flexible living space and is a standout feature of this home. Recent improvements include a new roof installed in 2025, new HVAC system, new hot water heater, new dryer, and new microwave, adding to the comfort and convenience this home has to offer. Conveniently situated just off Route 50 for an easy commute and close to Downtown Easton, shopping, local restaurants, and everyday conveniences. With four bedrooms, multiple flexible living areas, a main-level primary suite, home office, abundant natural light, and an attached two-car garage, this home offers a wonderful combination of space, updates, versatility, and location. Come see everything this Lakelands at Easton home has to offer!

29009 Superior Cir, Easton

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

3 Beds ⋅ 3 Baths

Charming and beautifully updated, this circa-1900 Colonial offers an inviting blend of historic character and refined, comfortable living in the heart of downtown Oxford. Surrounded by lovely gardens, mature trees, and established plantings, the property enjoys a picturesque setting just moments from the waterfront, with water views looking down the street and all the charm of this beloved Eastern Shore village close at hand. Inside, beautiful hardwood floors and thoughtfully updated interiors create a warm and welcoming atmosphere. The beautiful sun-lit living room offers a gracious space for relaxing and gathering, while the spacious gourmet kitchen serves as the heart of the home, featuring a large center island, premium stainless appliances, and a generous casual dining and sitting area overlooking the garden. A formal dining room provides an elegant setting for entertaining, while a comfortable sitting room opens to the screened porch, extending the living space outdoors. A full bath with a glass-enclosed shower completes the main level. Upstairs, the private primary suite is distinguished by vaulted, beamed ceilings and an ensuite bath with a double-sink vanity, glass-enclosed shower, two closets, and convenient access to the laundry. Two additional guest bedrooms share a half bath, with plans available upon request for conversion to a full bath. Outside, a wonderful screened porch and adjoining deck overlook the lush gardens and mature trees, creating a peaceful setting for outdoor dining and relaxation. A rare detached one-car garage offers additional workshop space, while the stone driveway provides ample off-street parking. Located in the heart of historic Oxford, the home is ideally positioned for enjoying the town’s waterfront parks, marinas, restaurants, and scenic streets, along with the relaxed pace and enduring character that make Oxford one of the Eastern Shore’s most treasured waterfront communities.

100 Tilghman St, Oxford

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

5 Beds ⋅ 5 Baths

EXPANSIVE SOUTHWESTERN VIEWS OF THE TRED AVON AND CHOPTANK RIVERS. A distinguished waterfront residence in Oxford, thoughtfully designed to embrace its extraordinary setting. Exceptional craftsmanship is evident throughout, with exquisite moldings and millwork, Brazilian Cherry hardwood floors, elevated and vaulted ceilings, abundant natural light, and an open floor plan oriented toward the water. The main level is equally suited to gracious entertaining and comfortable everyday living. A formal dining room opens to a refined gourmet kitchen with a generous center island and breakfast bar, premium stainless-steel appliances, wine storage, and a six-burner gas range. The kitchen flows seamlessly into the spacious living room with gas fireplace and continues to a screened porch and adjoining covered porch with outdoor grill, overlooking the pool and river. A well-appointed guest bedroom with ensuite bath and powder room complete the main level. Upstairs, a spacious sitting area with custom built-ins provides a quiet retreat. The waterside primary suite is exceptionally private, with a sitting area and gas fireplace, private balcony overlooking the river, and two cedar-lined walk-in closets with custom cabinetry. A discreetly integrated refreshment bar with wet sink and beverage refrigerator adds an elegant touch. The ensuite bath features a jetted tub, dual-sink vanity, and glass-enclosed walk-in shower. Three additional guest bedrooms include two sharing a Jack-and-Jill bath and a third with an ensuite bath. The waterfront grounds are designed for both relaxation and entertaining, with a pool and hot tub positioned to take full advantage of the expansive river views. A natural shoreline, small sandy beach, and private dock with boat lift and approximately 3' MLW extend the living experience to the water. A large two-car garage provides generous parking and storage. An exceptional Oxford offering with commanding river views, refined interiors, extensive outdoor living, and a private waterfront setting—an elegant retreat with all the elements for sophisticated Eastern Shore living.

808 S Morris St, Oxford

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

3 Beds ⋅ 2 Baths

Welcome to “Oaklands”, a charming property ideally located just off Oxford Road and only 3 miles from downtown Easton. Enjoy the best of Eastern Shore living with convenient access to a community dock with boat slips available, as well as a community waterfront lot perfect for launching canoes, kayaks, and paddleboards or simply relaxing by the water. The property features a one-level, 3-bedroom, 2-bath home with a spacious screened rear porch overlooking the private yard—an ideal setting for morning coffee, entertaining, or enjoying peaceful evenings outdoors. A detached 2-car garage provides plenty of room for vehicles, boats, water toys, or additional storage. With its combination of comfortable one-level living, outdoor space, garage storage, and community waterfront access, “Oaklands” offers a wonderful opportunity to enjoy the Eastern Shore lifestyle just minutes from all that downtown Easton has to offer.

