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28475 Pinehurst Cir, Easton
$355,000
3 Beds ⋅ 2 Baths
Welcome to easy Eastern Shore living in the desirable Easton Club. This 3-bedroom, 2-bath townhome offers a peaceful, low-maintenance setting with a wooded backdrop and convenient access to everything Easton has to offer. A major renovation in 2016, along with more recent updates, has created a fresh and comfortable interior featuring newer flooring, newer paint, and newer stainless steel appliances. The inviting floor plan includes a main-level bedroom, spacious living and dining areas, and a well-appointed kitchen with abundant cabinetry and workspace. Natural gas serves both the heating system and cooking, while two mini-split units provide supplemental heating and cooling for bedrooms two and three. A Rinnai tankless hot water heater adds everyday efficiency and convenience. Step outside to the rear deck and enjoy the privacy of the surrounding trees, with refreshed landscaping enhancing the setting. Easton Club residents enjoy community amenities including a pool and tennis/pickleball courts, along with maintained grounds and lawn mowing for a more carefree lifestyle. Just minutes from historic Downtown Easton, with its restaurants, boutiques, galleries, theaters, medical facilities and everyday conveniences, the location also offers easy access to the waterways, kayaking, biking, walking trails, parks, and outdoor recreation that are such a part of the Eastern Shore lifestyle. This home combines a tranquil residential setting with quick access to town and the many ways to enjoy the surrounding area.

28475 Pinehurst Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

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:

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:

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:

29316 Will St, Easton
$349,000
3 Beds ⋅ 2 Baths
🏡 Cute as a button Updated Rancher Easton – 29316 Will Street 🏡 Welcome to this adorable, move-in ready rancher that perfectly blends comfort, functionality, and style! Nestled in a convenient Easton location, this well-maintained home shines with thoughtful updates throughout. Step inside to discover a warm and inviting interior, ideal for everyday living or entertaining. Major improvements include a brand-new roof and newer HVAC system, giving you peace of mind for years to come. Outside, you’ll love the versatility this property offers: Detached garage complete with a private office space— Additional bonus room for storage, hobbies, or flex space Fenced backyard ideal for privacy Lovely patio area ready for outdoor dining and gatherings Whether you're downsizing, starting out, or looking for a low-maintenance retreat, this adorable home checks all the boxes. Don’t miss your opportunity to enjoy easy living with extra space where you need it most! 📍 Conveniently located near all that Easton has to offer—shops, dining, and more!

29316 Will St, Easton

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

31066 Skipton Cordova Rd, Cordova
$340,000
2 Beds ⋅ 3 Baths
Move-in ready and beautifully renovated. This charming colonial offering 3-bedroom home in the Chapel School District that has been extensively remodeled from top to bottom. With so many major improvements already completed, this is a wonderful opportunity for a first-time homebuyer looking for an updated home without the projects and added expense that often come with an older property. Step inside to a bright, fresh interior featuring new LVP flooring, a completely remodeled kitchen with new cabinetry and appliances, and beautifully updated bathrooms. Major exterior improvements include a new roof, new windows, and new siding, adding to the home's move-in-ready appeal. Need extra space? The upstairs features a versatile bonus room that could serve as a home office, guest room, hobby space, playroom, or potential third bedroom. This home offers a comfortable country setting while remaining convenient to Easton and surrounding Mid-Shore communities. Whether you're purchasing your first home, downsizing, or simply looking for a property where the work has already been done, this one deserves a closer look.

31066 Skipton Cordova Rd, Cordova

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

11994 Cordova Rd, Cordova
$340,000
2 Beds ⋅ 1 Baths
Charming and move-in ready, this updated 2-bedroom, 1-bath home with a flexible office space that could easily serve as a third bedroom is perfect for first-time homebuyers, downsizers, or anyone seeking comfortable, low-maintenance living. Major improvements include a new roof and siding completed in 2020, along with a whole-house generator for added peace of mind. Inside, you'll find tasteful updates throughout, creating a warm and inviting atmosphere. The oversized detached 2-car garage offers endless possibilities, providing ample space for vehicles, storage, hobbies, or the ideal workshop. Award winning school district. Conveniently located just minutes from Easton and nearby public boat ramps, this home offers easy access to shopping, dining, and all the outdoor recreation the Eastern Shore has to offer.

11994 Cordova Rd, Cordova

Listing courtesy of Coldwell Banker Realty. Contact:

21524 Chicken Point Rd, Tilghman
$339,000
4 Beds ⋅ 2 Baths
Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "W" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

21524 Chicken Point Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact:

4096 Main St, Trappe
$335,000
6 Beds ⋅ 3 Baths
Historic Farmhouse with Significant Value-Add Potential Built in 1919 and offering approximately 3,448 square feet, this stately farmhouse sits on a .44-acre lot and presents a rare opportunity for investors or renovation enthusiasts to restore a historic property with substantial upside. The home features many original architectural elements, including hardwood floors, crown molding, multiple fireplaces, wood pocket doors, and a grand staircase that highlight the craftsmanship of the era. The spacious main level includes two large sitting rooms, a formal dining room with floor-to-ceiling windows overlooking the wraparound porch, and a large kitchen with walk-in pantry. Additional features on this floor include a laundry area, half bath, and a secondary staircase leading to the upper level. Upstairs you’ll find five bedrooms and two full bathrooms, along with multiple linen closets and a long hallway lined with original wood doors. The third floor offers a sixth bedroom and an additional flex space, providing even more potential for added living area. With 3 levels of living space and a large footprint, this property offers an excellent canvas for renovation or restoration. Homes in the area that have been updated command significantly higher values, making this a compelling value-add investment opportunity. Property is being sold strictly as-is.

