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$559,000
4 Beds ⋅ 3 Baths
A myriad of possibilities come with this unique property. Two homes for the price of one. The main house offers three bedrooms with two full baths plus an attached in-laws/au-pair with two bedrooms, family room with brick hearth fireplace, one full bath, kitchen and sunroom. The main house has gleaming wood floors, kitchen with breakfast area, formal dining and living room with fireplace. Spacious primary suite with walk-in closet. The third floor is great for a workroom, studio, crafting and kids playroom. Situated on 2.1 +/_ acres with a detached 4-car garage and storage shed in a quiet country setting and just minutes to a Talbot County boat ramp.

6253 Middle Point Rd, Neavitt

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$879,000
4 Beds ⋅ 3 Baths
An Exceptional Custom Built Choptank River Waterview Retreat. Masterfully crafted in 2021 by the owner, an experienced custom home builder, this modern farm style home is a true showcase of exceptional craftsmanship, timeless architecture, and refined luxury. Every detail was thoughtfully designed to create a residence that is both elegant and inviting, where breathtaking Choptank River views and spectacular sunset skies become part of everyday living. Offering approximately 3,000± square feet on .95± acres, this remarkable home captures panoramic water views from nearly every room. Expansive windows fill the interiors with natural light while framing the ever changing beauty of the river, creating a serene backdrop for both relaxation and entertaining. Surrounded by beautiful mature landscaping with irrigated lawn, the grounds provide a private and picturesque setting with thoughtfully designed outdoor spaces that enhance the timeless appeal of the home and create a truly tranquil retreat. Designed with lifestyles of today in mind, the open concept living spaces are ideal for gathering with family and friends. Soaring cathedral ceilings, brick fireplace, and walls of windows create a stunning great room that flows seamlessly into the dining area and gourmet kitchen. The chef inspired kitchen is the centerpiece of the home, featuring elegant quartz countertops, a striking leathered granite island, premium finishes, and a spacious entertaining bar. The thoughtful design provides the perfect setting for preparing meals, hosting guests, and enjoying conversation while taking in beautiful views of the Choptank River. The luxurious main level primary suite offers a private oasis with a spa inspired bath featuring a large custom tiled shower, relaxing soaking tub, expansive walk in closet, and conveniently placed laundry nearby. Two additional bedrooms share a beautifully appointed full bath on the main level along with custom designed private office space and mudroom that showcase exceptional storage, woodworking details, and craftsmanship throughout. The upper level provides a spacious fourth bedroom with captivating bird’s eye views of the river and generous walk in attic storage. Outdoor living is equally impressive with spaces designed for unforgettable entertaining and relaxation. While taking in river views at all times of day, enjoy morning coffee on the deck, cocktails on the patio, and prepare and indulge in meals in the beautifully appointed outdoor kitchen and bar area. After a day on the boat, unwind beneath colorful sunset skies in the refreshing outdoor shower. The backyard creates the perfect backdrop for hosting family and friends while enjoying the beauty of the Eastern Shore. The exterior of the home reflects its custom quality with classic board and batten siding, Bermuda shutters, wooden gable accents, and designer lighting. Ideally located to enjoy the best of Eastern Shore living, take your golf cart to Ferry Point Marina for boating access or pick up fresh local seafood from TL Morris Seafood before returning home to enjoy dinner with breathtaking sunset views over the Choptank River. This sanctuary is placed a short drive away from the desirable towns of Easton and Saint Michaels, where gourmet restaurants, historical sites, and boutique shopping await. Ocean beaches can be reached in just over one hour and Washington D.C. in about one and a half hours. This is more than a home, it is a thoughtfully crafted retreat designed for gathering, entertaining, and embracing the beauty of every season. A rare opportunity to own a custom residence where luxury finish, exceptional craftsmanship, and captivating water views come together to create an extraordinary lifestyle.

29629 Ferry Point Dr, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,100,000
4 Beds ⋅ 3 Baths
Location, Location, Location. Oxford corridor with 50 Ft. of waterfront plus a small dock on Peachblossom Creek and a beautiful pond. Peaceful 3.5 acre waterfront lot with plenty of room for a pool and tennis courts. Rancher style home being sold As Is. 4 bedrooms and 3 full baths, oversized garage as well as a large detached garage. First time offered in 50+ years. This property is ready for your design. Bring your architect and make this your forever home.

