Refine Search
Map
Sort by
24645 Long Haul, Saint Michaels
$2,200,000
4 Beds ⋅ 5 Baths
Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for entertaining. Gleaming hardwood floors enhance the home's inviting ambiance. The primary suite is a serene escape with a stunning bath, while the upper level offers generous space ready to be transformed to match your vision. Outside, the property unfolds into a private waterfront playground, complete with a charming cottage ideal for guests or extended family, and a detached two-car garage with a one-bedroom apartment awaiting restoration. Bring your imagination! An exceptional opportunity for boating, entertaining, and relaxed coastal living. Just minutes from fabulous restaurants, boutique shopping, and the quaint charm of St. Michaels.

24645 Long Haul, Saint Michaels

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Benson & Mangold, LLC.

203 Chew Ave E, Saint Michaels
$2,125,000
5 Beds ⋅ 6 Baths
Significant Price Improvement!!! Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully re-imagined through comprehensive renovations completed in 2023 and 2024. See virtual tours above. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms and 5 and a half baths, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm— located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four en-suite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace—framed by expertly trained David Austin climbing roses—a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.

203 Chew Ave E, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Monument Sotheby's International Realty.

27877 Bent Farm Ln, Oxford
$2,100,000
4 Beds ⋅ 4 Baths
This Island Creek waterfront home located on deep water with a southern exposure and long shoreline is being sold for the first time since built in 1999. Situated on 3.8 acres, every detail was thought out and executed by the owners and a top rate builder. The house consists of 4,469 sq. ft. of living space plus a two car garage. The house has an open floor plan, featuring a large eat in kitchen with views over Island Creek, the dock and an expansive well landscaped lawn that drops to the shoreline. The kitchen is well appointed with top end appliances, tons of storage areas, pantry and is close to the laundry room and shop. There is a primary bedroom suite on the first floor, a second bath, and three bedrooms and two full baths on the second floor. There is a deck, patio and screened porch facing SW, all meticulously maintained. The property is located in the “X” flood zone. This is an extraordinary waterfront property located in the Oxford zip code on one of the best deep water creeks in Talbot County.

27877 Bent Farm Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

8240 Tricefield, Saint Michaels
$2,100,000
5 Beds ⋅ 6 Baths
Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds. Built with quality and designed for comfortable living, the home features two spacious primary suites, including one conveniently located on the first floor. Large walk-in closets provide abundant storage throughout. An attached in-law suite offers flexibility for extended family, guests, or multi-generational living. The impressive foyer welcomes you into a thoughtfully designed floor plan featuring mostly hardwood floors throughout. Enjoy a spacious dining room perfect for large family gatherings, a comfortable living room anchored by a cozy brick fireplace, dedicated office space, and a separate craft room. A large utility room provides exceptional functionality with space for an extra freezer and refrigerator, while multiple HVAC zones ensure comfortable heating and cooling throughout the home. Outdoor amenities are equally impressive. Relax by the pool, entertain on the waterfront, or take advantage of the private dock with approximately 4 feet of mean low water depth. The property also includes a substantial workshop with tractor storage, ideal for hobbyists, boaters, or those needing extra workspace. Recent improvements provide peace of mind, including a roof that is just two years old and a paved driveway completed within the last year. This is a rare opportunity to own a solidly built waterfront retreat offering space, functionality, and timeless Eastern Shore charm just moments from the shops, restaurants, and waterfront attractions of St. Michaels.

8240 Tricefield, Saint Michaels

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

Selling Office: Benson & Mangold, LLC.

3750 Windy Hill Rd, Trappe
$2,100,000
0-3750 Windy Hill Rd- 139 acre Tract Located in the heart of Maryland’s Eastern Shore, this 139± acre farm in Talbot County offers a rare combination of highly productive agricultural land, proven hunting opportunities, and long-term investment potential. With a strong history of crop production and no conservation easements, this property provides flexibility for farming, recreation, and future development. The property is predominantly comprised of fertile, tillable acreage that has been successfully farmed in a rotation of soybeans, corn, and wheat. The soils in this region are known for their productivity, making this tract well-suited for continued agricultural use. Portions of the property have previously been enrolled in CRP programs, presenting an opportunity for future income diversification through conservation programs while maintaining active farming operations. Access is a standout feature, with dual road frontage along both Kates Point Road and Clarks Wharf Road. This allows for efficient equipment movement, multiple entry points, and potential homesite, subject to local regulations. The layout of the property is functional and open, offering expansive fields with excellent visibility and ease of management. For outdoor enthusiasts and investors alike, the recreational value is significant. The farm includes an established pit specifically designed for Canada goose and snow goose hunting, with the surrounding area known for strong seasonal waterfowl migration. The open fields and agricultural setting create ideal feeding conditions, making this a reliable hunting destination. In addition to waterfowl, the property supports a consistent population of whitetail deer. Surrounded by large tracts of timber, this farm serves as a natural feeding and transition area, increasing deer movement throughout the property. This balance of agriculture and nearby cover creates an ideal setup for both hunting and wildlife observation. The rural and private setting offers peace and seclusion while still being conveniently located near the towns of Easton and Cambridge. These nearby hubs provide access to shopping, dining, healthcare, and other essential services, making the property both practical and accessible. With no conservation easements in place, the property maintains maximum flexibility for future use. Whether you are looking to expand a farming operation, establish a premier hunting property, or build a private residence, this tract offers multiple pathways to meet your goals.

