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$455,000
3 Beds ⋅ 3 Baths
Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a bright and open living area with gas fireplace, custom built-ins, and seamless access to a private rear patio overlooking peaceful common space. The stunning kitchen has been completely transformed with quartz countertops, soft-close cabinetry, and newer stainless steel appliances. A main-level bedroom with its own ensuite bath provides flexible living options for guests or primary use. Upstairs, the spacious owner’s suite features a private balcony, a spa-like bath, and generous closet space, along with a second guest suite offering its own private bath. Additional improvements include fresh interior and exterior paint, a newer HVAC system (within the last five years), updated carpeting, refinished hardwood floors, and recently installed 6” gutters. The property includes a one-car garage with attic storage,plus paved parking. Backing to open common area for added privacy and tranquility, and located near The Links at Perry Cabin with no town taxes, this home delivers comfort, convenience, and exceptional value.

9518 Quail Hollow Unit #702, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$7,500,000
6 Beds ⋅ 8 Baths
Set along the peaceful waters of Caulk Cove, this extraordinary waterfront estate offers luxury, privacy and natural beauty across more than 10 acres. The property features open farm fields and professionally landscaped, park-like grounds, with a tree-lined driveway creating a breathtaking approach to the residence. Built in 2013, the custom-designed home encompasses nearly 8,500 square feet of thoughtfully curated living space, positioned to capture sweeping waterfront views. A gracious front porch welcomes you into a grand foyer, setting the tone for the exceptional craftsmanship found throughout. The main level offers soaring 12-foot ceilings, rich hardwood floors, expansive windows and doors and custom millwork including crown molding, coffered and tray ceilings and elegant board-and-batten detailing. At the heart of the home, the living room serves as a remarkable gathering space with a dramatic floor-to-ceiling stone fireplace, custom built-ins, coffered ceilings, a wet bar and access to the rear porch. The kitchen is a stunning focal point, featuring a diamond coffered ceiling, custom handmade walnut cabinetry, two oversized islands, white and leathered granite countertops, and a Wolf six-burner, dual-oven range. A fully equipped butler’s pantry offers extensive cabinetry, generous counter space, a secondary refrigerator, dual dishwashers, a wine refrigerator and an electric oven. The open dining area flows seamlessly between the kitchen and living room. The primary suite is a private retreat with a tray ceiling, wood-burning fireplace, expansive walk-in closet with custom built-ins and vanity and a luxurious bath featuring heated floors, a jetted soaking tub, separate vanities, an open tile-and-glass shower and a private water closet. The suite is completed by a private sitting room with fireplace and wet bar, along with a private screened porch overlooking the gardens and serene waterfront. Four additional ensuite bedrooms each offer unique and luxurious bath designs. A well-appointed laundry room with ample cabinetry and generous counter space enhances everyday convenience and leads directly to a functional mudroom with access to the attached two-car garage. The second level features 9-foot ceilings and is anchored by a spacious family room with a stone hearth wood-burning fireplace and built-in window seating, flowing into a billiards area with wet bar, creating an ideal space for entertaining. The sixth bedroom currently includes custom built-in bunk beds but was originally designed as a home office and offers flexibility to be restored to its original use. The home’s exceptional design extends seamlessly outdoors, with a spacious screened porch leading to an open-air porch with a wood-burning fireplace and outdoor entertainment setup. Bluestone walkways and patios lead to a 20’ x 40’ lagoon-style Gunite pool with a waterfall feature, an outdoor kitchen and a waterside fire pit offering stunning sunset views over the cove. The property also includes a charming one-bedroom guest house with a luxury kitchen, open living area with fireplace and screened porch. A private dock with approximately 6’ MLW offers two boat slips, a floating dock and access to waterfront dining and premier fishing throughout the Chesapeake Bay and surrounding tributaries. Additional highlights to the home include a greenhouse with raised garden beds, a fenced garden area, professional landscaping with accent lighting, and a full irrigation system. This exceptional estate is truly one-of-a-kind!

