luxury houses for sale Fairfield County, United States (page 10)

Welcome to 36 Richmond Drive! Tucked into a great Darien neighborhood, this three-bedroom, two-bath ranch is close to everything, bike to Cherry Lawn Park, walk to local shops and restaurants, or hop on the train in minutes. The home sits on a level, corner lot of over half an acre, with stone patios, a built-in grill, and plenty of yard space for play and entertaining. Inside, you'll find a lower level that's perfect for hanging out, with a playroom, bar, and a cozy wood-burning stove. Whether you're ready to update and make it your own, or you're looking for a project with great potential, this home is a terrific opportunity. All in the award-winning Ox Ridge Blue Ribbon School district!

Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens, from the heated gunite pool surrounded by an oversized terrace and through the walls of glass throughout the home. From the moment you enter, prepared to be wowed by this concrete, glass and bamboo structure, as you flow through the stunning open living spaces into the private first floor Primary Bedroom, then up to the well thought out second floor. Rare and remarkable, this noteworthy home was designed by Specht Harpman and artfully built in 2010 by Michael Greenberg in the bucolic setting of Weston, CT. Enjoy best of both worlds- living in secluded waterfront serenity with effortless access to the areas shopping, restaurants and beaches in Westport and neighboring communities.

Beautifully refreshed, this inviting 4-bedroom home blends classic character with modern comfort just moments from downtown Greenwich. As one of only two homes in a Planned Unit Development, this charming home features an updated kitchen that opens to a comfortable family room, along with a welcoming living room and formal dining room - ideal for both everyday living and entertaining. The second floor hosts a lovely primary bedroom suite, 2 additional bedrooms, a full bath and a spacious laundry room. The third floor bedroom with it's own full bath provides a perfect retreat for guests or flexible bonus space. With a detached garage and parking, plus a prime location minutes from Metro-North, local restaurants, and shops, this home offers the best of Greenwich living.

Set on 1.21 acres, this beautifully maintained home has exceptional indoor and outdoor living designed for entertaining. Home was completely taken down to the studs in 2017. The freshly painted interior offers top-of-the-line finishes and a flexible floor plan. The main level features a private office with Murphy bed, dining room with soaring ceilings, and a cozy living room with wet bar and fireplace. Open-plan gourmet kitchen, breakfast area, and family room flow seamlessly to an expansive terrace with multiple seating areas, an outdoor kitchen, and fire pit, creating an ideal setting for gatherings throughout the year. The gorgeous primary suite features a spa bath with sauna, walk-in closet, and floor-to-ceiling windows overlooking the property. Two additional bedrooms share a full bath, while two versatile bonus rooms can be customized to fit your needs. They would make a great nursery, playroom, second office, or gym. Other highlights include an outdoor shower, space for a climbing frame and golf net, and an attached two-car garage. This property provides privacy and convenience to everything Greenwich has to offer.

Set on 2.19 private acres in a prime Darien location, 222 Brookside Road offers exceptional space, privacy, and opportunity just minutes from town and Cherry Lawn Park. With more than 7,000 square feet above grade, plus an additional 3,000 square feet on the lower level, this expansive 4-bedroom, 5.5-bath residence provides an incredible canvas to create a home tailored to your vision. Generously proportioned rooms and tall ceilings create a wonderful sense of scale throughout, while a flexible floor plan offers endless possibilities, including the potential for a first-floor in-law or guest suite. The exceptionally spacious lower level provides abundant room for entertaining, relaxing, and recreation. Outdoors, the expansive property is highlighted by a pool and well-appointed pool house featuring a full bath, laundry hookups, and full kitchen with a range and space for a refrigerator-creating a private setting for summer gatherings and relaxation. An attached four-car garage, plus an additional detached two-car garage, provides parking for six cars and even more flexibility. A rare opportunity to enjoy significant acreage, remarkable space, and endless potential in an incredibly convenient Darien location.

Beautifully reconstructed and expanded modern home in downtown Greenwich offering 4-5 bedrooms, 5 baths, and four levels of light-filled living. The open floor plan features a designer kitchen with quartz island, gas range, walk-in pantry, family room with fireplace, dining room, living room with fireplace, and a mudroom. The luxurious primary suite includes vaulted ceilings, dual walk-in closets, fireplace, and a balcony. Four additional bedrooms, finished lower level with full bath, and outdoor terraces with fireplace provide exceptional living and entertaining space. A separate 416 sq. ft. climate-controlled studio/office plus detached garage make this a rare in-town opportunity just moments from train, parks, dining, and shopping. Sonos ready speaker system and generator ready panel.