3750 Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Meredith Fine Properties.

26090 Royal Oak Rd, Royal Oak
$2,000,000
4 Beds ⋅ 5 Baths
Welcome to Terrapin Point, an extraordinary waterfront estate nestled in the heart of Royal Oak, Maryland—one of Talbot County’s most coveted and picturesque settings. Built in 1890, this timeless Victorian residence evokes the charm of a bygone era, blending old-world elegance with the serene beauty of Maryland’s Eastern Shore. Set gracefully on a private point along the tranquil waters of Oak Creek, the property offers sweeping, uninterrupted waterfront views and a rare sense of peace and seclusion. With minimal boat traffic and protected waters just off the Miles River, Terrapin Point is a true sanctuary for those seeking quiet coastal living and the wonders of nature. A long, tree-lined driveway creates a grand and memorable approach, opening to a storybook setting reminiscent of a Norman Rockwell painting. The home itself is filled with natural light and architectural character, including soaring ceilings, elegant archways, and a stunning dining room with exposed beams that overlooks the water—perfectly framing the estate’s breathtaking surroundings. Designed for both relaxation and entertaining, the home features a spacious kitchen and dining area ideal for hosting, along with an oversize screened porch that invites you to unwind while enjoying gentle breezes off the creek. Outdoors, a beautifully positioned in-ground pool sits just at the water’s edge, offering a resort-like vacation experience. On the edge of the trees sits a beautifully designed potential "glamping" cabin, art or music studio where you can enjoy the birds singing and watch the light through the trees. Perfectly located, the property sits equidistant between the charming towns of Easton and St. Michaels, allowing effortless access to renowned dining, shopping, and cultural attractions while maintaining a peaceful, tucked-away feel. The 12 acre point of land and home embodies the quintessential Eastern Shore lifestyle—refined yet relaxed, elegant yet inviting. A rare offering where timeless architecture, premier waterfront, and an exceptional location come together to create a truly unforgettable property. *Seller currently resides at the property in the main floor primary suite. Several pictures have been visually enhanced with virtual staging.

26090 Royal Oak Rd, Royal Oak

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

Selling Office: TTR Sotheby's International Realty.

938 Marea Ter, Saint Michaels
$2,000,000
4 Beds ⋅ 6 Baths
Fabulous in-town St. Michaels waterfront property – This coastal style waterfront residence, built in 2020, offers approximately 3,000 square feet of thoughtfully designed, sophisticated yet relaxed waterfront living space on San Domingo Creek. Located within town limits, the property enjoys direct access to the St. Michaels Nature Trail, allowing effortless walkability to shops, dining, and cultural amenities—no car required. Designed for both comfort and entertaining, the light filled interior features an open floor plan with high ceilings, a well-appointed chef’s kitchen, and a welcoming fireplace. Four private bedroom suites – including a primary suite on the main level - make it a breeze to accommodate larger family gatherings and visiting friends. A spacious screened waterside porch, heated inground pool, deck and Bocce Court extend the living space to the outdoors for seasonal entertaining and warmer weather fun. A separate pool house/studio, connected by the screened porch and breezeway, includes a full bath and offers flexibility for use as a home office, creative space or additional guest quarters. The 2.3 acres lot is located at the edge of the San Domingo Cove community and is adjacent to protected woodlands, providing privacy, and offers with public water and sewer and a fully fenced backyard. Boating enthusiasts will appreciate the dock (shared with one neighboring property), offering two dedicated slips and a floating dock per owner and water depths of approximately 4–4.5 feet at the slips and 3 feet at the floating dock. From here it is easy to boat to Tilghman Island and Oxford, and San Domingo Creek is also great for kayaking and canoeing. An exceptional and rare opportunity to enjoy refined, in town waterfront living in one of Talbot County’s most sought after communities.