28221 Widgeon Ter, Easton

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

$470,000
3 Beds ⋅ 3 Baths
Tucked away among the farmland of Talbot County, this charming Cape Cod offers a peaceful Eastern Shore setting while still being conveniently located just outside of Easton. Set on more than two acres with mature trees, established gardens, nearby ponds, and quiet winding roads, the property offers privacy and plenty of room to enjoy the outdoors. Inside, the home features three bedrooms, two full baths, and a flexible floor plan. The main level includes a living room, separate dining room, spacious kitchen with an oversized island, and a first-floor primary suite with private bath. A dedicated laundry room with half bath adds convenience, while a separate space just off the garage entry makes an ideal drop zone, mudroom, or additional storage area. Upstairs are two additional bedrooms, a full bath, and an open bonus area perfect for a playroom, home office, or second living space. Outside, established flowers gardens, Black-eyed Susans, berry bushes, and mature trees create a gardener's dream with plenty of space to make your own. Enjoy the privacy of country living with the shops, restaurants, and conveniences of Easton just a short drive away. Professional photos coming soon!

5935 Bay Acres Dr, Trappe

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

$249,990
2 Beds ⋅ 1 Baths
This charming 2-bedroom bungalow, remodeled kitchen with granite counters, large island, new floors throughout, appliances, hot water heater & HVAC. All major units have been replaced. Home offers a unique blend of classic character and modern convenience. With 1,014 sq. ft. of thoughtfully designed space. Enjoy the convenience of main floor laundry hookups, enhancing everyday living. The detached structure sits on a generous 0.17-acre lot, providing ample outdoor space for relaxation or gardening. Parking is hassle-free with a dedicated driveway. This property is perfect for those seeking a cozy home with potential for customization. Experience the charm of a historic bungalow. Don't miss the opportunity to make this your own!

4070 Hennisee Ln, Trappe

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$389,900
4 Beds ⋅ 2 Baths
Charming Cape Cod home, built in 1986, offers a perfect blend of comfort and community. With 1,950 sq. ft. of living space, it features 4 spacious bedrooms and 2 full bathrooms, ideal for gatherings or quiet evenings. Large 4 season room located off kitchen/dining area. Nestled on a generous 0.46-acre lot, the property boasts a detached garage with ample storage, perfect for hobbies or outdoor gear. Enjoy the convenience of main-floor laundry, enhancing your daily routine. Located in a welcoming neighborhood, residents benefit from nearby parks, excellent schools, and vibrant community events. The area is known for its friendly atmosphere and easy access to public services, ensuring a fulfilling lifestyle. Embrace the warmth of this home and the joys of community living, where every day feels like a retreat.

14013 Old Wye Mills Rd, Wye Mills

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$3,295,000
5 Beds ⋅ 5 Baths
Welcome to this exceptional 4/5 BR/4.5BA waterfront residence overlooking picturesque Town Creek in the historic waterfront town of Oxford. Built in 2023, this home is privately set on 1.71 acres (very rare for Oxford) surrounded by mature trees, extensive landscaping and thoughtfully designed hardscaping that complement the natural beauty of its serene waterfront setting. Designed with extraordinary attention to detail, the home showcases soaring vaulted ceilings, expansive windows, and multiple decks and balconies that capture tranquil water views from nearly every room. The grand living room, anchored by a gas fireplace, flows effortlessly into the dining area and an extraordinary chef’s kitchen featuring a large center island, separate casual dining space, a well-appointed butler’s pantry, and a screened porch just off the kitchen - perfect for outdoor dining and enjoying the peaceful waterfront setting. A private office with an adjacent full bath offers flexibility as a guest suite. The desirable main-level primary suite is a luxurious retreat, complete with a spa-inspired bath, private sitting room, and sliding doors opening to a peaceful screened waterside porch. The second floor offers three additional guest bedrooms, including one with an ensuite bath and two connected by a Jack & Jill bath, providing comfortable accommodation for family and guests. Outdoor living is equally impressive, featuring a waterside slate patio with expansive views, ideal for relaxing or entertaining while enjoying the serene waterfront setting. A new pier with two slips and 4’ MLW provides convenient boating access, while a thoughtfully integrated rainwater harvesting and management system was incorporated as part of the property’s environmental site design. Located just a short stroll from downtown Oxford, this beautiful waterfront home offers the perfect blend of luxury, comfort, and small-town coastal living. *Home built out of flood zone: Elevation certificate available *Room for pool; plans available for pool and pool house.

