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$559,990
2 Beds ⋅ 2 Baths
Welcome to the Kelly, a beautifully designed home that pairs an open-concept layout with timeless classic elements. Offering 2 bedrooms, 2 baths, and a 3-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. 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 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.

7582 Ward Brothers Cir, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$425,000
2 Beds ⋅ 1 Baths
Welcome to this charming Jack’s Point bungalow, where classic style, modern updates, and thoughtfully restored Craftsman details come together in a warm, bright, and inviting home. Tastefully refreshed throughout and fully furnished the residence features newer flooring, a newer roof, and updated appliances, offering modern comfort while maintaining its timeless appeal. The thoughtfully designed floor plan includes one bedroom, one bathroom, a versatile den, and an open concept living area that is ideal for both everyday living and effortless entertaining. A screened-in porch provides the perfect space to relax and enjoy the outdoors year-round. The open kitchen showcases beautifully restored original pine cabinetry, blending vintage charm with modern functionality. Outside, the yard features a lovely rose garden and plenty of room to garden, unwind, or entertain. Ideally located near Oxfords restaurants, marinas, parks, and scenic trails, this delightful home offers the perfect combination of character, comfort, and convenience.

104 Bonfield Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$989,000
3 Beds ⋅ 3 Baths
Beautifully renovated, this turn-of-the-century home is ideally situated on Brookletts Avenue in Easton's sought-after Historic District. Designed to maximize natural light and fresh air, the home features a welcoming wraparound porch, along with a beautifully landscaped, fully fenced backyard complete with perennial gardens, a patio, and access to a two-car carriage/garage house with a renovated space to use for home office, gym, children's playroom, plus additional alley parking. Inside, you'll find gracious living spaces that flow seamlessly while maintaining distinct, inviting rooms. Rich hardwood floors, soaring ceilings, classic architectural moldings, original hardware, custom built-ins, and a stunning staircase showcase the home's timeless character. The renovated kitchen perfectly blends style and functionality with custom-finished concrete countertops, premium appliances, a farmhouse sink, a spacious island, and thoughtfully designed storage. The charming powder room makes a statement with hand-painted Portuguese tile and a one-of-a-kind custom concrete sink. Upstairs, a unique staircase landing provides privacy by separating the primary suite from the front bedrooms. The primary bathroom has been freshly updated with stunning details to be admired by sophisticated buyers. The guest bathrooms are beautiful with carefully selected finishes that complement the home's historic charm. This home has been meticulously maintained, with new boiler, HVAC and hot water heater, and newer dishwasher these added updates should give a new buyer peace of mind. The low-maintenance exterior features durable vinyl and cement board siding. A rare opportunity to own a beautifully restored historic home with modern conveniences in one of Easton's most desirable neighborhoods. Schedule your private showing today!

204 Brookletts Ave, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$299,999
3 Beds ⋅ 1 Baths
Charming 3-bedroom, 1-bath home conveniently located in Easton with easy access to Route 50 and just minutes from historic downtown Easton, shopping, restaurants, parks, and all the town's amenities. Recent owner improvements include updated kitchen flooring and the addition of a rear patio. Other notable features include architectural shingle roofing, an updated heat pump, replacement vinyl windows, and 200-amp electrical service. Ready for immediate occupancy, this property presents an excellent opportunity for first-time homebuyers, downsizers, or investors alike.

122 Prospect Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$295,000
3 Beds ⋅ 2 Baths
Mc Daniel Rancher - This 3 Bedroom and 2 Bathroom rancher in the community of Mc Daniel, is conveniently located approximately 5 miles to St. Michaels. Close to half an acre of land, this property offers plenty of space for gardening and relaxing or grilling on the back deck. Just over 1400 square feet of living space, the dining room opens to the living room creating a generous space for gathering or entertaining. Newer vinyl plank flooring in bedrooms, living and dining rooms. Being sold "as is" condition.

