luxury houses with terrace for sale Saint Michaels, United States

Beautifully positioned on 2.41 acres overlooking the coveted Miles River, this exceptional 4BR/4.5BA coastal residence offers sweeping water views, light-filled interiors, beautifully cultivated gardens, and an impressive array of waterfront amenities. From the moment you enter, your eye is drawn through the home to the Miles River beyond, with abundant natural light creating a serene and inviting setting. Beautiful hardwood floors, crown molding, recessed lighting, and thoughtfully appointed interiors enhance the home’s refined yet relaxed coastal character. The waterside living room is centered around a gas fireplace, with sliding doors opening to the expansive back deck and framing the river beyond. The gourmet kitchen features premium appliances, a breakfast bar, beverage bar with wine storage, and spacious eat-in dining area, ideal for both everyday living and entertaining. The formal dining room accommodates up to 14 and is beautifully appointed with chandelier lighting, crown molding, and chair rail. A powder room and large laundry room with an adjoining full bath add convenience to the main level. The main-level primary suite is a private retreat, offering a generously sized bedroom with doors opening to the back deck, an expansive walk-in closet with custom built-ins, and a luxurious bath with dual-sink vanity, glass-enclosed walk-in shower, and jetted tub. Upstairs are three additional bedrooms, including one with an ensuite bath, while two guest bedrooms share a full hall bath. A large bonus room with separate exterior access provides excellent storage and additional possibilities. An oversized attached two-car garage includes a dedicated workshop area. Equally impressive are the grounds, where mature trees, lush landscaping, colorful flowering gardens, and beautifully maintained garden beds create an exceptional setting throughout the seasons. Extensive hardscaping complements the landscape and leads to the waterfront amenities, including an in-ground pool surrounded by an expansive patio and pool deck, along with a large deck overlooking the river. Beyond, 308’ of riprapped shoreline, a private pier with two slips and floating dock, approximately 3.5' MLW, and wide-open Miles River vistas complete this extraordinary Eastern Shore waterfront property, designed to be enjoyed equally indoors and out. Remarks - Office Private 4000 left

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.

This is more than a waterfront estate - it is an invitation to experience one of Maryland's Eastern Shore's most treasured lifestyles. Step from your private dock onto your boat, and within minutes, you will be cruising the scenic waters of the Wye River and Eastern Bay. Renowned for exceptional crabbing and fishing, the Wye River offers endless opportunities to pull crab pots, teach the kids to fish, or spend memorable days exploring the waterways. At home, your private beach provides the perfect setting for swimming, kayaking, relaxing along the shoreline, and gathering with family and friends to watch spectacular sunsets over the bay. The property's private lighthouse - a truly distinctive feature that conveys with the home - creates an unforgettable backdrop for entertaining, peaceful evenings, and panoramic water views. When it is time for dinner, shopping, or a change of scenery, historic St. Michaels is just a 10-minute boat ride away. One of the Eastern Shore's most beloved waterfront towns, it is known for award-winning restaurants, charming boutiques, picturesque marinas, and year-round events. Whether you are boating across the Wye River and Eastern Bay, enjoying world-class crabbing, fishing with the family, or ending the day with a sunset from your private beach or lighthouse, this property captures waterfront living at its finest - a rare Eastern Shore experience few homes can offer.

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!

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 historic home was built by members of the Neavitt family, for who the village was named. The present owner bought it in 1999 and renovated and updated it 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 Some furniture conveys

Current owner/architect was in process of large upscale renovation when planes changed. The property has received Talbot County approval for a new 5-6 bedroom septic system. Fully permitted architectural and structural plans , along with a full-color exterior fly-through video The approved plans provide additional options for future improvements and may be modified to suit a buyer’s preferences. See the document panel for floor plans showing the proposed large addition and an alternative one-level living design.

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.