104 East St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$2,295,000
3 Beds ⋅ 6 Baths
With its central Talbot County location and effortless one‑story layout, this move‑in ready waterfront retreat offers a rare blend of convenience, comfort, and stunning natural beauty. Set on more than two acres on Trippe Creek with 185' of water frontage—directly across from Talbot Country Club—the property enjoys an elevated vantage point with broad water views, a private pier, and a heated pool and hot tub all just minutes from the amenities of both Oxford and Easton. The 3,100‑plus square‑foot home is designed for easy living, with sweeping waterside views and a newly renovated primary suite featuring a luxurious private bath with a steam shower. Two additional bedrooms, a bunkroom plus three full baths provide ample space for guests. The gourmet eat‑in kitchen, formal dining room, large living room with fireplace, separate family room create a warm, flexible layout for everyday living and entertaining. A screened porch offers the perfect spot to enjoy the breeze off the creek. Thoughtful updates throughout the home preserve its beautiful hardwood floors, moldings, and character while introducing a fresh coastal palette, contemporary kitchen and baths, new roof and Hardie board siding, and numerous additional improvements. The grounds are exceptional—one of the most beautiful settings in the county—with mature specimen trees, curated landscaping, full yard and garden sprinkler system, invisible dog fence and uncommon topography that enhances both privacy and views. The dedicated nature preserve directly across the street ensures no future building. A waterfront property of this quality, setting, and convenience with no flood insurance required is a rare find. Added bonus--enjoy a front row seat without leaving your own property to enjoy TCC's incredible 4th of July fireworks! Don’t miss the opportunity to make 5920 Oxford Road your own.

5920 Oxford Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$319,000
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: (410) 745-0415
$1,195,000
4 Beds ⋅ 4 Baths
Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright living spaces. This home offers four spacious bedrooms, generously sized bathrooms, and ample storage, providing comfort for family and guests alike. The rear yard is a private retreat designed for both relaxation and entertaining. Tucked into the lush landscaping (which includes an in-ground irrigation system) is a fully finished, detached accessory building. This versatile, light-filled structure is perfect for a dedicated craft studio, hobby workshop, private home office, or fitness room. This property also includes rare, highly coveted off-street parking. Situated just steps from San Domingo creek and less than a block from Talbot Street, the house provides quick access to the waterfront park/kayak launch and the nature trail as well to the town's maritime attractions, local ice cream parlors, and fine dining. An 1850 historic treasure in a premier in-town location doesn't come along often-schedule your private tour today and make the magic of the Eastern Shore your reality.

114 W Chestnut St, St Michaels

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

$3,495,000
4 Beds ⋅ 5 Baths
Located at the end of a private, gated, park-like lane, mid-way between Easton and Oxford: This gracious home is situated on one of the premier sites in Talbot County, MD...2.3-acre point of land, providing Westerly (SUNSET) views looking directly down Trippe Creek toward the Tred Avon River. The recently updated brick home provides exceptional water views from most rooms, especially from the living room, dining room and brick-floored glassed "River Room." The floor plan (see downstairs and upstairs plans in the attached photos) features 2-bedrooms down stairs (including a "Primary" Bedroom) and 2 bedrooms upstairs (Including another "Primary" - take your pick!). A total of four large bedrooms, four bathrooms and one half-bath. Lots of living and entertaining spaces downstairs, including a spacious living room, family room, library and River Room. Recent updates include a new BAT septic system; encapsulated crawl space; refinished wood floors throughout; fresh paint inside and out; new kitchen countertops; new kitchen appliances; updated bathrooms and more. This is a true "turn-key" home. For boating, there is a substantial private pier (6' x 135') which provides 6+ ft of depth at low tide (MLW). By boat, the town of Oxford and the open waters of the Choptank River are just a short, scenic 5-mile boat ride downstream. By car, this prime location is conveniently located approx. 5-miles to Easton or 5-miles to Oxford.

