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$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
$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
$479,000
4 Beds ⋅ 2 Baths
Nestled in the serene Chapel Woods subdivision, this charming traditional home offers a perfect blend of comfort and functionality. With four spacious bedrooms and two full bathrooms, this residence is designed to meet your needs for both relaxation and entertaining. Step inside to discover a warm and cozy ambiance throughout. Enjoy the tranquility of your surroundings with picturesque views of trees and lush greenery right from your windows. Outside, the expansive 2.13-acre lot provides ample space for outdoor activities or simply enjoying nature. The detached garage offers plenty of room for your vehicles, toys, and tools, as well as additional storage on the second level of the garage. This home is not just a place to live; it's a sanctuary where you can create lasting memories. Experience the perfect blend of comfort, style, and nature in this delightful property.

11598 Malvern Ln, Cordova

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

$849,000
3 Beds ⋅ 4 Baths
An Exceptional Opportunity! Unexpectedly available once again due solely to a change in the buyers' personal circumstances, this exceptional property is available through no fault of the home. If you missed it the first time, here's your opportunity to own one of the area's most distinctive and beautifully maintained residences. Ideally situated just four miles from the heart of charming St. Michaels, this timeless home offers peaceful country living with easy access to boutique shopping, exceptional dining, marinas, and the Chesapeake Bay lifestyle. Just moments from Claiborne Landing, you'll enjoy convenient public boat access for effortless days on the water, whether your passion is cruising, fishing, crabbing, or simply exploring the beauty of the Chesapeake Bay. Built in the early 1900s and thoughtfully renovated over the past two decades, this remarkable residence seamlessly blends historic character with today's modern conveniences. Situated on a picturesque half-acre lot, the home offers three spacious bedrooms, each with its own private bath, plus the flexibility for a fourth bedroom, home office, or guest suite. Several bedrooms also enjoy access to private balconies, adding to the home's unique charm and appeal. The beautifully updated kitchen features granite countertops, stainless steel appliances, tile flooring, and generous workspace, making it ideal for both everyday living and entertaining. Gleaming hardwood floors flow throughout the home, showcasing its warmth, craftsmanship, and attention to detail. Step outside to enjoy the beautifully landscaped grounds, complete with a charming potting shed and an additional storage building. The true showpiece, however, is the extraordinary 1,500-square-foot attached garage. This impressive two-story space features three oversized garage bays, a dedicated office, and abundant room for multiple vehicles, boats, workshop space, hobbies, collections, and projects of every kind. Whether you're a car enthusiast, woodworker, craftsman, artist, entrepreneur, or someone who simply enjoys tinkering and creating, this exceptional space offers endless possibilities rarely found in a property of this caliber. Rich in history, impeccably maintained, and completely move-in ready, this one-of-a-kind property offers the perfect blend of timeless elegance, modern comfort, and exceptional versatility. Whether you're searching for a full-time residence, a weekend retreat, or a home with unmatched garage and workspace, this remarkable property delivers. Don't miss this exceptional opportunity to make it yours.

10494 Rich Neck Rd, Claiborne

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

$595,000
3 Beds ⋅ 3 Baths
Nestled in the charming THREAD HAVEN community, close to the YMCA, Idlewild Park with easy access to Easton Bypass for commuters. This delightful traditional home offers a perfect blend of comfort and functionality. With 1,970 sq. ft. of thoughtfully designed living space, this residence features three 2nd floor spacious bedrooms and two and a half bathrooms, ideal for both relaxation and entertaining. Step inside to discover an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm atmosphere for gatherings. Upgraded kitchen countertops, an island for additional prep space, and a cozy breakfast area, making it a culinary haven. Enjoy the elegance of wood floors throughout, enhancing the home's inviting ambiance. The primary suite offers a private retreat with an en-suite bathroom, while the additional bedrooms provide ample space for guests or a home office. A charming fireplace in the living area adds a touch of warmth on cooler evenings. Outside, the expansive 0.57-acre lot backs to serene trees, providing a peaceful backdrop for outdoor activities. The wrap-around porch and deck invite you to savor morning coffee or evening sunsets in your own private oasis. A convenient shed offers extra storage for gardening tools or outdoor equipment. With an attached two-car garage and a concrete driveway, parking is a breeze. This home is not just a place to live; it’s a sanctuary where memories are made. Experience the perfect blend of comfort, style, and nature in this lovely property.