9745 Tilghman Island Rd, Mcdaniel

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$394,793
4 Beds ⋅ 3 Baths
Welcome to this beautifully maintained end-unit townhome in the highly desirable Lakelands community of Easton. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed floor plan, this home provides the perfect blend of comfort, space, and convenience. The sun-filled main level features a spacious primary suite with a large en-suite bath and an oversized walk-in closet. The gourmet kitchen is appointed with granite countertops, stainless steel appliances, and a breakfast bar that flows seamlessly into the dining area and inviting living room, complete with a cozy gas fireplace. A private office or den offers an ideal space for working from home, reading, or pursuing hobbies. Upstairs, you'll find three generously sized bedrooms, a full bath, and an expansive bonus family room that can easily serve as a media room, playroom, home gym, or additional gathering space. Step outside to enjoy a fully fenced backyard backing to mature trees, creating a peaceful setting with added privacy. The front of the home overlooks the community pond, offering scenic views and a welcoming streetscape. Residents of Lakelands enjoy access to the community swimming pool and beautifully maintained common areas. Conveniently located just minutes from historic downtown Easton, shopping, dining, healthcare, and Route 50, this home also provides easy access to the waterfront charm of St. Michaels. Don't miss this opportunity to own one of Lakelands' desirable end-unit homes with exceptional space, privacy, and location!

29281 Superior Cir, Easton

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$990,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained 3-bedroom, 2-bath ranch home located on more than an acre in the peaceful waterfront community of Glebe Villa. With a view of the Tred Avon River this property offers the perfect blend of privacy, comfort, and Eastern Shore charm. With over 2,100 square feet of thoughtfully designed living space, you’ll immediately appreciate the inviting layout. A welcoming foyer opens to a bright and comfortable living room filled with natural light. The spacious country kitchen features stainless steel appliances, ceramic tile flooring, crown molding, a breakfast bar, and plenty of room for everyday living and entertaining. Enjoy casual meals in the breakfast area or host family gatherings in the separate formal dining room. One of the home’s standout features is the expansive four-season sunroom, highlighted by a beautiful exposed wood beam and walls of windows that bring the outdoors in. Whether you’re enjoying your morning coffee, reading a favorite book, or relaxing after a busy day, this space is sure to become a favorite. The private primary suite offers a spacious bedroom and its own en-suite bath, while two additional bedrooms and a second full bathroom provide comfortable accommodations for family and guests. Step outside to a large rear deck overlooking the peaceful backyard—an ideal setting for outdoor dining, entertaining, or simply enjoying the tranquil surroundings. The property offers access to the Tred Avon River, offering opportunities to kayak, canoe, fish, or simply take in the beauty. If you’ve been searching for a well-cared-for home in a quiet location with room to spread out and enjoy the outdoors, this Eastern Shore gem is ready to welcome you home. Schedule your private showing today!

8992 Glebe Creek Rd, Easton

Listing courtesy of Harlan C. Williams Co.. Contact:

$411,000
5 Beds ⋅ 3 Baths
This Richmond model features 5 bedrooms, including a convenient 1st floor bedroom, making it a great option for guests, multi generational living or a home office. This particular home includes Washer and dryer, 16x10 Paver Patio, quartz Countertops and white cabinetry. Features and amenities of the community include: outdoor community pool, bathhouse and fitness studio, multi-racquet sports courts (including tennis and pickleball), play ground, Bark Park/dog park, walking and biking trails, central community lake and gathering ares and open green spaces. Lakeside at Trappe is conveniently located just off Route 50, about 8 miles south of Easton, providing easy access to shopping, dining and the Eastern Shore beaches. The Builder is offering closing costs with the use of Lennar Mortgage and Title.