28161 Harleigh Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$640,000
4 Beds ⋅ 3 Baths
Welcome to Ingleton, a waterfront community ideally situated along the Miles River and Hunting Creek. Set on 2.7± acres with a Miles River water view, this traditional two-story home offers 4 bedrooms, 2.5 baths, an attached one-car garage, and a 16' x 24' pole barn with lean-to. Major renovations and improvements were completed in late 2021/2022, including a new 50-year roof, new HVAC system, new water heater, and a completely renovated kitchen and breakfast area featuring granite countertops, a center island/breakfast bar, stainless steel appliances, updated cabinetry and flooring, recessed lighting, and an under-sink reverse osmosis system. Hardwood floors extend throughout the principal living areas, and the spacious living room features a wood-burning fireplace and mantel. A sunroom opens to the expansive backyard, bordered by mature trees and tall pines. Additional improvements include a renovated first-floor powder room, semi-conditioned crawlspace with vapor barrier and new sump pump, smart thermostat, graded and top-dressed driveway, and concrete slab at the pole barn. The two full baths upstairs are ready for your vision and future renovation. The voluntary Ingleton HOA is reported at $120 annually and maintains the community waterfront access lot on Hunting Creek, offering kayak-depth water, along with mosquito spraying. Approximately 6 miles to Easton and 10 miles to St. Michaels, with convenient access to Route 50 and the Bay Bridge corridor.

8235 Ingleton Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$3,000,000
4 Beds ⋅ 3 Baths
Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its westerly orientation delivers spectacular sunsets every evening, complemented by expansive water views and abundant wildlife. Offered completely turnkey—furnishings, linens, fully equipped kitchen and everything shown in the photographs convey. Additional features include a saltwater pool, pool house, three-car garage and even a separate, fenced “tiny house” for the dogs! The property fronts Broad Creek, a tidal tributary of the Choptank River and Chesapeake Bay, and is not located within a FEMA-designated flood zone

23820 Mount Pleasant Landing, Saint Michaels

Listing courtesy of Engel & Volkers Annapolis. Contact: (443) 292-6767
$339,999
3 Beds ⋅ 2 Baths
This move-in-ready Easton rancher offers approximately 1,400 square feet of comfortable one-level living with 3 bedrooms and 1.5 baths. The home features a spacious living area, an open kitchen and dining space, a generously sized primary bedroom, and good natural light throughout. Set on an oversized, nearly half-acre lot, the property offers a large fenced backyard with plenty of room for outdoor enjoyment, along with a concrete patio, storage shed, and ample driveway parking. Important improvements are already in place, including flooring in 2019, a new roof in 2021, and HVAC in 2022. Public water, sewer, and natural gas add to the convenience. Well maintained and ready for its next owner, this is an appealing opportunity for comfortable single-family living in Talbot County.

29245 Corbin Pkwy, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$480,000
3 Beds ⋅ 3 Baths
Welcome to this beautifully maintained McDaniel model in Easton Club East, a sought-after 55+ active adult community in Easton. Offering 3 bedrooms and 2.5 baths, this spacious home features a well-designed floor plan with a first-floor primary suite, generous living spaces, and an attached two-car rear-entry garage. A welcoming foyer opens to the formal dining room and leads into the great room, where vaulted ceilings create a bright and open feel. Just beyond, the sunroom offers additional living space with abundant natural light. The kitchen features rich cherry cabinetry, granite countertops, ceramic tile flooring, double wall ovens, an electric cooktop, and a comfortable breakfast area. The first-floor primary suite includes a walk-in closet and private bath with a soaking tub and separate walk-in shower. Two additional bedrooms and a full bath provide comfortable space for guests. Additional features include an irrigation system and intercom system. Easton Club East offers an impressive array of community amenities centered around its 11,000-square-foot clubhouse, with a fitness center, ballroom, library, billiards and game spaces, card room, and arts and crafts room. Outdoor amenities include a swimming pool, tennis and pickleball courts, bocce courts, recreational paths, pocket parks, and scenic ponds. Lawn care and snow removal are also provided by the community association, making it easy to enjoy a low-maintenance lifestyle close to the shopping, dining, cultural attractions, and conveniences of Easton. (More photos coming by Friday!)

