luxury houses for sale Talbot County, United States

New Price! Transformative renovation in Martingham! This beautifully updated 2-bedroom, 2-bath single-level Gull Wing Villa overlooks the 6th fairway at Links at Perry Cabin, offering a serene golf course setting just minutes from the heart of St. Michaels. Thoughtfully redesigned, the home features new flooring throughout, a fully renovated kitchen and baths, and a reimagined layout that enhances both flow and functionality. The kitchen now opens seamlessly to the living area—ideal for modern living and entertaining. The primary bath has been expanded and now includes a large vanity. The smart design choices resulted in the addition of a generous extra closet in the primary suite. Additional updates include a new roof (2025), providing peace of mind for years to come. Located in the desirable Martingham community, residents enjoy access to a waterfront park with beach which is only about a 15 minute walk away. All of this is just moments from St. Michaels’ renowned shops, restaurants, and harbor.

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

Beautifully maintained Whitman model in the sought-after Easton Club East community. Offering spacious living and thoughtful updates throughout, this home features a formal living room, dining room, office/den, large kitchen, sunroom and laundry room on the main level. Also on the first floor are two bedrooms and two full baths, including a spacious primary suite with a walk-in closet and private ensuite bath. The kitchen is designed for both everyday living and entertaining featuring a large center island with seating for four and ample space for casual dining. Upstairs a private bedroom and full bath are complemented by a generous loft area, ideal for a home office, guest retreat or additional living space. Filled with natural light, the home also benefits from recent improvements including a roof (2021), HVAC system (2022) and engineered hardwood flooring throughout the main living areas (2022). Conveniently located near downtown Easton, shopping, dining, golf, medical facilities, and all the amenities of Maryland's Eastern Shore

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.

Don't miss this easy-care, charming 3 br, 2 bath home in the heart of Easton!!! Renovated by the current architect/owner, it features a gracious floor plan with abundant natural light. Public spaces feature two major seating areas, two dining areas, hall bath, open kitchen with generous counter space, plus a large porch and deck. A hallway leads to two bedrooms on the left. On the right, there is a full bath, a pantry with refrigerator-freezer and abundant storage, plus a laundry room. Beyond is a spacious primary suite with private tile bath and large walk-in closet.

A magnificent, stately, Daffin-built, Chesapeake Bay Brick Estate exudes excellent design and craftsmanship in this 5 bedroom (suites), 5.5 bath 6,500 sq. ft brick home that majestically sits on 21.7 acres facing the Chesapeake Bay. Excellent construction quality and design are evident throughout this magnificent estate. Geothermal system on 1st and 2nd floors; Heat Pump for the 3rd floor; Ductless units for 1st floor porch and 2nd floor porch, 3 hot water heaters. Double porches allow you to embrace arguably the most spectacular sunsets on the Eastern Shore. The front of the property is abundant with trees that offer ultimate privacy, and all but 4 acres are taxed under agricultural use, conveniently located between St. Michaels and Tilghman Island, this Chesapeake Bay oasis will far surpass your expectations. No For Sale sign on property but the property’s name ‘Baycup’ is on a small sign at the entrance.

PRICE IMPROVEMENT*** Discover the charm of Lakelands at Easton, where community spirit meets modern living in this stunning coastal-style townhouse. Built in 2010, this beautifully maintained home boasts 4 spacious bedrooms and 3.5 bathrooms, offering ample space for relaxation and entertainment. The inviting exterior features well-kept sidewalks that encourage evening strolls and friendly neighborly chats. Step outside to enjoy the community amenities, including basketball courts and a refreshing outdoor pool, perfect for summer gatherings and active lifestyles. The vibrant neighborhood is designed for connection, with parks nearby that provide green spaces for picnics, playdates, and outdoor activities. The community's commitment to safety and convenience is evident, with public services readily accessible, making daily life a breeze. Inside, the home features a cozy gas fireplace, ideal for creating warm memories during chilly evenings. The improved basement offers additional living space, while the attached garage and driveway provide ample parking for guests. With a lot size of 0.09 acres, this property strikes the perfect balance between manageable upkeep and outdoor enjoyment. Embrace a lifestyle where community, comfort, and convenience come together seamlessly in Lakelands at Easton. Don't miss your chance to make this delightful townhouse your new home! **New AC 2024, Five New windows with warranty, New Roof Ridge top peak and vents through Marasun 2025, Gas Fireplace-all new parts 2026, 2019 Replaced wood Decking with Trex decking, Only One of 4 units that has 4 bedrooms.**

