luxury houses with pool for sale Guilford, United States

CUSTOM MADISON ESTATE: Private 2.11-Acre Oasis with Heated Inground Pool. Custom-built in 2001 for the original owners, this exceptional Madison estate offers over 5,400SF of meticulously designed living space set on a private 2.11-acre lot. Designed for both refined daily living and high-end entertaining, the home boasts 4 bedrooms, 4.5 bathrooms, and an ideal layout for modern flexibility. At the heart of the main level, an oversized family room features dramatic vaulted ceilings and a cozy wood-burning fireplace, creating an inviting space to gather. Distanced remote work is effortless with two dedicated home office spaces. The expansive floor plan spans 4,421 square feet between the 1st & 2nd floors, supplemented by an additional 998 square feet in the partially finished basement-perfect for a rec room, craft area, home gym, or media center. A rare highlight is the versatile bonus room above the garage, complete with its own dedicated full bath and laundry area-making it ideal for an au-pair suite, guest quarters, or a private creative studio. Outdoors, step into your own private New England retreat. The professionally landscaped grounds feature a heated inground pool surrounded by lush greenery, offering complete tranquility and an idyllic summer setup. Over 7 acres of Land Trust are located behind the home. Conveniently located near Rt 80, for easy access to New Haven and all points north, this turn-key custom home represents shoreline living at its finest!

More than a residence, this is a world unto itself. Encompassing 6.57 acres, this singular Branford estate offers the space to shape an extraordinary lifestyle. Zoning allows for up to six horses, with a four-stall barn offering a loft, lower level ideal for a wine cellar, and versatility for three additional stalls or conversion to an approximately ten-car garage-an opportunity for equestrians and car collectors alike. The acreage lends itself well to a private vineyard, gardens, recreation, or quiet enjoyment. A spectacular inground pool, hot tub, waterfall feature, and pool house create the ambiance of a private resort. Dating to the early 1900s, the six-bedroom, five-and-a-half-bath home is rich in warmth and character, with an expansive floor plan for everyday living and gracious entertaining. Formal living and dining rooms are complemented by a sunroom where the landscape becomes part of the interior experience. Fireplaces across both levels bring architectural presence and an inviting sense of home. The main level also offers a private study and generous en-suite bedroom, creating flexibility for guests or first-floor living. Upstairs, a spacious primary suite joins additional well-proportioned rooms, while a second staircase enhances the home's distinctive flow. A partially finished lower level adds space. Convenient to New York City by highway or train, this timeless, versatile estate offers a rare opportunity to live beautifully, without ever needing to get away.

A truly unforgettable and exceptionally rare offering-Rogers Island presents an exciting opportunity to own a private island paired with a mainland residence, delivering the perfect balance of seclusion and convenience. The mainland property includes its own dock, parking, and support space, making access to the island with a 5-minute boat ride, seamless and effortless. Just offshore, the island unfolds into a peaceful, panoramic retreat surrounded by water views in every direction. Designed for both relaxation and entertaining, the estate features a 10-bedroom main residence with 6 full and 2 half baths, a 4-bedroom/2.5 bathroom guest house, artist's studio with half bath, and dedicated staff quarters. A mahogany wraparound porch invites you to take in the scenery, while meandering granite pathways guide you thru the grounds which offer an exceptional collection of amenities: an in-ground heated pool with pool house and separate bath house, tennis court, Nicklaus-designed putting green, koi pond, greenhouse and two docks. A charming gazebo sits at the edge of the property-perfectly positioned to capture sweeping views for miles. Quiet, expansive and thoughtfully designed, Rogers Island is a legacy property where generations can gather with ease, hosting everything from intimate weekends to large-scale entertaining, all set against a backdrop of uninterrupted water views, timeless coastal beauty and a sense of privacy that's increasingly impossible to find.

