luxury houses with pool for sale Old Lyme, United States

Rare opportunity on 2.5+ private acres in premier Deans Ridge! Prime, secluded location offers effortless commuting near top schools, beaches, & dining. This sprawling 4-bed, 4.5-bath Cape Cod with attached 2-car garage features a grand 2-story foyer, formal dining with crown molding & shiplap, and a home office with built-ins and custom recessed lighting throughout. The chef's kitchen boasts honed granite & a Quadra-Fire pellet stove with an incredible brick surround, opening to a front-to-back family room with custom built-ins & a walk-in pub with wet bar. Upstairs offers a primary suite with dual closets & custom walk-in tile shower, a 2nd ensuite bedroom, plus 2 bedrooms sharing a double-vanity bath. Ideal for multi-generational living, the lower level provides a private refuge with home/garage access, rec room, full bath, in-law flex space, & ample dry storage. Wood and pellet stoves paired with solar yield supreme efficiency ($0 electric bills in peak months!). Designed for seamless outdoor living, the home features strategic exterior uplighting that highlights the front facade. The fully fenced yard delivers added ease for pet owners, featuring an expansive 44-foot deck with a dedicated gazebo, ceiling fan, and integrated lighting, all overlooking the peaceful backyard and in-ground pool for a complete outdoor destination.

Overlooking the hills of Lyme, Connecticut, Hilltop Estate combines old world elegance with modern luxury. The fully renovated stone and stucco main house, spacious guest cottage, pool and barn complex are set on nearly 50 acres. Made up of five separate parcels with potential for equestrian pursuits, farm to table living or sellable individually. The barns include a workshop fully convertible to living space, artist studio or entertainment space. Contiguous to the barns is an Alitex greenhouse manufactured in England with its own dedicated, fully equipped potting room. The property is surrounded by manicured gardens, stone walls, privet hedges and mature plantings. The three bedroom, two and one half bath main house exudes historic character with detailed moldings, refined finishes, antique chestnut floors, custom built-in cabinetry, grass cloth wallpaper, hand-hewn exposed beams, multiple fireplaces, decorative painting and light-filled interiors. The gourmet kitchen features two stoves (Wolf and Gaggeneau) and a Sub-Zero refrigerator. Enjoy the outdoor terrace for six months a year; warmed by its stone fireplace and protected by fully retractable roller screens in the summer. The two bedroom en-suite guest cottage complete with a full kitchen provides a luxurious escape for family and friends. Meandering trails throughout the property provide a peaceful hiking experience for enjoyment year-round. The property is equidistant to New York City and Boston.

Steeped in history and thoughtfully maintained, this exceptional antique residence beautifully blends timeless New England character with modern comfort. Nestled on a picturesque property in the heart of Lyme, this remarkable 5 bedroom home showcases the craftsmanship and architectural details that define a true Connecticut antique. Rich hardwood floors, original beams, multiple fireplaces, and beautifully preserved period features create an inviting atmosphere throughout. Designed for both everyday living and entertaining, the home offers gracious living spaces, including a spectacular oversized bonus room perfect for gatherings, a media room, studio, or recreation space. A sun filled sunroom overlooks the grounds, providing the perfect place to relax year round. The outdoor setting is equally impressive, featuring a sparkling in ground pool, expansive stone patio, and beautifully landscaped grounds that create an ideal backdrop for entertaining or quiet enjoyment. Combining historic charm, generous living space, and exceptional outdoor amenities, this one of a kind property offers a rare opportunity to enjoy the beauty and lifestyle of one of Connecticut's most picturesque towns.

Set in a magnificent North Cove waterfront location, this exquisitely designed and masterfully crafted residence captures striking views of the Connecticut River and Long Island Sound, all just moments from the Village of Essex. Built in 2014 with exceptional attention to detail, the nearly 6,000-square-foot home offers a timeless architectural aesthetic, beautifully balanced living spaces, and expansive walls of windows and French doors that frame the inspiring water views. Spacious stone terraces extend the living areas outdoors, while professionally landscaped grounds feature mature gardens, specimen plantings, and graceful shade trees. Inside, custom moldings, wood, tile, and marble flooring, along with a state-of-the-art hydro-air heating and cooling system, reflect the home's quality and thoughtful design. A separate finished bonus room with its own staircase offers exceptional flexibility as an au pair suite, private studio, or home office, while a three-bay garage provides ample space and convenience. The spectacular waterfront grounds are designed for both entertaining and relaxation, featuring expansive bluestone terraces, an outdoor gas fire pit, and a stunning pool and spa complex, all set against the breathtaking backdrop of North Cove and the Connecticut River. Completing this exceptional offering is a shared dock with a slip accommodating a boat up to 25 feet, making this a truly distinctive waterfront retreat.