Carrigan Homes introduces our newest model, the “Talbot”, a 2610 sqft 4 bedroom, 2.5 bath custom home with a 1st floor primary suite, gourmet kitchen, 2nd floor bonus family room and oversized garage. This home is packed with generous standard and energy-saving features, and is to be built on one of the last remaining lots in Easton Village. Buy now, make every selection and color choice and move in by early 2027! The 1st floor entry is defined by glass French doors which reveal the private study. Beyond, the dining room opens into a light-filled family room with cathedral ceiling, natural gas fireplace and views of the south facing backyard. In the kitchen, an expansive island centers the surrounding workspace with stainless steel appliances, including a double oven, microwave, dishwasher and 36” natural gas cooktop and just beyond is the laundry room with pantry and workspace cabinetry. Gleaming 1st floor finished-on-site hardwood floors and stairs, solid core interior doors, Adams trim, quartz countertops and other upgraded finishes announce the high quality that Carrigan is known to deliver. The carpeted second floor family room leads to three additional bedrooms with generous closets, and a shared bath completes the space. The Talbot features a brick-topped full front porch, brick to grade on all sides, durable Hardie lap siding, and an oversized garage with workshop space. Add an optional brick-topped screened porch to create more outdoor living! Energy-saving features include two-zone Bosch 20 seer HVAC with inverter, 2x6 exterior wall construction and double-hung windows. A conditioned crawl space provides ample storage accessed by interior stairs. The spacious backyard boasts sunset views and can be fenced for pets or privacy. Easton Village amenities include a community pier on the Tred Avon River, boat slips, extensive walking trails, an outdoor pool, kayak storage and launch, and close proximity to the towns of Easton, St. Michaels and Oxford. Visit the lower, slower Eastern Shore to see why you will want to call this place home!

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.

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!

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.

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 Wi-Fi controlled front/rear irrigation system. The superbly designed and crafted home offers an open floorplan 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!

Known as the William J. Wrightson House, this distinguished circa 1897 residence in the heart of St. Michaels beautifully blends timeless elegance and refined architectural detail with the comforts and conveniences of modern living. Lovingly restored from top to bottom, the home has undergone extensive renovations and improvements, including all new HVAC systems, tankless hot water system, updated wiring, crawlspace encapsulation, new roof and gutters, recessed lighting, high-end appliances, three fully renovated baths, a custom butler’s pantry, complete interior and exterior painting, and new patio grading and drainage, among many others. A full list of improvements is available. Ideally situated just steps from the waterfront, marinas, boutique shops, waterfront dining, and renowned local restaurants, the property offers an exceptional in-town lifestyle in one of the Eastern Shore’s most beloved waterfront communities. Filled with natural light throughout, the beautiful 3BR/3BA residence showcases heart pine and yellow pine flooring, custom millwork, and thoughtfully renovated living spaces designed for both everyday comfort and effortless entertaining. The welcoming living room, anchored by a new gas fireplace/stove, flows seamlessly into a gracious formal dining room ideal for gatherings with family and friends. The gourmet kitchen features quartz countertops, top-tier appliances, abundant cabinetry, and custom built-ins, effortlessly combining style and functionality. At the rear of the home, a stunning sunroom addition serves as a true focal point, featuring vaulted ceilings, a shiplap accent wall, wet bar and custom butler’s pantry with beverage chiller and bar sink, custom built-ins, a renovated full bath, and French doors opening to the picturesque gardens and brick patio beyond. Upstairs, the comfortable primary suite offers a peaceful retreat, complemented by a luxurious bath with a clawfoot soaking tub, Carrara Bella marble flooring (in shower as well), custom antique vanity, and glass-enclosed walk-in shower. Two additional guest bedrooms and a beautifully renovated bath with marble tile flooring, granite-topped vanity, and Perrin & Rowe fixtures provide inviting accommodations for family and guests. The outdoor spaces are equally enchanting, highlighted by a stunning English garden filled with roses, crepe myrtles, and hydrangeas, all enclosed by a charming French Gothic lattice shadowbox fence, creating a private and storybook setting.

