Talbot County Homes under $500,000

Talbot County Homes under $500,000

Welcome to Talbot County, Maryland – a hidden gem nestled on the Eastern Shore, where history, natural beauty, and a vibrant community come together. Known for its picturesque landscapes, charming waterfront towns, and rich cultural heritage, Talbot County offers an idyllic setting for those seeking a peaceful yet engaging lifestyle.

With its stunning views of the Chesapeake Bay and miles of scenic waterways, Talbot County is perfect for outdoor enthusiasts. Whether you enjoy sailing, fishing, or simply taking leisurely strolls along the waterfront, this area provides endless opportunities to connect with nature. The county is also home to a variety of parks and nature reserves, making it easy to explore the great outdoors.

One of the most appealing aspects of Talbot County is its diverse real estate market, particularly for those looking for homes under $500,000. Here, you can find charming single-family homes, cozy townhouses, and even some waterfront properties that offer both comfort and affordability. This makes Talbot County an attractive option for first-time homebuyers, families, and retirees alike.

In addition to its beautiful homes, Talbot County boasts a vibrant arts scene, with galleries, theaters, and cultural events that reflect the community's rich history. The county’s towns, such as Easton, St. Michaels, and Oxford, are filled with delightful shops, restaurants, and cafes that add to the warm, welcoming atmosphere.

Discover the charm of Talbot County, where you can find your dream home without breaking the bank. Come explore the possibilities and make this enchanting area your own!

Newest Talbot County Homes under $500,000

8490 Tilghman Island Rd, Wittman
$354,900
3 Beds ⋅ 2 Baths
🏡 COMING SOON — 8490 Tilghman Island Rd Welcome to this extensively renovated 3-bedroom, 2-full-bath home, offering approximately 1,539 sq. ft. of living space on a spacious, level 0.69-acre lot. ✨ Recent updates include: • New flooring throughout • Fresh interior and exterior paint • Updated kitchen with new countertops and appliances • Updated bathrooms • New deck • New dishwasher • New washing machine • New AC unit Move-in ready with plenty of room inside and out, this home offers comfortable living in a peaceful Eastern Shore setting—approximately 10 minutes from St. Michaels and 5 minutes from Tilghman Island Beach 3 Bedrooms | 2 Full Bathrooms | 1,539 Sq. Ft. | 0.69 Acres

8490 Tilghman Island Rd, Wittman

Listing courtesy of Johnson-Needham Realty LLC. Contact:

29349 Woodridge Dr, Easton
$499,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully updated 4-bedroom, 2.5-bath home nestled in a private, tree-lined setting just outside of town. With an oversized two-car garage and an impressive list of recent improvements, this home offers space, comfort, and privacy. The main level features a spacious living room, dining area, kitchen with a large pantry and breakfast bar, an additional family room with fireplace offering the perfect place to relax, and an enclosed porch with pellet stove. The generous primary suite offers custom built-ins, while the additional bedrooms offer plenty of space for family, guests, or a home office. The backyard has been completely transformed, creating a beautiful outdoor space to enjoy. Extensive tree work and stump grinding have also been completed throughout the property. The many updates include renovated bathrooms, fresh paint and new trim throughout, new fixtures, dishwasher, front door and door to the enclosed porch, new HVAC motors for both units, new roof and water softener, newer windows, new exterior light poles, an encapsulated crawl space, and a replaced crawl-space support beam. A bar/game room is conveniently located off the garage, providing additional space for entertaining or relaxing. Enjoy peaceful wooded views while being just minutes from Easton and surrounding areas. Conveniently close to town without town taxes, this property offers a great combination of privacy, space, and location with many thoughtful improvements already completed.

29349 Woodridge Dr, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

10225 Ocean Gtwy, Easton
$350,000
4 Beds ⋅ 2 Baths
Great opportunity in Easton! This spacious 4-bedroom, 2-bath rancher offers nearly 2,000 square feet of comfortable one-level living on approximately half an acre. The inviting floor plan features a generously sized kitchen with quartz countertops, ample cabinetry, a large pantry and plenty of space for everyday living and entertaining. The primary bedroom offers a vaulted ceiling, skylight, huge walk-in closet and private full bath with custom shower. Three additional bedrooms provide flexibility for family, guests or a home office. Outside, enjoy the spacious yard, patio/deck area and storage shed. The attached one-car garage provides additional storage and convenience. Ideally located with easy access to Easton, shopping, dining, St. Michaels, airport, new hospital and golf course! A wonderful opportunity to enjoy space, comfort and one-level living just minutes from all that Easton has to offer!