1471 Lake George Ln, Trappe

Listing courtesy of EXP Realty, LLC. Contact: 8333357433
$350,000
4 Beds ⋅ 2 Baths
Coming Soon!!! Beautifully updated, stylish split-level residence blends thoughtful design with everyday comfort. A 3 or 4 bedroom, 2 full bath home that feels both welcoming and well cared for. Numerous upgrades can be found throughout. The main-level features an open floor plan with the kitchen flowing into the living room, and updated flooring extends throughout. The lower level expands the living space with a comfortable 4th bedroom or family room or bonus room ideal for a home office, and a large utility room with laundry and abundant storage. large and private fenced rear yard with storage shed. Ideally located on Petunia Drive, this home enjoys easy access to historic downtown, local parks, shopping, dining, and major routes - offering a perfect balance of small-town charm and everyday convenience. Don't miss this one!

29397 Petunia Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,500,000
4 Beds ⋅ 3 Baths
Open Sunday, August 2nd from 1:00 to 3:00pm. A stunning Farmhouse completely restored/rebuilt by reknown Architect Greg Wiedemann on two glorious acres meticulously maintained on a serene Choptank River Setting. it is the Quintessential "Getaway" from the hustle/bustle of life. The focus of each room is the River. There are patios, balconies and porches galore for your leisure enjoyment and viewing pleasure. The center of the home is the Dining and Kitchen area. You enter from the side porch and exit through either twin glass doors which border large windows which overlook the River onto a flagstone patio where you can enjoy outdoor dining or just relaxing by the River. Off of the Kitchen you will find the "Mud Room" and/or Laundry Room. You will find a stackable Washer Dryer and Utility Sink in this area. Also next to the Laundry room you will find a large full bath with shower. The actual Front Door to the home is on the side of the house off of the welcoming porch with a swing. The Main entrance opens to the Living Room with Large windows which front to the Choptank. One of the four bedrooms in the home is on the first floor with a large ensuite bath, There are actually two large primary bedrooms. One can use the primary bedroom on the first floor for a large family room as the upstairs bedrooms are very spacious. The second floor primary enjoys both a balcony and a screened porch. The home is in excellent condition. The two zone air conditioning systems have just been replaced. On the grounds you will find two sheds, one for utilities and the other serves as a Workshop and storage, Enjoy a 1000 foot private beach front with a dock. Within the photos, please take the time to gaze upon the variety of seasonal trees and flowering plants that adorn this two acre paradise.

31720 Ayres Dr, Trappe

Listing courtesy of Weichert, REALTORS. Contact: afitzgerald@weichertrealtors.net
$484,900
4 Beds ⋅ 3 Baths
Beautifully maintained two-story Colonial in Matthewstown Run.  Situated on a large lot that backs to a farm with a peaceful spring fed pond, offering privacy and picturesque views, offering endless possibilities for a pool and outdoor living, from entertaining and gardening to play areas and recreation. There are 4 bedrooms, 2½ updated bathrooms, and a beautifully renovated kitchen This is the model with the laundry room addition between kitchen and garage. with attached two-car garage. BONUS this home has a basement - 1/2 finished and 1/2 awesome storage. Plus all of the mechanicals, including tankless hotwater heater..  Roof, HVAC, appliances, all updated. Even the siding was replaced in 2011. There is not a lot original in this home. Seller would like October settlement, but will consider earlier for the right situation. These were the premium lots when the community was developed and the owners along that strip have made the layout very nice.

29803 Standish St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$349,900
3 Beds ⋅ 3 Baths
Bright and inviting, this Easton Club townhome offers a comfortable two-level floor plan designed for everyday living. The main level features a bright living room, an eat-in kitchen with a pantry, a convenient powder room, & sliding glass doors leading to a rear deck. Upstairs, the primary suite includes a walk-in closet and en-suite bath, accompanied by 2 additional bedrooms & a full hall bath. Residents of Easton Club enjoy community amenities including a swimming pool, tennis court, and beautifully maintained common grounds, all just minutes from downtown Easton, shopping, dining, & Route 50.