11 Londonderry Dr, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$359,900
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: 4108226665
$1,495,000
5 Beds ⋅ 5 Baths
Some homes check the boxes. Others create a lifetime of memories......Welcome Home to 28091 Oaklands Circle Perfectly situated on over 2.5 beautifully landscaped acres in the highly desirable Oaklands community, this exceptional five-bedroom, four-and-a-half-bath custom home offers the rare combination of luxury, comfort, privacy, and a truly move-in-ready lifestyle. From the moment you arrive, you’ll appreciate the mature trees, manicured landscaping, fresh mulch, and natural privacy that surround this beautifully maintained property. Every detail reflects years of thoughtful care and pride of ownership. Inside, timeless craftsmanship meets thoughtful updates. Rich hardwood flooring flows throughout the home, complemented by replacement windows, recessed LED lighting, custom built-in shelving, window seats with hidden storage, and pocket doors that add both character and functionality. At the heart of the home is the beautifully updated kitchen featuring granite countertops, generous island workspace, coffee bar, breakfast area with lots of natural light and an inviting layout designed for everything from family dinners to holiday gatherings. With five spacious bedrooms, 4 1/2 bathrooms, great room, formal areas, and a fully finished bonus room above the attached three-car garage, the flexible floor plan easily accommodates growing, blended, or multi generational families, overnight guests, a home office, fitness room, or recreation space. Comfort can be found in every season. Enjoy the warmth of both a gas fireplace and a traditional wood-burning fireplace, or gather around the fire pit on cool evenings during cooler months. Just outside you will discover your own private retreat. Relax on the screened-in covered porch, multiple decks, spend afternoons and weekends lounging by the sparkling swimming pool with diving board, featuring a new pool cover and new pool pumps. Explore the custom tree fort and zip line, or simply enjoy the open green space that makes this property so special. Relax on any one of the multiple deck spaces overlooking the peaceful backyard or just simply soak up the AC in the summertime. A large storage shed provides plenty of room for lawn equipment, tools, and outdoor gear. Significant improvements—including replacement windows, approximately three-quarters of the roof replaced, and a whole-house backup generator—offer lasting value and peace of mind. A state-of-the-art security, alarm, and surveillance system adds another level of comfort for today’s homeowners. Located just minutes from historic downtown Easton or the waterfront town of Oxford, both with outstanding restaurants, boutique shopping, access to local healthcare, schools, and the waterfront lifestyle of Maryland’s Eastern Shore, this home offers the perfect balance of convenience and tranquility. Beautifully updated, meticulously maintained, and designed for everyday living as well as unforgettable entertaining, 28091 Oaklands Circle is more than a home—it’s where birthdays are celebrated, holidays are shared, and lifelong memories are made. Come experience the warmth, quality, and lifestyle that make this remarkable property truly one of Easton’s finest.

28091 Oaklands Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$395,000
2 Beds ⋅ 2 Baths
Comfortable living spaces can be found in this well-maintained 2BR/2BA townhome located just minutes from downtown Easton. Features include hardwood floors, wood-burning fireplace, newer kitchen appliances, washer and dryer. Carpeting was replaced a couple years ago. Convenient location with quick access to the Easton bypass and Rt 50, hospital and downtown.

1175 S Washington St Unit #18, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$324,990
3 Beds ⋅ 3 Baths
August Delivery! Discover the Elmwood, a luxury three-story townhome offering 2,254 square feet of thoughtfully designed living space in Lakeside at Trappe. This move-in ready home features 3 bedrooms, 2.5 baths, and a 2-car garage with a private driveway. The entry level includes a spacious recreation room with direct access to the outdoor patio, providing the perfect space for entertaining or relaxing. The main level showcases an open-concept design where the kitchen, dining area, and Great Room flow seamlessly together. The designer kitchen is appointed with quartz countertops and stainless steel appliances, creating both style and functionality. Upstairs you'll find two secondary bedrooms, a full bath, and a luxurious owner's suite complete with a walk-in closet and private en-suite bathroom. Backing to open green space, this home offers a peaceful setting while providing modern comfort and convenience. Don't miss this opportunity for luxury townhome living at Lakeside at Trappe.