Elevated on a dramatic rise above the Connecticut River, this captivating property, aptly named "River Knoll," showcases one of the most breathtaking private settings on the river. The historic home has been featured in multiple publications such as Veranda and CTC&G for its exceptional beauty. Stunning landscape design frames every vista from the river's edge to the meticulously tended grounds that flow effortlessly into the natural surroundings. At the heart of the property is an 18th-century Cape, artfully expanded with architectural additions that honor the home's original character while delivering modern luxury. Step inside to discover the soul of the home: original hand-hewn beams, rich paneled walls, and wide-plank flooring that whisper stories of centuries past. Yet, every room has been thoughtfully enhanced with upscale improvements that marry history with today's lifestyle demands. The chef's kitchen, complete with a butler's pantry, is designed for serious cooking and effortless entertaining. Updated bathrooms throughout reflect refined taste and functionality. The primary suite is a private sanctuary with extraordinary river views that unfold in quiet splendor.

A rare opportunity to own a meticulously designed enclave set on nearly three private acres overlooking the Connecticut River. The main house has over 4600 square feet of beautifully scaled living space with elegant architectural finishes throughout. The first floor features a welcoming entryway which leads to a well-equipped kitchen, breakfast room, formal dining room, and both a living room and family room with fireplaces. Each room has plenty of windows that bring in natural light and showcase incredible views of the CT River. An elegant curved stairwell leads to the second floor, which is designed with privacy in mind. It features a separate wing for the primary bedroom suite, and another for two guest bedrooms and baths. An elevator services the entire structure, so every room is accessible to all and offers a possible working option for multigenerational living. The compound also features a separate spacious guest house with a full kitchen, sitting room, bedroom, and one- and one-half bathrooms situated next to the inground Gunite pool, offering another private retreat for guests, visitors, or family members to enjoy

The Benjamin F. Post House, c. 1801, has been thoroughly and thoughtfully updated to provide all the amenities of modern living while respecting the historical integrity of the home. A sidewalk just steps from the property leads directly into the heart of Essex Village, an approximately 20-minute walk to its shops, restaurants, marina, and waterfront. Set on a .48-acre professionally landscaped lot backing up to a quiet wooded area, the fenced-in backyard boasts a beautiful gunite pool and a generous pool deck/patio, perfect for both relaxing and entertaining. Inside on the first floor, there is a light-filled chef's kitchen, well-appointed with upscale appliances including a commercial-grade six-burner range, a large center island, and ample counter space. There is also a formal dining room, a living room with a wood-burning fireplace, and a library with a gas fireplace and built-in floor-to-ceiling bookshelves. An additional room with its own exterior entrance could serve as an office or a potential first-floor bedroom. A lovely four-season sunroom overlooks the pool deck and features a convenient wet bar complete with a beverage chiller. There is also a powder room on the first floor. Upstairs, the primary suite has an updated ensuite bathroom with marble finishes, a large walk-in closet, and a spacious sitting area. There are also two more bedrooms, another den/office area, a second updated bathroom, and laundry. Offering historic character, modern comforts, privacy, and

Welcome to 83 Old Post Road in Old Saybrook. This antique colonial offers a unique blend of historical charm and great potential, nestled on a sprawling 1.7-acre lot within walking distance to the heart of town. Boasting 5+ bedrooms and 2.5 bathrooms, this spacious home exudes timeless character with features such as wide pine wood floors, covered porches, period details, and abundant natural light throughout. The true allure of this property lies in its potential for expansion and possible subdividing. With 1.7 acres of land at your disposal, there's ample room to bring your vision to life and create the ultimate dream home. Whether you're looking to add a pool, a guest house, or explore the option of subdividing, there are endless possibilities. Conveniently located within walking distance to town, this exceptional property enjoys easy access to local shops, restaurants, beaches, and more. Don't miss your chance to own a piece of Old Saybrook history and start imagining the possibilities!