This home allows for a 3.12% FHA Assumable Loan! Welcome to easy Eastern Shore living in the charming waterfront town of St. Michaels! This 3-bedroom, 2 bath, 1,232 sq. ft. home is located in the desirable community of Rio Vista offering direct access to the Miles River, complete with a community dock, boat slips, and boat ramp — perfect for boating, crabbing, paddleboarding, or sunset cruises. Enjoy the relaxed coastal lifestyle just minutes from shops, restaurants, marinas, and everything that makes St. Michaels so special. Residents also enjoy access to a community pool for summer fun. Whether you’re looking for a full-time residence, weekend getaway, or investment opportunity, this home offers the ideal blend of comfort, location, and waterfront amenities.

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.

Carrigan Homes introduces our newest model, the “Talbot II”, a 2400 sqft 3 bedroom, 2.5 bath custom home with a 1st floor primary suite, gourmet kitchen, 2nd floor bonus family room and oversized garage.This home is packed with generous standard and energy-saving features, and is to be built on one of the last remaining lots in Easton Village. Buy now, make every selection and color choice and move in by early 2027! The 1st floor entry is defined by a glass door which reveals the private study. Beyond, the dining room opens into a light-filled family room with cathedral ceiling, natural gas fireplace and views of the south facing backyard. In the kitchen, an expansive island centers the surrounding workspace with stainless steel appliances, including a double oven, microwave, dishwasher and 36” natural gas cooktop, and just beyond is the laundry room with pantry and workspace cabinetry. Gleaming 1st floor finished-on-site hardwood floors and stairs, solid core interior doors, Adams trim, quartz countertops and other upgraded finishes announce the high quality that Carrigan is known to deliver. The carpeted second floor family room leads to two additional bedrooms with generous closets, a flex space for your personal use, and a shared bath completes the space. The Talbot features a brick-topped full front porch, brick to grade on all sides, durable Hardie lap siding, and an oversized garage with workshop space. Add an optional brick-topped screened porch to create more outdoor living! Energy-saving features include two-zone Bosch 20 seer HVAC with inverter, 2x6 exterior wall construction and double-hung windows. A conditioned crawl space provides ample storage accessed by interior stairs. The spacious backyard boasts sunset views and can be fenced for pets or privacy. Easton Village amenities include a community pier on the Tred Avon River, boat slips, extensive walking trails, an outdoor pool, kayak storage and launch, and close proximity to the towns of Easton, St. Michaels and Oxford. Visit the lower, slower Eastern Shore to see why you will want to call this place home!

PRICE IMPROVEMENT*** Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019

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. Built by a member of the Neavitt family c.1870, this home was extensively updated yet retains its historic charm. Specific updates include: a new two-story addition with full baths on each floor, new closets/utility spaces, new windows, new HVAC, new wiring, new appliances, new cabinets, two new sheds, new water filtration, extensive landscaping and more. MOST FURNITURE CONVEYS. There are no St Michaels or waterfront taxes, a savings of thousands of dollars each year.