7412 Tour Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,625,000
3 Beds ⋅ 3 Baths
Welcome to White Barn at Middlespring, a remarkable 8-acre Eastern Shore estate offering the perfect blend of historic charm, modern updates, privacy, and country living. Set at the end of a quarter-mile private drive surrounded by picturesque farmland, this exceptional property features three distinctive structures: a beautifully restored 1824 manor home, a 3-car detached garage with finished bonus space above, and a historic 40' x 63' barn. Additional highlights include a new metal roof, new windows, composite decking, updated kitchens and bathrooms, irrigation for the rear lawn and landscape beds, landscape lighting, and thoughtfully renovated living spaces, creating a truly move-in-ready retreat just minutes from downtown Easton. Built in 1824 on land first patented in 1663, the manor home has been thoughtfully renovated to preserve its historic character while embracing modern comfort. Wide-plank pine floors, original architectural details, and three wood-burning fireplaces create warmth and timeless elegance throughout. At the heart of the home, the beautifully renovated farmhouse kitchen is designed for gathering, featuring a large center island, professional 8-burner range, farmhouse sink, and recently updated fixtures that blend seamlessly with the home's period character. All kitchen and bathroom fixtures throughout the home have been thoughtfully updated within the past three years, offering today's conveniences while preserving the home's historic integrity. A spacious mudroom with utility sink adds everyday functionality, while the newly constructed sunroom addition showcases exposed wood beams and a cozy propane stove, creating the perfect space to relax and enjoy the surrounding landscape in every season. Outside, enjoy peaceful mornings from the composite deck overlooking eight scenic acres. The beautifully maintained rear lawn and landscape beds are serviced by an irrigation system, while landscape lighting highlights the mature trees, historic outbuilding, and walkways, creating an inviting setting well into the evening. Offered fully furnished, the home includes a beautifully curated collection of furnishings and lighting from Restoration Hardware, Arhaus, and Pottery Barn, allowing the next owner to enjoy a seamless transition into the Eastern Shore lifestyle.

32137 Discovery Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$569,990
4 Beds ⋅ 4 Baths
Under Construction | Late Summer Move-In! Backing to a serene tree line, this beautifully designed home offers privacy, style, and exceptional living. A private office, designer powder room, and sun-filled open layout are complemented by upgraded oak stairs and artisan railing. The chef’s kitchen shines with premium KitchenAid appliances, a stainless hood, oversized quartz island, and elegant designer finishes. Upstairs, a spacious loft provides flexible living space, while the luxurious primary suite features dual walk-in closets and a spa-inspired bath with a soaking tub and frameless shower. A private guest suite with its own bath creates the perfect retreat for visitors. Located in the resort-style Lakeside at Trappe community, enjoy easy access to a pool, fitness center, sports courts, playground, dog park, and the natural beauty of Maryland’s Eastern Shore—all just minutes from Easton. Ask about builder incentives! Please note interior photos are similar while under construction

1951 Silver Lake Ln, Trappe

Listing courtesy of Brookfield Mid-Atlantic Brokerage, LLC. Contact: (703) 420-3322
$995,000
3 Beds ⋅ 3 Baths
Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive landscaping with full irrigation and so much more!

101 Seymour, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$2,850,000
6 Beds ⋅ 6 Baths
This exceptional waterfront estate was thoughtfully designed and custom built by its current owner after years of meticulous research and planning, drawing architectural inspiration from the timeless elegance of Colonial Williamsburg. Constructed with an uncompromising commitment to quality and authenticity, this remarkable residence is a true showcase of enduring craftsmanship. Offering 6 bedrooms, 5 full baths, 1 half bath, and an impressive 7 fireplaces, the home is rich with period-inspired architectural details. From the Flemish Bond brickwork and cypress plank siding to the one-of-a-kind, 2.5-inch-thick solid cherry and mahogany entry door, every element was carefully selected to reflect both beauty and longevity. Exceptional custom woodwork is found throughout the home, complemented by stunning Brazilian Teak, Brazilian Cherry, and White Oak hardwood flooring. Adding to the home’s distinction are custom light fixtures crafted by Virginia MetalCrafters, among the final pieces ever produced by the renowned Virginia manufacturer. The chef’s kitchen was designed with both elegance and functionality in mind, featuring custom cherry cabinetry, dual sinks, dual dishwashers, dual Sub-Zero refrigerator and freezer units, and abundant workspace for entertaining or everyday living. The inviting living room showcases custom built-in cabinetry and a magnificent fireplace designed to accommodate both a traditional open hearth and a wood-burning stove. The spacious first-floor primary suite offers a private retreat complete with a luxurious en-suite bath featuring a jetted soaking tub, walk-in shower, and generous walk-in closet. Upstairs, five additional bedrooms enjoy abundant natural light, southern exposure, and beautiful water views. Nearly every principal living space throughout the home captures breathtaking southern-facing waterfront vistas, creating a seamless connection between the interior and its spectacular setting. Outdoor living is equally impressive. A gracious waterside patio with elegant bifurcated brick steps leads to the expansive 720-square-foot swimming pool, creating an ideal space for relaxing or entertaining. Beyond, the riprap-protected shoreline leads to a custom private dock with approximately 3 feet of water depth at mean low water (MLW), providing convenient access to the water. A rare offering on Maryland’s Eastern Shore, this extraordinary waterfront home blends historic architectural inspiration with modern comfort and exceptional craftsmanship. Designed and built to stand the test of time, it is a legacy property meant to be enjoyed for generations.

