luxury property for sale Tilghman, United States

Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio A Short-term Rental application is underway. Ask owner for details. Some furniture conveys

Bolton Farm, available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 115-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated entrance and mature tree-lined drive create a gracious approach to the main residence while highlighting the property’s stunning water views, natural beauty with mature landscaping and specimen trees. The generous porch-front manor house blends classic architecture with relaxed coastal style with newly updated kitchen and baths. The expansive waterside living room features brick flooring and floor-to-ceiling windows and French doors that flood the space with natural light and showcase stunning water views. A formal living room and dining room sit adjacent, seamlessly connecting the rooms. The well-appointed kitchen and family rooms include a large center island, breakfast area, wet bar, high-end stainless appliances, built-ins and fireplace. A waterside screened porch extends the living space outdoors, perfect for dining and relaxation. The main floor also offers a guest or owners suite with an en-suite marble bath. The paneled mudroom and powder room complete this floor. Upstairs, the hall landing provides access to the generous primary suite which includes built-ins and a beautifully appointed en-suite marble bath. Two additional bedrooms are connected by a renovated bath. The oversized fourth bedroom suite includes a sitting room, en-suite bath and stunning views. This floor is completed with a laundry room. The third floor provides two additional guest bedrooms and a shared full bath. The lower-level basement offers excellent storage. The charming brick guest house, circa, 1790 has two-bedrooms featuring a new cedar shake roof, center hall, high ceilings, wood floors, moldings, full kitchen and renovated bath. The Equestrian and agricultural amenities include a new four-stall barn with loft game room, fenced pastures, a wooded forest, two equipment barns, and a greenhouse/garden shed. Meandering paths connect the main house, guest house, and barns. The property includes a parcel across from the main entrance to ensure additional privacy. The outdoor features give the farm the opportunity for large family occasions with numerous areas to gather and enjoy the stunning sunsets. Features include a waterside pool, covered pavilion, private tennis court, two ponds, a pier and hiking trails throughout the expansive grounds. An adjacent 37+-acre waterfront parcel (included in the total acreage) has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

This exceptional waterfront cottage is set on two private acres and offers sweeping sunset views over the Choptank River to the Chesapeake Bay. Completely renovated from crawl space to roof, the home features over 2,600 square feet of beautifully finished living space with three bedrooms and three full baths. The interior showcases renovated kitchen and baths, complemented by extensive custom finish-work throughout. There is a detached garage with metal roof and second floor storage and gravel circular driveway with ample parking. Improvements on this home include an encapsulated crawl space, new roof, siding, multiple premium sliding glass doors and windows, all valuable upgrades that enhance both style and energy efficiency. The grounds have been thoughtfully transformed with curated shrubs, trees, and perennials that highlight the existing landscape, concrete pool, and pergola, creating an ideal setting for outdoor relaxation and entertaining. Enjoy easy boating access just 10 minutes to Oxford and 15 minutes to Tilghman, while by land the property is ideally situated between Easton and St. Michaels. Enjoy the protection of high property elevation (no flood insurance required) with a sturdy rip-rapped shoreline, beautiful sandy bottom, and a private L pier with two new boat lifts. 24878 W. Ferry Neck Road offers the perfect blend of privacy, comfort, and Eastern Shore waterfront living on the Choptank River. Co-listed by Rob Lacaze of TTR Sotheby's International Realty and Janet Larson of Benson and Mangold.

Welcome to 107 E. Chestnut, a beautifully restored circa-1870 residence nestled in the heart of St. Michaels. From the moment you step inside, you are greeted by the perfect blend of timeless character and modern sophistication, where original architectural details have been thoughtfully preserved and seamlessly integrated with extensive renovations. The spacious entry combines an elegant living and dining area, featuring wood floors, a gas fireplace flanked by custom built-ins, and custom shutters have been added to each window. Throughout this home you will find historic charm and craftsmanship are evident at every turn. At the rear of the home is a full bath and designer kitchen that opens to the family room highlighted by soaring ceilings and an abundance of windows that fill the space with natural light year round. This inviting area flows to the screened-in porch and brick patio, creating the perfect setting for indoor-outdoor living. Beyond the patio lies a garden oasis featuring lush landscaping, colorful perennials, pond and large detached shed/storage building. The current owner has worked with the Town of St. Michaels to obtain approvals for converting this structure into a separate guest suite, and architectural plans are available for the next owner. The second level offers two generously sized bedrooms and a beautifully redesigned full bath. The rear bedroom includes an overlook of the family room, which offers additional space that could easily be transformed into a private sitting area, dressing room or walk-in closet. The front bedroom features a dedicated dressing room and oversized closet, providing the potential to create an en-suite bath. Both rooms offer cathedral ceilings with exposed rafters adding to the rooms architectural interest and charm. This is a true gem in historic St. Michaels that includes off street parking. Don't miss this exceptional opportunity to own a home in the one of the most popular towns on the Eastern Shore.