Welcome to your own private retreat! This exceptional custom 3-bedroom Cape Cod home sits on 2 sprawling, peaceful acres and offers the perfect blend of modern upgrades and ultimate outdoor living. Step inside to a main floor designed for both everyday comfort and effortless entertaining. Remodeled Kitchen: The heart of the home features updated cabinetry and finishes, anchored by a cozy wood-burning stove. Family Room: Highlighted by a handsome warm fireplace, creating an inviting space to gather. Formal Dining Room: Elegant layout perfect for hosting dinners and holiday gatherings. Formal living room ,also with wood burning fireplace adds to your entertaining experience Primary Suite: Features a warm fireplace and a beautifully remodeled full en-suite bath. Additional Bedrooms: Two generously sized bedrooms, each featuring direct access to an attached full bathroom. Resort-Style Backyard & Grounds Step outside to an outdoor haven engineered for relaxation, recreation, and pet-friendly living. In-Ground Pool Compound: Complete with a stone waterfall feature, expansive barbecue area, separate dressing room, and a summer kitchen for poolside dining. Outdoor Entertaining: Enjoy crisp evenings around the fire pit or relax in the covered picnic area. Covered Porch: Overlooks the entire pool area, offering a shady vantage point to unwind. Fully Fenced in back yard keep your furry friends close by

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.

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!

Opportunity knocks! Available for the first time since it was built on .93 acre on the cul-de-sac, this stately Colonial offers turn-key living. Open the front door to the welcoming foyer and your eye is drawn to the detail work that surrounds you. A formal living room is to the right and the dining room to the left opens to the family room with gas fireplace and then to the kitchen which will thrill the most discerning cook. The island provides plenty of workspace as well as abundant seating for family and friends. Entertaining for holidays or watching a game is fun and easy with this floor plan design. The covered porch provides additional entertaining space. Outside is a spectacular private outdoor oasis designed for ultimate relaxation and entertaining. The centerpiece of the backyard is a stunning in-ground pool, surrounded by a concrete patio and an expansive composite deck. There is endless space for unwinding at home or hosting large gatherings. Seamlessly connecting the indoor and outdoor living areas, this backyard is built for creating memories. Upstairs features a magnificent primary suite, a second family room, and three additional spacious bedrooms. Second floor laundry room features another half bath. Enjoy phenomenal storage, an attached, oversized 3-car garage, plus a vast walk-out basement perfect for a gym or playroom. In addition to the main house, a versatile one bedroom in-law suite is accessed via deck, driveway and garage.

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!

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.

Positioned moments from the shoreline and local marina, 15 Linden Shores delivers a masterfully reimagined coastal retreat combining thoughtful upgrades, expansive layout options, and impressive community perks. Spanning 2,800 square feet, the open-concept main floor is flooded with sunlight from soaring vaulted ceilings and multiple skylights. Anchoring this primary gathering space is a gourmet chef's kitchen along with a warm gas fireplace. For effortless indoor-outdoor living, glass doors open onto an oversized deck and gazebo, where you can unwind against a backdrop of tranquil marshland and harbor views. Designed for true main-level living, the residence offers a first-floor primary bedroom suite complete with a luxurious ensuite bathroom featuring radiant heated floors and a Bain Ultra soaking tub. Upstairs, a versatile loft provides additional flexible living space. The fully finished walk-out lower level acts as a self-contained suite-ideal for guests, extended family, or a dedicated sanctuary-comprising a private bedroom, home office, workout area, lounge, steam shower, and dedicated laundry space with Speed Queen appliances. Every mechanical and technology system throughout the home has been meticulously updated for effortless modern living. Integrated features include an 11-zone Sonos sound system, Ring security, Nest smart thermostats, Hunter Douglas window treatments, updated HVAC, whole-house water filtration, a full-home backup generator, custom deck lighting

This magical light-filled New England 7,945 s.f. "cottage" takes full advantage of its private waterfront location overlooking LIS and a wildlife estuary. Sited in a private community on 1.27 acres with 300' of water frontage provides panoramic water views of sunrises and sunsets from most rooms. A heated swimming pool, two beaches and mooring rights guarantee outdoor pleasures. There is also room for a tennis court. The house was expanded from its original 1912 footprint and fully renovated over 3 years (1987-1990) with the best curated materials including Tischler high impact windows throughout. French doors in the 18' ceilinged living room, dining room and family room all open to a flagstone terrace. The 6+ bedrooms, all but one with ensuite bathrooms, can be accessed by elevator or front and back stairs. There is also a separate handicapped accessible apartment. The impressive, newly renovated kitchen with table sitting up to eight is equipped with top of the line appliances. Privacy, gracious living space and endless recreation possibilities make this special property an ideal retreat. Check floor plans for more details.