7250 Maxmore Creek Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$344,000
2 Beds ⋅ 3 Baths
This attractive end-unit townhouse is located in the desirable Easton Club community offering well-maintained, move-in ready living just minutes from historic downtown Easton. The home features a welcoming front porch that leads to the foyer and spacious kitchen, complete with granite counters, a pantry, breakfast bar, ample cabinet and counter space and appliances that are all less than two years old. The spacious living room offers flexible space for both living and dining and features two sliding glass doors leading to the rear deck overlooking ponds and a wooded setting. Upstairs, the primary suite features a large walk-in closet and spacious private bath, while the second bedroom also includes its own full bath and walk-in closet. Bedroom-level laundry adds everyday convenience. An attached outdoor storage shed provides ample space for tools, bikes, seasonal decor or any of your storage needs. A new roof was installed in June 2026 giving a buyer peace of mind for years to come. Residents of Easton Club enjoy a newly refinished in-ground pool, newly refinished tennis and pickleball courts and multiple ponds throughout the community, all just minutes from downtown Easton's charming boutiques, restaurants and local attractions. Downtown Oxford is approximately 10 minutes away where you can enjoy local waterfront dining, the beach at “The Strand” and so much more.

28491 Pinehurst Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$465,000
2 Beds ⋅ 2 Baths
Chesapeake by Del Webb. Thurston model single-story in the Easton Club East, 55+ active adult community. This rarely available, single-owner home is move-in ready and boasts the comfort of a recently upgraded kitchen and HVAC system with exceptional views of the Lyons family farm. This desirable model features a spacious layout with Southern exposure and plenty of large windows. The spacious Florida room overlooks the backyard and pastural views. Enjoy every sunset from the comfort of the brick patio surrounded by luscious, mature vegetation. This house features a chef-inspired, open kitchen, plenty of cabinetry and a pantry for storage. Recently upgraded appliances and a gas stove will make meal-prep a cinch. The family room features a gas fireplace, making the room warm and cozy in the wintertime. Entertaining is fun and easy with a pony-wall surrounding the kitchen. On the other side of the kitchen is the formal dining room. The sleeping quarters are separated by the common areas, providing excellent privacy for guests. The main bedroom is in the back of the house with large windows allowing afternoon light into the spacious bedroom and plenty of room for your biggest bed. Unwind in the jetted tub while watching the sunset. Two sinks, lots of bathroom storage and an additional shower make getting ready easy. The suite is made complete with a spacious walk-in closet. The second bedroom is perfect for guests or as an office or craft room. And the second bathroom features a tub and shower combo. Roof (2021) and HVAC (2024). Landscaping is made easy with irrigation. The 2-car garage off of the main street makes running errands quick. The community amenities include Clubhouse, pool and tennis/pickleball courts. Care-free maintenance means the HOA fees take care of yard work and snow removal, so the only thing you’ll have to worry about is living.