Enjoy the distinctive coastal lifestyle of Stamford's sought-after Shippan neighborhood in this distinguished Tudor home, offering approximately 6,000 square feet of timeless architectural character, sophisticated modern updates, and a thoughtfully designed 2016 renovation by Granoff Architects. With 5 bedrooms, 3 full and 2 half baths, the home is rich in detail, including original stained glass, oak paneling, unique solid oak arched interior doors, and three wood-burning fireplaces. Custom millwork, a Vermont slate roof, and new Marvin windows throughout further showcase the home's exceptional craftsmanship. Beautifully renovated second-floor bathrooms feature custom cabinetry, marble showers and countertops, and heated floors. In addition to the generous living and entertaining spaces, the home also includes a finished lower level, a third-floor loft with water views (currently used as a home gym), and an attached greenhouse that adds to the home's classic charm. Outside, a 40' x 20' gunite pool and spa, expansive patio, and mature garden create a picturesque private oasis. Beautifully landscaped and exceptionally private, the grounds provide an idyllic backdrop for sun-filled summer days, evenings spent poolside and memorable gatherings with family and friends. An exceptional Shippan offering with remarkable space, character and versatility. ** Also available for purchase with the adjacent lot at 1688 Shippan Avenue (MLS 24189415). Properties may be purchased separately

Set prominently along the coveted shoreline of Rowayton, this extraordinary residence is a true architectural masterpiece that defies the standard coastal trope. Designed by award-winning Cardello Architects, the home is a fortress of design-a structural marvel built with an uncompromising integrity that feels as permanent as the tides. The silhouette is bold and commanding, yet every element reflects a sophisticated functional design that breathes with the rhythm of the Long Island Sound.

Originally the sole residence on Wildcat Road, this distinguished 1925 stone manor blends timeless architectural elegance with a commanding setting. Located within Darien's coveted Delafield Island private association, the property is approached by a sweeping circular drive and surrounded by mature landscaping offering a rare sense of privacy, grandeur, and permanence, just minutes from downtown Darien, the Metro-North train, beaches, and Great Island. Rich in character and craftsmanship, the residence showcases architectural details rarely found today, including soaring 12-foot ceilings, a dramatic circular staircase, five fireplaces, Juliet balconies, vintage servant bells, graceful arches, skylights, and a sun-filled glass solarium. Thoughtfully designed for both grand entertaining and comfortable everyday living, the spacious country kitchen opens to an expansive deck overlooking the surrounding natural landscape. Adding to the property's exceptional appeal, several acres of protected land trust border the rear of the home, preserving a tranquil backdrop and enhancing the estate-like setting. Whether hosting family gatherings, entertaining guests, or simply enjoying the peace and beauty of its surroundings, 15 Wildcat Road offers a unique opportunity to own one of Delafield Island's most distinctive and historic homes.

Exceptional opportunity in the heart of Old Greenwich! A rare opportunity to own a flat, build-ready lot in the heart of Old Greenwich, offering the perfect setting to expand the existing home or create a stunning new custom residence. Set on a level lot in a highly sought-after neighborhood, this spacious 4-bedroom, 2.1-bath Colonial offers over 2,346 square feet of living space with generously sized rooms. The main level features a welcoming foyer, large living room with fireplace, formal dining room, expansive sunroom, and a spacious family room. The eat-in kitchen provides ample workspace and storage, with a conveniently located half bath nearby. Upstairs offers four generously sized bedrooms, two full baths, multiple walk-in closets, and additional closet space throughout. The home's functional layout, oversized rooms, and abundance of living space provide excellent flexibility for everyday living and entertaining.

Sport Lovers Dream - Set at end of a quiet cul-de-sac on Stillman Lane, this custom-built 2013 residence offers 4 finished levels of thoughtfully designed living space on 1.2 level acres w putting green. High ceilings, abundant natural light and seamless flow define the main level, where formal living and dining rooms connect effortlessly to an expansive open-concept kitchen and family room with fireplace. Upstairs, find a primary suite with spa-inspired bath with heated floors, whirlpool tub + steam shower plus 4 en-suite bedrooms. The walkout LL is centered around recreation + wellness w gym, golf simulator, indoor putting area, glice for skating on, rec room + wine rooms. Professionally designed landscaping by James Doyle, expansive flat lawn + outdoor kitchen complete the property.

Located moments from Wilton Town Center, this fully reimagined 6-bedroom, 5.2-bath residence blends timeless character with modern luxury. Set on more than two pristine acres with a designated pool site and overlooking the Silvermine River, the home has been extensively renovated, showcasing exceptional craftsmanship and thoughtful design throughout. The interior features 9-foot ceilings, Brazilian cherry floors on the main level, red oak upstairs, and custom millwork. Designer finishes, modern lighting, and integrated smart-home technology complement a spacious layout ideal for entertaining and everyday living. The lower level offers two large rooms, each with walk-out access, a fireplace, a full bath, and an additional room that could serve as a bedroom, providing flexible space for nanny or in-law use, guest quarters, recreation, or a private home office. Bespoke cabinetry, premium fixtures, and top-tier appliances elevate each room. Additional highlights include commercial-grade mechanical systems, a Kohler true full-house 48 KW generator, advanced home technology and security, and a lifetime shingle roof with warranty and copper flashing. Outdoors, refreshed landscaping, new plantings, a mahogany deck and porch, and upgraded hardscaping create a private, inviting setting for gatherings or quiet enjoyment.