1410 Lake Geneva Dr, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$3,100,000
4 Beds ⋅ 4 Baths
Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and direct access to some of the Eastern Shore’s finest boating and sporting waters. A scenic, tree-lined drive leads to the residence, where the water immediately takes center stage. Thoughtfully renovated in 2019, with numerous additional upgrades completed in subsequent years, the home is designed for both relaxed everyday living and effortless entertaining. The main level features a waterside primary suite with an exquisite ensuite bath, along with an additional guest bedroom and adjacent full bath(with sauna). The spacious living room is anchored by a brick fireplace with pellet stove insert, custom built-ins, and sliding doors opening to the waterside patio, creating a seamless connection to the remarkable setting. A well-appointed kitchen with stainless steel appliances and granite countertops adjoins the separate dining room, where spectacular water views provide a memorable backdrop for gatherings. Two other main-level rooms offer flexibility for an office, family room, exercise room, or other living needs, while a generous laundry room with built-ins and a secondary staircase adds everyday convenience. Upstairs are two additional guest bedrooms and two en-suite baths along with an adjoining bonus room ideal for guests or hobbies, and a second staircase. A true sportsman’s paradise, the property offers deep water, excellent fishing, private hunting, and endless opportunities for boating and recreation. The private pier, completed in 2023, features three slips, a boat lift, and a jet ski lift. With approximately 7' MLW, a newly riprapped shoreline, sandy beach, new BAT septic system installed in 2019, and a new roof completed in 2026, this exceptional waterfront retreat is perfectly suited for those seeking the very best of Eastern Shore living. *Approximately 24 acres are enrolled in a Forest Stewardship Plan. * Please do not drive in without an appointment-security monitoring.

26279 Deep Water Harbor Rd, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$272,500
3 Beds ⋅ 3 Baths
Tired of paying rent? This move-in-ready 3-bedroom Easton home lets you start building equity immediately—with exterior maintenance handled for you. The main level features an eat-in kitchen, spacious living room, and convenient half bath. Upstairs you'll find a primary suite with built-ins, two additional bedrooms, and two full baths. Outside, enjoy the private patio overlooking a peaceful backyard.

29595 Dutchmans Ln Unit #58, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$410,000
4 Beds ⋅ 3 Baths
Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air conditioning system, offering peace of mind and modern comfort. Combining historic waterfront charm with thoughtful updates, this property presents a rare opportunity to enjoy the best of Chesapeake Bay living, whether as a full-time residence, weekend getaway, or investment property. The owner is a licensed Maryland Real Estate agent.