938 Marea Ter, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Washington Fine Properties, LLC.

8670 Bozman Neavitt, Saint Michaels
$1,950,000
3 Beds ⋅ 3 Baths
The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A What's special The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A long, pine-lined entrance drive carries you toward a first glimpse of Harris Creek ahead — water framed by tall pines, open and still. Then the drive sweeps gently to the left, and then, almost as a surprise, the cottage — modest, elegant, perfectly placed. It makes no attempt to impress. It doesn’t need to. The cottage is quiet and handsome — simply elegant in the way that only genuine character produces. Nothing oversized, nothing imposing. Just a well-proportioned, beautifully maintained home that belongs exactly where it sits. That first view of the house — unhurried, understated, perfectly at home in its setting — tells you everything about what kind of place this is. THE PROPERTY Few waterfront properties in Talbot County can offer what Rose’s Garden delivers: 6.87 private acres along Harris Creek, with approximately 400 feet of rip-rap shoreline in excellent condition. That kind of scale — within the Saint Michaels area — is simply not available anymore. And the west-facing orientation means sunsets over open water every evening, looking out across largely undeveloped land on the opposite shore. The views are clean, natural, and remarkably unspoiled. For a property this close to Saint Michaels, that is genuinely extraordinary. A private dock with 4 feet of water provides direct access to the creek and the Chesapeake Bay beyond. The home has been comprehensively renovated — new roof, refinished hardwood floors, updated kitchen, two fully remodeled baths, and complete HVAC throughout. A buyer arrives to something turnkey, not a project. THE LIFESTYLE Morning coffee on the primary bedroom deck with the creek glassy and still, nothing but natural shoreline across the water. Afternoons in the saltwater pool with the scent of pines and the sound of the water nearby. Evenings at the waterside pavilion as the sky turns orange over Harris Creek — unobstructed, undeveloped, all yours to take in. The rose garden and large, beautiful mature trees spread across the property give the grounds a park-like, tended quality that simply cannot be manufactured — it accumulates over decades, and here it already exists. At night, subtle landscape lighting illuminates those trees from below, casting the grounds in a quiet, warm glow. It is the kind of lighting that enhances rather than announces — a property that is just as inviting after dark as it is at sunset. And yet Saint Michaels — its restaurants, the Chesapeake Bay Maritime Museum, the Miles River Yacht Club — is just minutes away. The seclusion is real. The convenience is too. That combination is what makes Rose’s Garden so difficult to replicate. WHY THIS PROPERTY IS RARE Properties like Rose’s Garden do not come together by accident. The acreage, the frontage, the dock, the unspoiled views, the mature landscape — each of these alone would make a property noteworthy. Together, and this close to Saint Michaels, they represent something that simply does not come to market often. The renovation means a buyer inherits none of the headaches that typically accompany older waterfront homes — the deferred maintenance, the aging systems, the compromises. The work is done and done well. Rose’s Garden is ready for its next chapter. AT A GLANCE 6.87 private acres — Saint Michaels area — Waterside pavilion — Pine-lined entrance drive w/ creek views — New roof — Large mature trees throughout grounds — Primary bedroom deck w/ water views — Subtle up lighting on mature trees — Full HVAC — central + mini-splits — Unspoiled views — largely undeveloped opposite shore — Both baths fully remodeled — 400 ft Harris Creek frontage — Refinished hardwood floors — Rip-rap shoreline — excellent condition — Updated kitchen w/

8670 Bozman Neavitt, Saint Michaels

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

Selling Office: Unrepresented.

Oxford Road, Oxford
$1,875,000
Welcome to an amazing farm opportunity located 3 miles from Oxford, Maryland, one of the Eastern Shore’s most treasured waterfront towns, where timeless charm meets an exceptional opportunity to create your dream home. Set along the shores of Goldsborough Creek, this premier waterfront parcel offers northwestern exposure, delivering breathtaking sunset views across tranquil waters. The preferred waterfront building site allows for construction with a 100-foot setback, providing nearly 180 degrees of waterfront views on Goldsborough Creek. A proposed 150-foot private dock site would provide approximately 2.5 feet at mean low tide. A recent septic application with the Talbot County Health Department has been submitted for a four-bedroom residence. Soil evaluations indicate excellent conditions for a generous sewage disposal area, offering flexibility for a substantial home and the potential for future improvements. Engineering analysis also supports the possibility of identifying additional SDA locations should subdivision be pursued, subject to county approvals. Preliminary estimates show the potential for 2 waterfront and 1 inland building site, to be confirmed with Talbot County Planning and Zoning. The farm is located within a historic waterfowl staging area providing habitat for wintering Canada Geese and Ducks. Adjacent woodland and contiguous farm fields complement this coveted rural setting with ample opportunity to enhance the natural features and create a haven for the outdoors and nature enthusiasts. This unique waterfront farm opportunity provides an extraordinary setting to design and build a custom waterfront retreat in a location defined by the natural beauty where land and water combine.

Oxford Road, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Coldwell Banker Realty.

9788 Pintail Pl, Saint Michaels
$1,840,000
4 Beds ⋅ 3 Baths
Nestled on 2.3 private acres in the sought-after Martingham neighborhood, this beautifully updated waterfront home offers one level living with the perfect blend of comfort, style, and outdoor living. Overlooking Porter Creek, the property features a private pier with lift and rip-rapped shoreline, where you can enjoy breathtaking sunsets, and endless days enjoying the water. Inside, the open floor plan flows effortlessly from the spacious living areas, open dining area, to the fully renovated kitchen, complete with quartz countertops, custom cabinetry, and modern appliances. The expansive waterside owner’s suite has a luxurious bathroom with heated tile floors, and generous closet space. Two additional bedrooms, plus a den that could serve as a fourth bedroom and custom bathroom. Step outside to a screened porch with awning or lounge beside the tiled gunite heated saltwater pool, Pebblesheen finish and surrounded by a custom deck—perfect for entertaining or quiet relaxation. Additional highlights include a two-car garage with attic storage, a laundry room with utility sink, stacked washer/dryer, and a 4-ton Legacy heat pump for year-round comfort. This is a rare opportunity to own a meticulously maintained home in one of St. Michaels’ most desirable communities, where privacy, luxury, and a waterfront lifestyle come together beautifully. Experience life alongside one of Maryland’s finest golf courses - across the street of the award-winning Links at Perry Cabin Golf Course—a premier golf destination designed by the legendary Pete Dye.