205 Cherry Street is one of the most prestigious addresses in historic St. Michaels. Originally built as a single-family residence, it currently operates as an Inn. It is being marketed both as a 7 bedroom inn and also as a single family residence, offering 5 bedrooms (including the first floor primary bedroom suite). The original living room/office with fireplaces on the first floor are currently being used as bedrooms for the inn but can easily be converted back to living areas. (see virtual images in photos). The beautiful front lawn provides a park-like setting with one-of-a-kind water-views overlooking St. Michaels Harbor. There is also a 2 bedroom, 2 bath guest cottage on the property. The property directly across the street (FKA The Hambeleton Inn) was purchased as a private residence and serves as a second home to its owner. This is a wonderful opportunity to own a landmark historic inn or primary or second home in the heart of St. Michaels.

Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for relaxing, entertaining and enjoying life on the water. Inside, a gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Property is offered as part of an estate and is being sold as is.

Improved Pricing ! Make this Charming Oxford Gem your new home. This well-maintained 4-bedroom, 2.5-bath home offers a comfortable blend of classic style and Eastern Shore charm in a prime Oxford location. Whether you're looking for a first home, a retirement retreat, a weekend escape, or an investment property, this inviting residence is designed to fit a variety of lifestyles. Tucked away on a quiet cul-de-sac, it features welcoming indoor and outdoor spaces ideal for year-round living, with plenty of room to transform/grow and make it your own. Inside, the foyer opens to spacious living and dining areas featuring Brazilian cherry hardwood floors, vaulted ceilings, and abundant natural light. French doors lead to a flexible room that can serve as a first floor guest room or home office. The living room flows into a large kitchen with a bright breakfast room and an adjacent dining area, making it ideal for casual mornings and gatherings with family and friends. Just off the kitchen, a half bath and a large family room provide added convenience and direct access to a spacious backyard. Upstairs, the primary suite offers a peaceful retreat with a large walk-in closet and an en-suite bath featuring double sinks, a Jacuzzi tub, and a walk-in shower. Two additional bedrooms share a generous hall bath with double sinks and a tub-shower combination. A second-floor bonus room adds even more flexibility and can be used as a playroom, home gym, game room, or private retreat. Outdoor living is equally appealing, with a front and back decks, patio with fire pit and a fully fenced backyard. One of the largest yards in the neighborhood, with plenty of room for a pool. Located just a short walk from downtown Oxford, the home offers easy access to local shops, restaurants, the waterfront park, Oxford Market, and Scottish Highland Creamery. Move-in ready and full of character, this Eastern Shore gem delivers exceptional value. Move-in ready and full of character, this Eastern Shore gem offers the best of Oxford living at an exceptional value. Recent Upgrades include: A new roof installed in August 2025, Stainless-steel appliances less than two years old, encapsulated crawlspace.

Envisioned for a premier waterfront setting along the Tred Avon River, this exceptional TO-BE-BUILT coastal residence by award-winning firm - Pacquin Design Build, presents a rare opportunity to create a refined Eastern Shore retreat on a remarkable 4.18-acre homesite within the exclusive Morgan’s Point community of Oxford. Thoughtfully designed in classic shingle-style architecture, the proposed home is perfectly oriented to capture sweeping river views, abundant natural light, and a seamless connection between indoor and outdoor living. The proposed floor plan balances timeless elegance with everyday comfort, featuring open yet well-defined living spaces that flow effortlessly toward the waterfront. A chef’s kitchen anchors the main level, opening to inviting gathering areas and expansive terraces overlooking the river. Walls of glass frame the ever-changing water views, while a main-level bedroom suite offers flexibility for guests or convenient single-level living. The upper level is designed as a private retreat, highlighted by a serene primary suite with elevated river views and additional bedrooms thoughtfully arranged for family and guests. Outdoors, the concept plan showcases a resort-inspired setting with a waterfront pool, generous patios, and sweeping lawn leading to approximately 389 feet of rip-rap shoreline. Boating, paddleboarding, and relaxed days by the water are central to the lifestyle this property affords. The lot is fully usable, offers ample mean low water depth, has an approved perc, and does not require flood insurance, making it an ideal canvas for a custom estate, family compound, or legacy retreat. Lot can be purchased separately for $2,250,000 (MDTA2012470) Set within the natural beauty and refined charm of Talbot County, and just moments from the Chesapeake Bay, this extraordinary offering combines privacy, scale, and location. A rare chance to bring a bespoke coastal vision to life on one of the Eastern Shore’s most desirable riverfront parcels—perfect as a year-round residence or second-home sanctuary. Located 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!