10225 Ocean Gtwy, Easton

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

705 S Morris St, Oxford
$499,000
2 Beds ⋅ 2 Baths
Embrace an effortless coastal lifestyle in the heart of Oxford, where days are shaped by the water and some of the town’s most beloved destinations are just a short stroll from home. Ideally located near beach access, waterfront dining, marinas, tennis and pickleball courts, and a local church, this beautifully refreshed cottage offers a rare combination of walkability, privacy, and Eastern Shore charm. Set on a generous 16,988+/- square foot lot, the 1,200+/- square foot, two bedroom, two full bath residence has been thoughtfully updated with a fresh coastal sensibility. The remodeled kitchen features new stainless steel appliances, while renovated baths, new luxury vinyl plank flooring throughout, windows and doors, custom window treatments, and efficient ductless heating and cooling create a polished, comfortable interior designed for easy living. A wooden deck extends the living space outdoors, providing a relaxed setting for morning coffee, meals with friends and family, and evening relaxation after a day on the water. The grounds offer room to entertain and enjoy the outdoors, complemented by ample parking and a two story outbuilding with electricity, offering potential with exceptional storage and versatility. Additional improvements include a new hot water heater and French drain installation, while affordable utility costs add to the home’s low maintenance appeal. A history of short term rental income provides additional flexibility for buyers seeking a coastal retreat with income potential. What truly distinguishes this property is its location. From 705 S. Morris Street, the waterfront lifestyle of Oxford is within easy reach. Walk to the beach, stroll to enjoy dinner overlooking the river, head to the marina for an afternoon on the Chesapeake, or spend the morning on the tennis and pickleball courts and many walking paths. Situated in sought after Talbot County, Oxford offers the understated elegance and slower pace that have long made Maryland’s Eastern Shore a coveted destination. Conveniently positioned between Washington, D.C. and the Atlantic Ocean, this inviting cottage presents an opportunity to enjoy a refined yet relaxed coastal escape in one of the Shore’s most charming waterfront towns.

705 S Morris St, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

9144 Honeysuckle Dr, Easton
$250,000
3 Beds ⋅ 1 Baths
Bring your vision and your renovation plans to 9144 Honeysuckle Drive in Easton! This three-bedroom, one-bath split-foyer home is being offered at $250,000 and presents an opportunity for investors, contractors, or buyers looking to create a home tailored to their own style. The property needs a full rehab, but the potential is here. The existing layout offers three bedrooms, one full bath, and the versatility of a split-foyer design. Out back, an in-ground swimming pool adds an attractive feature that could become the centerpiece of the finished property. Located in Easton, this property offers the opportunity to transform an existing home into something special while taking advantage of the area's established residential setting. Property is being sold as-is. Buyers should conduct their own due diligence regarding condition, renovations, permits, and the pool.

9144 Honeysuckle Dr, Easton

Listing courtesy of EXP Realty, LLC. Contact:

6207 Landing Neck Rd, Easton
$70,000
3 Beds ⋅ 1 Baths
Tucked right off Route 50 in Easton, this property offers unparalleled convenience with a structure that is ready for a total overhaul. Whether you are looking for a massive foundational rehab project or a site to build your brand new dream home, the geography cannot be beat. Enjoy seamless access to the Bay Bridge for DC/Baltimore trips, a straight shot to the DE/MD beaches, and immediate access to downtown Easton's shops and dining. The property is priced for the land and location. Enter at your own risk. Strictly AS-IS, inspections are for knowledge only. Buyers and buyers agents' to do all due diligence.

6207 Landing Neck Rd, Easton

Listing courtesy of Keller Williams Realty. Contact:

64 Park Ln, Easton
$30,000
2 Beds ⋅ 2 Baths
ONLINE AUCTION: Bidding begins 10/08/2026 @ 10:00 AM. Bidding ends 10/12/2026 @ 11:50 AM. List Price is Suggested Opening Bid. Deposit: $5,000. This auction takes place on the Ashland Auction Group Website Bidding Platform. Pre-auction offers may be accepted. Mobile Home located in the Active 55+ Hyde Park Community in Talbot County. Enjoy the convenience of Easton's historic downtown, dining, shopping and arts scene. Easy access to parks, trails and the Tred Avon River. Easy access to major traffic artery US-50 (Ocean Gateway). Property is vacant.