4096 Main St, Trappe

Listing courtesy of Coldwell Banker Realty. Contact:

28491 Pinehurst Cir, Easton
$329,000
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:

347 N Washington St, Easton
$325,000
2 Beds ⋅ 1 Baths
Charming Cape Cod Near Historic Downtown Easton <br> Warm, welcoming, and full of character, this beautifully updated Cape Cod offers comfortable living spaces and a wonderful location just a short stroll from historic downtown Easton. <br> Inside, beautiful hardwood floors add warmth and character, while the bright, inviting kitchen and updated HVAC provide everyday comfort. The spacious second level offers exceptional flexibility with a large bedroom, separate office or sitting area, walk-in closet, and abundant additional storage, ideal for a home office, reading nook, hobby space, or quiet retreat. Outdoor living is just as inviting. Enjoy morning coffee or watch the world go by from the classic front porch and porch swing. In the beautifully landscaped backyard, a newer deck and patio provide plenty of space for outdoor dining, entertaining, gardening, or simply relaxing. A large storage shed with attic space offers excellent additional storage for bikes, tools, hobbies, and seasonal items. <br> Best of all is the location. Downtown Easton’s restaurants, boutiques, galleries, and year-round events are close at hand, with parks, shopping, schools, and major routes conveniently nearby. <br> Move-in ready, full of charm, and close to the heart of Easton, come take another look and see all this home has to offer. <br><br> Advance notice required for showings - please contact your agent to schedule your appointment.

347 N Washington St, Easton

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

9531 Quail Hollow Dr Unit 405, St Michaels
$319,900
2 Beds ⋅ 3 Baths
Located in the desirable Martingham community, this two-bedroom, two-and-a-half-bath condominium offers comfortable living just minutes from historic downtown St. Michaels. The main level features a spacious living room with hardwood flooring and a wood-burning fireplace, a convenient half bath, and a full-season sunroom overlooking the backyard with direct access to the outdoor space. A detached one-car garage provides additional parking and storage. Upstairs, both bedrooms feature en-suite baths, including a rear bedroom with a private balcony overlooking the backyard and The Links at Perry Cabin Golf Course. Brand-new carpeting has just been installed throughout the upper level, and the home also features a brand-new water heater. Conveniently located near shopping, dining, waterfront parks, and the many attractions of downtown St. Michaels, this property offers an excellent opportunity to enjoy Eastern Shore living.

9531 Quail Hollow Dr Unit 405, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

508 Cynwood Dr Unit A, Easton
$315,000
Located in the heart of Easton’s medical and healthcare district—and just moments from Route 50—this 1,500± sq. ft. end-unit commercial condo offers an exceptional opportunity for medical, dental, or professional office use. If you’re ready to own instead of rent, this space delivers the flexibility, infrastructure, and location your business needs. Thoughtfully designed with a highly functional layout, the unit features a welcoming waiting room, dedicated reception area, two restrooms, five office/exam rooms, break room, equipment room, sterilization area, and mechanical room. Every treatment room includes a sink and is fully plumbed for dental chairs with water, suction, and air at both ends. Wiring is already in place for digital dentistry, panoramic X-ray, and data systems. All rooms also include Radon fans installed during COVID to create negative pressure—an added layer of safety and value. Additional perks include 220V service for autoclaves and laundry hookups. Interior walls can be easily reconfigured to suit your practice or workflow. Recent updates include a new roof and freshly repaved parking lot. Shared operating costs—trash, lawn care, landscaping, and water—are divided among the four units based on square footage.With ample parking and a prime location surrounded by established healthcare providers, this space is a rare chance to elevate your business while building equity. Perfect for medical, dental, therapy, or professional users looking to stop paying rent and secure a smart long-term investment. Bring your buyers. Bring your business.

508 Cynwood Dr Unit A, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

6136 Tilghman Island Rd, Tilghman
$300,000
REAL ESTATE AUCTION featuring ON SITE and SIMULCAST BIDDING!! Online Bidding Opens - Thursday, October 29, 2026. Live On Site Auction - Friday, October 30, 2026 at 12:00 noon. List price is opening bid only. Live Auction Bidders – A $40,000 deposit, payable by cashier’s check, will be required of the purchaser at time and place of sale. Online Auction Bidders – A $40,000 deposit, payable by cashier’s check or wire transfer, is due from all online bidders prior to bidding platform approval. That deposit to be applied to the purchase price for the purchaser, and all other deposits returned within 1 business day. A once in a lifetime opportunity to purchase a waterfront restaurant building with tiki bar in one of the most sought after locations on Maryland’s Eastern Shore. Located at the gateway to Tilghman Island and facing the Tilghman Island Drawbridge, considered to be the busiest on the East Coast, the property features ample exposure to both boat and vehicle traffic. The auction provides an opportunity for both users and investors to purchase a trophy waterfront property in a truly unique, desirable location with extensive long-term potential.