This elegant and updated historic colonial is tucked away on a quiet road on 1.4 acres. The original two-story structure was built in the mid 1800s, and the additional first-story wing was later added in 1974. The main house has a cozy living room with a fireplace, a formal dining area with a window seat, reading room, a family room/den, and a powder room. The updated galley kitchen features upscale stainless-steel appliances, lots of cabinet space for storage, and plenty of counter space. There is a sunny breakfast nook just off of the kitchen. Upstairs are two bedrooms, including the primary with ensuite bath along with another bedroom and full bathroom. The addition offers a private and separate living space, with a kitchen, living room, bedroom with ensuite bath, a den and another full bathroom. As it is connected to the original house by a breezeway, it offers a good option for use an in-law apartment or for a multi-generational living arrangement. The main house has beautiful wide-plank floors and the apartment has hardwood floors. There is a spacious two-car garage located at the end of the addition. Outside is a lush mixture of mature landscaping, lawns, and shady trees. You can enjoy the outdoor setting from the covered front porch, a patio area off of the breakfast nook, or another patio by the pool area shaded by a vine-draped pergola leading directly to the sparkling in-ground gunite pool.

This charming and updated historic colonial is tucked away on a quiet road on 1.4 acres. The original two-story structure was built in the mid 1800s, and the additional first-story wing was later added in 1974. The main house has a cozy living room with a fireplace, a formal dining area with a window seat, reading room, a family room/den, and a powder room. The updated galley kitchen features upscale stainless-steel appliances, lots of cabinet space for storage, and plenty of counter space. There is a sunny breakfast nook just off of the kitchen. Upstairs are two bedrooms, including the primary with ensuite bath along with another bedroom and full bathroom. The addition offers a private and separate living space, with a kitchen, living room, bedroom with ensuite bath, a den and another full bathroom. As it is connected to the original house by a breezeway, it offers a good option for use an in-law apartment or for a multi-generational living arrangement. The main house has beautiful wide-plank floors and the apartment has hardwood floors. There is a spacious two-car garage located at the end of the addition. Outside is a lush mixture of mature landscaping, lawns, and shady trees. You can enjoy the outdoor setting from the covered front porch, a patio area off of the breakfast nook, or another patio by the pool area shaded by a vine-draped pergola leading directly to the sparkling in-ground gunite pool.

Discover the charm and comfort of this beautifully maintained Cape, ideally situated on a quiet cul-de-sac off School House Road in one of Old Saybrook's desirable locations. Offering over 2,700 square feet of finished living space, this inviting home is just across from The Preserve trail access and moments from Clark Park, making it easy to enjoy nature, recreation, and the outdoors. Inside, gleaming hardwood floors, a spacious living room with a wood-burning fireplace, and a formal dining room create a warm, welcoming atmosphere. The updated kitchen features rich cherry cabinetry and granite countertops and opens to a cozy family room with a Garrison wood stove. Sliders lead to a cedar-paneled three-season room overlooking the private backyard, deck, and patio-perfect for entertaining or relaxing outdoors. Upstairs, the spacious primary suite features an en-suite bath with a custom shower and tons of storage, along with two additional bedrooms and a full bath. The finished lower level offers flexible space for a home office, gym, media room, or additional living area. Thoughtful updates include Andersen replacement windows, newer garage doors, enhanced attic insulation, and ice dam heating cables. Blending classic New England charm, versatile living spaces, and an exceptional location near trails and recreation, this move-in-ready home is a wonderful place to enjoy the best of Old Saybrook living.

Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with Sub-Zero refrigerator, new double wall oven, and cooktop. A butler's pantry adds a second refrigerator and dedicated wine fridge. Four bedrooms with private en suite bathrooms, including a reimagined primary suite with spa-level finishes. Two home offices. An inviting Family Room. A spectacular Living Room. And a Sunroom - a fully restored 1920s porch with original terra cotta floors and sweeping estate views. Every room is professionally curated with bespoke wallcoverings and custom light fixtures. Steps from the Ivoryton Playhouse, The Copper Beech, and Prive Swiss. Minutes to Connecticut River marinas. Long Island Sound 15 minutes beyond. A truly unique property located in what Yankee Magazine ranks as the #1 small town in New England.

Selden Farm, a landmark 1690s property steeped in history and set in a picturesque corner of Lyme, is once again available for new stewardship. Upheld by only three families since 1695 when it sat on over 6,000 acres, it presents a rare opportunity to own a beautiful country Antique home now set on 9 pastoral acres abutting conservation land with sweeping views of Selden Cove and the CT. River. At its heart is a gracious and authentic 5-bedroom Colonial which exudes history, charm and character. House features include a tavern room, wide board floors, original paneling & moldings, 6 fireplaces and an abundance of windows which invite lovely views and light into each room. Adjacent to the home is a 3-bay garage with self-sufficient guest accommodation for visiting family and friends. Dotted throughout the property are a renovated barn used as a studio/office/ gym, several outbuildings, a greenhouse and sunny open meadow for animals or farming. Two privately situated guest houses (one needing renovation) are ideally suited for in-law, caretaker, or income purposes. Relax by the large saltwater pool with patio and full-service cabana or play tennis on the all-weather court. The land is open, tranquil, and beautifully sited, offering long views, privacy, and a deep sense of place. Rarely does a property combine this level of authenticity, acreage, outbuildings, and river-valley setting in Lyme. Ideal for buyers seeking history, creative space or a generational retreat.