Coveted location between Easton and St. Michaels with breathtaking Tred Avon River views!!!!Set on 3.3 private acres in the established community of Travelers Rest, this beautifully restored brick home enjoys water views from nearly every room. The thoughtfully designed one-level floor plan is comfortable and easy to live in, while the classic character of the original home has been complemented by extensive updates from the current owners. A substantial attic runs the full length of the house, offering excellent storage and the potential for future expansion. The three-bedroom, three-bath home has been updated throughout, with beautiful hardwood floors, a renovated kitchen, new HVAC system, Rinnai tankless water heater, new deck, 2017 roof, and numerous other improvements. The spacious waterside primary suite has a generous ensuite bath, ample closet space, and additional storage, while two privately situated bedrooms share a full bath for family or guests. The living spaces are warm and inviting, with large windows bringing the river setting indoors. The living room centers around a wood-burning fireplace framed by custom built-in bookshelves, and the formal dining room is well suited for entertaining. The renovated kitchen, with its large center island and premium appliances, flows into the comfortable family room and the waterside enclosed sunroom, complete with a full bath and beautiful river views. An adjoining bonus room offers additional flexibility for a butler’s pantry, hobby or craft room, or storage. An oversized attached two-car garage connects conveniently to the expansive attic, while a detached, climate-controlled studio provides wonderful flexibility for an art studio, home office, workshop, or other uses. The outdoor spaces make the most of the waterfront setting. A gunite pool, added in 2020, is surrounded by hardscape and fencing and offers a private place to relax and entertain. The dock was completely rebuilt in 2024 and includes two slips, a floating dock, and approximately 6' MLW, providing excellent access to the Tred Avon River and by boat to Oxford and the Choptank River. With its beautiful setting, extensive improvements, exceptional boating access, and convenient location between Easton and St. Michaels, this is a special Eastern Shore property that offers privacy, character, and an easy waterfront lifestyle.

Set on the coveted shores of the Tred Avon River, this extraordinary waterfront estate is a rare offering, combining deep-water boating, a private sandy beach, a substantial main residence, separate guest accommodations, and an exceptional collection of lifestyle amenities. From the first approach, the property unfolds as a private Eastern Shore compound, where elegant architecture, sweeping river views, and resort-caliber amenities are seamlessly integrated into a singular waterfront setting. The four-bedroom, five-and-a-half-bath main residence is both impressive and inviting. A dramatic two-story living room features hardwood floors, a fireplace, custom millwork, and abundant natural light, while the waterside den offers a more intimate retreat with a gas fireplace, custom bookshelves, and a wall of glass framing views across the Tred Avon. A spacious screened porch and expansive Ipe decking extend the living spaces outdoors and provide direct access to the waterfront. At the heart of the home, the kitchen is equipped with a Sub-Zero refrigerator, gas cooktop, double ovens, stainless steel dishwasher, granite countertops, and white cabinetry, along with generous space for casual dining. A first-floor office and laundry room add everyday convenience, while dual staircases provide easy access throughout the home. The first-floor waterfront primary suite is a private sanctuary with its own fireplace, sitting room with custom bookshelves, two walk-in closets with custom shelving, and a beautifully appointed bath featuring a waterside soaking tub, dual vanity, and walk-in steam shower. Each additional bedroom is en suite, creating comfortable and private accommodations for family and guests. Outside, the property transforms into a private waterfront retreat. A heated lap pool, hot tub, and sandy beach create distinct places to relax along the river, while a scenic walking path winds through wildflower gardens and open space, reinforcing the estate’s remarkable sense of privacy and scale. The pool house makes outdoor entertaining effortless, with a full kitchen, stainless steel appliances, gas range, laundry facilities, and an outdoor shower. A separate three-bedroom, two-bath guest residence provides exceptional additional accommodations with hardwood floors, a full kitchen, laundry, garage, and a large deck overlooking the Tred Avon—ideal for extended family, guests, or multi-generational living while preserving the privacy of the main residence. For those drawn to the water, the property delivers. A private pier offers 6+ feet of water at mean low water, three slips, two boat lifts, water and electric—providing exceptional deep-water access for a wide range of vessels. From here, spend the day cruising the Tred Avon and exploring the waterways of the Chesapeake Bay. A rip-rapped shoreline provides protection while preserving the property’s connection to the river. With a three-car garage, irrigation system, extensive custom millwork, guest and pool houses, heated pool, sandy beach, and substantial boating infrastructure, this is far more than a waterfront home. It is a complete Eastern Shore estate—a private compound where the residences, grounds, and waterfront amenities come together to create an exceptional lifestyle on the Tred Avon.