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

‘Eagle’s Nest’ is an exceptional waterfront retreat overlooking Island Creek, just minutes from historic Oxford. Prime location with guest house and deep water (6.5' MLW). Privately sited on more than four acres amid mature trees and meticulously landscaped grounds, this impressive main residence (5324 SF)—completely rebuilt by Ilex Construction in 2008—offers four bedrooms, four full baths, and two half baths. Every room is generously sized and thoughtfully designed to capture expansive water views while providing elegant yet comfortable living. The main level features beautifully appointed living spaces, including a formal living room with coffered ceiling, wood-burning fireplace, custom built-ins, wet bar, and sliding doors opening to the waterside patio. A formal dining room, enclosed by French doors, offers an inviting setting for entertaining. At the heart of the home, the gourmet kitchen showcases a cathedral ceiling, large center island, top-of-the-line appliances, gas fireplace, spacious walk-in pantry, and custom built-ins—creating a warm and functional gathering space. The adjoining sunroom is filled with natural light and features vaulted ceilings, slate tile flooring, and sweeping water views, with glass doors opening to the patio and pool area. Nearby, a well-equipped mudroom, laundry room, and half bath add everyday convenience, along with a covered breezeway to the two-car garage. The desirable main-level primary suite serves as a private retreat with tranquil water views, dual walk-in closets, and a luxurious en suite bath. Just off the primary suite corridor, a private office with custom built-ins and an additional powder room enhance the home’s thoughtful design. Upstairs, three generously sized guest bedrooms each include en suite baths. A comfortable sitting area opens to a balcony overlooking Island Creek—an ideal place to relax and take in the serene setting. In addition, a coveted one-bedroom, one-and-a-half-bath guest house (968 SF) includes a full kitchen, living room, and attached two-car garage—perfect for visitors, extended family, or flexible use. Outdoor living is equally impressive, highlighted by a gunite swimming pool, expansive brick patio, mature landscaping, and extensive hardscaping designed to complement the waterfront setting. The private pier features two slips and a boat lift with 6.5' MLW along a protected, riprapped shoreline. ‘Eagle’s Nest’ presents a rare opportunity to enjoy refined Eastern Shore waterfront living just moments from Oxford. New roof on main house (2025). New pool cover: Aqua pool service contract paid for-2026

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.

Welcome to ‘Drake’s Landing’! Beautifully sited on 20 picturesque acres on the shores of Irish Creek, this 4,602 sq. ft .completely renovated (2021) waterfront estate offers the perfect blend of casual elegance and thoughtful design. The main level welcomes with expansive water views and features a guest bedroom with ensuite bath, a cozy family room (or den/office), and a gracious living room anchored by a large brick hearth and woodburning fireplace. The gourmet kitchen is the center of the home - outfitted with upgraded appliances, a center island with breakfast bar, and additional dining space. Adjacent is a second kitchen - ideal for effortless indoor/outdoor entertaining. A formal dining room and large waterside sunroom complete the main living spaces. Upstairs, two spacious primary suites anchor each end of the home, offering privacy and comfort, with two additional guest bedrooms (one with ensuite bath) and a hall bath in between. Step outside to enjoy westerly water views from the elevated deck, or gather on the enclosed screened porch, perfect for crab feasts and sunset dining. Outdoor amenities include a charming 2BR/1.5BA guest cottage (540 sq. ft.), a new dock with two slips, stunning waterside pool, waterside firepit, and barrel sauna. A 3-bay equipment garage is connected to an enclosed game room and workshop - creating a complete retreat for relaxation, recreation, and unforgettable waterfront living. The property with its acreage is also great for hunting. This is Eastern Shore living at its best – spacious, serene, and set up for year-round enjoyment. *Furnishings may be available for sale.

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.

Charming 2-3BR/2BA coastal cottage with tranquil water views of Black Walnut Cove and the Choptank River - ideal for easy full-time living or a relaxed weekend retreat. Beautiful hardwood floors run throughout, complementing the home’s warm, welcoming character and comfortable scale. The living room, anchored by a wood-burning fireplace, offers a cozy gathering space, while the kitchen is thoughtfully designed with a large center island, wet bar, and French door access to a beautiful screened porch overlooking the cove - perfect for morning coffee, quiet afternoons, or casual evening entertaining. The primary suite is a peaceful retreat, featuring an ensuite bath, walk-in closet, and convenient laundry cubby. An adjoining second bedroom offers flexibility as a private office, sitting room, or additional sleeping space. A third bedroom and full hall bath provide comfortable accommodation for guests. Additional highlights include a garden shed and a fully conditioned “she shed” with heat and AC, currently used as an art studio – a versatile space for hobbies or creative pursuits. Numerous improvements include a new roof, Pella architectural windows, encapsulated crawlspace, 3-zone Mitsubishi mini-split system, reverse-osmosis water filtration, and more. This thoughtfully updated cottage offers the best of Eastern Shore living with a relaxed, waterside feel.