7508 Cooper Point Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$1,679,000
4 Beds ⋅ 4 Baths
Significant price improvement! Welcome to your private waterfront retreat just minutes from the charming, historic town of St. Michaels, Maryland. Tucked away on a quiet cul-de-sac in the serene Oakwood Park community along San Domingo Creek, this one-story residence offers four bedrooms, three and a half baths, and a harmonious blend of space and comfort. With approximately 2,839 finished square feet, all on the main level, the home is designed for convenience and ease of living. Inside, generous rooms are enhanced by rich custom yellow pine floors, premium carpeting, and tile. At the heart of the home, the living room impresses with a vaulted ceiling, exposed beams, custom built-ins, and a rustic wood-burning fireplace. A waterfront family room flows into the dining area, while the country kitchen features handsome cabinetry, premium countertops, modern appliances, and a pantry with washer and dryer. The waterside primary suite offers a fireplace, walk-in closet, and a spacious bathroom with dual vanities. On the opposite side of the home, a second bedroom includes an ensuite bath and walk-in closet, complemented by two additional bedrooms with ample closet space (one used as den) and a full bath. The exterior showcases cedar shake siding, a welcoming covered front porch, a private patio between the main bedrooms, a large rear waterside deck, a two-car detached garage, and a wide gravel driveway with ample guest parking. The property is served by a private well and septic system, with public sewer hookup approved and coming soon, offering flexibility for future expansion or renovation. This home is part of a unique five-property HOA (fees $600/year) with each property owning 20% of a central community lot, a deepwater dock with five slips, and a historic pavilion available for member events and leisure. Residents also enjoy a kayak rack and a small sandy beach for launching boats or paddle boards. The setting provides not only a comfortable home but a lifestyle of Chesapeake Bay waterfront living. According to research, the grounds of the five lots and the “Oakwood Association” belonged long ago to the Oakwood Inn, a prominent retreat in the early 20th century. Known for its scenic harbor views and role in local leisure culture, the inn appeared in postcards from the 1930s and was a hub for skating, swimming, pleasure boating, regattas, and log canoe races. Its legacy adds a rich historical dimension to the property, connecting today’s residents to St. Michaels’ vibrant past as a sailing and leisure destination. There are photos of two pieces of memorabilia at the end of the photo section of this listing for your enjoyment. See attached documents for HOA information ($600/year per property), easement information, C&Rs, Contract Disclosures, etc. Flood Zone X, no flood insurance required. Three-bedroom septic, public sewer hookup available near future.

24390 Oakwood Park Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$659,000
3 Beds ⋅ 2 Baths
The one-of-a-kind Ryan model is set to be the largest one-story home constructed on Sandy Lane, brought to life by Developer Sandy Lane, LLC and renowned local builders Stansbury and Sons. Like all ten homes in this thoughtfully designed new downtown Easton community, the Ryan will be a custom, stick-built residence backed by a one-year builder’s warranty and outfitted with brand-new appliances and systems—allowing homeowners to enjoy their new space without the constant burden of "old house" maintenance. The Ryan's convenient single-level layout includes three bedrooms, two full baths, and a spacious living room with vaulted ceilings that flows seamlessly into the dining area and a beautifully appointed kitchen. A cook's dream, the kitchen features custom cabinetry, including a large pantry cabinet, solid surface countertops, and stainless-steel appliances. The luxurious primary suite offers a private bath with a tiled shower, double sink vanity and a generous walk-in closet. The two additional bedrooms on the opposite side of the floorplan share a stylish hall bath with tub/shower. There is also a dedicated laundry area—strategically placed between the kitchen, primary suite and garage entrance—which completes the interior. Outside, the home boasts a one-car attached garage with an electric car charger, a concrete driveway with parking for two, custom front foundation landscaping, a fully sodded yard, and a rear patio. Sandy Lane homes are built with premium features such as encapsulated, climate-controlled crawl spaces suitable for storage, superior framing and finish work, certified IECC Energy Efficient insulation (R-49 ceiling, R-21 walls), luxury vinyl flooring throughout, ample closet space, and multiple contemporary ceiling fans and fixtures. The Ryan’s flexible design makes it ideal for retirees, remote workers, singles and families alike. All infrastructure costs—including surveys, permits, site work, utilities, and street improvements—have been prepaid by the developer, eliminating typical new construction extended yearly front foot fees for buyers. Located off N Washington Street in Easton, Sandy Lane offers easy access to downtown amenities such as Easton Utilities (electric, water, sewer, cable, and high-speed internet), weekly trash and recycling pickup, and a wealth of recreational options including parks, sports fields, trails, playgrounds, tennis and pickleball courts, a community pool, and a dog park. Easton and Talbot County provide abundant waterfront access, fire and police services, medical facilities, cultural attractions such as the Avalon Theater, The Academy Art Museum, and Maritime Museum, premium shopping, and some of the best dining on the East Coast. The community is subject to Covenants and Restrictions but carries no HOA or associated fees. Developer: Sandy Lane, LLC (MHBR 9512). Builder: Stansbury and Sons Home Improvement Inc. (MHBR 8351). Builder Contract required.

