TTR Sotheby's International Realty (page 2)
Listings of the agency
Listings for sale: 21 to 40 / 51
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House with terrace Oxford (United States)
Unrivaled Architecture and Design! Exceptional waterfront living on picturesque Town Creek in the historic village of Oxford. Built in 2023 and privately set on 1.71 acres—an extraordinary offering in Oxford—this 5-bedroom, 4.5-bath residence is surrounded by mature trees, refined landscaping, and beautifully executed hardscaping. Designed with exceptional attention to detail, the home features soaring vaulted ceilings, expansive windows, and multiple decks and balconies that frame tranquil water views throughout. The grand living room with gas fireplace opens to the dining area and extraordinary chef’s kitchen, appointed with a substantial center island, casual dining area, and butler’s pantry. A screened porch extends directly from the kitchen, creating an effortless setting for outdoor dining and entertaining. The main-level primary suite is a private retreat with a spa-inspired bath, separate sitting room, and direct access to a screened waterside porch. A private office with adjacent full bath offers flexibility as a fifth bedroom or guest suite. The second floor offers three additional bedrooms, including an ensuite guest room with private balcony, and two bedrooms connected by a Jack-and-Jill bath. Outside, a waterside slate terrace takes full advantage of the setting, while a new pier with two slips and 4' MLW provides convenient boating access. The property also features an integrated rainwater harvesting and management system as part of its environmental site design. Just a short stroll from downtown Oxford, this exceptional property offers a rare combination of architectural distinction, privacy, acreage, and waterfront access. Built outside the flood zone; elevation certificate available. Room for a pool, with plans available for a pool and pool house.
…$3,295,0005bedrooms5bathroomsland 0.7haBy Ttr Sotheby's International Realty
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Property Easton (United States)
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.
…$2,995,0004bedrooms4bathroomsland 11.3haBy Ttr Sotheby's International Realty
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House with pool Chester (United States)
Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.
…$825,0004bedrooms4bathroomsland 0.1haBy Ttr Sotheby's International Realty
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House with pool and garden Saint Michaels (United States)
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.
…$2,395,0004bedrooms5bathroomsland 0.6haBy Ttr Sotheby's International Realty
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House Oxford (United States)
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.
…$629,9004bedrooms3bathroomsland 0.1haBy Ttr Sotheby's International Realty
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House with pool Oxford (United States)
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 enjoying life on the water. Fabulous 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. Sold As Is
…$1,499,0003bedrooms3bathroomsland 0.1haBy Ttr Sotheby's International Realty
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House Neavitt (United States)
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!
…$399,0003bedrooms2bathroomsland 0.2haBy Ttr Sotheby's International Realty
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House with terrace Cambridge (United States)
Why wait for new construction?!? Built in 2025, this like new popular Dune model overlooks the golf course and enjoys sweeping fairway views and western sunsets. Offering 4 bedroms and 3.5 baths with first floor primary suite, the thoughtfully designed floor plan is ideal for everyday living and entertaining. The main level features a spacious great room, dining area gourmet kitchen and the first-floor primary suite with a large walk-in closet. A screened porch with a fireplace extends the living space and provides a comfortable place to relax or entertain. Upstairs are three additional bedrooms, a bonus room and an expansive covered deck with panoramic golf course views, the perfect place to enjoy morning coffee or take in the sunset. Located in Tides at River Marsh, adjacent to the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina, this home offers the convenience of nearby dining, golf, shopping and scenic walking paths. Community amenities continue to expand with a pool, clubhouse and pickleball courts slated to open soon.