29720 Lyons Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$295,000
3 Beds ⋅ 1 Baths
Welcome to 21647 Camper Circle in the charming waterfront community of Tilghman Island. This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle.

21647 Camper Cir, Tilghman

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$6,375,000
2 Beds ⋅ 3 Baths
Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land itself is remarkable. With significant acreage enrolled in the Conservation Reserve Program, over 185± acres provide restored habitat for wildlife and waterfowl. Another 50± acres remain under active cultivation, sustaining the farm’s agricultural heritage. The balance of the property presents a diverse mix of wetlands, mature woodland, wooded buffers, upland habitat, and scenic fields. These varied landscapes support habitat restoration and sporting use, while offering beautiful vistas in every season. A carefully maintained network of trails, and farm lanes provide access throughout the property, making it well-suited for recreation, hunting, and conservation management. At the heart of Duvall Farm is Duvall Lodge, constructed in 2006 by Ilex Construction. Drawing inspiration from Tennessee Pioneer architecture, the lodge is both timeless and inviting. The design embraces rustic authenticity while incorporating every modern comfort. Inside, the great room makes a dramatic impression with soaring ceilings, reclaimed timbers, wide-plank wood floors, and a massive stone fireplace that anchors the space. Exposed beams and natural materials create a warm ambiance, while broad windows and doors seamlessly connect the interior to the surrounding landscape. One of the lodge’s defining features is its full wraparound screened porch, offering sweeping views over a tranquil pond, stocked with bass and with a small pier. Whether for quiet mornings or gatherings with friends, the porch underscores the property’s seamless blend of indoor and outdoor living. Nearby, a hand-hewn log guest cabin extends the accommodations, creating a setting well suited to hosting family and friends. The improvements are understated yet thoughtful, designed to complement rather than dominate the landscape. They reflect the same stewardship evident across the farm itself — an approach that values authenticity, conservation, and the enduring character of the land. Duvall Farm is more than acreage; it is a complete environment, where agricultural productivity, habitat diversity, and architectural charm intersect. Few properties on Maryland’s Eastern Shore offer this combination of size, recorded parcels, conservation value, and a central lodge that feels historic with modern amenities. The location, just minutes from Easton and Oxford, places Duvall Farm within easy reach of the region’s cultural and culinary attractions, while the sheer scale of the farm ensures privacy and a retreat-like atmosphere. For those seeking a legacy property, conservation showcase, sporting retreat, or family compound, Duvall Farm represents an unparalleled opportunity. With its rich mix of land, water, and architecture, it is a property of enduring importance — one that honors the past while offering a wide horizon for the future. Please Note, tax ID and Property Taxes are showing the information on record for the improved parcel. Please contact agent for additional parcel information.

Oxford Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$437,000
3 Beds ⋅ 4 Baths
Enjoy the combination of privacy, convenience, and low-maintenance living in this beautifully updated townhome just minutes from downtown. Nestled against a peaceful wooded backdrop, this home offers a rare sense of seclusion with an exceptionally private balcony-style deck overlooking the trees. Inside, hardwood floors enhance the main level’s open-concept design, featuring a bright kitchen with stainless steel appliances, a dining area, and spacious living room. The upper level offers a private primary suite with a full bath, walk-in closet, and versatile loft space, along with two additional bedrooms and a full bath. The lower level provides even more space with a cozy family room, half bath, laundry area, and convenient garage access.

300 Dixon St Unit #505, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,095,000
3 Beds ⋅ 3 Baths
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.