9788 Pintail Pl, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

222 Chestnut, Saint Michaels
$1,825,000
3 Beds ⋅ 3 Baths
Where the harbor meanders to a close and drifting ducks replace the bustle of boats, this 2,284 square foot colonial captivates as serene dockside stillness gives way to elevated coastal personality. Whether welcoming guests from its end-of-lane circular drive or stepping ashore from one of your four boat slips, your restful retreat pampers with beautifully renovated interiors by local shop, Come By Chance’s, design team. Across living spaces, you’ll enjoy quiet refinement of the original 1996 construction as hand-scraped hardwoods, tailored millwork, crisp coastal hues, and light-filled windows frame seasonal harbor moments. Host visiting guests near your wood-burning hearth where built-ins hold favorite reads, collected shells, and travel mementos. Here, both curated and comfortably lived-in personality mirror mornings with coffee and dinner aromas from your breezy kitchen of high-end appliances, stone surfaces, and a central island. While everything from simple breakfasts to generous crab feasts overlook nautical views from your sunlit sitting room, you’re sure to linger long after meals from either of the double balconies. Here, let casual conversation entertain, then settle within either of your three serene bedrooms letting two full and one half baths refresh. Outside, toss yard toys for a four legged friend, cast off kayaks towards quiet coves, or set sail into the open expanse of the Chesapeake Bay. Closer to home, afternoons unfold, just a stroll’s-distance away toward daily discoveries within nearby St. Michaels shops, cafés, museums, and the yacht club.

222 Chestnut, Saint Michaels

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

Selling Office: Unrepresented.

106 E Division St, Oxford
$1,800,000
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:

Selling Office: TTR Sotheby's International Realty.

4491 Bachelors Point Rd, Oxford
$1,800,000
3 Beds ⋅ 3 Baths
Discover your own Eastern Shore retreat at 4491 Bachelors Point Road in Oxford, MD. This exceptional 29-acre waterfront estate offers unrivaled privacy, 2,100 feet of pristine shoreline on Boone Creek, and effortless access to the Choptank River. The thoughtfully designed residence—completed initially in 2003 and extensively updated—features over 2,000± sq. ft., three bedrooms, and a newly completed 2023 primary suite with a walk-in closet and spa-style bath. Enjoy sweeping water and wildlife views from the expansive screened porch and spacious deck. A separate apartment above the detached garage provides flexible space for guests, a home office, or rental income. The property also includes a 100-foot dock with water and electric (replanked in 2025) and sheltered waters ideal for small boats, kayaking, paddleboarding, and swimming. Set within the highly sought-after Bachelor’s Point community, residents enjoy proximity to deepwater boat slips, a full-service boatyard, and Oxford’s charming boutiques, restaurants, festivals, and recreational amenities. Mature trees, abundant wildlife, and protected conservation acreage create a serene, low-maintenance setting perfect for a private getaway, hunting retreat, or investment opportunity.

4491 Bachelors Point Rd, Oxford

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

Selling Office: Benson & Mangold, LLC.

23857 Ebb Point Rd, Bozman
$1,780,000
4 Beds ⋅ 4 Baths
*Furniture and decor included in sale* Experience elevated coastal living in this impeccably renovated 2,250 sq ft post-and-beam home, reimagined as a coastal modern contemporary masterpiece by interior designer Hollace Kutay. Known as Oyster Cove for its picturesque 2.5 acre location on Broad Creek, this home is perfectly situated for boaters and kayakers seeking both adventure and tranquility. Enjoy expansive water views from nearly every room, and take full advantage of the private dock outfitted with an electric boat lift—complete with both water and electric hookups for seamless waterfront living. Featuring 4 bedrooms and 3.5 baths—including dual primary suites upstairs and down—this designer showcase comes fully furnished (except 2 bedrooms) with curated, unique pieces included in the sale. The chef's kitchen features beautiful black and gold appliances, including a 48-inch duel fuel range. A stunning 9-foot island anchors the room, perfect for casual dining or entertaining, while the separate prep kitchen is equipped with a second refrigerator, sink, and dishwasher, ensuring both efficiency and style. The under-stair wine room with one-of-a-kind wallpaper as well as a dedicated office/lounge add both charm and function. The powder room features a custom artisan octopus sink crafted by designer and artist Hollace Kutay. Enjoy seamless indoor-outdoor living with generous dining spaces perfect for gatherings. This is a rare turnkey opportunity to own a furnished, design-forward home that’s as livable as it is luxurious. Owner is a Maryland licensed realtor.

23857 Ebb Point Rd, Bozman

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: Long & Foster Real Estate, Inc..