Where Architectural Inspiration Meets the Majesty of the Connecticut River. Perched majestically on 15.22 acres along the eastern bank of the Connecticut River, 89 River Road offers a rare convergence of architectural pedigree, natural beauty, privacy, and fully realized lifestyle design. Designed, owned, and meticulously crafted by one of America's leading architects, this 12,836-square-foot compound, completed in 2018, was conceived to inspire creativity, wellness, and a connection to the outdoors. Protected by parkland, Nature Conservancy, and Land Trust preserves, the heart of the home is defined by extensive, floor-to-ceiling glass walls that command uninterrupted, panoramic vistas of the Connecticut River while a scenic jeep road offers direct access to Chapman Creek and the River beyond. A seamless flow connects the breathtaking entertaining and living areas with a variety of outdoor decks and terraces. The estate offers a rare sanctuary designed to fuel both the mind and the body. It features an unparalleled suite of dedicated, professional- grade spaces that defy the ordinary. The Creative Hub: Fulfill your creative inspirations in one of four dedicated studios: a sky-lit art studio, a sky-lit writing/drawing studio, a fabrication studio, and a fully equipped woodworking shop.

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a "to be built" opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

This Traditional 4-bedroom, 2.5-bath home sits near Orient State Park and the Cross Sound Ferry. The private, landscaped backyard has a heated pool and patio, plus a large deck with glass doors to the open-plan kitchen and family room, making it ideal for entertaining. The first floor is completed with a private living room, a dining room, laundry, and a powder room. Upstairs, the primary ensuite has a full bath with views of the backyard and pool. Three more bedrooms and a full bath complete the second floor. The finished lower level offers a large recreation space. This home is ideal year-round living or for enjoying North Fork summers.

PRIVATE COASTAL CLINTON, CT RETREAT WITH POOL. Welcome to your private oasis in Clinton! Built in 2003 and set on almost 2 private acres, this beautifully designed 4-bedroom, 2.5-bath home offers an ideal balance of functional interior space and exceptional outdoor living. The main level features a fluid floor plan including formal living and dining rooms, a dedicated home office, and a generous kitchen complete with a walk-in pantry. Gather in the cozy family room anchored by a wood-burning fireplace insert, or relax in the light-filled sunroom overlooking your private backyard. Above the garage is a finished bonus room, ready for all sorts of entertainment. Step outside to an outdoor paradise featuring a back deck leading down to an in-ground vinyl pool surrounded by mature greenery for maximum privacy. Additional features include a whole-house generator for uninterrupted peace of mind, shed for outdoor storage, and an unfinished basement offering massive potential for custom expansion, storage, or a home gym. This home offers comfort, independence, and timeless coastal Connecticut charm.

Gracefully blending timeless architecture with exceptional everyday living, this beautifully appointed Colonial offers thoughtfully designed open spaces both inside and out. A welcoming wraparound porch creates an elegant first impression, while the interior unfolds into an open floor plan ideal for entertaining. The chef-inspired kitchen features a generous center island, double ovens, and a sunny breakfast area that opens seamlessly to the expansive family room. Anchored by a cozy fireplace, this space extends effortlessly through sliding doors to an expansive deck overlooking the private backyard. The outdoor setting is a true retreat. Highlighted by a sparkling inground pool and a built-in fire pit nestled on an upper terrace-creating the perfect setting for summer gatherings, relaxing evenings, and outdoor entertaining. The primary suite offers a peaceful sanctuary with abundant natural light, a spacious walk-in closet, and an ensuite bath featuring a whirlpool soaking tub, separate walk-in shower, and dual vanities. Three additional bedrooms provide exceptional flexibility, including an impressive 23' x 23' suite above the garage with hardwood flooring, double closets, independent heating and cooling, and endless possibilities as a guest retreat, home office, fitness studio or Bonus living space. Upper-level laundry adds everyday convenience, while the walk-out lower level includes a partially finished area ready to be customized to your lifestyle. Welcome Home!

Meticulously restored Craftsman on coveted Orchard Street in the heart of Orient Village. The private 0.55-acre lot offers an 18x40 heated in-ground pool, an original two-car garage and an outbuilding. A covered front porch opens to a welcoming foyer, which flows into a living room with a wood-burning fireplace and on to the dining room and eat-in kitchen. A mud room with laundry and a powder room complete the first floor. Upstairs is a primary suite with full bath and two additional bedrooms sharing a second full bath. Stroll to the village shops, country store, post office and yacht club, and enjoy the breezes off Orient Harbor. Professional photography coming.