Set along the peaceful shores of Chews Creek, this beautifully renovated waterfront home delivers the quintessential Eastern Shore lifestyle, where spectacular sunsets, endless water views, and effortless indoor-outdoor living take center stage. Thoughtfully updated throughout, the home offers five bedrooms and four full baths with a layout designed for both comfortable everyday living and exceptional entertaining. Hardwood floors flow throughout the main level, while abundant natural light and an open floor plan create a bright, inviting atmosphere. At the heart of the home, the gourmet kitchen features a large center island, Silestone countertops, Sub-Zero refrigerator, Viking gas cooktop, Miele built-in espresso maker, beverage refrigerator, nugget ice maker, stainless steel appliances, and ample space for gathering with all your guests. The kitchen opens seamlessly to the living and entertaining spaces, all oriented to capture beautiful water views. The main level offers tremendous versatility with a first-floor bedroom, dedicated office space, formal dining room accented by designer wallpaper, and an elegant living room with fireplace. A spacious waterside family room provides the perfect setting to relax, entertain, and enjoy the ever-changing waterfront scenery. Upstairs, the waterside primary suite serves as a private retreat overlooking the creek. Additional guest accommodations include generously sized bedrooms and a large bunk room ideal for hosting family and friends. Beautifully renovated baths feature custom tile work, dual vanities, and oversized walk-in showers. Outdoor living is equally impressive. A large waterside deck overlooks the heated and cooled salt-water swimming pool, creating a resort-like setting for summer gatherings. The outdoor amenities also feature a private outdoor spa/hot tub for year-round enjoyment. Professionally landscaped grounds, mature plantings, and multiple outdoor entertaining areas enhance the property’s relaxed waterfront lifestyle. Additional highlights include a detached two-car garage with an additional office space/bonus room,, roof less than ten years old, updated finishes throughout, and a setting that showcases some of the most breathtaking sunset views on Maryland’s Eastern Shore. Whether enjoying a quiet evening by the pool, entertaining guests on the deck, or watching the sun disappear over the water, this exceptional waterfront property offers a rare opportunity to experience Kent Island living at its finest.

Escape to this rare waterfront retreat on Brooks Creek in Cambridge, offering Two Thousand ft of water frontage with sandy beaches, Private pier and Pond. The property features a Four Bedroom, Two and One half Bath Colonial-style main home plus a Three Bedroom, Two Bath guest house with great potential. Enjoy a large barn, pond, and multiple outbuildings, ideal for hobbies, storage, or fishing. With serene views, abundant space, and endless opportunities, this property blends waterfront living with country charm.

LOCATION and CHARM! Set on 2.32 glorious acres overlooking Dixon Creek, this beautifully and lovingly maintained 1915 residence offers timeless character, refined comfort, and exceptional waterfront living. Original hardwood floors run throughout much of the home, while expansive windows bathe the traditional floor plan in natural light and frame expansive water views from nearly every room. The main level features gracious formal living and dining rooms, a gourmet kitchen with a beautiful center island and top-tier stainless appliances, and a welcoming family room with wood-burning fireplace. Custom built-ins are thoughtfully integrated throughout the home, reflecting quality craftsmanship and attention to detail. Upstairs, the waterside primary suite offers a fireplace, dual walk-in closets and a luxurious ensuite bath with soaking tub and glass-enclosed shower. Two additional guest bedrooms include one with an ensuite bath and another with access to the hall bath. The third level provides a small loft style BR /flexible bonus room, ideal for an office or studio. Outdoor living is equally inviting, with a waterside screened porch, a poolside screened patio with wet bar, and an additional open deck off the dining room—perfect for enjoying the tranquil setting. The beautifully landscaped grounds feature mature trees, lush plantings, and extensive hardscaping, anchored by a stunning gunite pool with expansive deck and surrounding gardens. Additional structures include a charming former icehouse (currently used as a storage shed) and a larger outbuilding once used as tenant quarters. An attached 2-car garage and a full encapsulated basement offer excellent functionality and versatility. With 280 feet of natural shoreline, a private pier with two slips, boat lift, and 3.5–4' MLW, this property captures the essence of Eastern Shore waterfront living. *Septic replaced in 2020 and is for 4 bedrooms-owners have plans for proposed first floor primary suite where existing south side porch currently is.