29812 Dustin Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$895,000
3 Beds ⋅ 3 Baths
Oxford. One owner 2,858 sq. ft home built in 2006 is just off the Strand only a block from the Tred Avon River. Features living room and dining rooms, den, family room with woodburning fireplace off open kitchen with island and granite countertops, powder room. Second floor offers 3 spacious bedrooms including a primary suite with walk-in closet and 2 guest bedrooms and guest bath. Exterior offers 2 balconies, HardiPlank siding, paver driveway and more on a .18 acre lot. Hardwood flooring throughout most of the home (except 2 guest bedrooms) and 2 energy efficient heat pumps. Located in the Oxford’s historic district. This home preserves the historic character while offering a modern floor plan with 9’ ceilings and modern upgrades. Professional photos coming in September

104 Stewart Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$725,000
3 Beds ⋅ 2 Baths
A Charming Eastern Shore Retreat located between Easton and Saint Michaels with Water Access & Endless Possibilities! Welcome to 5735 Irish Creek Road, a beautifully updated property offering a wonderful blend of Eastern Shore charm, modern improvements, water access, and incredible potential. Set in the peaceful countryside of Royal Oak, this distinctive property is ready for its next owner to bring their vision to life. Inside the main residence, a renovated gourmet kitchen provides a stylish and functional centerpiece for everyday living and entertaining. The inviting sunroom features a vaulted ceiling, creating a bright and airy space to relax and enjoy the surrounding setting. Recent improvements include a new hot water heater, new air conditioning system, new septic system, and updated flooring throughout. A newly added front brick porch enhances the home's curb appeal and creates a welcoming spot to enjoy the peaceful surroundings. The property also offers exceptional flexibility with a guest cottage and a carriage house/detached garage—perfect for guests, a studio, home office, workshop, additional storage, or whatever your imagination envisions. With water access, this property is ideally suited for enjoying all that the Eastern Shore lifestyle has to offer—from boating, kayaking, fishing, crabbing, and paddleboarding to simply spending leisurely days by the water. Whether you're looking for a peaceful full-time residence, a weekend escape, or a unique property with room to create something truly special, 5735 Irish Creek Road offers an exciting opportunity to make your Eastern Shore dreams a reality. Come discover the charm, embrace the possibilities, and make this one-of-a-kind property your own!

5735 Irish Creek Rd, Royal Oak

Listing courtesy of Compass. Contact: (301) 298-1001
$679,000
4 Beds ⋅ 2 Baths
Nestled in the charming High Banks community, this delightful Cape Cod-style home offers a serene retreat with 220 feet of waterfront along, and its own private dock to The Pond at High Banks. Or sit out on the wrap around porch overlooking the pond. To enter you drive down a tree lined lane and expansive lawn to a house literally out of a story book. Imagine mornings spent sipping coffee on your porch, listening to the gentle sounds of nature. With 4 spacious bedrooms and 2 full baths, this residence is designed for comfort and relaxation. The main bath is as elegant as you can make, with a built in vanity for pampering one self. The back yard area is fenced in with access from side and back of house. Remodled kitchen with induction stove, air fryer are the features a cook will appreciate. Community is known for its friendly atmosphere and well-maintained surroundings, making it a perfect place to call home. Local schools are highly regarded, ensuring quality education for all ages. Enjoy the convenience of nearby amenities, including shopping and dining options, all while being surrounded by the beauty of nature. This home is not just a property; it's a lifestyle that embraces tranquility and community spirit. Experience the joy of waterfront living in a neighborhood that feels like home. Please note the tax records do not reflect the second floor, the square footage came from the appraisal from when the owners bought. Any question buyer responsible to do there own verification . Shed and shop have electricity. All information is estimates based on the information given verify all and any questions on the above discription.

32659 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777
$730,000
3 Baths
28309 Village Lake Way is a two-story Easton home with connected living spaces suited to everyday routines. The kitchen combines wood cabinetry, stainless steel appliances, and a center island that adds prep space and casual seating. The adjoining living area includes a fireplace that anchors the room, and a separate dining area sits nearby for gatherings. The primary bedroom holds two windows for natural light and a walk-in closet, while the primary bathroom includes a double vanity and a separate shower. Outside, a fully fenced backyard and covered porch extend usable space. An attached two-car garage completes this well-maintained residence with practical amenities throughout every room.