PRESQUILE MANOR HOUSE – An extraordinary waterfront estate steeped in history, architectural distinction, and timeless elegance. Magnificently positioned along the Wye River with breathtaking panoramic views and coveted western exposure, this distinguished circa-1800 manor house offers an exceptional combination of historic character, refined luxury, and unparalleled waterfront living. Originally part of the historic Lloyd family holdings, the 10.48-acre estate has been meticulously renovated by renowned Peter Zimmerman Architects and West & Callahan Construction, reflecting an extraordinary commitment to preserving its architectural heritage while incorporating the finest modern appointments. The magnificent 7BR/6FB/3HB manor house showcases exquisite craftsmanship throughout, with exceptional millwork, beautifully proportioned rooms, soaring ceilings, rich hardwood floors, elegant fireplaces, and graceful architectural details. Expansive windows fill the interiors with natural light while framing spectacular views of the river and surrounding grounds. A stunning curved staircase with a beautifully crafted wood handrail serves as an architectural centerpiece. Gracious formal living and dining rooms provide elegant spaces for entertaining, while inviting gathering areas offer warmth and comfort for everyday living. The extraordinary gourmet kitchen features extensive custom cabinetry, an expansive center island, premium appliances, and beautifully appointed finishes. Seven generously appointed bedrooms and beautifully renovated baths provide exceptional comfort and privacy for family and guests. Throughout the residence, sophisticated finishes and thoughtful design reflect a remarkable balance between the home's distinguished history and contemporary luxury living. Beyond the residence, the spectacular grounds provide a setting of extraordinary beauty and tranquility. Expansive lawns sweep toward the river, complemented by magnificent mature trees, formal gardens, and beautifully maintained landscaping. A waterside swimming pool offers an idyllic setting for relaxation and outdoor entertaining, while a private tennis court adds to the property's outstanding recreational amenities. Extensive riprapped shoreline and a coveted deepwater boathouse provide exceptional access to the Wye River and surrounding Chesapeake Bay waterways. Sweeping river vistas and magnificent western sunsets create a breathtaking backdrop for this remarkable waterfront retreat. Rarely does a property of such historical significance, architectural refinement, and exceptional waterfront presence become available. Presquile Manor House represents a remarkable opportunity to own one of the Wye River's most distinguished estates, where centuries of history, extraordinary craftsmanship, and the natural beauty of Maryland's Eastern Shore come together in a truly exceptional offering. The estate is approached by an impressive, tree-lined entrance drive extending across approximately 7.1 additional acres, with access secured by a perpetual easement.

New 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!

Charming and beautifully updated, this circa-1900 Colonial offers an inviting blend of historic character and refined, comfortable living in the heart of downtown Oxford. Surrounded by lovely gardens, mature trees, and established plantings, the property enjoys a picturesque setting just moments from the waterfront, with water views looking down the street and all the charm of this beloved Eastern Shore village close at hand. Inside, beautiful hardwood floors and thoughtfully updated interiors create a warm and welcoming atmosphere. The beautiful sun-lit living room offers a gracious space for relaxing and gathering, while the spacious gourmet kitchen serves as the heart of the home, featuring a large center island, premium stainless appliances, and a generous casual dining and sitting area overlooking the garden. A formal dining room provides an elegant setting for entertaining, while a comfortable sitting room opens to the screened porch, extending the living space outdoors. A full bath with a glass-enclosed shower completes the main level. Upstairs, the private primary suite is distinguished by vaulted, beamed ceilings and an ensuite bath with a double-sink vanity, glass-enclosed shower, two closets, and convenient access to the laundry. Two additional guest bedrooms share a half bath, with plans available upon request for conversion to a full bath. Outside, a wonderful screened porch and adjoining deck overlook the lush gardens and mature trees, creating a peaceful setting for outdoor dining and relaxation. A rare detached one-car garage offers additional workshop space, while the stone driveway provides ample off-street parking. Located in the heart of historic Oxford, the home is ideally positioned for enjoying the town’s waterfront parks, marinas, restaurants, and scenic streets, along with the relaxed pace and enduring character that make Oxford one of the Eastern Shore’s most treasured waterfront communities.