64 Park Ln, Easton

Listing courtesy of Ashland Auction Group LLC. Contact:

29424 Corbin Pkwy, Easton
$415,000
3 Beds ⋅ 3 Baths
Nestled in the Stoney Ridge community, this exquisite split-level residence offers a harmonious blend of modern luxury and timeless comfort. With a major renovation completed in 2015, this home has been updated to provide an upgraded living experience. As you step inside, you are greeted by an inviting atmosphere enhanced by luxury vinyl tile flooring that flows seamlessly throughout the main living areas. The spacious layout features three generously sized bedrooms and three full bathrooms, ensuring ample space for relaxation and privacy. The heart of the home is the beautifully appointed kitchen, equipped with energy-efficient appliances, including a built-in range, microwave, and a sleek cooktop. The upgraded countertops and built-ins create a perfect setting for culinary creativity and entertaining. The bathrooms are thoughtfully designed, showcasing a stall shower and a walk-in shower, providing a spa-like retreat right at home. The presence of cedar closets and walk-in closets adds a touch of luxury and practicality, ensuring that storage is never a concern. Natural light pours in through replacement windows, illuminating the inviting spaces and enhancing the overall warmth of the home. The daylight basement, complete with a walkout level and workshop space, offers endless possibilities for customization, whether it be a home gym, office, or additional living area. Set on a generous 0.25-acre lot in an urban setting, this property provides a serene escape while remaining conveniently close to the vibrant lifestyle that Stoney Ridge has to offer. Off-street parking ensures ease of access, while the surrounding community boasts a rich array of amenities and attractions. This residence is not just a house; it's a sanctuary that embodies a luxurious lifestyle, where every detail has been thoughtfully curated for comfort and elegance. Experience the perfect blend of modern living and classic charm in this stunning home, where you can create lasting memories for years to come.

29424 Corbin Pkwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

3908 Harrison Cir, Trappe
$225,000
3 Beds ⋅ 2 Baths
This one level home offers more than meets the eye! Not a drive-by, this is a must see to appreciate. Cathedral ceilings in the living area creating spacious open feeling. Previous owner had hair salon with separate side entrance, could be a 4th bedroom or familyroom. Kitchen, A/C & siding updated 2002, roof in 2014, washer/dryer 2020. Screened porch overlooking the fenced backyard which backs to farmland. Shed w/elec. needs a new roof. Zoned R-2.

3908 Harrison Cir, Trappe

Listing courtesy of Meredith Fine Properties. Contact:

29301 Pin Oak Way, Easton
$354,900
3 Beds ⋅ 2 Baths
Interior Photos Soon! Welcome to your next home in desirable South Beechwood. Lovingly maintained by its original owner. This spacious rancher features cozy family room, a bright sunroom, and primary bedroom with private bath. Recent major improvements include a newer roof, HVAC system, and appliances. Outside, enjoy a spacious yard backing to trees and a protected area. A large garden shed adds convenient space for tools, lawn equipment, and outdoor belongings. Both comfortable and affordable - Whether you're a first-time buyer looking to get started or ready to simplify and scale down, this rancher is ready for its next chapter! Public records does not reflect square footage of sunroom.

29301 Pin Oak Way, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

29595 Dutchmans Ln Unit 702, Easton
$275,000
3 Beds ⋅ 3 Baths
Discover the charm of this inviting Colonial townhouse style condominium in the desirable Stoney Ridge community. With 1,584 sq. ft. of thoughtfully designed space, plus the finished family room in the basement, this home features three cozy bedrooms and two and a half baths, perfect for comfortable living. The heart of the home boasts a galley kitchen with upgraded cabinets, granite countertops and tile backsplash, equipped with modern appliances, including a built-in microwave and dishwasher, seamlessly flowing into a family room ideal for gatherings. The HVAC was replaced in 2023. Enjoy the warmth of an electric fireplace in the living area, and the convenience of a main-floor laundry. The community offers well-maintained common areas, with services like lawn care and snow removal included in the association fee. Stoney Ridge is conveniently located near parks, providing ample opportunities for outdoor activities, and is served by reputable schools both public and private. With easy access to public services and a friendly neighborhood atmosphere, this home is a perfect blend of comfort and community. Experience the joy of living in a place that truly feels like home!

29595 Dutchmans Ln Unit 702, Easton

Listing courtesy of Meredith Fine Properties. Contact:

1258 Lake Michigan Dr, Trappe
$450,999
3 Beds ⋅ 2 Baths

1258 Lake Michigan Dr, Trappe

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

Start Your Search