100 Pier St W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,849,000
4 Beds ⋅ 4 Baths
Simply Sensational! Sunrise views over Town Creek set the tone for this beautifully designed four-bedroom waterfront home, where contemporary architecture meets the warmth of a waterfront cottage. The main living areas include a formal living room and dining room, each with a fireplace, a bright eat-in kitchen and an inviting family room, where walls of windows frame the water views and fill the home with natural light. Two first-floor bedrooms offer the convenience of main-level living. Upstairs, two ensuite bedrooms open to the second-floor sun deck, including a spacious primary suite with floor-to-ceiling windows overlooking Town Creek.An expansive waterside patio and pool create the perfect setting for relaxing and entertaining. The separate one-bedroom guest house/pool house and detached workshop provide additional space for family, guests, hobbies or a home office. The private pier, complete with a boat lift and floating dock for kayaks and paddleboards, provides easy access to the Tred Avon River and the Chesapeake Bay. Located in the historic waterfront village of Oxford, this exceptional home captures the beauty, charm and relaxed waterfront lifestyle that define Maryland's Eastern Shore. The property is offered with its furniture allowing for an effortless transition.

106 E Division St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$750,000
3 Beds ⋅ 4 Baths
Extremely private 3 BR 3 1/2 BA house on 4 acres with a pool! This property features a huge, finished bonus/game room over the garage with separate hvac zone, large family room with vaulted ceiling, first floor mater suite with an extremely well-done tile bathroom and absolutely complete privacy!

30420 Deep Branch Rd, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$250,000
4 Beds ⋅ 3 Baths
Welcome to 3759 Rumsey Drive, Trappe, MD, located in the “La Trappe Heights” community; within the town limits of Trappe and connected to public water and sewer. This spacious home offers 4 bedrooms and 2.5 bathrooms, making it an excellent opportunity for buyers looking to add their personal touches. Being sold strictly sold AS-IS! This property is being sold strictly AS IS. The seller will make no repairs or improvements. Buyers are encouraged to conduct any inspections they deem necessary for informational purposes. This is a great opportunity for investors, renovators, or buyers looking to build equity while enjoying the convenience of an in-town location. The main level features a comfortable spacious living area with a wood-burning fireplace, a formal dining area, along with a kitchen/dining combo area as well. A convenient half bath, and access to the rear deck, perfect for relaxing or entertaining. The home also includes an attached one-car garage for parking and additional storage. Upstairs, you'll find all four bedrooms. The primary suite includes a private bathroom with a walk-in shower, while the second full bathroom, located off the hallway, features a tub/shower combination to accommodate family and guests. Outside, enjoy a spacious rear yard complete with a storage shed for lawn equipment, tools, or seasonal items. Please note that the HVAC system provides heating and cooling to the first floor only that was installed six years ago. The hot water tank is two years old. With some TLC this home is truly a gem in the lovely town of Trappe, Maryland.

3759 Rumsey Dr, Trappe

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$510,000
3 Beds ⋅ 3 Baths
Welcome to easy living in one of Easton's most sought-after 55+ communities. Situated on a desirable corner lot with mature landscaping, this well-maintained Thurston model offers a thoughtfully designed floor plan with a first-floor primary suite, an additional main-level bedroom and full bath, a spacious family room open to the kitchen, and a bright sunroom. Upstairs offers a private guest suite and versatile loft, perfect for visitors or a home office. Recent updates include fresh paint in select rooms. Additional highlights include hardwood flooring throughout the main living areas, a two-car garage, irrigation system, and private patio. Community amenities include a clubhouse with a fitness center and game rooms, an outdoor pool, tennis courts, and walking trails. Conveniently located just minutes from downtown Easton, shopping, restaurants, and medical facilities.

29833 Hillary Ave, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$459,900
4 Beds ⋅ 4 Baths
This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.