Refined waterfront offering on Maryland’s Eastern Shore, 7871 Avon Court has been completely transformed into a sophisticated modern farmhouse blending timeless design and convenience. Thoughtfully renovated to a like-new standard, the residence offers approximately 2,000 square feet with 3 bedrooms, 2.5 baths and a private office/flex space. Dramatic vaulted living spaces, wide-plank flooring, custom finishes and a beautifully reimagined kitchen create interiors that feel both elevated and inviting. Expansive windows frame views of the Tred Avon River from nearly every room, seamlessly connecting the home to its exceptional waterfront setting. Set on a high-bank waterfront site with approximately 360± feet of shoreline and 3± feet MLW, the property is ideally suited for boating, kayaking, paddleboarding and waterfront entertaining. Private pier, sandy beach, mature trees and expansive lawn create a rare park-like setting just minutes from downtown Easton and within easy reach of Washington, Northern Virginia, Philadelphia and surrounding Mid-Atlantic destinations. A compelling waterfront retreat offering privacy, style and effortless Eastern Shore living. Room for pool subject approvals.

Easton Club - Comfort and Convenience! Beautiful natural light, a spacious end-unit setting and the ease of first-floor living. This four-bedroom, three-bath townhouse features a generous great room with gas fireplace opening to the kitchen and dining area with Corian countertops—an inviting space for everyday living and entertaining. The first-floor primary suite offers a private bath with walk-in shower and dual vanities, while an additional main-level bedroom, full bath and laundry add to the convenience. Upstairs, two bedrooms, a family room and a large storage room provide plenty of space and flexibility. Enjoy outdoor living on the patio and in the fenced yard, with a corner lot and attached one-car garage completing the property. Ideally located along the desirable Oxford Road corridor, Easton Club offers a community pool and tennis/pickleball court, just a short drive from downtown Easton and Oxford.

Motivated Seller and Improved Pricing! Discover an exceptional opportunity to enjoy life in historic Oxford, Maryland. Ideal as a peaceful escape, retirement retreat, or full-time residence with room to grow, this inviting three- to four-bedroom home is located on a quiet cul-de-sac in the Jacks Point neighborhood, just a short distance from the waterfront. Vaulted ceilings and an open-concept layout create a bright, airy feel, while continuous Brazilian cherry hardwood floors add warmth and character throughout. The first-floor living space offers a generous foyer, flexible office or guest space, a separate dining room, a living room, a half bath, and an eat-in kitchen. The main second floor includes three bedrooms and two full baths, while a separate staircase provides access to a bonus room that can serve as a playroom, entertainment space, or private retreat. Beyond these rooms, a garage conversion completed before the current owner’s 2007 purchase expands the home with a large, light-filled family room and a separate storage area with interior and exterior access, providing ample room for lawn, garden, athletic, and marine equipment. The well maintained 28-year-old home has received steady updates, including a new roof in 2025, new appliances in 2024, first-floor HVAC system replacement in 2022, an encapsulated crawlspace, and more. It is move-in ready and priced to give the next owner flexibility to personalize the finishes and pursue future updates. Set on a quarter-acre lot with a fully fenced yard, the property offers ample space for outdoor living, a swimming pool, a shed, or an expanded garden. Endless possiblities! Just steps from the Oxford Community Center, Jacks Point Marina, Play Ball Dog Park, and the town center, the home also places shops, cafés, the museum, library, ice cream shop, yacht club and ferry within easy reach. The relaxed rhythm of Oxford life begins just beyond your front door.