7421 Quaker Neck Rd, Bozman
$1,750,000
6 Beds ⋅ 5 Baths
Offered for the first time in over 50 years, this 13+/- acre waterfront property on Broad Creek presents a rare opportunity to own an expansive estate with exceptional shoreline frontage. With more than 960+/- feet of waterfront, the setting provides unobstructed water views and a private pier, offering direct access to the creek and surrounding natural landscape. A tree-lined private driveway leads to the residence, positioned to take full advantage of its waterfront location. The home features 6 bedrooms and 4 full/1 half baths. The main level includes a screened-in porch entry, welcoming foyer, spacious living room with fireplace, formal dining room with a second fireplace, and a flexible study or office with built-in shelving and water views. The updated eat-in kitchen is equipped with granite countertops, a large breakfast bar, gas cooktop, stainless steel appliances, and a spacious pantry. A main-level half bath completes the floor. Both a primary staircase and a secondary staircase provide access to the upper levels. All six bedrooms are located on the second floor. The owner’s suite includes a fireplace, ensuite bath, and access to a front-facing balcony. Front-facing secondary bedrooms also have balcony access. The third level offers additional living space, including a large bonus room, entertainment room, three additional rooms, completed drywall and electrical work, and a full bath with shower. Additional property features include a detached garage with parking and storage, an externally accessed basement for storage, a wide exterior pad suitable for boat or RV storage, hardwood floors, a waterside deck, and a private pier. This property combines acreage, extensive waterfront frontage, and a spacious residence ready for its next owner.

7421 Quaker Neck Rd, Bozman

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Porter House International Realty Group.

12633 Connelly Rd, Cordova
$1,723,750
3 Beds ⋅ 2 Baths
Bridgewater Farm - 12633 CONNELLY ROAD, CORDOVA MD 21625 137± Acres - consisting of approximately 105± tillable, 20± acres of woodland, and the balance around the house, driveway, and hedges. The property is improved by a circa 1870 brick farmhouse with a basement and several sheds, barn, well, and septic. Health Department information on file showing 1980 septic and 1986 well. Property sold ‘as-is’. **Existing farm lease. Contact agent for details. The residence provides late-19th-century architecture that is remarkably intact for a rural brick farmhouse. Significant features include the 13 cornices along the northern portion of the house, thick masonry walls, and brick lintel detailing above the windows. Later additions include the kitchen wing with a bedroom above and a three-season porch. There are two basements with a dirt floor and shoring with an interior concrete block retaining wall. The underside of the house is accessible to witness the condition and assess for renovation. Additional structures include a period barn and sheds. Offers considered beginning 5.13.26 to allow adequate time on the market. Showing by appointment only.

12633 Connelly Rd, Cordova

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Meredith Fine Properties.

22707 Marshall Ln, Wittman
$1,700,000
5 Beds ⋅ 4 Baths
Now Offered at $1,895,000 | Private Harris Creek Waterfront Private Harris Creek waterfront with pool, pier, boat lift and deep-water access—crafted for boating, kayaking and the best of Eastern Shore living. This five-bedroom, three-and-a-half-bath residence offers a rare blend of privacy, comfort and wide water views just minutes from St. Michaels and Easton. Sun-filled interiors feature red oak floors, custom built-ins, multiple fireplaces and an inviting layout designed for everyday living and entertaining. The kitchen is the heart of the home with KitchenAid appliances, granite countertops, oversized island seating, butler’s pantry and dry bar. Main-level living includes a waterside primary suite with fireplace, private guest suite, office or den, and additional gathering spaces. Upstairs offers three bedrooms, full bath and spacious family room. Outdoor living shines with a screened porch, expansive waterside deck, saltwater pool and firepit patio overlooking Harris Creek. Private pier with boat lift and deep-water access opens the door to endless days on the water. Additional features include a two-car garage with workshop, whole-house generator and new septic system (2025). An exceptional waterfront opportunity at an outstanding new price.

22707 Marshall Ln, Wittman

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

Selling Office: Unrepresented.

121 Pier, Oxford
$1,695,000
3 Beds ⋅ 3 Baths
Welcome to Tred Avon Point, an extraordinary waterfront property on a stunning point of land in the picturesque, historic town of Oxford, MD. Strategically sited only 25 feet to the waters edge on three sides to capture breathtaking views of the Tred Avon River & amazing western sunsets! Maritime inspired post & beam, open design visually connects the views to the space. The character & depth of the architecture blurs the lines between indoor & outdoor living. The abundance of the wood toned palette play with the hue & saturation of the natural landscape. The space easily transitions from entertaining friends & family to a respite for homeowners. The perfect vantage point to watch the boats, sailing races & watermen go by. Two primary suites on each level can be reached by the nautically designed wood spiral staircase or elevator. Gorgeous custom designed kitchen renovation done in 2019. The guest suite on the first level enjoys the views from its private deck. The rooftop cupula offers a stunning 360 degree birdseye view of the town & water. All season beauty can be enjoyed even in winter in front of the recently installed, high-end brick fireplace. The property includes a shared lot with a 7ft MLW deepwater multislip dock with lift. Perfectly located near dining, yacht club & marinas yet still invoking quiet & privacy. The included furniture, fine art & accessories create a move-in ready primary, 2nd home or vacation rental. Truly a one of a kind home!