28420 Oaklands Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

4 Beds ⋅ 5 Baths

Holly Point on prestigious World Farm Road offers an unparalleled waterfront lifestyle. This charming three bedroom, two and a half bath Eastern Shore Cape Cod features an open floorplan, a main-floor primary suite, two ensuite bedrooms and a loft area on the second floor, and breathtaking, broad views across Island Creek. Outdoor amenities include an oversized waterside pool and a deep-water dock with 6 feet MLW. Additionally, the property boasts private guest quarters situated above a detached garage, ensuring ample space for visitors. Located in a highly desirable, protected shoreline setting, this rare gem requires no flood insurance.

4471 World Farm Rd, Oxford

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

3 Beds ⋅ 2 Baths

“High Banks” Welcome to 32525 Discovery Dr. in Easton, MD. This offering consists of just over 2 acres of lush landscaping in a peaceful, parklike setting with pond access. Inside, you’ll find a move-in-ready 2-bedroom, 2-full-bath home. Please note that while the home is set up as a 3-bedroom home, the septic system is approved for only 2 bedrooms. Enjoy easy, one-level living with numerous upgrades, including a renovated bathroom, granite countertops in the kitchen, crawlspace encapsulation completed in 2019, a new roof in 2020 with 30-year shingles, a new HVAC system in 2020, and a new well pump in 2020. The primary bedroom was upgraded in 2021 with a shower enclosure and granite countertops, and a new front door was installed in 2024. Be sure to check out the 3-season rear sunroom, where you’ll want to spend much of your time overlooking the private rear yard. With its spacious grounds, peaceful setting, and thoughtful updates, “High Banks” offers the perfect combination of comfort and privacy.

32525 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

3 Beds ⋅ 2 Baths

Beautifully crafted, turn-key "Oxford Cottage" built in 2023 offering high-end finishes and classic Eastern Shore charm with NO HOA! Step off the welcoming front porch into a light-filled open-concept main level featuring hardwood floors throughout. The generous-sized eat-in kitchen boasts custom cabinetry, upgraded countertops, stainless steel appliances, and a seamless transition out to a spacious screened-in sunroom—ideal for outdoor dining and entertaining. The main floor offers an entry-level full bath and a versatile flex room perfect for a primary bedroom, home office, or den. Upstairs features two generous-sized bedrooms with dramatic vaulted ceilings, a full bath, and a dedicated laundry area. Outside, cedar-raised flower beds frame the home alongside a low-maintenance 0.11-acre lot and a detached frame garage with ample room for vehicles, water toys, or a workshop. Located just blocks from the Strand beach, waterfront parks, local dockside dining, the historic Oxford-Bellevue Ferry, and the Scottish Highland Creamery!

101 Tilghman St, Oxford

Listing courtesy of The Parker Group. Contact: 3022176692

3 Beds ⋅ 3 Baths

Prime Oxford Road location! This distinctive one level contemporary home offers a desirable split bedroom floor plan and an exceptional setting just minutes from Talbot Country Club, Easton, and Oxford. Set on a wooded lot, the property combines privacy and comfortable one-level living. Inside beautiful wood floors extend throughout the main living spaces. The thoughtfully designed layout offers a comfortable family room and dining area, along with a large living room with fireplace. A dedicated office/library provides a quiet space for work or study, while two primary owner suites offer exceptional flexibility and privacy. With 3 bedrooms and 3 full baths, the home provides ample room for guests and everyday living. Outdoor living takes center stage with front and rear porches, a charming breezeway and an in-ground swimming pool. A rare four-car garage provides exceptional space for vehicles, storage, hobbies, or recreational equipment. A sought after Oxford Road address, generous indoor and outdoor spaces, and convenient access to both Easton and Oxford make this a special Eastern Shore opportunity. Property being sold as-is. Inspections for informational purposes only.

6028 Millington Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

2 Beds ⋅ 2 Baths

Updated 2-bedroom, 2-bath home featuring a number of improvements and upgrades completed since December 2023. A bright front sunroom provides an inviting entry and features a custom built-in window bench seat. The adjoining living and dining areas offer comfortable everyday living space, accented by a custom stained-glass window. The renovated kitchen features new custom cabinetry, quartz countertops, stainless steel appliances, new flooring, a pantry, and a breakfast nook. The primary bedroom includes an en-suite bath with a glass-enclosed shower and double vanity. A second bedroom and full bath complete the home's living spaces. Additional improvements include upgraded electrical, new vinyl replacement windows, a new mini-split heating and air conditioning system, new water heater, ceiling fans, and a new front storm door. Just off the kitchen, the carport provides convenient covered parking with the flexibility to serve as additional outdoor living or entertaining space. Vinyl fencing and gates help define this area from the spacious backyard, offering plenty of room to enjoy the property outdoors. Some furniture and furnishings are available. Conveniently located with quick access to Route 50, the home offers an easy connection to downtown Easton, Cambridge, St. Michaels and surrounding Mid-Shore destinations.

29336 Hawkes Hill Rd, Easton

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

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