Fabulous home in Oaklands, ideally located along the highly desirable Oxford Road corridor! Beautifully updated and designed for effortless entertaining, this four-bedroom Colonial offers light-filled interiors, hardwood floors, geothermal heating and cooling and exceptional indoor-outdoor living. The living room features a fireplace flanked by custom built-ins and a large bay window. A separate family room provides a more relaxed setting with exposed wood beams and raised-hearth brick fireplace. At the heart of the home, the renovated kitchen features an oversized island, abundant cabinetry, a gas range, generous storage and a dining area. Just beyond, the light-filled sunroom is a standout with a wet bar, beamed ceiling and custom built-ins making it an inviting space for gatherings throughout the year. Upstairs, the oversized primary suite includes an updated ensuite bath and expansive walk-in closet. The second bedroom features hardwood floors and its own sitting area, while two additional bedrooms and an updated full bath complete the second floor. Outside, the backyard is an entertainer’s dream, featuring a saltwater in-ground pool, outdoor kitchen, fire pit and an impressive 1,532 square feet of terraced patio space. Two sheds offer additional storage and versatility, while a separate pump house accommodates the pool equipment. An oversized attached two-car garage provides ample space for vehicles, storage and hobbies. A 26 kW whole-house generator provides added comfort and peace of mind. Residents of Oaklands also enjoy community water access and use of the community pier, completing this exceptional Oxford Road property. Please do not go down driveway without an appointment.

Filled with natural light and offering an exceptional floor plan, this spacious Easton Club home combines comfortable first-floor living with an open setting and western exposure. Hardwood floors extend through much of the main level, where a generous great room features a raised-hearth fireplace, deck access and expansive views. The formal dining room and spacious chef’s kitchen are ideal for entertaining, with an island, breakfast bar, separate breakfast area and abundant custom cherry cabinetry.The first-floor primary suite includes a walk-in closet and spacious bath with dual vanities, a soaking tub and walk-in shower. Two additional bedrooms, a full bath and a large laundry room are also located on the main level. A screened porch, deck and patio with a motorized retractable awning provide multiple spaces for outdoor living, relaxing and enjoying the western sunsets.Upstairs, an expansive bonus room offers tremendous flexibility as a recreation room, home office, studio or overflow guest space, along with additional walk-in attic storage. Carefully maintained by only its second owner, the home also features an attached two-car garage and an HVAC system replaced in 2020. Conveniently located close to downtown Easton with access to the Easton Club community pool and pickleball court.

EXPANSIVE SOUTHWESTERN VIEWS OF THE TRED AVON AND CHOPTANK RIVERS. A distinguished waterfront residence in Oxford, thoughtfully designed to embrace its extraordinary setting. Exceptional craftsmanship is evident throughout, with exquisite moldings and millwork, Brazilian Cherry hardwood floors, elevated and vaulted ceilings, abundant natural light, and an open floor plan oriented toward the water. The main level is equally suited to gracious entertaining and comfortable everyday living. A formal dining room opens to a refined gourmet kitchen with a generous center island and breakfast bar, premium stainless-steel appliances, wine storage, and a six-burner gas range. The kitchen flows seamlessly into the spacious living room with gas fireplace and continues to a screened porch and adjoining covered porch with outdoor grill, overlooking the pool and river. A well-appointed guest bedroom with ensuite bath and powder room complete the main level. Upstairs, a spacious sitting area with custom built-ins provides a quiet retreat. The waterside primary suite is exceptionally private, with a sitting area and gas fireplace, private balcony overlooking the river, and two cedar-lined walk-in closets with custom cabinetry. A discreetly integrated refreshment bar with wet sink and beverage refrigerator adds an elegant touch. The ensuite bath features a jetted tub, dual-sink vanity, and glass-enclosed walk-in shower. Three additional guest bedrooms include two sharing a Jack-and-Jill bath and a third with an ensuite bath. The waterfront grounds are designed for both relaxation and entertaining, with a pool and hot tub positioned to take full advantage of the expansive river views. A natural shoreline, small sandy beach, and private dock with boat lift and approximately 3' MLW extend the living experience to the water. A large two-car garage provides generous parking and storage. An exceptional Oxford offering with commanding river views, refined interiors, extensive outdoor living, and a private waterfront setting—an elegant retreat with all the elements for sophisticated Eastern Shore living.