121 Pier, Oxford

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

Selling Office: Benson & Mangold, LLC.

29328 Matthewstown Rd, Easton
$1,695,000
Premier Car Wash Facility in Easton This is an exceptional opportunity to acquire a highly successful car wash business with a large and loyal customer base. Located on one of Easton's busiest arterial roads, the facility enjoys excellent visibility and a high traffic count, ensuring a steady flow of customers. Key Features: **New Tunnel Installed in 2016:** The car wash is equipped with a state-of-the-art tunnel system installed in 2016, offering efficient and high-quality cleaning services. The equipment is well-maintained, ensuring smooth operations and minimal downtime. **Cutting-Edge Washify POS System:** In 2023, the business upgraded to a modern Washify POS system, enhancing the customer experience with a streamlined payment process and efficient service management. This system also offers valuable data analytics for business optimization. **Prime Location:** The car wash boasts a strategic location on a highly trafficked arterial road in Easton, providing excellent visibility and accessibility. The location attracts a steady stream of both regular and new customers. **Ample Waiting Area:** The facility includes a spacious and comfortable waiting area for customers, enhancing their experience while they wait for their vehicles to be serviced. **Office and Storage Spaces:** The property features well-organized office and storage spaces, providing ample room for administrative tasks and inventory management. **Business Potential:** With its modern equipment, prime location, and established customer base, this car wash is poised for continued growth. The business has a strong reputation in the community, and its recent upgrades ensure it remains competitive in the market. **Investment Opportunity:** This is a turnkey operation with significant potential for expansion. The business is ideal for investors looking to enter the car wash industry or existing operators seeking to expand their portfolio. **Financial Information:** Detailed financial information is available upon request for serious inquiries with signed NDA.

29328 Matthewstown Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

Morgans Point Drive, Oxford
$1,650,000
Discover the rare opportunity to own one of the Eastern Shore's finest waterfront parcels: Lot 5, an exceptional 4.18-acre homesite in the exclusive Morgan's Point community of Oxford, Maryland. This home site has an approved prec, and flood insurance is not required. Tucked along the serene Tred Avon River, this buildable waterfront gem offers expansive privacy and boundless potential, thanks to its generous scale and direct river access with 389 feet of rip-rap shoreline. Perfect for your custom estate, family compound, or legacy retreat, this sanctuary marries natural splendor with the refined charm of Talbot County's coastal haven. Spanning 4.18 acres, a fully usable lot provides versatile space to build your future home with breathtaking river vistas. Boasting direct frontage on the Tred Avon River with ample mean low water depth In a market where waterfront estates command premiums, this rare 4+ acre offering represents an unparalleled canvas for your vision. Nestled in the tranquil town of Oxford, this estate offers privacy and serenity while remaining conveniently close to shopping, dining, entertainment, medical facilities, and the Chesapeake Bay. Major commuter routes provide easy access to Washington, DC; Northern Virginia; Annapolis; and Philadelphia, with four major airports: BWI (71 miles), DC (74 miles), Dulles (112 miles), and Philadelphia (113 miles). Embrace the Eastern Shore lifestyle and live the Bay Life in unparalleled luxury!

Morgans Point Drive, Oxford

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

Selling Office: Benson & Mangold, LLC.

32137 Discovery Dr, Easton
$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:

Selling Office: Maryland Heritage Properties.

106 E Division St, Oxford
$1,625,000
4 Beds ⋅ 4 Baths
Oxford Cove – A truly rare offering, this extraordinary waterfront property is a study in serenity, privilege, and timeless eastern shore beauty. Surrounded by sweeping, uninterrupted water views to the south and east, the property captures the beautiful sunrise, immersing you in the everchanging light and rhythm of the tides. The main residence- graciously scaled with four bedrooms-embraces a refined yet relaxed aesthetic, designed for effortless living and seamless indoor-outdoor flow. Expansive terrace with a waterside pool, creates an idyllic setting for both quiet reflection and elegant entertaining. A charming one bedroom guest house/pool house offers a private haven for visitors, while a separate workshop provides space for creativity or collection. For the avid mariner, the property is exceptionally equipped with a private pier with a boat lift and a floating dock for kayaks and canoes- delivering immediate access to the finest waters of the Chesapeake Bay. Set in the historic village of Oxford,, one of the Eastern Shore’s most treasured enclaves, “Oxford Cove” offers a rare balance of seclusion and proximity. Here, life is defined by understated luxury, natural beauty, and the enduring allure of the waterfront.