28309 Village Lake Way, Easton

Listing courtesy of Open Door Brokerage, LLC. Contact: 4804625392
$1,075,000
4 Beds ⋅ 4 Baths
This spacious 4-bedroom, 3.5-bath home offers a peaceful rural setting just minutes from downtown Easton. Set on 2+/- acres with an additional 5.92+/-acre non-buildable lot included in the sale, the property offers plenty of space both inside and out. The main level features a large living room with a stone-surround gas fireplace, formal dining room, sunroom, and a well-appointed kitchen with stainless steel appliances, and a large island that makes gathering and entertaining easy. A first-floor office or library adds flexibility, while A whole-home Sonos sound system adds another layer of convenience for everyday living and entertaining. Upstairs, the spacious primary suite includes a private bath with a tile-surround shower and soaking tub, along with three additional bedrooms, two of which have attached baths. The full basement is a standout feature, offering a dedicated workshop with ample space for projects, tools, and storage. Outside, the entertaining space continues with a large back porch, pool, hot tub, oversized shed, extended driveway, and lush landscaping. With a secluded country feel, generous indoor and outdoor gathering spaces, and easy access to downtown Easton, this property offers an exceptional balance of privacy, space, and convenience.

29747 Easton Farms, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$549,900
3 Beds ⋅ 3 Baths
Chesapeake by Del Webb. The Hillsboro model offers an exceptional combination of space, convenience, and comfortable living. Located directly across from the Community Center and pool, this home features more than 3,400 square feet of thoughtfully designed living space. The main level includes two generously sized bedrooms and two full bathrooms, along with a separate office, living room, family room with fireplace, and bright sunroom. Upstairs, you'll find an additional bedroom, full bathroom, and spacious living area—ideal for guests, family members, or a private retreat. Step outside to the rear patio, where extensive landscaping creates a beautiful setting for outdoor entertaining, relaxing, or enjoying the surrounding views. With its versatile floor plan, abundant living space, and highly convenient location, the Hillsboro is a home designed for both everyday comfort and entertaining. Recent improvements include a new roof, HVAC system and a new hot water heater

29580 Charles Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$749,900
4 Beds ⋅ 3 Baths
Welcome to this beautifully maintained 4-bedroom, 2.5-bath home in Master's Village at Easton Club. A welcoming wraparound front porch and beautifully landscaped front yard set the tone for the inviting spaces found throughout the home. Hardwood flooring extends through most of the main level, where the light-filled living room features high ceilings, a gas fireplace, and built-in cabinetry. The highly sought-after entry-level primary suite offers a private retreat with direct access from the bedroom to the back deck, along with a spacious bath featuring a soaking tub, separate shower, and double vanities. Just off the kitchen, the sunroom opens to the deck with an awning, creating an ideal space for indoor-outdoor living and entertaining, with a stone patio providing additional outdoor space. Upstairs, the hallway landing doubles as a comfortable sitting area or potential home office and leads to three additional bedrooms. A large bonus room offers plenty of flexibility as a recreation room, family room, or additional gathering space. An additional stairway from the second level leads to a dedicated storage room, providing convenient extra storage. Located in the desirable Easton Club community, residents enjoy access to community amenities including a swimming pool and tennis courts, all just minutes from the conveniences of downtown Easton. Roof New August 2026 HVAC- Downstairs new 2026, upstairs new 2020.