Rare opportunity to own a uniquely private 7.49-acre bay front estate in Orient Village. This exceptional waterfront property features a spacious 5700 sq ft main residence with 6 bedrooms, 7 baths, three wood burning fireplaces, three bay garage, expansive front and rear covered porches and panoramic bay views. The 20 x 44 heated pool is complemented with a 860 sq ft pool house featuring open common area, kitchenette, full bath, laundry, two changing rooms, outdoor shower, & porch – creating an ideal setting for entertaining and summer living. A fully fenced clay 60 x 120 ft tennis court is expertly sited, so sun glare is never an issue. The property offers an additional free-standing two-bay garage with second floor bonus space providing flexible options for recreation, boat/bike storage or studio space. The 195 ft wide private walkout bay beach offers sweeping Harbor views of Long Beach State Park, Bug Light House and Orient Yacht Club. The property is ideally located within walking or biking distance to the Village of Orient, Orient Yacht Club, local marinas, Post Office, the Country Store, Oysterponds Historical Society and all village amenities.

This storybook circa 1858 cottage captures the very essence of North Fork living: cozy, charming, and effortlessly inviting. Rich in history and timeless appeal, this beautifully preserved home blends the simplicity of a bygone era with thoughtful modern updates, creating a warm and welcoming retreat. Inside, random-width wide plank flooring adds authentic character throughout. The first floor offers a spacious primary bedroom, a second bedroom or home office, an inviting living room, formal dining room, and an eat-in kitchen with a convenient laundry area. Upstairs, two additional bedrooms and a half bath provide comfortable accommodations. Architectural details enhance the home's enduring charm, from the welcoming semi-wraparound covered front porch to the side deck with a new retractable awning overlooking beautifully landscaped gardens. A pergola with a slate patio creates the perfect setting for outdoor dining, entertaining, or simply relaxing on a summer evening. Adding to the property's appeal is a detached 2-car garage and a delightful artist's or hobby studio, complete with its own pergola-covered sitting area nestled among lush gardens. Privately tucked behind a classic white picket fence, the beautifully landscaped .5-acre property is an exceptional outdoor sanctuary. The backyard features a heated free-form Gunite pool with a cascading waterfall, a pool shed with deck, two additional storage sheds, mature trees, and an abundance of seasonal flowering plantings, creating a peaceful and private oasis. Ideally located just minutes from pristine beaches, golf courses, marinas, renowned wineries and breweries, county parks, farm stands, Hampton Jitney and popular local eateries. This special property also enjoys close proximity to Historic Greenport, where waterfront dining, boutique shopping, and galleries await. The backyard abuts a nature preserve that leads to Marion Lake County Park. Nothing can be built behind it. Whether you're enjoying a quiet morning coffee on the porch, spending the afternoon poolside, or entertaining friends after a day at the beach, this one-of-a-kind North Fork treasure offers the perfect blend of historic character, modern comfort, and relaxed coastal living.

RARE OPPORTUNITY in the highly sought-after Barberry Farms Association! With only 2 MLS sales since 2021, homes in this premier beach community seldom become available. Enjoy private access to a wonderfully wide & deep sandy beach that has storage bins & an area for kayaks & small sailboats to make life easier. BIG home, BIG rooms. Spanning 4,833 sq ft, this 10 room Colonial features hardwood floors throughout. Off the formal entry foyer sits a den/library w/ built-ins, ideal for a home office, & a formal living room centered by a wood-burning fireplace. The main level also boasts a formal dining room w/ a bow window, & a center island chef's kitchen w/ granite counters, double ovens & a real walk-in pantry. Adjacent to the kitchen, a natural light filled family room offers a gas fireplace, a bow window & sliders out to a broad bluestone patio for outdoor entertaining. Upstairs features cathedral ceilings, a vaulted game room, a large laundry room w/ utility sink that is super convenient, & 4 bedrooms, 3 w/ walk-in closets. Highlights include 2 ensuites! The primary retreat has a spacious bathroom with deluxe spa tub, oversized glass shower, long double vanity, even an English heated towel rack. Set on professionally landscaped grounds, the flat open backyard is ready for lawn games or a future pool. Features include 4 full/2 half baths, a full basement, 8-zone (!) natural gas heat, city water & a 3 car garage. Exceptional coastal living. Don't wait another 5 years!