Architect-designed contemporary waterfront home on nearly 18 private acres across two parcels with approximately 1,400 feet of shoreline on Greenwood Creek. Positioned to capture 180-degree western views, the property offers privacy, deep water, and a setting that is increasingly difficult to find on Maryland’s Eastern Shore. A custom pivoting front door creates a striking first impression and sets the tone for the home's thoughtful design. The home was designed to take advantage of the surrounding water and landscape, with floor-to-ceiling windows, open gathering spaces, and strong indoor-outdoor connections throughout. The kitchen opens to the main living areas and features a glass accordion door that connects directly to the screened porch, creating a seamless transition between indoor and outdoor spaces. The layout flows easily between the kitchen, dining areas, family room, porch, and pool area, making the home equally well suited for everyday living and entertaining. The primary suite is set apart from the rest of the home by a glass-enclosed walkway and includes a private office, large dressing room, en-suite bath, and private porch access. In addition to the primary suite, the main level includes three additional bedrooms, each with access to a private bathroom. The finished lower level includes a home theater, billiards room, bar area, workout room, additional bedroom and full bathroom, along with unfinished basement space for storage. Outdoor features include a solar-heated pool, private beach, and deep-water pier with two boat lifts. The protected shoreline and direct access to Eastern Bay make this an ideal property for boating and waterfront living. A three-bay outbuilding with workshop space and additional storage provides room for equipment, hobbies, or car and boat storage. Located just outside Queenstown, the property is convenient to Easton, Annapolis, Washington D.C., Baltimore, and Philadelphia while offering the privacy and pace of the Eastern Shore.

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.

Price reduced SIGNIFICANTLY!! Beautiful views of Harris Creek and the Choptank River beyond provide a stunning backdrop for this beautifully maintained home in the established community of Tilghman on Chesapeake. A welcoming front porch framed by mature landscaping and colorful gardens leads into a bright, light-filled interior featuring soaring two-story ceilings, hardwood floors, crown moldings, and abundant natural light. Designed for both everyday living and entertaining, the gourmet kitchen opens to a spacious family room with a gas fireplace, breakfast area, and inviting sunroom. The adjoining rear deck, complete with a hot tub, provides a wonderful setting for outdoor entertaining while overlooking the beautifully landscaped grounds and tranquil water views. The main level also includes gracious formal living and dining rooms, as well as a private office. The upper level overlooks the family room below and features a spacious primary suite with a private balcony and luxurious ensuite bath with a jetted tub and walk-in shower. Three additional bedrooms—one currently used as a library—share a full hall bath. An attached two-car garage provides convenient parking and storage. Residents of Tilghman on Chesapeake enjoy an exceptional array of amenities, including a waterfront clubhouse, swimming pool, picnic area, community pier, and private boat slips available for lease, offering residents an ideal opportunity to enjoy the waterfront lifestyle of Maryland’s Eastern Shore.

Located in the desirable Cooke’s Hope community, 28706 Hope Circle offers approximately 4,172 square feet of finished living space, including three bedrooms and four bathrooms. The home combines classic Eastern Shore character with spacious living areas, thoughtful updates, and appealing indoor and outdoor amenities. The first floor features a private primary suite, complemented by a large first-floor laundry facility. The main-level family room includes a gas fireplace and provides a welcoming setting for relaxing or entertaining. Additional first-floor spaces include a separate formal dining room and a separate dedicated sitting/piano room, offering versatile areas for formal gatherings, quiet relaxation, or enjoying music. A wraparound porch adds curb appeal and provides multiple areas for enjoying the outdoors. The recently refreshed kitchen features new appliances and countertops, along with a dedicated kitchen dining area ideal for casual meals. A separate coffee and bar area provides additional storage and serving space, making it perfect for morning coffee, entertaining, or evening cocktails. The second floor includes two bedrooms, two bathrooms, a dedicated office area, and a second large family room. This flexible space is well suited for movie nights, watching sports, hosting guests, or creating a comfortable retreat for family and friends. Two dedicated second-floor storage areas provide convenient space for important household items. The backyard is a private oasis, featuring a heated pool, professionally landscaping, and a Hunter sprinkler system. The thoughtfully landscaped setting provides a peaceful and inviting environment for relaxing, entertaining, and enjoying the outdoors. Additional features include a new roof and a heated and cooled two-car garage with 9-foot-wide doors. The second floor of the garage provides an additional large finished storage area with potential for flexible use. The expansive garage offers ample room for vehicles, equipment, hobbies, seasonal items, or a workshop. The combination of generous interior spaces, abundant storage, updated features, and attractive outdoor amenities makes this home ideal for both everyday living and entertaining. Cooke’s Hope amenities include a community dock, canoe storage and launch, walking and exercise trails, tennis and pickleball courts, a private community mailroom, and a fitness center. Conveniently located near downtown Easton, the property offers a peaceful neighborhood setting with easy access to the area’s shops, restaurants, cultural attractions, and waterfront destinations.