7583 Easton Club Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$985,000
4 Beds ⋅ 3 Baths
Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

21477 Island Club Rd, Tilghman

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to the William J. Wrightson House, a beautifully restored c. 1897 residence where historic St. Michaels charm meets exceptional modern comfort. Located in the heart of town and just steps from the waterfront, marinas, shops, and restaurants, this distinctive 3-bedroom, 3-bath home offers an extraordinary opportunity to enjoy the very best of Eastern Shore living. Extensively renovated with an emphasis on quality and craftsmanship, the home has been updated from top to bottom. Improvements include new HVAC systems, tankless hot water heaters, updated wiring, encapsulated crawl space, new roof and gutters, recessed lighting, high-end appliances, three renovated baths, a custom butler’s pantry, complete interior and exterior painting, and improved patio drainage and grading. Natural light fills the gracious interior, highlighting heart pine and yellow pine floors, custom millwork, and beautifully appointed living spaces. The living room, anchored by a new gas fireplace, flows naturally into the formal dining room and gourmet kitchen, which features quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins. At the rear of the home, the extraordinary sunroom overlooking the English garden, provides an inviting space for relaxed gatherings or entertaining. Vaulted ceilings, shiplap wall treatment, custom built-ins, and butler’s pantry with beverage chiller and bar sink make this room the heart of the house. French doors open to the brick patio and beautifully landscaped gardens. The second floor offers a serene primary suite with a luxurious marble bath, clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a beautifully renovated hall bath provide comfortable accommodations for family and guests. Outside, a private English garden creates a picturesque retreat, with roses, crepe myrtles, and hydrangeas framed by a charming French Gothic lattice shadowbox fence. Beautifully restored, thoughtfully designed, and ideally located, this is historic St. Michaels living at its finest.

202 E Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$775,000
4 Beds ⋅ 4 Baths
Welcome to 30300 Kings Meadow Place! This spacious home is what peaceful country living is all about! Located on 1.5 acres just outside Easton town limits, you will enjoy nature at its best. A beautiful 3200+ sq. ft. home loaded with amenities - wood floors throughout the main level, with a recently renovated kitchen that now boasts an open floorplan to the Living room with a gas fireplace surrounded by built-in bookcases & Breakfast area with direct access to the rear covered porch. You will enjoy Quartz countertops, stainless steel appliances including a gas oven/range to prepare your meals that you can serve in the large formal dining room for those special guests. The Primary bedroom is located on the opposite side of the house than the other bedrooms for privacy & boasts a spacious spa-like bath, double walk-in closet and access to the rear covered porch. Two additional en-suite bedrooms on the main floor and a powder room give your guests or other family members their own privacy! A main floor fully-equipped laundry room is ideal! Did I mention that there is a covered front porch as well? Upstairs you will find a spacious loft that overlooks the kitchen which can be a whatever you desire - a family room, an office, a workout space. Also you will find the 4th bedroom and another room that could be a game room or play room. There is lots of storage in the house but you will love the attached 3 car garage with a workbench and even more storage. Currently there is no pool but there is certainly plenty of room to add one! If you are in the market for a lovely home in a peaceful country setting, you don't want to miss this one! Some of the furnishings may be purchased separately as well as great Harley Davidson motorcycle!

30300 Kings Meadow Pl, Easton

Listing courtesy of Shore Living Real Estate. Contact: 4102515291
$949,000
4 Beds ⋅ 3 Baths
Beautifully upgraded and thoughtfully designed, custom finishes, and every modern convenience. The gourmet kitchen features dual fuel gas cook top and electric oven in professional grade stove, quartz countertops, professional grade appliances, and premium appointments, flowing seamlessly into warm hardwood floors and a cozy gas fireplace beneath a striking coffered ceiling. Beautifully curated designer wallpaper accents throughout this stunning model home! Offering 4 bedrooms and 2.5 baths, the home includes a first‑floor primary suite with an ensuite spa bath, custom shower, and generous walk‑in closets. Additional highlights include Hardie Plank siding, custom black windows, a Trex deck, paved driveway, 1‑car garage, and excellent storage throughout. Located just a short walk to the heart of St. Michaels, you’ll enjoy easy access to charming shops, restaurants, waterfront activities, and year‑round festivals.

111 Chesapeake Ave, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$379,990
2 Beds ⋅ 2 Baths
Welcome to the Pacifica 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. 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 an optional freestanding tub and 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.

