luxury houses with pool for sale Guilford, United States

Welcome to a truly exceptional living experience at The Residences at 66 High Street! This stunning three-bedroom, two-and-a-half-bathroom condo presents a rare opportunity for those seeking luxury and convenience in one of Guilford's most desirable locations. Spanning an impressive 3,148 square feet, this custom single-level home offers elegant design and modern amenities, ensuring comfort and style at every turn. Step inside to discover an exquisite open floor plan highlighted by two-inch marble and black walnut countertops, complemented by high-end finishes from Waterworks and custom built-ins throughout. Enjoy the culinary delight of a gourmet kitchen equipped with Subzero appliances, a 48 Wolf range, and two spacious walk-in pantries. The inviting living area features a gas fireplace for cozy evenings and a state-of-the-art Full Swing sports simulator that also serves as a perfect media room. This smart home boasts temperature-controlled fresh air and is easily managed via iPad. Step outside to your covered private terrace and be captivated by stunning marsh and Long Island Sound views, accompanied by refreshing salty breezes. The vibrant community offers a heated pool, fitness center, fire pit, dog park, and more, making it an ideal setting for relaxation and recreation. With easy access to the marina, beach, dining, shopping, and cultural experiences in downtown Guilford, this property epitomizes Connecticut shoreline living at its finest.

Welcome to 177 Warpas Road, a beautifully rebuilt 4 bed, 2.1 bath coastal colonial set on 1.84 acres, bordered by 185 acres of protected land trust. A lighted stone column entrance sets the tone for this home where New England style meets thoughtful modern updates. Set well back from the road, enjoy a rare sense of privacy, complemented by a fresh, updated exterior with new windows, siding, entrance portico, roof and refinished flooring (all 2025). Inside, the 1st floor layout is designed for easy living and effortless entertaining. The den with custom built-ins opens to a bright, eat-in kitchen with captivating property views. The dining area, living room and family room also offer views of the perfectly manicured and landscaped grounds. A stone fireplace and cathedral ceiling detail the family room and a wall of glass frames views of the resort-like backyard. The second floor offers an updated primary bedroom with tray ceiling. A newly created attic space provides a valuable head start for expansion with potential to add additional square footage. A roomy two-car garage adds convenience year round. Outdoors, an expansive two level patio incorporates a 2-year-old 630 square foot Timbertech deck with automatic awning that creates a shady outdoor living space. Across the lush lawn, a saltwater pool and a putting green create a true country club atmosphere. A full property irrigation system keeps the professionally maintained lawn and landscaping looking beautiful!

An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town neighborhoods. Close to sandy beaches, charming town center and the Madison Country Club, recreation and everyday conveniences are right at your doorstep. Traditional by design with ten foot ceilings, abundant natural light and generously scaled rooms that create an airy feel, ideal for relaxing or entertaining. Five well appointed bedrooms offer private welcoming guest options. A main level open concept perfectly connects the dining, living and kitchen areas, a purposeful layout that flows beautifully. custom millwork and thoughtful finish details everywhere will not disappoint. The expansive great room is perfect for movie nights, casual get togethers or a quiet evening by the fire. Outside the property transforms into your own private resort. Lush landscaping surrounds a very private bluestone patio with outdoor fireplace for an inviting setting for year-round entertaining. Enjoy the heated saltwater pool and chic pool house with its own bath and outside shower. Meticulously maintained this much admired home offers and exceptional balance of scale, sophistication and warmth in the heart of Madison. (Town field card being adjusted to show correct above grade sf 5837)

Set on over 20 breathtaking, wooded acres, this property offers a rare blend of privacy, natural beauty, and flexible living. This contemporary split-level home is filled with natural light and thoughtfully positioned to capture sweeping hillside views from nearly every angle. With five bedrooms and 3.5 baths, including a private in-law suite with its own entrance, the home provides exceptional versatility for multi-generational living or guest accommodations. Outdoors, the property unfolds into a true retreat-meandering private hiking trails, a serene spring-fed pond, and open fields dotted with fruit trees create an idyllic country setting. Entertain with ease around the in-ground cement pool, surrounded by a stamped concrete patio, or host unforgettable gatherings beneath the stunning pergola dining area. Recent improvements, including a new roof make this move in ready. With its unmatched acreage, scenic vistas, and boundless potential, this is a unique opportunity to create a truly special lifestyle property in the heart of Durham.

A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.