21406 Dogwood Cove Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166
$814,990
4 Beds ⋅ 5 Baths
The Brentwood: True Executive-Style Luxury on the Eastern Shore ​Experience unparalleled scale and sophisticated design in the Brentwood, a magnificent 3,736-square-foot executive residence designed for modern luxury living. Set within a premier community featuring expansive, large home sites, this estate offers a rare and highly coveted feature for the Eastern Shore: a massive, full unfinished basement providing endless potential for future customization, a home gym, or unparalleled storage. ​The architectural design prioritizes ultimate privacy and comfort, boasting spacious bedrooms, each complete with its own private, dedicated en-suite bath. The crowning jewel of the home is the sprawling Owner’s Suite—a private sanctuary featuring an exclusive owner's sitting room, a massive walk-in closet, and a specialized wardrobe storage area designed for the ultimate organizer.Designed to blend grand indoor living with the coastal lifestyle, the Brentwood offers flexible structural options, including a sun-drenched morning room or a spacious three-car garage. Step outside to create your own private outdoor oasis on a generous home site, all while being just minutes from the scenic river for premier boating, kayaking, and outdoor water activities. The Brentwood isn’t just a home; it’s an elevated lifestyle. ​Feature & Highlight Lists ​🌟 Executive Structural Highlights ​Massive Footprint: 3,736 sq. ft. of expertly designed, wide-open living space. ​The Eastern Shore Unicorn: Rare, full unfinished basement offering incredible structural storage or future finished square footage. ​Ultimate Family/Guest Privacy: Every single bedroom features its own private, dedicated en-suite bathroom. ​Flexible Footprint: Customization options to add a bright, open morning room or expand to a 3-car garage. The Owner’s Retreat ​Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. ​Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. ​🌊 Community & Lifestyle ​Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). ​Scenic River Access: Located just minutes from the river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. The Owner’s Retreat ​Private Sitting Room: A dedicated relaxation space tucked inside the primary suite. ​Expansive Walk-In Closet: A massive, boutique-style layout with a dedicated wardrobe storage area. ​🌊 Community & Lifestyle ​Large Home Sites: Generous lot sizes with ample room to engineer a custom outdoor oasis (pool, outdoor kitchen, or extensive hardscaping). ​Scenic River Access: Located just minutes from the scenic Wye river, offering instant access to boating, paddleboarding, and coastal outdoor recreation. "Limited time" Up to $20,000 closing cost assistance if buyer uses a Koch Homes preferred lender and tile company. Talbot County maintains the communities shared treatment facility.. The other fee listed reflects the public works facility fee (sewer fee)for ongoing operation, maintenance, administration and engineering.

0000 Rustling Oaks Dr, Wye Mills

Listing courtesy of Koch Realty, Inc.. Contact: 410-320-6422
$374,900
3 Beds ⋅ 3 Baths
Enjoy the freedom of main-level living without giving up the space to host family and friends. This beautifully maintained Lakelands home offers a first-floor primary suite, generous guest accommodations, flexible loft space, a private fenced yard, and the low-maintenance lifestyle so many Easton buyers are searching for. HVAC replaced in 2025. Additional features include multiple storage closets, a dedicated laundry room, a two-car garage, and a fully fenced backyard with patio ideal for outdoor entertaining, pets, or gardening.

29053 Superior Cir, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$489,000
3 Beds ⋅ 3 Baths
Beautiful end-unit townhome in desirable Easton Club, offering a rare combination of natural light, flexible living space, and sweeping, peaceful nature views. Thoughtfully positioned on one of the larger lots among the original Easton Club townhomes, this home features added side windows that bring in wonderful natural light while capturing the surrounding nature views. The main level offers an inviting living room with solid wood flooring, crown molding, higher baseboards, and a gas fireplace with marble hearth and mantel. An arched opening leads to the formal dining room, creating a gracious flow for everyday living and entertaining. The kitchen features white cabinetry, composite countertops, tile backsplash, tile flooring, newer appliances, and recently installed LED under-cabinet lighting. A spacious first-floor family room provides excellent flexibility and could also serve as a main-level primary bedroom suite, with a full bath and closet for added convenience. Upstairs, the large primary bedroom with sitting area features a walk-in closet, updated walk-in shower, and access to a private balcony with newer polymer membrane, privacy screen, posts, and railings. A second upstairs bedroom and additional full bath complete the upper level. Outdoor spaces include a rear patio overlooking a peaceful lawn, mature trees, and open green space, plus a private balcony for relaxing above it all. Additional conveniences and updates include an attached one-car garage, a newer roof with GAF Silver Pledge warranty, newer gutters and downspouts, newer furnace, newer washer and dryer, recently installed wool stair runner, and an encapsulated crawlspace with dehumidifier. Charming garden accents, including the front yard armillary and backyard concrete bird bath, convey with the home. Enjoy the ease of Easton Club living, where tree-lined surroundings, open green space, panoramic view of expansive open land, and neighborhood amenities create a quiet and convenient setting. The community offers a pool, tennis and pickleball courts, sidewalks, and easy access to downtown Easton, Oxford, shops, dining, and waterfront recreation. With its desirable end-unit location, versatile floor plan, beautiful natural light, and scenic setting, this home is a special opportunity in one of Easton’s established communities. Schedule your private showing today.