106 E Division St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: TTR Sotheby's International Realty.

3750 Windy Hill Rd, Trappe
$1,600,000
3 Beds ⋅ 2 Baths
Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a range of buyers. It's l Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750 Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

3750-A Windy Hill Rd, Trappe
$1,600,000
Talbot County Farm With Country Home, Multiple Outbuildings And Tillable Ac This exceptional farm in Talbot County, Maryland, presents a rare opportunity to own a highly productive Eastern Shore property that combines agricultural value, quality improvements, and premier recreational appeal. Situated in a region known for its fertile soils and strong farming history, this 90 acre home farm offers a balanced mix of tillable acreage, improved structures, and wildlife habitat, making it well-suited for farming operations, outdoor recreation, and long-term land investment. The property has a proven track record of row crop production, including corn, soybeans, and wheat. A diverse and productive soil profile supports continued agricultural use, with primary soils consisting of Mattapex silt loam and Nassawango silt loam across the majority of the fields. Additional areas include Mattapex-Woodstown soils located within previously enrolled CRP sections and wooded portions of the farm. These soils are well regarded across the Eastern Shore for their consistency and productivity, providing a solid foundation for both commercial farming and conservation practices. The farm is zoned agricultural, allowing flexibility for a variety of uses, including crop production, recreational enjoyment, and potential enrollment in conservation programs. A large portion of the acreage is tillable, offering income potential or lease opportunities, while the remaining mix of timber and habitat enhances the property's recreational value. At the center of the property sits a well-maintained 1,966 square foot brick ranch-style home built in 1997. The residence offers three bedrooms and two full bathrooms and has been thoughtfully designed for both comfort and functionality. The main living area features a spacious living room with a knotty pine accent wall and bowed window that brings in natural light. The dining room includes chair rail detailing, tongue-and-groove paneling, and a built-in glass-front cabinet, creating a functional and inviting setting. The kitchen is well-appointed with wood cabinetry extending to the ceiling, crown molding, stainless steel appliances, and a center island with seating. A pass-through connects the kitchen to the dining area, improving flow for daily use and gatherings. French doors lead to a sunroom that overlooks the surrounding farmland and wooded edges, providing a consistent view of the property throughout the seasons. The primary suite includes a private bathroom with a deep jetted soaking tub. Additional features of the home include a covered front porch and an attached two-car garage. Supporting the agricultural operation are several outbuildings, including a milk house and two additional structures, highlighted by a custom-built steel building. These improvements provide space for equipment storage, workshop use, and potential game processing. From a recreational standpoint, this Talbot County farm offers strong hunting opportunities. A large pond, complete with a strategically placed hunting pit, is heavily utilized by migratory Canada geese during the season. The combination of open ground, water, and surrounding timber creates an ideal setup for waterfowl hunting. The property also supports a healthy population of whitetail deer, adding to its appeal for hunting and outdoor recreation. For buyers seeking additional acreage, an adjoining 82.54 acre tract is also available. This parcel includes a large portion of tillable ground, with sections previously enrolled in CRP. The additional tract provides an opportunity to expand the farming operation, increase recreational use, or secure additional investment acreage. It may be purchased together with the home farm or separately, offering flexibility for a r Property taxes shall be based on the acreage as determined by the Buyer’s survey and the acreage conveyed. Taxes will be prorated proportionally from the total parent tract of 582 acres.

3750-A Windy Hill Rd, Trappe

Listing courtesy of LPT Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

6905 Pea Nck, Saint Michaels
$1,595,000
4 Beds ⋅ 3 Baths
Nestled beneath a canopy of mature pines along the protected waters of Solitude Creek, this beautifully renovated waterfront retreat captures the timeless appeal of Maryland's Eastern Shore. Occupying approximately 2.745 private acres with nearly 200 feet of shoreline, the property offers an exceptional blend of privacy, boating, and relaxed luxury—just minutes from the historic waterfront town of St. Michaels. Renovated in 2020, the residence pairs classic coastal architecture with bright, contemporary interiors designed to embrace natural light and peaceful water views. Spanning approximately 2,100 square feet, the home offers four bedrooms and two-and-a-half baths, all arranged on a single level for effortless everyday living. Warm hardwood floors, custom millwork, and an inviting fireplace create an atmosphere that is both elegant and welcoming, while expansive windows frame the surrounding landscape and shimmering creek beyond. At the heart of the home, a beautifully appointed gourmet kitchen features custom cabinetry, granite countertops, a generous center island, and vaulted ceilings that flow seamlessly into open dining and living spaces. Created for gathering with family and friends, these light-filled interiors extend naturally onto an expansive waterside composite deck—an ideal setting for morning coffee, sunset cocktails, or alfresco dinners overlooking the water. The primary suite offers a beautifully finished bath, while three additional guest bedrooms provide comfortable accommodations for family and visitors. Every room reflects a timeless aesthetic that complements the property's serene waterfront surroundings. A private pier with a 9,000-pound boat lift and approximately 6 feet of mean low water offers exceptional boating for a wide variety of vessels. The property's seamless connection to the Choptank River and surrounding tributaries creates a waterfront lifestyle defined by both privacy and adventure. Whether arriving by boat or by car, few locations offer such a remarkable balance of seclusion, convenience, and direct access to some of the Eastern Shore's most celebrated waterways. A detached two-car garage with loft space above provides abundant storage and flexibility for hobbies, a workshop, or future possibilities. Mature landscaping, towering pines, and exceptional privacy complete this rare waterfront offering. The adjacent 3.21± acre waterfront lot to the north is also available for purchase at $895,000. Additional information is available from the listing agent upon request