This is not simply waterfront living. This is a waterfront lifestyle unlike any other. Tucked within the coveted enclave of Sachem's Head, this extraordinary estate commands direct Long Island Sound frontage with unobstructed harbor views and breathtaking sunsets. Masterfully crafted in 2003 and transformed by the current owners with uncompromising quality, the 6,000 SF+ residence is defined by Dramatic walls of glass framing endless water views from virtually every room offering seamless indoor-outdoor living. You will be immediately wowed by the jaw dropping great room with an incredible fireplace & soaring ceiling. At the heart of the home lies a stunning Poliform kitchen, the pinnacle of modern luxury, thoughtfully appointed with premium appliances and designed to delight the most discerning chef. Oversized dining area that effortlessly steps right onto the expansive Ipe deck for additional outdoor waterfront entertaining. The all glass-enclosed family room overlooks the sound as well as the heated saltwater pool. Upstairs, a dramatic suspended gallery leads to an octagonal office and private outdoor captain's walk with endless vistas. The primary suite is a sanctuary with panoramic water views, balcony, fireplace, custom closets, and a spa-inspired bath with oversized shower and infrared sauna. A separate wing offers three en-suite bedrooms with stunning new baths and custom bunks for additional guests. Exceptional boating amenities include a permanent pier of concrete

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.

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!

Experience some of the most peaceful and breathtaking views of Long Island Sound from this beautiful Cliff House; condo, tucked away in a secluded corner of Harbour Village condominium community in Branford. A long gradual stairway leads to a million-dollar view that's worth every step. Enjoy your own personal paradise with private gardens, a large shaded deck that offers an inviting setting in all seasons. Step out for your morning tea, watch the boats Lindsey Cove or take a quiet walk through the garden, a daily reminder that this is more than a home, it's a lifestyle. Residents of Harbour Village enjoy access to a private beach, heated pool, waterfront clubhouse, fitness center, library, cozy fireplace, commercial kitchen, outdoor grill and patio, ideal for entertaining or relaxing year-round. Kayak enthusiasts have access to seasonal beachside kayak racks. The condo itself blends warmth and comfort with a working fireplace, hardwood floors throughout the main level, and a bright galley kitchen with granite countertops. The spacious, sun-filled primary suite offers vaulted ceilings, plush wall-to-wall carpeting, and a beautifully renovated bathroom with large soaker tub and window to the water. A large second bedroom and newly renovated bathroom with walk-in shower completes this serene retreat where you can wake to changing colors of the sunrise and water every day! Easy travel to NYC, minutes from Branford train station and Tweed New Haven Airport.

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.

Nestled in Westbrook, Connecticut, 331 Dennison Road is a quintessential private retreat that seamlessly blends indoor comfort with outdoor splendor. This casual residence features a bright, open floor plan highlighted by a grand great room with a cozy fireplace, perfect for quiet evenings or lively gatherings. The kitchen opens directly onto a charming patio, ideal for alfresco dining overlooking the pool and woods. Outside, an inviting inground pool is encircled by a meticulously curated flower garden, while a dedicated, fenced-in vegetable garden with raised beds and a custom shed awaits the home gardener. With the convenience of a spacious first-floor primary suite, this home offers a thoughtful layout designed for modern living in a serene, park-like setting. Offering geothermal heating/cooling system and owner owned solar panels for a very efficient low cost utilities.

This 4-bedroom Colonial offers the perfect combination of space, comfort & location. Ideally situated in a subdivision close to shopping, restaurants and major highways. The main level welcomes you with a spacious eat-in kitchen featuring abundant cabinetry, perfect for cooking & gathering. Sliders from the kitchen lead out to an oversized deck, creating a seamless indoor-outdoor flow for hosting. The kitchen opens directly to a large family room with built-ins & fireplace, making it the perfect spot to unwind. A formal dining room for special occasions and a bright living room that offers additional flexible living space. The second floor features four generously sized bedrooms and two full bathrooms. The spacious primary suite includes its own private full bath and an impressive walk-in closet. The additional bedrooms are well-proportioned and ideal for family members, guests, or home office space. The finished walk-out lower level adds over 1,100 square feet of additional living space & includes another full bathroom. This versatile area is perfect for a guest suite, gym, office, media room, or playroom. With sliders to the private backyard, you have easy access to the above ground pool. Additional highlights include a two-car garage, central air, & a beautifully landscaped lot. Plus...City water & sewers and economical solar panels to keep your electric bill way down. With its generous layout and excellent location, this home truly offers the best of comfortable living.

Welcome to 8 Meeting House Road, a secluded and serene retreat. This special property was the former Reverend John Marsh parsonage circa 1818. It has been privately owned for the last 41 years by the same family and is now ready for a new steward. This gracious historic home features a light-filled eat-in kitchen, a fabulous enclosed sunporch overlooking verdant views of the property, and multiple fireplaces. There are several multifunctional rooms including a library with built-in bookcases, a music room, and a generously sized great room with beamed cathedral ceilings. There are also five spacious bedrooms and 2.5 updated bathrooms. The property is set on over four acres with stone walls running throughout, and outbuildings, including a carriage house that has plenty of space for a workshop, a studio, or an office. Behind the carriage house you'll find a natural in-ground gunite pool in a lush private setting. This is a rare opportunity to own an intact historic property with this kind of heritage in the Connecticut River Valley.

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.