Welcome to 200 Wye Road, an exceptional waterfront estate set on over two private acres along the Wye River, directly across from the protected natural beauty of Wye Island. Here, scale, setting, and thoughtful design converge to create a truly elevated Eastern Shore lifestyle. Spanning more than 8,100 square feet across three finished levels, the residence offers a refined yet highly livable floor plan designed to capture water views from nearly every room. Expansive living spaces, a formal dining room with handpainted custom wallpaper from the U.K., and a reimagined gourmet kitchen create an environment equally suited for everyday living and large-scale entertaining. The kitchen has been thoughtfully redesigned with updated cabinetry, statement lighting, and a full suite of premium appliances, including Wolf, Sub-Zero, and Bosch. The home offers exceptional flexibility, including an optional first-floor primary suite, a dedicated home gym, two laundry rooms, and an oversized mudroom designed for seamless day-to-day living. Two wood-burning fireplaces add warmth and character, enhancing the home’s sense of comfort and timeless appeal. The primary suite serves as a private retreat, complete with two walk-in closets and a fully renovated, spa-inspired bath featuring heated flooring, a soaking tub, a glass-enclosed shower, and its own gas fireplace, delivering a level of comfort and detail rarely found. Since 2024, the property has undergone extensive upgrades that enhance both performance and long-term value, including a new Owens Corning roof with a transferable warranty, three fully replaced Trane HVAC systems, a whole-home water filtration system, and comprehensive renovations throughout the bathrooms and interior spaces. Outdoor living is where the property truly distinguishes itself. A newly renovated 20x40 waterfront pool with a pebble finish and automatic cover anchors the setting, complemented by expansive hardscaping, manicured grounds, and multiple areas designed for entertaining or quiet relaxation. The shoreline has been improved with 250 feet of stone rip rap, and the deep-water dock is outfitted with new electrical service and lighting, featuring a new 25,000 lb boat lift and a 12,000 lb one along with two additional slips, providing effortless access to the Wye River and beyond. Whether enjoying sunrise coffee on the screened porch, hosting summer gatherings by the pool, or heading out by boat to St. Michaels or the Kent Narrows, this property offers a lifestyle defined by ease, privacy, and connection to the water. Conveniently located in Queenstown, just minutes from shopping, dining, and Route 50, with easy access to Annapolis and Easton, 200 Wye Road represents a rare opportunity to own a turnkey waterfront estate in one of the Eastern Shore’s most sought-after settings.

Enjoy the Chesapeake Bay lifestyle from this charming 2-bedroom, 3-bath cottage offering beautiful Bay views and direct access to the water just across the street. Situated on more than .6 acres, the property combines a relaxed coastal setting with a spacious, private backyard that is flat and ideal for outdoor living and entertaining. After a day on the water, unwind in the hot tub, rinse off in the outdoor shower, or simply enjoy the privacy of the backyard. A storage shed provides convenient space for kayaks, paddleboards, bikes, and other outdoor gear. Just across the street, direct access to the Chesapeake Bay and a sandy beach makes it easy to launch a kayak or paddleboard, spend the day along the shoreline, or simply take in the Bay. While the property is non-waterfront, the combination of water views and convenient Bay access offers an exceptional opportunity to enjoy the Eastern Shore lifestyle. Whether you're looking for a weekend getaway or a full-time Shore home, 101 Chesapeake Bay Drive offers an inviting retreat with space, privacy, water views, and the Chesapeake Bay just steps away.