13 Sandy Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$699,000
3 Beds ⋅ 3 Baths
Broker and Public Open 4/23 from 10am to Noon! OCCUPANCY PERMIT in hand, move right in! Nestled in the charming town of Easton Maryland, this exquisite new construction offers a perfect blend of modern luxury and traditional elegance. The sixth of Sandy Lane's ten total homes to be built, this design is the first two story that includes a first-floor primary suite with gorgeous en-suite bath and a huge walk-in closet. There are two additional bedrooms up and a 320sf family room, providing a second spacious gathering place for tv watching, reading, homework, pool table, games, the works! It is a thoughtfully designed custom layout providing plenty of space for privacy, relaxation and entertainment. Step inside to discover an inviting open floor plan that seamlessly connects the gourmet kitchen to the dining and living areas. The kitchen as designed is a cook's dream, with an island providing ample workspace and seating for four. The kitchen is equipped with custom cabinetry and elegant countertops as well as stainless appliances. The kitchen island serves as a focal point for gatherings, while recessed lighting and ceiling fans enhance the ambiance throughout the home. The interior is fitted with luxurious vinyl plank flooring and carpeting, creating a warm and comfortable atmosphere. The first-floor primary suite features a huge walk-in closet and a private, beautifully finished bathroom with a custom-tiled shower. Next to the interior entrance to the garage, you will find a convenient, dedicated laundry room and private powder room. Outside, the property is equally impressive. The extensive hardscape and beautifully landscaped front yard create a picturesque setting, with a rear patio and front porch perfect for outdoor entertaining or quiet evenings spent enjoying the neighborhood views. In addition to an encapsulated and climate-controlled crawl space, features include energy-efficient double-pane windows, Certified IECC Energy Efficient insulation (R-49 ceiling, R 21 walls), exterior lighting, and a well-designed gutter system, ensuring both functionality and aesthetic appeal. Whether you are retired, work from home or have a growing family, this flexible floorplan will suit your needs. Parking is a breeze with an attached garage with electric car charger, driveway space for two vehicles, and additional on-street parking available. Located on a cul-de-sac, this home offers a sense of privacy while still being in the heart of downtown, where the vibrant community life of Easton awaits. You can experience the luxury of modern living in a prime downtown Easton location, where every detail has been meticulously crafted to provide comfort and elegance. Don't miss the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle offered on Sandy Lane. Sandy Lane homes are subject to recorded Covenants and Restrictions (attached in docs) but there is no HOA or fees. Developer: Sandy Lane, LLC, MHBR 9512. Builder: Stansbury and Sons Home Improvement Inc., MHBR 8351. BUILDER CONTRACT REQUIRED.

18 Sandy Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$745,000
4 Beds ⋅ 4 Baths
Back on market due to BUYER not being able to sell their house! Clean inspections so READY for YOU! This beautifully sited end-unit townhouse has serene field views, and offers 2,433 sq. ft. of elegant living with 4 bedrooms, 3 full baths, and 1 half bath. Designed with an open concept, the living room, dining room, and kitchen flow seamlessly together, creating a warm and inviting space for entertaining or everyday living. Soaring two-story ceilings, skylights, and expansive windows flood the home with natural light, while a gas-burning fireplace is the focal point of this inviting space. The main-level primary suite serves as a private retreat with an ensuite bath, complemented by two walk-in closets. A cozy den and convenient powder room complete the main level. An upper-level loft overlook adds architectural charm and provides additional space for relaxation. Upstairs, one guest bedroom enjoys its own ensuite bath, and two additional bedrooms share a connecting full bath. Outdoors, a beautifully landscaped backyard framed by mature trees provides a tranquil setting, while the attached 2-car garage offers convenience. Cooke’s Hope residents enjoy an unmatched lifestyle with ponds, tennis courts, walking trails, a dog park, fitness center, picnic pavilion, and a community dock—making this one of Easton’s most desirable communities.

28933 Jasper Ln, Easton

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$475,000
4 Beds ⋅ 3 Baths
Private backyard in Vibrant Community. Get lost in this backyard oasis close to downtown Easton in the very exciting neighborhood of Mulberry Station. Minutes from downtown Easton, you will get lost in all the special nooks and crannies hiding in your hidden paradise. Lose yourself in a book under the Crepe Myrtles, Zen out next to the manmade Koi ponds with water features. Who needs a sound machine with the peaceful sounds of leaves rustling and babbling brooks babbling? A huge inground pool with a designated firepit area can make any evening special. This thoughtfully designed outdoor space needs to be seen to really be appreciated. Inside, you will find ample room to spread out. The lovely kitchen/family room combo features a gas fireplace to cozy up to. Indoor/Outdoor dining with sliders that open up from your kitchen onto your beautiful large deck with electric awning. Upstairs, Double doors open to your very large primary suite with walk-in closet and en-suite. Three other large bedrooms and bathroom round out the upstairs.

8862 Roundhouse Cir, Easton

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

$334,290
3 Beds ⋅ 3 Baths
Large 3 bed Townhouse 2,254 sq ft - July Delivery! Open plan kitchen, Stainless steel appliances. Photos are for illustration purposes. Agents must accompany buyer during first visit to the community.

1217 Loch Ness Ln, Trappe

Listing courtesy of Builder Solutions Realty. Contact:

$8,750,000
6 Beds ⋅ 6 Baths
Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 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 and appreciation for the scope of this offering. 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 is 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. The revised offering of The Wilderness, providing 234 acres comprised of 5 recorded parcels with over 3,000 feet of shoreline is a remarkable opportunity to witness life on the Shore.

27295 Southside Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255