Welcome To 5-7 Haddam Dock Road Located in Haddam, Connecticut. Discover A Rare Riverfront Opportunity Offering Two Homes On One Lot, Breathtaking River Views Of The Connecticut River, and Your Own Private Boat Dock. This Property Is Perfect For Multi-Generational Living, Guest Accomodations, Or Rental Income. The Main House Showcases Soaring Windows That Frame The Picturesque Waterfront, Filling The Living Spaces With Natural Light While Creating A Seamless Connection To The Outdoors. This Home Offers 4 Large Bedrooms With Private Baths and Plenty Of Closet Space For Storage. Step Outside To An Expansive Entertaining Area Featuring A Sparkling Gunite in Ground Pool, Spacious Patio, Full Outdoor Kitchen, and Multiple Areas Designed For Relaxing Or Hosting Family and Friends. The Second House Provides Privacy and Flexibility, Making It Ideal For Visitors, Extended Family, A Home Office, Or An Income-Producing Rental. This High Ranch Style Home Has An Open Concept Floor Plan With High End Wolf Appliances, Wide Plank Tile Throughout, and Custom Built Ins Accenting Most Of The Rooms, and Has Double His and Her Walk in Closets. Situated On Beautifully Landscaped Grounds, This Exceptional Prroperty Also Features Direct River Access With A Private Dock, Allowing You To Enjoy Boating On The Connecticut River, Fishing, Kayaking, Or Simply Taking in The Peaceful Waterfront Setting From Your Own Backyard.

Amazing custom built Nantucket style Cape situated on sprawling grounds, terraced high above a picturesque great yard & overseen by natural highlands. The setting is nothing but breathtaking! Inclusive is an inground pool engulfed by the primary hardscape which walks-out from the lower level & is situated high above the great yard. A magnificent carriage house featuring a 4 bay garage & significant apartment with full kitchen, large living room, bedroom & full bath. The primary home is a masterpiece of open flowing spaces & painstakingly milled trim, woodworking & built-in's throughout! The chef's kitchen boasts incredible cabinetry & built-in hutches that harness the expansive island & fine appliances to include Dacor gas cooktop & wall ovens as well as blended Subzero & walks-out to a blue stone patio. The great room just embraces the theme with incredible wood work, gas fireplace & French doors which open to a veranda above the pool & yard beyond an epic terrace stone wall. The main level is completed with the finely appointed primary bedroom suite as well as additional bedroom suite & mudroom with half bath. The upper level is inclusive with a 3rd suite ideal as guest space. The lower level is charming & includes a tavern room with a full custom wood bar, family room with gas fireplace, rec room & a full bath. Additional enhancements include Viessmann on-demand hot water, Buderus boiler, home-run plumbing, full house on-demand generator & much, much more!!!

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.

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

Tucked away from the road and set above the CT river on over three acres, this amazing waterfront home is also a secluded personal resort, complete with a pool, spa, and private beach. Designed to showcase river views from every vantage point, the home features high ceilings, floor to ceiling windows, and an expansive open-concept floor plan that brings in an abundance of natural light. A living room with a fireplace, formal dining area, and family room all lead out to a large deck, which offers plenty of room for outdoor entertaining or just admiring the scenic waterfront setting. A well-appointed chef's kitchen with a center island and plenty of storage space faces the family room. A first- floor primary bedroom offers an office/sitting area with another fireplace, a generous ensuite bathroom with both a soaking tub and walk-in shower. A spacious laundry/mud room leads from the kitchen to the three-car garage. A sunroom overlooks the pool deck, which includes a gunite in-ground pool, a large patio area, and a fantastic outdoor kitchen with a built-in grill and bar area perfect for al fresco dining. The second-floor landing is open to the first floor below, and has two bedrooms both with ensuite bathrooms, and sitting area. The finished walk-out lower level leads to another patio area overlooking the private beach. A large family room, a full kitchen, two more bedrooms and a full bathroom complete the lower floor, offering plenty of room for visitors.

Dreaming of a stylish country retreat with history? Look no further than the charming Captain Elijah Johnson house, nestled in the bucolic village of Middle Haddam, CT and located just two hours from New York City and Boston. This property blends modern amenities, including a swimming pool, with the carefully restored original features of a house built in 1780 and listed on the National Registry of Historic Places. Set on a picturesque 0.7 acres, this waterfront home with a difference boasts a private waterfall and brook, cocooned by old-growth oak and maple trees. From the back deck or the saltwater gunite pool you enjoy the peaceful sights and sounds of water, making it an ideal spot for unwinding. A remote-operated irrigation system draws directly from the brook, ensuring that the gardens never face drought. Just three minutes' walk away the Connecticut River provides opportunities for boating, kayaking, and even enjoying a yellow sand beach. This spacious home features 4+ bedrooms, providing ample space for family or guests, with multiple living areas that provide flexibility for many uses. The first floor includes the primary bedroom with fireplace, making single-level living an option. Two new bathrooms complement the home layout, and the eat-in country kitchen is filled with charm, providing a warm and welcoming space to cook and gather. The spacious living room with original oak paneling and fireplace makes the perfect retreat for winter nights.

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.