28542 Congressional Ct, Easton

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com
$403,540
5 Beds ⋅ 2 Baths
The Richmond by Lennar is a popular new construction home on Maryland’s Eastern Shore, offering approximately 2,238 square feet of thoughtfully designed living space. This spacious floor plan features 5 bedrooms and 3 full bathrooms, providing plenty of room for family, guests, or a home office. The open-concept layout showcases a large kitchen and dining area, highlighted by elegant quartz countertops and ample space for entertaining. Enjoy outdoor living with a rear patio, perfect for relaxing or hosting gatherings.

1467 Lake George Ln, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$328,940
3 Beds ⋅ 3 Baths
Backing to open space for added privacy, this beautiful new construction townhome offers the perfect blend of comfort, style, and convenience. Residents enjoy exceptional community amenities, including a clubhouse, resort-style swimming pool, fitness center, walking and biking trails, playground/tot lot, pickleball and multi-sport courts, dog park, and a scenic lake woven throughout the neighborhood. Ideally located near Easton, waterfront destinations, shopping, dining, and major commuter routes. This luxury three-story townhome at Lakeside at Trappe features a 2-car garage, 3 bedrooms, 2 full baths, and 1 half bath, along with versatile recreation spaces perfect for entertaining, working from home, or relaxing with family. The gourmet kitchen is highlighted by a spacious quartz center island, walk-in pantry, stainless steel appliances, and luxury vinyl plank flooring throughout the main living areas. The spacious owner’s suite offers a large walk-in closet and private bath. Additional features include ceiling fan prewiring in the bedrooms and main living areas, plus smart home technology with a Ring video doorbell and smart front door lock.

1416 Lake Geneva Dr, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$385,000
3 Beds ⋅ 3 Baths
Come experience this beautifully maintained townhome offering an impressive 2,520 square feet of living space, featuring an open-concept floor plan designed for comfortable everyday living and entertaining. The spacious main-level primary suite includes a large walk-in closet, while the inviting second floor loft provides the perfect space to relax, read, or enjoy hobbies. You'll also appreciate a dedicated office/study room on the main level. Additional highlights include a fenced rear yard, cozy gas fireplace, attached garage, Brand-New roof (2026), and a convenient huge walk-in storage room - no attic stairs required. The community's private swimming pool is included with the HOA, providing a wonderful place to cool off and unwind during the summer months. Ideally located with quick and easy access to downtown Easton, you'll enjoy shopping, dining, entertainment, and all the charm that the Easton lifestyle has to offer. Schedule your tour today!

29049 Superior Cir, Easton

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$679,900
4 Beds ⋅ 3 Baths
Nestled in the coveted Cooke’s Hope community, 28839 Jasper Lane offers the perfect blend of comfort, charm, and scenic surroundings. This spacious end-unit townhome features 4 bedrooms and 2.5 baths, including a desirable first-floor primary suite with a walk-in closet and spa-like soaking tub designed for easy everyday living. The airy, light-filled interior is highlighted by a soaring vaulted ceiling in the living room, where a cozy gas fireplace creates a warm and welcoming focal point. A thoughtfully designed layout provides both functionality and flexibility, while the attached 2-car garage adds convenience. Out back, the home truly shines with a beautifully landscaped patio overlooking a peaceful pond setting — a rare and calming backdrop that adds to the property’s unique appeal. The tranquil water views create an ideal setting for outdoor dining, quiet mornings, or simply enjoying the beauty of nature right from your backyard. As part of the beloved Cooke’s Hope neighborhood, residents enjoy access to walking trails, scenic green spaces, ponds, tennis courts, a dog park, and a strong sense of community, all just moments from the shops, restaurants, and charm of historic Easton.