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.

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.

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.

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 150 Joshuatown Road in Lyme, a stunning, custom built residence sited on over 30 acres of bucolic land, with specimen trees, beautiful landscaping, and over 1/4 mile of impressive rebuilt stone walls. The main level features a welcoming foyer, Chef's kitchen with breakfast room, a cherry paneled library with vaulted ceiling and warming fireplace, commodious dining room, living room with separate seating areas, and a first floor primary suite. The second level has additional bedrooms and a beautiful family room, currently used as an art studio. In addition to the Main house, there is an incredible Guest house, fully functioning with full kitchen and adequate bedroom space. This is a property that needs to be seen to be believed! Simply amazing!

Your Beach Retreat Awaits! Completely renovated and thoughtfully redesigned, 86 Fenwood Drive offers the perfect opportunity for a year-round residence or summer getaway. Ideally located just minutes from the kayak launch, cove, and beach, this charming home sits on a beautifully landscaped, level lot filled with mature plantings and inviting outdoor spaces. Step inside to discover a stunning custom kitchen featuring GE Cafe appliances, white shaker cabinetry, quartz countertops, and character-grade flooring that flows throughout the home. The bright and welcoming front living room is anchored by a cozy wood-burning fireplace, creating the perfect gathering space. At the rear of the home, the spacious family room showcases soaring ceilings, exposed beams, shiplap accents, and an abundance of windows overlooking the backyard. This versatile space could easily be converted into an additional bedroom if desired. Adjacent to the family room is a beautifully updated full bath featuring a new vanity with marble top and a stylish tiled shower. Convenient first-floor laundry is located just off the hallway leading to the bedroom wing. Both bedrooms offer generous proportions, while the primary suite boasts an oversized walk-in closet and a luxurious en-suite bath complete with heated floors, a soaking tub, updated vanity, and a large walk-in shower. The updates continue throughout the property, including a new propane tank, new septic tank, central air condition

Experience shoreline living at its finest in this beautifully updated home offering breathtaking 180-degree water views. The home features a light and bright kitchen with stainless steel appliances and blends modern updates with timeless coastal charm. The well-designed floor plan features spacious, light-filled rooms with a natural flow, while walls of windows frame and showcase the incredible water views throughout. A welcoming covered front porch with beautiful mahogany decking provides the perfect spot to relax and take in the coastal surroundings. Step outside to your private backyard retreat featuring an inground pool, stunning bluestone patio, and plenty of space for relaxing or entertaining against a picturesque Long Island Sound backdrop. A finished lower level offers potential for an in-law setup, adding valuable flexibility to the home. Whether enjoying your morning coffee on the front porch or unwinding by the pool overlooking the water, this home delivers the perfect coastal lifestyle. Ideally located just minutes from Milford's beaches, downtown restaurants and shops, the train station, and major highways, this exceptional property offers the perfect blend of tranquility, convenience, and modern living.

Welcome to Greystone, a masterpiece of modern architecture. Bordered by a protected wildlife area, this 4500 sf smart home offers peace and privacy. The main level features an open living room, dining area and kitchen, den, office, half bath, laundry room and primary bedroom suite. Two ensuite bedrooms and a rooftop deck comprise the upper level. The lower level affords access to the backyard and has finished space for a gym or home office as well as a rough-in for a full bath. The kitchen boasts a 10' x 4' island and large walk-in pantry and is well appointed with Wolf and Sub-Zero appliances. An expansive white limestone wrap-around deck and spacious lawn---with an irrigation system---are perfect for relaxing or entertaining. The attached two-car garage is heated. White oak radiant-heated flooring complements the oak Unilux windows and exterior doors. Interior pocket doors and custom cabinetry continue the sleek contemporary look. Kitchen and bathroom countertops are quartzite, some with waterfall edging. Bathrooms feature limestone floors and unique tadelakt plaster walls. Designed with energy efficiency in mind, Greystone uses a geothermal system for heating and cooling. Smart home technology includes programmable LED lighting, motorized shades, security system, and wiring for audio and AI systems. A whole-house generator connects automatically during power outages.