104 Madison Ave, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$5,295,000
4 Beds ⋅ 7 Baths
First time offering in Morgans Point. Custom built estate designed by architect Lauren Dianich of Atelier 11, this elegant Georgian-style brick and shingle residence offers over 5,200± square feet of thoughtfully designed living space filled with natural light and panoramic water views of the Tred Avon River. Set on 5± acres, the home is crafted for both refined entertaining and private, relaxed waterfront living. The heart of the home is the River Room, surrounded by windows that frame sweeping views of the Tred Avon River. Hardwood floors by Universal Floors in D.C. feature an inlaid compass medallion that points to magnetic north, creating a distinctive focal point. A fireplace anchors the space, with a screened-in porch with its own fireplace just beyond, perfect for enjoying chilly evenings. The chef’s kitchen is equipped with professional-grade appliances including a Wolf range and double wall ovens, Sub-Zero refrigerator, Asko full-size dishwasher, and Fisher & Paykel dishwasher drawers. A large island offers a wine fridge and illuminated display cabinetry, while the butler’s pantry—complete with an additional refrigerator and charming porthole windows framing water views—enhances the home’s functionality. Additionally, a custom-built oval wet bar with a two-drawer Sub-Zero refrigerator offers substantial cabinetry. This space provides a natural gathering point for entertaining. A large mudroom with powder room provides convenience for busy households. Also on the main level are a library with floor-to-ceiling shelving and a wood-burning fireplace, a fitness room with water vistas, a formal half-bath, and a first-floor en-suite bedroom ideal for guests. A dedicated utility entrance allows for discreet service and maintenance without entering the main living spaces. A 25kW standby generator provides reliable backup power for the main residence, offering peace of mind during outages. Upstairs, the primary suite with a gas fireplace serves as a retreat, with its spacious bathroom offering a shower, jetted soaking tub, and two walk-in closets—one with its own half-bath. Additional bedrooms include an upper-level en-suite and family-friendly accommodations, all supported by a conveniently located laundry room. Completing this floor is a private office with a gas fireplace and panoramic river views, offering an inspiring space for work or study. A generously sized, detached three-car garage includes a second-floor guest quarters with a kitchenette, washer and dryer, and en-suite bedroom, where windows capture tranquil water views. Outdoors, enjoy resort-like amenities including a heated pool with a fully retractable cover and a pool pavilion with its own bathroom and outdoor shower. The grounds are beautifully landscaped and designed for relaxation, with serene river views visible from nearly every room of the property. This rare offering seamlessly blends architectural pedigree, modern luxury, and a spectacular setting on the Tred Avon River—an exceptional opportunity to experience Eastern Shore living at its finest.

5381 Morgans Point Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,299,000
This commercial property in St Michaels presents a unique investment opportunity. Situated on a 2.24-acre lot, the property benefits from a prime highway location, ensuring high visibility and accessibility for future tenants or customers. This property lends itself to a variety of business ventures. the flexibility of parking options enhance its attractiveness for commercial use. Investors can capitalize on the growing demand for commercial spaces in this area, leveraging the strategic location while the focus remains on land utilization and development potential. This property is ideal for those looking to invest in a versatile space with the opportunity for appreciation and income generation.

941 S Talbot St, St Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$249,500
2 Beds ⋅ 3 Baths
BUYER MUST FILL OUT APPLICATION AT HYDE PARK OFFICE AND BE APPROVED. NEW ROOF JUST INSTALLED MAY 2026! This charming and well maintained 2-bedroom, 3-bath rancher is located in the desirable Hyde Park 55+ community. Offering one-level living on one of the largest lot in the entire community. this home features a welcoming front porch that leads into a spacious living room. The open kitchen includes ample cabinet and counter space, a pantry, and a breakfast bar that overlooks the family room, perfect for everyday living and entertaining. The primary suite boasts a walk-in closet with separate full baths with a shower/tub combo and linen closet. The second suite features a large closet. A large sunroom overlooks the backyard has a separate HVAC system. Additional highlights include a huge 1-car garage with room for a workshop, additional storage room off the primary with access to the back yard and a shed with electric. The vibrant Hyde Park community offers fantastic amenities included with the ground rent, such as an outdoor pool, a clubhouse for social gatherings, fitness center, dog park, 9-hole disc golf course and shuffleboard courts. Property taxes, water, sewer, and trash services are all included, along with snow removal on paved streets and maintenance of common areas. Onsite office management provides added peace of mind. Don’t miss this opportunity to enjoy low-maintenance living in a welcoming, active adult community! Conveniently located just minutes from Easton’s shopping, dining, and entertainment options!

1 Victoria Ct, Easton

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