28839 Jasper Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$2,495,000
4 Beds ⋅ 4 Baths
Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal Living, the residence reflects exceptional design and offers gracious living spaces, including four bedrooms with three updated en-suite baths and three fireplaces. A custom great room with wood-burning fireplace, built-ins and fine wood cabinetry anchors the home, complemented by formal living and dining rooms each with fireplaces. The gourmet custom kitchen includes custom cabinetry, quartz countertops, KitchenAid appliances and dual pantries. Outdoor amenities include a 30,000-gallon pool, expansive lawns, mature trees, irrigation system, partial rip-rapped shoreline and private pier with electric and water. Ideal for boating, kayaking, paddleboarding and waterfront entertaining, this exceptional property offers privacy, comfort and enduring Eastern Shore appeal. Two Osprey nesting platforms convery with the property. Some furniture available under separate contract. Boat Lift sold As Is. Do not come down driveway without an appointment.

3770 Leonard Cove Lane Ln, Trappe

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$359,990
3 Beds ⋅ 3 Baths
MOVE-IN-READY Home with Quartz Designer countertops and stainless steel appliances.

1680 Lake Placid Dr, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$465,000
Fully leased duplex in-town Easton. Each unit (104 & 106) offers 3 bedrooms, 1 full bath, and 1 half bath, along with a living room, dining room, and kitchen. Bedrooms are located on the second floor, with walk-up attic access above for additional storage. Each unit has a basements with interior access, basements house the washer/dryer, oil furnaces, and hot water heaters. Interior features include a mix of wood and tile/laminate flooring. Each unit also has front porch and a rear kitchen entrance that leads to a shared backyard. On-street parking is available, along with two detached outbuildings/garages accessed from the alley. Heating is oil-fired with separate systems for each unit. Both units are tenant-occupied. Conveniently located near Idlewild Park and Easton’s Rails-to-Trails.

104/106 Stewart St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$5,995,000
6 Beds ⋅ 6 Baths
Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton, Cambridge, and St. Michaels, The Wilderness is sure to please the discerning buyer. Sited among large waterfront estates, The Wilderness enjoys privacy and a commanding presence with old-growth trees, broad southerly views, and deep water. The scope of improvements includes the primary residence, waterside guest cottage, beach house, pool, pier, tennis court, early 20th-century barn, and a host of accessory structures for life on the farm. Visit the virtual tour for an inside look. The main house has great historical significance not only for the original owner’s grandson who lived there and served two terms as the Governor of Maryland but also for its place in the development of Maryland’s domestic architecture, as noted on two markers from the Maryland Bicentennial Commission and the Maryland Historical Society. The smaller and original of the two brick wings dates from the late 18th century and the larger wing from the early 19th century. The house’s architecture is unusual in that the 19th-century wings telescope up, instead of down, from the original wing. The white brick, black shutters, and historical olive green trim color are a serene palette against the house’s majestic specimen trees around the property, including a gigantic Sycamore that was at one time, the largest of its species in Maryland. The long white gravel drive under the sheltering canopy of mature trees passes by the barn and other outbuildings then curves around the front of the house. Brick steps lead up to the front porch of the early 19th century wing opening into a gracious foyer and stair hall with an elegant elliptical arch that rests on pilasters at the side walls to separate the public from private areas of the house. A French door at the rear of the foyer frames a vista of the lawn and Choptank River. To the side of the foyer are two identical parlors at the front and rear corners of the house. Both rooms have magnificent fireplace mantles and surround; one is a 1740 hand-carved mantel by noted English artisan woodcarver Grinnling Gibbons and the other is a 1780 mantel surrounded by the famous English architect and artisan, Robert Adam. The main floor of the 18th-century wing contains a spacious living room, dining room, original kitchen, and larger kitchen, pantry, two powder rooms, and a stunning sunroom connecting to a terrace along the rear of the house overlooking the Choptank River. Part of this wing was the final addition to the original home. The second floor of the 19th-century wing contains two bedrooms over the two parlors below with fireplaces and walk-in closets and two baths. The 18th-century wing and later addition contain an artist’s studio with cabinetry and sink that has a myriad uses– TV room, arts and crafts room. The primary suite is located at the rear corner of this wing. It has a fireplace flanked by single windows and another window on the rear wall for panoramic views of the mature landscape and the Choptank River. Two baths complete the suite, with one bath off a hall for access from the art studio. Two stairs access the attic level; one in the 18th-century wing leads to two bedrooms and one bath. The main stair in the 19th-century wing leads to a large game room and another cozy bedroom ensuite.