6136 Tilghman Island Rd, Tilghman

Listing courtesy of A.J. Billig & Company. Contact:

8186 June Way Unit 307, Easton
$299,900
3 Beds ⋅ 2 Baths
Welcome home to this charming 3-bedroom, 2-full-bath home offering a comfortable and functional layout with the convenience of a main-level primary bedroom. The spacious primary bedroom features a private full bath and direct access to the deck, creating an easy connection to the outdoors. The main level also offers a welcoming living area, kitchen and dining space, along with convenient main-level laundry. The kitchen and dining area provide additional access to the deck, making outdoor entertaining or enjoying your morning coffee a breeze. Upstairs, you’ll find two additional bedrooms and a full bathroom, providing plenty of space for family, guests, a home office or flex space.This desirable end-unit home offers added privacy and extra outdoor space, including a side yard and backyard—perfect for relaxing, entertaining, or enjoying some fresh air. Updates include an HVAC system that is only one year old and a new washing machine, providing added peace of mind. Come see all this home has to offer!

8186 June Way Unit 307, Easton

Listing courtesy of Coldwell Banker Realty. Contact:

313 Linden Ave, Easton
$299,000
3 Beds ⋅ 2 Baths
This charming Colonial is ideally located in downtown Easton, just off the Rails to Trails, only a block from Idlewild Park and conveniently located between both of Easton's YMCA facilities. Inside, the welcoming first floor offers a spacious living room with French doors opening to a cozy den that could also serve as a home office, playroom or quiet retreat. The kitchen flows into a large dining area with French doors leading to a bright sunroom overlooking the fenced rear yard. A spacious laundry/mudroom and updated half bath complete the first floor. Upstairs, three comfortable bedrooms share an updated full bath. Original hardwood floors flow throughout most of the home, adding character to the inviting interior. A large walk-up attic provides abundant storage space for seasonal items. The fenced backyard offers a brick patio for outdoor entertaining, a separate fire pit area ready to be brought back to life and a storage shed. Beyond the rear fence, a private alley presents the opportunity to create off-street parking, an added bonus in town. The roof was replaced in 2017. With its convenient location, flexible living spaces and inviting outdoor areas, this charming Easton home offers the best of in-town living with close proximity to parks, trails, dining, boutique shops and everyday amenities just moments away.

313 Linden Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

22314 Pot Pie Rd, Wittman
$295,000
Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home on 0.84± commercially zoned acreage with premier road frontage presents a compelling opportunity for investors seeking rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights • 3 Bedrooms 2 Bathrooms split between two units • 0.84± acre parcel with generous yard space • Two accessory structures (retail/storage in need of repair + versatile workshop ) • Strong long-term rental market supported by local workforce and regional amenities • Minutes to marinas, dining, recreation, and Chesapeake Bay attractions • Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable rental property in the Eastern Shore’s highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

22314 Pot Pie Rd, Wittman

Listing courtesy of Meredith Fine Properties. Contact:

108 Miles Ave, Saint Michaels
$295,000
A rare opportunity in the heart of St. Michaels: this half-acre+ wooded parcel offers the privacy of a tucked-away retreat with the everyday convenience of an in-town location. Restaurants, shops, seasonal events, waterfront parks, and the character of the historic district are all close at hand, yet the setting feels quiet and natural. Approximately three times the size of a typical in-town lot, the property provides remarkable flexibility for home placement, architectural style, and outdoor living spaces. The generous buildable envelope allows for a variety of layouts, and driveway access can be configured from Miles Avenue, Canton Street, or both, depending on the design. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

22314 Pot Pie Rd, Wittman
$295,000
3 Beds ⋅ 2 Baths
Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining conveniently located near St. Michaels, Easton, and Tilghman Island. Investment Highlights • 3 Bedrooms 2 Bathrooms split between two units • 0.84± acre parcel with generous yard space • Two accessory structures (retail/storage (in need of repair) + versatile garage/ workshop) • Strong long-term potential rental market supported by local workforce and regional amenities • Minutes to marinas, dining, recreation, and Chesapeake Bay attractions • Quiet rural location with easy access to surrounding towns and services An excellent offering for investors seeking a stable potential rental property in the Eastern Shore’s highly regarded Talbot County market. Property is being sold As-Is. Showings by appointment only. BUYER RESPONSIBILITY TO PERFORM DUE DILIGENCE REGARDING PROPERTY LOCATION, USE, RESTRICTIONS, AND TAXES.

22314 Pot Pie Rd, Wittman

Listing courtesy of Meredith Fine Properties. 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: