luxury houses for sale Talbot County, United States

Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation system.The superbly designed and crafted home offers an open floor-plan with 4 bedrooms and an office, 3.5 designer baths with heated floors,, a magnificent gourmet kitchen, upper and lower level living areas providing outstanding functionality. Breathtaking water- views and protected shoreline! This is an outstanding turn-key property that comes beautifully furnished !

NEW PRICE!! Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design. A welcoming front porch with a classic porch swing sets the tone before stepping inside to a light-filled interior featuring soaring vaulted ceilings and an open-concept floor plan designed for effortless everyday living and entertaining. Rich hardwood flooring flows throughout, complemented by a beautifully appointed chef’s kitchen, three well-proportioned bedrooms, and two elegantly finished full baths—all conveniently situated on a single level. Virtually every component of the home has been renewed, allowing the next owner to enjoy a truly turnkey property with the peace of mind that comes with comprehensive renovation. Outside, professionally designed landscaping surrounds a private backyard, creating a tranquil setting for outdoor dining, entertaining, or quiet relaxation. Ideally located in the heart of St. Michaels, the home is just moments from the town’s renowned boutiques, acclaimed restaurants, waterfront parks along the Miles River, the community pool, and the YMCA. Offering the rare combination of like-new construction and one of Maryland’s most desirable small-town settings, 803 New Lane presents an exceptional opportunity to enjoy Eastern Shore living at its finest.

Waterfront Living Reimagined in San Domingo Cove! Coastal influences, exceptional craftsmanship and meticulous attention to detail define this immaculate custom waterfront home. Dramatic two-story family room, soaring ceilings, walls of windows and an open staircase with stainless steel cable railings create a striking architectural statement. The second-story catwalk and loft overlook the main living area, while expansive windows frame the pool and water views beyond. Designed for both everyday living and entertaining, the chef's kitchen features quartz countertops, stainless steel appliances and extensive soft-close cabinetry. An oversized island provides generous prep space and seating, while the bright eat-in dining area and separate beverage station offer exceptional space for casual dining and entertaining. Bamboo flooring extends throughout the living spaces, adding warmth and continuity to the home's contemporary coastal design. The thoughtfully designed floor plan includes a first-floor primary suite overlooking the pool and San Domingo Creek, two additional ensuite bedrooms and a spacious bonus room with a full bath, ideal as a guest suite, home office, studio, media room or fourth bedroom. Outside, beautifully landscaped grounds frame the waterside pool and expansive patio, while the shared private pier with a boat lift and floating dock provides easy access for boating, kayaking and paddleboarding. An oversized three-car garage offers ample space for vehicles, storage and recreational equipment. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the St. Michaels Nature Trail. This distinctive property combines waterfront privacy with convenient access to the shops, restaurants, marinas and waterfront attractions of St. Michaels.

Unbelievable price reduction! Located about 12 miles from St Michaels, Neavitt is a charming village of 60+ houses at the end of a peninsula. The village has a park and playground, public landing with a launch for canoes, and an active community association that stages events and operates its own lending library. 6403 was renovated and expanded in 2011 and the layout adapted for modern living, with light-filled rooms, a cleverly updated floor plan, and direct views of Balls Creek. Features include a skylit first floor primary suite, spacious great room, an eat-in kitchen with Kraftmaid cabinets...but no St Michaels taxes! The two adjacent properties are being renovated. Each will be valued at over $900,000 when completed!

A masterpiece of Eastern Shore living, this Tidewater colonial estate is set against sweeping, panoramic views where the Choptank River, Chesapeake Bay, and three creeks converge. Showcasing breathtaking sunsets, the private oasis features a waterside pool, a main floor primary suite built in 2023, rich hardwood floors, and a detached 3-car garage. Tucked away in the desirable Ferry Neck enclave of Royal Oak, this estate offers the ultimate waterfront lifestyle. As you approach via tree-lined W. Ferry Neck Road, you enter Tranquility and are greeted by a circular driveway, mature landscaping, and a profound sense of privacy. Designed for classic Eastern Shore comfort, Tranquility offers impressive water perspectives from every room. The Main Level features gleaming hardwood floors, formal living room and dining room, gourmet kitchen with walk-in pantry, screened porch, sunroom, two wood-burning fireplaces, and two convenient powder rooms. The spectacular first-floor primary suite offers an exceptional private sanctuary. The Second Level boasts three well-appointed, ensuite bedrooms, ensuring privacy and comfort for family and guests. Structural Updates: The home also features a brand-new roof installed in 2023. Beyond the main residence, the 3-car detached garage ideal for car enthusiasts has an upper level that presently serves as an office and a substantial storage room. Tranquility truly provides the best of both worlds. For just under three acres, the property's privacy is unmatched. The endless water views , the close proximity to the sandy bottom shore, the pier with water, electric, and boat lift, all contribute to the perfect retreat. Furthermore, the convenience to Oxford by boat or the Bellevue Ferry, as well as a 15-minute car ride to both Easton and St. Michaels, define the perfect Talbot County location.

Motivated Seller and 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.

Major Price Improvement! 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.

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.

Welcome to Holly House – A Rare Waterfront Legacy Estate on the Miles River Holly House presents an extraordinary opportunity to own one of the Upper Miles River’s most captivating waterfront estates. Set gracefully on five spectacular, beautifully landscaped acres, this contemporary French-inspired residence offers approximately 150 feet of private shoreline, panoramic water views, and unforgettable sunsets. Designed for effortless one-level living, the impeccably constructed brick home blends timeless architecture with endless potential. The current residence features a gracious living room, formal dining room, inviting den, spacious kitchen, sunroom, private office, study/optional bedroom, an elegant waterfront primary suite with dual bathrooms and separate walk-in closets, two additional en-suite bedrooms, a powder room, unfinished basement, and an attached two-car garage. Outdoor living is equally impressive. A waterside 8-foot-deep swimming pool, expansive terrace overlooking the Miles River, private 150-foot pier, tennis court, and oversized outbuilding create an exceptional setting for entertaining, recreation, and peaceful waterfront living. Whether you choose to thoughtfully refresh the existing home or create a spectacular new estate, Holly House offers an unmatched canvas to realize your vision. The property has also received its long-awaited approval from Talbot County for a new 5-6 bedroom septic system, allowing construction to begin immediately. Fully permitted architectural and structural plans, along with a stunning full-color exterior fly-through video, are included with the sale. For those wishing to personalize the design, the approved plans can be modified to reflect a buyer’s individual style and lifestyle needs. This is more than a home—it’s a once-in-a-generation opportunity to create a landmark waterfront estate in one of the Eastern Shore’s most coveted location See document panel for floor plans for large addition and another for one level living

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

LOCATION, CHARM, and beautifully RENOVATED!!!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 porch 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 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. *Roof- 2011, new siding, new boiler, renovated kitchen and primary bath, encapsulated basement, redecked pier, plus more1!-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.

Stock Range Farm spans 350 acres of prime waterfront and is available for purchase in its entirety OR with reduced acreage including the main residence, if the buyer so chooses. Options include selling main residence with 20+ acres, 40+ acres, and 100+ acres. **CALL listing agent for more information! The property is free of easements and includes development rights, subject to all applicable Talbot County zoning regulations. With vast working farmland and resort-style amenities, this rare gem truly combines luxury and sophistication with seclusion and tranquility. The 12,000+ sq. ft. primary residence showcases the breathtaking stylings of acclaimed architect Peter Jay Zweig and exemplifies the pinnacle of luxury living. Built by Ilex Construction, striking architectural details and unparalleled craftsmanship are demonstrated throughout, seamlessly integrating with the breathtaking beauty of the landscape. This magnificent home is filled with an abundance of natural light and boasts panoramic views, thanks to soaring glass walls that overlook the tranquil waters of Pickering Creek, expansive fields, and picturesque vineyards. The thoughtfully curated interior includes spacious living areas, a stunning owner's wing that offers privacy and comfort, and a separate guest wing that features a full kitchen, providing ideal accommodations for family and visitors. High-end features abound, including a gourmet kitchen, recreation room complete with kitchen and bar for entertaining, full exercise room, 5 car garages, elevator, heated limestone floors, Venetian plaster walls, and multiple outdoor decks. At every turn, this property exudes the loving care it has received. Outside, the resort-style amenities include a large, heated infinity pool, complete with waterfall and hot tub, stunning pool pavilion with full outdoor kitchen, stone fireplace, and two TV’s and AV system. Along with the waterside tennis/pickleball court, tranquil koi pond, and private pier with 4-5’MLW, the opportunities for outdoor fun and relaxation are boundless. In addition is the beautifully renovated 4-bedroom guesthouse with views of the vineyards, providing comfortable accommodations for family and friends. A well-equipped 9-stall barn includes a tack room/office, kitchenette, and a riding ring, complemented by 20 acres of fenced pastures. There is also a 3-4 BR caretaker's home, a fully outfitted greenhouse, large equipment barn complete with an office and full workshop, and hay barn for storage. The property also offers excellent hunting opportunities, making it a versatile retreat for outdoor enthusiasts. The highlights of this extraordinary property continue through every acre, including sweeping landscapes and hardscapes, 200 acres of working farmland, 5 acres of vineyards, and a 6-acre stocked pond with private island. Unparalleled in its mix of tranquility and luxury, the opportunity to experience the very best of the Eastern Shore’s refined lifestyle and natural beauty is only possible at Stock Range Farm. Please don't drive in driveway as there are security cameras and alarm. All appointments must be made with listing agent and additional information and details are available upon request.

Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick residence enjoys sweeping views of the Tred Avon River from nearly every room. Thoughtfully designed for one-level living, the home combines classic architectural character with extensive updates by the current owners and a floor plan that is both comfortable and highly functional. The interior has been carefully updated while retaining the character of the original home. Improvements include beautiful hardwood flooring, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new roof (2017), new deck, and numerous additional enhancements. A complete list of improvements is available from the listing agent. The three-bedroom, three-bath residence includes a spacious waterside primary suite with a generous ensuite bath, ample closet space, and additional storage. Two additional bedrooms share a full bath and are privately positioned for family or guests. The main living spaces take full advantage of the river setting. The generously proportioned living room features a wood-burning fireplace framed by custom built-in bookshelves, while the formal dining room provides a gracious setting for entertaining. The renovated kitchen features a large center island and premium appliances and opens directly to the family room, where a wood stove, breakfast area, and wall of built-in bookshelves create a comfortable gathering space. An adjoining bonus room offers exceptional flexibility and could serve as a walk-in butler’s pantry, hobby or craft room. The enclosed sunroom, with its attached full bath, is a particularly appealing space from which to enjoy the expansive water views. An oversized attached two-car garage provides convenient access to extensive attic storage that runs the full length of the house. A detached climate-controlled studio adds valuable additional space for an art studio, home office, workshop, or other uses. Outside, the property is equally well appointed. A gunite pool, added in 2020, is surrounded by extensive hardscape and fencing, offering a private setting for outdoor enjoyment. The new dock, completed in 2024, includes two slips, a floating dock, and approximately 6'MLW, providing excellent access to the Tred Avon River for boating and fishing. With its coveted location, private acreage, substantial improvements, exceptional water access, and panoramic Tred Avon River views, this is a distinctive Eastern Shore waterfront property that offers both privacy and a relaxed, livable setting.

Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

Set on 31 private acres along the peaceful waters of Hunting Creek, this exceptional Eastern Shore estate combines timeless architecture with modern sophistication. With over 1,000 feet of waterfront and approximately 6 feet of mean low water, the property offers deep-water access, stunning views, and an unmatched sense of privacy. The five-bedroom, five-and-a-half-bath residence has been completely renovated from top to bottom, showcasing impeccable finishes, custom millwork, and thoughtfully designed spaces throughout. Sunlight pours through large windows that frame panoramic views of the creek and surrounding landscape. The home features two luxurious primary suites, each offering a private retreat with refined finishes, spa-inspired baths, and generous closets. Two additional bedrooms share a beautifully designed ensuite bathroom, while a first-floor bunk room with its own bath provides the perfect space for guests. Outside, the saltwater pool overlooks the water, surrounded by manicured lawns and mature trees that extend to the shoreline. A long, tree-lined driveway creates an impressive approach to the home, setting the tone for the peaceful retreat that awaits. Located just minutes by car to Easton and St. Michaels—and even closer by boat—this Hunting Creek estate captures the very best of the Chesapeake Bay lifestyle: elegance, tranquility, and effortless connection to the water.

Beautifully positioned as an end-unit with southern field views, this townhouse offers 2,433 square feet of living space with 4 bedrooms, 3 full baths, and 1 half bath. Recently painted throughout, the home features gorgeous hardwood floors throughout the first floor and a well-designed floor plan for everyday living and entertaining. The open-concept living and dining areas connect to the kitchen, while two-story ceilings, skylights, and large windows provide abundant natural light. A gas fireplace is the focal point of the main living area. The first-floor primary suite includes two walk-in closets and an ensuite bath. A den, true laundry room, and powder room complete the main level. The upper-level loft overlooks the main living area and provides flexible space for a home office, sitting area, or reading nook. One guest bedroom has an ensuite bath, while two additional bedrooms share a second full bath—making this the only townhouse currently available with two full bathrooms on the upper level. Ample walk-in attic storage provides additional space for seasonal items and storage. The landscaped backyard overlooks open fields and is bordered by mature trees, offering privacy and pleasant views. An attached two-car garage adds everyday convenience. Located in Cooke's Hope, residents enjoy access to ponds, walking trails, tennis courts, a fitness center, dog park, picnic pavilion, and a community dock, all just minutes from downtown Easton.

Brand New Home Ready for Move-In! Step into this stunning two-story home designed for modern living, offering the perfect blend of style, comfort, and functionality. The open-concept layout features upgraded lighting, hardware, and railings throughout, complemented by a premium exterior color package. The gourmet kitchen includes a large island, walk-in pantry, and stainless steel appliances, flowing seamlessly into a bright and spacious family area ideal for entertaining. The main level features a private primary suite with a luxurious en suite bath, along with a convenient half bath and laundry room. Upstairs, you'll find three additional bedrooms and two full baths, providing plenty of space for family or guests. Located in Lakeside at Trappe, just minutes from Easton and Cambridge, this amenity-rich community offers a pool, fitness room, and dog park.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. 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 76+-acre waterfront estate 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. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

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 114+-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.

See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. 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 76+-acre waterfront estate 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. With nearly 4,000 feet of riprapped shoreline, “Bolton Farm” represents a rare offering on Maryland’s Eastern Shore.

This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.

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

Welcome to this extraordinary waterfront estate, gracefully sited on 6.92 lush, landscaped acres with sweeping views of Leadenham Creek. Designed by architect Alan Meyers, constructed by Ilex Construction, and masterfully styled by interior designer Skip Sroka, this 10,000+/-sq. ft. residence is a showcase of timeless craftsmanship and elevated design. The custom brick exterior is crowned by a new cedar shake roof with copper caps and bands, creating a refined profile that blends seamlessly into the natural surroundings. Double mahogany doors with full-view, artistically designed leaded glass open to a luminous foyer with immediate, breathtaking views of the water. Inside, riff-sawn red oak floors flow through expansive formal and informal living areas. Vaulted ceilings add architectural drama, while curated lighting provides warmth and sophistication throughout. The main level features formal living and dining rooms, a stunning gourmet kitchen, and multiple spaces designed for both relaxation and entertaining. The kitchen is a chef’s dream—equipped with top-tier appliances, a large center island, sitting area with fireplace, and an eat-in dining space. Just off the kitchen, a beautifully crafted screened porch with an octagonal ceiling offers a peaceful, year-round retreat. A walk-in pantry and custom-designed bar enhance both function and hospitality. Also on the main level is a striking private office wrapped in Anigre wood paneling, featuring custom built-ins and a circular backlit ceiling. A separate guest wing includes a spacious family/recreation room with spectacular river views and two guest suites with ensuite baths. The primary suite enjoys its own private wing, with serene water views, a cozy sitting area and fireplace, dual walk-in closets, and an elegant dressing hall. The luxurious, spa-inspired bath includes a soaking tub and glass-enclosed shower, creating a true sanctuary of comfort and privacy. Upstairs, dual wings on opposite sides of the home offer two additional guest suites with ensuite baths, a bonus/music room, and a dedicated fitness room. Five fireplaces handcrafted by Collecio Brothers Stone Masons bring warmth and timeless character throughout the home. Modern systems include geothermal heating and cooling, a new Honeywell HVAC control system, Vantage lighting automation, a fully encapsulated crawlspace, and a Generac generator. In addition to the oversized 3+ car attached garage, a separate detached two-bay garage offers equipment storage, a workshop, and a half bath. Outdoors, the estate is designed for both grand entertaining and quiet waterfront living. Features include an extended waterside patio, beautiful pool house with a fully equipped outdoor kitchen, two dressing rooms, an outdoor shower, and an in-ground pool with heated spa. Over 1,000 feet of riprapped shoreline and a 210-foot private dock with two slips, a floating dock, and 7-foot MLW offer direct access to the Chesapeake Bay. This remarkable estate was built for luxurious living, effortless entertaining, and a deep connection to the natural beauty of Maryland’s Eastern Shore. *Current taxes are based on homestead credit.