27293 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255
$299,900
3 Beds ⋅ 2 Baths
Huge price improvement 5/21/26! Welcome to 8186 June Way, #307 in Easton—a move-in ready, spacious and bright three-bedroom end townhome located just one mile from downtown Easton. This beautifully situated unit offers the best location in the townhome section of Waylands, featuring a large backyard bordered by trees and a private side deck off the kitchen/dining area overlooking peaceful greenspace. Inside, you’ll find a well-designed floor plan with a first-floor primary suite, open kitchen with breakfast bar flowing into the dining area, a large living room, and convenient laundry on the main level. Upstairs includes two generously sized bedrooms with plenty of closet space and a full hall bath. Additional highlights include ample storage in the attic, a large detached backyard shed, and crawl space access at the rear of the home. Conveniently located near shopping (Giant, Walmart, and more) and with quick access to Route 50 for commuters.

8186 June Way Unit #307, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$799,900
3 Beds ⋅ 3 Baths
***BRAND NEW & MOVE-IN READY*** this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!

807 Radcliff Ave, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 3019459010
$699,999
4 Beds ⋅ 3 Baths
PRICED TO SELL! SELLERS NOW OFFERING A $2500 CREDIT AT CLOSING FOR ANY BUYER TO PUT TOWARDS A CHAIR LIFT to more easily access upstairs bedrooms, should that be desired. 7586 Easton Club is an entertainer’s dream home—so much fun downstairs with open concept living, eat in kitchen with ample bar seating, natural gas fireplace, a salt water hot tub, private backyard and brick patio, garden seating area, huge driveway for lots of guest parking, and more! 1st Floor, bathrooms and primary staged by Wall to Wall Staging, bedrooms three and four are virtually staged. Rare opportunity to purchase this well-maintained turn-key Master's Village home in Easton Club on one of the most private backyard lots in the community, all walkable to the community pool and tennis/pickleball courts. It's not just a home; it's a lifestyle! Set back off the road and on a wide lot, the property is professionally landscaped with a rear yard that is among the most private in all of Easton Club, with professional landscaping including many large trees, underground sprinkler system throughout the yard, patio pavers and a separate outdoor seating area as well as a new salt water hot tub to use on those chilly nights or to relax any time of year. The brick front of the traditional home is stately. The front door entrance brings you into a grand two-story foyer which leads into a formal sitting area and dining room with tray ceiling to the right, powder room, laundry, interior access to the garage, family room with gas fireplace and eat-in chef's kitchen to the left with stainless steel appliances, large island, wall oven/microwave, wine fridge and enormous pantry. Ceilings are at a generous 9' height, with a higher vaulted ceiling over the eat-in area of the kitchen. The window shades by the eat-in area are electronic. Downstairs, over a half a dozen windows are new, put in by the current owners. Upstairs are all four sizable bedrooms. The large primary suite can easily accommodate a king sized bed with room to spare and offers vaulted ceiling, a custom built walk in closet. double vanity, heated floors, heated towel rack, large soaking tub, and walk in shower. Within the last few years the HVAC, kitchen and baths have been updated and the current owner has put new LVP floors throughout the entire upstairs, new LVP downstairs (the downstairs LVP flooring is not glued nor nailed and is over stunning hardwood cherry floors that match the powder room flooring, so should the buyer prefer hardwood, they are easily removed). The upstairs guest bathroom tile flooring was newly installed by the current owners. Sellers made some roof repairs early spring 2026. The roof is original and that is factored into the new listing price. Easton Club offers so many desirable amenities, including a clubhouse, pool, tennis court/pickleball, sidewalks, common areas with ponds and much green space & the community is mere minutes from Historic Downtown Easton's restaurants, shops, museums, doctor offices, hospital, and a short drive to Oxford and St Michaels and approximately 1.5 hrs to Washington DC, Bethesda and Baltimore, less than 1 hr to Annapolis!