…$549,0004bedrooms4bathroomsland 0.1haBy Ttr Sotheby's International Realty
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House Talbot County (United States)
Beautifully positioned on a quiet cul-de-sac in the sought-after community of Cooke’s Hope, this distinguished brick residence offers timeless architecture, generously scaled interiors, a beautifully landscaped private garden with green house, and a detached two-car garage with a private studio above. Designed for both everyday comfort and elegant entertaining, the home is filled with natural light and features a thoughtfully planned floor plan. The welcoming living room is defined by high ceilings, a gas fireplace, and ample space for multiple seating areas, including room for a grand piano. At the heart of the home, the expansive kitchen combines exceptional storage with a large center island, Corian countertops, quality appliances, and a casual dining area. A spacious library/family room with custom built-in shelving provides an inviting retreat, while the adjoining enclosed sunroom overlooks the garden and creates a seamless connection to the outdoors. An elevator provides convenient access to the second level (new carpet throughout), where the spacious primary suite features a tray ceiling and a large well-appointed bath with two walk-in closets, separate vanities, a generous walk-in shower, and towel warmers. Two additional bedrooms offer abundant closet space and share a skylit hall bath. Easily accessible attic space provides excellent additional storage. The mudroom and laundry room is thoughtfully equipped with built-in cabinetry, a utility sink, and direct access to the garden. Outside, mature landscaping, brick hardscaping, and a fountain create a private and tranquil setting. Above the detached garage, the studio with half bath offers exceptional flexibility as a home office, guest suite, fitness room, or creative workspace. Residents of Cooke’s Hope enjoy an outstanding collection of amenities, including scenic walking trails, ponds, tennis and pickleball courts, a fitness room, community gathering spaces, and a waterfront dock with slips and kayak storage. A rare opportunity to own a beautifully maintained home that offers timeless design, exceptional versatility, and the distinctive lifestyle of one of Easton’s premier communities.
…$1,150,0003bedrooms3bathroomsland 0.1haBy Ttr Sotheby's International Realty
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House with garden Chestertown (United States)
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.
…$750,0003bedrooms3bathroomsland 0.3haBy Ttr Sotheby's International Realty
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House Easton (United States)
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.
…$13,750,0005bedrooms9bathroomsland 140.2haBy Ttr Sotheby's International Realty
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Apartment Chestertown (United States)
**Listing price is for FOUR units for sale as an investment package! 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! 1A – three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! 1B – the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. 2A – a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. 2B - a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible.
…$1,500,0007bedrooms5bathroomsBy Ttr Sotheby's International Realty
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House with pool Cambridge (United States)
Waterfront Living with a Deeded Boat Slip on Cambridge Creek - Enjoy beautiful water views, three screened porches and a deeded deep-water boat slip in this spacious three-level residence in the desirable Waterside community. Thoughtfully designed with approximately 3,000 square feet of living space (per floor plans) the home offers the comfort of a single-family home with the ease of low-maintenance living. The main level features an open floor plan with spacious living and dining areas, well-appointed kitchen with granite countertops, stainless steel appliances, island seating and abundant storage plus a large screened porch overlooking the water. The entry level offers a flexible family room with a full bath and screened porch, ideal for guests, a home office or recreation. Upstairs, the waterside primary suite features vaulted ceilings, large walk-in closet, spacious bath, private screened porch and an adjoining office or sitting area. Just blocks from downtown Cambridge's restaurants, shops, marina and waterfront parks, this exceptional home offers easy access to Cambridge Creek and the Choptank River. Square footage is based on floor plans. Tax records may differ and buyers should verify.
…$549,9003bedrooms3bathroomsBy Ttr Sotheby's International Realty
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House with pool Easton (United States)
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.
…$729,0004bedrooms4bathroomsland 0.1haBy Ttr Sotheby's International Realty
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House with pool and garden Wittman (United States)
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.
…$5,995,0008bedrooms6bathroomsland 31.2haBy Ttr Sotheby's International Realty
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House with pool Wittman (United States)
"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.
…$7,900,0008bedrooms6bathroomsland 46.4haBy Ttr Sotheby's International Realty
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House with pool Wittman (United States)
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.
…$5,995,0008bedrooms6bathroomsland 31.2haBy Ttr Sotheby's International Realty
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House Chestertown (United States)
A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.
…$325,0004bedrooms2bathroomsland 0.2haBy Ttr Sotheby's International Realty
- 48Video
House Easton (United States)
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
…$2,995,0003bedrooms5bathroomsland 2haBy Ttr Sotheby's International Realty
- 50Video
House with pool Bozman (United States)
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.
…$6,800,0005bedrooms6bathroomsland 2.8haBy Ttr Sotheby's International Realty
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