6905 Pea Nck, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Benson & Mangold, LLC.

23776 Mount Pleasant Lndg, Saint Michaels
$1,550,000
3 Beds ⋅ 2 Baths
A wonderful opportunity to purchase an amazing one story waterfront home on an expansive 2.5 acre lot with western exposure on Broad Creek. Many upgrades have been done to make this a special home to enjoy your life of relaxation and pure enjoyment on the Eastern Shore of Maryland! Mount Pleasant is a very sought after St Michaels neighborhood with close proximity to the downtown historic area of great restaurants, museums and boutiques but no town taxes! You will love the upgraded gourmet kitchen with granite countertops, large center island, soft close cabinetry, broad water views with Samsung stainless steel appliances where you can make your favorite dishes to enjoy. Besides the kitchen, the large Sunroom is my other favorite room of the home with large windows on three sides for panoramic water views to enjoy nature, sunsets and waterfowl along with great access to the wrap around waterside deck through sliding glass doors. I think you will agree when you see it! You will find a bonus of lovely hardwood floors throughout the home and 2 full upgraded bathrooms as well as a double sided wood burning fireplace for the cooler nights on the Shore and we all know that last winter was colder than most so it was very much enjoyed! The property includes a heated workshop for hobbies as well as 2 other sheds for extra storage should you need it but also a screened waterside Gazebo for entertainment, wraparound deck, partially covered front porch and a deeded private dock on Broad Creek with 3+ MLW with multiple slips, a boat lift and a great place to catch some fresh crabs for dinner! What are you waiting for? This could be the one you have been waiting to come on the market!

23776 Mount Pleasant Lndg, Saint Michaels

Listing courtesy of Shore Living Real Estate. Contact:

Selling Office: Meredith Fine Properties.

St Michaels Rd, Newcomb
$1,540,000
20 acres off St Michaels Rd overlooking Newcomb Creek and out to the Miles River. Partially cleared shoreline offering expansive views of the water with beautiful sandy beaches and high elevation. During the summer, enjoy a quick boat ride to St. Michaels and all that the town has to offer. In the fall and winter, enjoy great goose and duck hunting. Approved for 6 bedroom SDA.

St Michaels Rd, Newcomb

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

216 E Chew Ave, Saint Michaels
$1,522,000
4 Beds ⋅ 4 Baths
PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is "move in ready" and ready to enjoy the Summer in Saint Michaels. 216 E Chew Ave. is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2-car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the "Conservatory". It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for spacious ground floor master suite as double closets and laundry plumbing already exist in addition to plumbing for a wet bar. Two sets of French doors open to either the front lawn or side yard for entertaining and outdoor grilling and dining. The side yard has a southern exposure and paver patios for a dining set and a fire pit. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the beautiful sunrises and sunsets. Now offered at a REDUCED PRICE, this home also has the lowest price per square foot for a Luxury, Waterview, in town home (under $450), making it a comparatively excellent value. This rare combination of location, quality, amenities and value cannot be replicated in the Saint Michaels market. Do not miss the opportunity to enjoy all that is special about Saint Michaels that comes with this special home.

216 E Chew Ave, Saint Michaels

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

Selling Office: Unrepresented.

7650 Ferry Cove Rd, Sherwood
$1,505,000
3 Beds ⋅ 4 Baths
Discover this stunning, custom-built waterfront Cape Cod nestled in Ferry Cove, Sherwood, a serene setting that is located right next door to a HGTV dream home! Newly constructed in 2024, this home offers the ultimate blend of luxury and comfort. Owners enjoy direct access to a beautiful sandy beach with 186 feet of waterfrontage on the Chesapeake Bay, creating the perfect space for both relaxation and entertaining guests. Step into the modern kitchen, which features ample storage, an oversized island, and an eye-catching glass backsplash. The open floor plan is designed for seamless entertaining, while a cozy fireplace provides warmth and ambiance on chilly evenings. The main level primary suite boasts breathtaking water views and an owner's suite that is sure to impress. Upstairs, a spacious loft opens to a second balcony deck that overlooks Ferry Cove—perfect for watching sunsets on warm evenings. Each of the two bedrooms includes a private bath, and the second room features a large bonus room situated above the oversized two-car garage. This flexible space offers numerous possibilities to suit your lifestyle needs. Set on over 5.5 acres, the property delivers privacy, water access, and the luxury of your own private sandy beach. There is also plenty of space for storage for your hobbies with a 36x42 pole barn added to the property in 2025. Experience modern amenities and an inviting coastal lifestyle in this exceptional retreat. Whether you seek a year-round residence or a getaway, this property offers an idyllic setting to enjoy the best of waterfront living.

7650 Ferry Cove Rd, Sherwood

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Meredith Fine Properties.

602 Landing Rd, Saint Michaels
$1,500,000
3 Beds ⋅ 3 Baths
Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home’s mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***

602 Landing Rd, Saint Michaels

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Unrepresented.

How much is your home worth?

Get instant property value now!