7586 Easton Club Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4107458060
$1,379,800
4 Beds ⋅ 4 Baths
Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan delivers comfort and ease. High‑end finishes include Shaw luxury vinyl plank flooring, a gourmet kitchen with a 48" dual‑fuel range, custom tile backsplash, quartz countertops, stainless steel appliances, and a spacious walk‑in pantry. The inviting living area features a fireplace and seamless access to the covered front and rear porches. The primary suite offers a true retreat with a spa‑inspired ensuite bathroom, soaking tub, walk‑in shower, sitting area, and a large custom closet. Additional highlights include a dedicated laundry room, public sewer, and thoughtful craftsmanship throughout. This beautifully designed home is a must‑see for anyone seeking luxury living in one of Maryland’s most charming waterfront towns.

7865 Pea Neck, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$276,995
3 Beds ⋅ 2 Baths
Conveniently located between Route 50 and historic downtown Easton, this charming 1950s cottage is being sold as and presents a fantastic opportunity for homeowners and investors alike. Set back from the street with a large, private backyard, the home offers timeless character and original details throughout. The first floor features a welcoming living room with hardwood floors and arched doorways, adding warmth and classic appeal. A nicely sized kitchen opens to the dining room, where sliding glass doors lead to the porch for easy indoor-outdoor living. Two spacious bedrooms and a full bath complete the main level. Upstairs, the second floor offers a generous primary bedroom with a full bath, creating a private retreat. This property is also an investor’s dream, having served as a profitable rental for many years with the potential to continue as such. With its flexible layout, it may also offer the possibility of conversion into a two-family property, with the second-floor functioning as a studio and the first floor as a two-bedroom unit. Owner will offer settlement assistance.

7 Judas St, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,195,000
4 Beds ⋅ 5 Baths
Enjoy historic in-town living in the heart of St. Michaels, where this beautifully maintained residence offers a rare combination of timeless architecture, a sought-after waterfront-adjacent location, and convenient access to the harbor, parks, trails, shops, and restaurants. Ideally located near the waterfront, scenic trails, park, kayak launch, and the town’s many amenities, the home provides easy access to the best of Eastern Shore living. Inside, warm and inviting interiors feature hardwood floors throughout, multiple living areas, and four wood-burning fireplaces that enhance the home’s historic character. The flexible floor plan includes four bedrooms, four and one-half baths, a dedicated office, custom built-ins, and generous storage, well-suited for a variety of living arrangements and lifestyle needs. Thoughtfully designed spaces offer both comfortable everyday living and additional room for guests, creative pursuits, work-from-home flexibility, or future customization. Outdoor features include a landscaped fenced yard designed for privacy and low-maintenance enjoyment, along with a spacious patio ideal for outdoor entertaining and relaxation. A detached cottage provides added versatility for use as a studio, workshop, or storage space. Off-street parking is an added convenience within the Historic District. Blending historic charm, adaptable living spaces, and an exceptional in-town location, this distinctive residence offers a unique opportunity to experience life in one of Maryland’s most desirable waterfront communities.

114 W Chestnut St, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$475,000
3 Beds ⋅ 3 Baths
Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor. Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful mornings from the expansive screened porch or spacious deck—perfect for relaxing or entertaining while taking in the natural beauty of the island. Inside, the home has been thoughtfully updated and features a bright, open living area and a beautifully renovated kitchen designed for both everyday living and gatherings with family and friends. The spacious primary suite offers a private bath and walk-in closet, along with panoramic water views and direct access to the second-story porch/deck with a retractable awning—an ideal place to unwind and enjoy the serene surroundings. Two additional guest bedrooms and a full bath complete the home’s comfortable and functional layout. Additional highlights include a charming screened porch, generous outdoor living spaces, a storage shed, and beautifully landscaped patios and walkways that enhance the home’s inviting coastal atmosphere. Located in the heart of Tilghman Island, this exceptional property offers the perfect opportunity to relax, boat, fish, and explore everything the Eastern Shore lifestyle has to offer.

5933 Tilghman Island Rd, Tilghman

Listing courtesy of Meredith Fine Properties. Contact: 4107149166