This move in ready five bedroom, two and a half bath home sits on a private lot in southern Anne Arundel County, with the space, updates, and outdoor living that today's buyers are prioritizing. Inside, the kitchen, bathrooms, living areas, and bedrooms have all been enhanced in 2026 with fresh paint, flooring, cabinetry, countertops, and more. The primary suite includes a walk-in closet and an en suite bath with a soaking tub, stand up shower, and double sink vanity, all overlooking the in ground pool below. The finished walkout basement adds a large family room and a bonus room with a window, well suited to a home office, gym, or guest space. Outside is where the property earns its keep: a covered front porch, a screened in back porch, extensive hardscaping, an in-ground pool with a storage shed, and private walking trails through the wooded backyard. It's a layout built for entertaining as much as for quiet mornings with coffee. The driveway offers ample parking for guests connecting to a two car garage. Tracys Landing puts you minutes from marinas, waterfront dining, and Chesapeake Bay access, with Annapolis, Washington, D.C., and Northern Virginia all within reach.

Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway. Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground, basketball court, and picnic areas. Conveniently located near local marinas, waterfront dining, parks, and Chesapeake Bay attractions, with easy access to Annapolis, Edgewater, Washington, D.C., and Baltimore. A great opportunity to enjoy a water oriented lifestyle in one of Southern Anne Arundel County's popular waterfront communities.

Experience the best of Annapolis living in the sought-after, amenities-rich community of Fishing Creek Farm. Perfectly positioned to capture beautiful water views and surrounded by lush lawns and mature landscaping, this handsome brick-front Colonial offers a rare combination of timeless architecture, flexible living spaces, and an exceptional neighborhood lifestyle. A gracious foyer welcomes you into formal living and dining rooms designed for entertaining, with the current living room serving as a billiards room. At the heart of the home, the bright white kitchen features quartz countertops, abundant cabinetry, and a sunny breakfast nook that flows seamlessly into the impressive family room with soaring vaulted ceilings, a fireplace, and easy access to the patio and expansive backyard. Whether hosting summer gatherings or enjoying a quiet evening outdoors, the spacious front and rear yards provide room to relax, play, and take in the peaceful surroundings. Designed for both convenience and versatility, the main level includes a spacious primary suite, while a second upper-level primary suite enjoys sweeping water views and creates an ideal retreat for owners or guests. Two additional bedrooms share a well-appointed hall bath, providing ample space for family and friends. The partially finished lower level offers additional living space, generous storage, and easily accessible crawl spaces. Life in Fishing Creek Farm extends far beyond the property itself. Residents enjoy one of Annapolis' most coveted waterfront communities, complete with a community marina, swimming pool, sandy beach, tennis and pickleball courts, and year-round social activities. Located on the Annapolis Neck peninsula between the South River and the Chesapeake Bay, this special neighborhood offers a peaceful waterfront setting just minutes from downtown Annapolis, Eastport, and major commuting routes to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., and the Eastern Shore. A wonderful opportunity to enjoy the Chesapeake lifestyle in one of Annapolis' most desirable communities. Welcome Home!

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!

Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along the water’s edge. Inside, the home unfolds across three levels with a thoughtfully designed four bedroom, four bath layout that offers both flexibility and comfort. A private bedroom and full bath on the entry level provide the perfect space for guests or a quiet home office. The main living level is designed for seamless everyday living and entertaining, highlighted by a warm and inviting living room with a gas fireplace that adds both comfort and ambiance. The upper level features two additional bedroom suites, including a serene primary retreat complete with its own gas fireplace. An elegant touch that enhances the sense of relaxation and retreat. Expansive windows frame captivating views over the marina and out to the Chesapeake Bay, filling the home with natural light and creating an ever-changing backdrop of boating activity and open water. As the day winds down, the setting truly comes to life with breathtaking sunsets that paint the sky and reflect across the water. An experience to be enjoyed from both the interior living spaces and outdoor areas. High-end finishes and a modern, open-concept design elevate the interiors, while the beautifully appointed gourmet kitchen and well designed baths enhance both form and function. Every detail has been curated to deliver a low-maintenance, lock-and-go lifestyle without compromising on luxury. Ideally positioned within walking distance to waterfront dining, including Libbey’s Coastal Kitchen & Cocktails and Knoxie’s Table, residents also enjoy immediate access to marina amenities, scenic walking paths, and the relaxed rhythm of life on the Bay. Sunset Wharf offers a rare opportunity to own a newly completed residence in a thoughtfully designed waterfront community where every day feels like a getaway. Welcome Home!