29403 Jobes St, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$559,900
3 Beds ⋅ 3 Baths
BRAND NEW & MOVE-IN READY, this spacious ranch home offers easy one level living and features high end finishes throughout, including a gourmet kitchen with stylish white and timber cabinetry, satin bronze hardware, quartz countertops, subway tile backsplash, and stainless steels appliances including a double oven, gas cooktop and range hood. The living room features a gas fireplace and large picture windows, providing an abundance of natural light. The owner's suite is equipped with a walk-in closet and luxurious bath with dual vanity, spacious shower w/dual shower heads and tile surround. Rounding out the main level is two additional bedrooms and a full bath with ceramic tile flooring and surround. Additional amenities include 9' ceilings, two car side load garage, LVP flooring, ceramic tile in all baths and laundry room, public sewer (no private septic), 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, and a spacious front porch. All of this in a convenient location in close proximity to both downtown Saint Michaels and Easton shops, restaurants and grocery. NO HOA or restrictive covenants. This property will not last long, schedule you private tour today!

26542 Royal Oak Rd, Easton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010
$865,000
5 Beds ⋅ 3 Baths
A distinctive Eastern Shore residence where historic character, generous living spaces and mature gardens come together in a setting that feels established and remarkably private. The home has evolved, creating a spacious interior with original architectural elements complemented by later additions designed to bring more light and garden views into the house, along with modern conveniences. Wood floors, substantial trim, original wood doors, exposed brick, built-in cabinetry, and bookcases preserve much of the home's character. The main level offers a series of interconnected gathering spaces rather than a conventional modern floor plan. A formal dining room provides a more traditional setting for entertaining, while the large kitchen offers a substantial center island, an informal dining area, and casual living space. The house opens dramatically toward the gardens. The family room is centered around a large brick fireplace and surrounded by built-in bookcases, while broad windows overlook the grounds. An adjoining garden room sits several steps below the principal living level and is wrapped in windows and glazed doors, creating an exceptional transition between indoors and out. Brick flooring reinforces the connection to the adjoining brick terraces and garden. Upstairs, the bedrooms are notably generous in scale, with abundant natural light and the irregularities and details that distinguish an older home from newer construction. Multiple baths serve the upper level, and wood flooring, traditional doors, and architectural details continue throughout. Outside, brick terraces extend the living areas into a mature landscape of lawn, established trees, perennial garden beds, and an ornamental pond. The grounds have the feeling of a garden developed over many years rather than newly installed landscaping. A detached two-car garage provides additional utility and storage with a conditioned second-floor fitness room or studio. Located minutes from downtown Easton and within the rural setting of Talbot County, this new offering is sure to please the discerning buyer.

30595 Kingston Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$1,150,000
3 Beds ⋅ 3 Baths
Beautifully positioned on a quiet cul-de-sac in the sought-after community of Cooke’s Hope, this distinguished brick residence offers timeless architecture, generously scaled interiors, a beautifully landscaped private garden with green house, and a detached two-car garage with a private studio above. Designed for both everyday comfort and elegant entertaining, the home is filled with natural light and features a thoughtfully planned floor plan. The welcoming living room is defined by high ceilings, a gas fireplace, and ample space for multiple seating areas, including room for a grand piano. At the heart of the home, the expansive kitchen combines exceptional storage with a large center island, Corian countertops, quality appliances, and a casual dining area. A spacious library/family room with custom built-in shelving provides an inviting retreat, while the adjoining enclosed sunroom overlooks the garden and creates a seamless connection to the outdoors. An elevator provides convenient access to the second level (new carpet throughout), where the spacious primary suite features a tray ceiling and a large well-appointed bath with two walk-in closets, separate vanities, a generous walk-in shower, and towel warmers. Two additional bedrooms offer abundant closet space and share a skylit hall bath. Easily accessible attic space provides excellent additional storage. The mudroom and laundry room is thoughtfully equipped with built-in cabinetry, a utility sink, and direct access to the garden. Outside, mature landscaping, brick hardscaping, and a fountain create a private and tranquil setting. Above the detached garage, the studio with half bath offers exceptional flexibility as a home office, guest suite, fitness room, or creative workspace. Residents of Cooke’s Hope enjoy an outstanding collection of amenities, including scenic walking trails, ponds, tennis and pickleball courts, a fitness room, community gathering spaces, and a waterfront dock with slips and kayak storage. A rare opportunity to own a beautifully maintained home that offers timeless design, exceptional versatility, and the distinctive lifestyle of one of Easton’s premier communities.

7040 Old School House Ln, Easton

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