Beautifully designed & maintained, this stylish home is tucked away on a quiet street in Old Greenwich. An inviting front porch welcomes you into well appointed interiors featuring soaring 12 foot ceilings in the living/dining rooms, a fireplace, custom built-ins, and abundant natural light. A gourmet chef's kitchen outfitted with high-end appliances, quartz countertops & a generous center island. The family room/playroom just off the kitchen creates the perfect setting for everyday living. Upstairs offers a primary BR along with 3 additional BRs & 2 full baths. Enjoy entertaining on the back deck or around the stone fire pit all surrounded by mature landscaping. Fenced yard & finished garage. Ideally located close to town, beach & schools. Move right in & enjoy the best of Old Greenwich!

190 Brookwood Lane is set in one of New Canaan's most unique and desirable residential settings - a bucolic landscape of rolling meadows, mature woodlands, and gently flowing streams set on just over 3 acres of quintessential New England beauty. Situated in the heart of New Canaan, the property offers a peaceful and established neighborhood setting where quiet roads, mature trees, and estate-scale properties create an atmosphere increasingly difficult to replicate. This extraordinary proposed residence blends timeless New England architecture with refined modern living. Designed by Tanner White Architects as the quintessential New Canaan colonial with gracious proportions and exceptional scale, the home is envisioned with approximately 7,500 square feet across the first and second floors, including expansive entertaining spaces, dramatic 10-foot ceilings on the main level, generously scaled bedrooms, and seamless indoor-outdoor living throughout. The proposed floor plan includes 6 bedrooms, 8 bathrooms, 3-car garage, and pool with the opportunity to finish attic and lower-level spaces for more than 10,000 total square feet. The oversized homesite provides exceptional flexibility for estate level outdoor amenities while maintaining tremendous privacy and natural beauty.

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sunroom, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

Set on 4.1 beautifully landscaped acres at the corner of Locust Road and Carpenters Brook, this exceptional Greenwich estate blends timeless elegance, privacy, and resort-style living. A sweeping circular driveway leads to the approximately 8,300-square-foot main residence, surrounded by mature trees, flowering gardens, stone walls, and expansive lawns designed by Wesley Stout Landscape Architects. Sun-filled formal and informal spaces feature coffered ceilings, antique oak floors, a dramatic double-height family room, chef's kitchen, and four fireplaces. The home offers six bedrooms, including a luxurious primary suite with spa-like bath, gym, walk-in closet, and private balcony. The finished lower level includes a wine cellar, home theater, recreation room, craft room, and cabana area. Outdoors, enjoy a heated gunite pool, vine-covered pergola, stone fireplace, multiple entertaining terraces, and a private par-three golf hole. A separate guest house with full bath and private driveway provides flexibility for guests, extended family, or a home office, all conveniently located to town, schools, dining, and transportation.

Classic four bedroom Colonial in a convenient Riverside location has been thoughtfully renovated and expanded over the years. Entertain in the spacious living room with fireplace and the sun-filled dining room leading to the open plan kitchen, breakfast area, and family room. Step out from both main rooms through French doors to the beautiful covered deck with fireplace and flagstone surround leading out to the professionally landscaped English country grounds. Primary suite with walk-in closet, large bath, gas fireplace, and expansive windows. Three additional bedrooms, three additional full baths, and laundry room complete the second level. Special features include new Marvin windows and exterior doors throughout, new chimney, noise reduction exterior walls, and updated electrical and plumbing. Exterior painting of the house and oversized two-car garage completed in 2025.

Classic New England charm meets modern luxury in this beautifully updated 1921 Colonial. Perfectly situated just minutes from the quaint Georgetown boutique shops , restaurants, and Route 7. Set on nearly half an acre lot, this home offers effortless living and entertaining inside and out. The heart of the home features a renovated eat-in kitchen with timeless marble countertops, a 4 seated island, and newer stainless-steel appliances. Entertain with ease in the formal dining room, unwind by the gas fireplace in the living room, or settle into the versatile sunroom - equally suited as a home office. Upstairs, the primary suite is a true sanctuary, complete with gas fireplace, a spacious walk-in closet and renovated spa-inspired bathroom with soaking tub. Two additional bedrooms and a well-appointed hall bath round out the second floor. The third level offers a wonderfully flexible carpeted family room - ideal as a playroom, media space, or guest retreat. Step outside to a stunning country backyard oasis with a fresh 1,200 square foot bluestone patio equipped with a built in DCS grill and cozy fire pit nook. With its flat, usable property, timeless architectural character, and every major update already done, this home is a rare find in one of Redding's most convenient locations.

Perfectly positioned just steps from downtown Darien, the train station, schools, and the vibrant new Corbin District, this beautifully updated Colonial offers the ideal blend of convenience, charm, and move-in-ready living. Freshly painted throughout with newly refinished hardwood floors, this 5-bedroom, 3.5-bath home features generous living spaces including a formal living room, dining room, family room, rec room, and an open kitchen designed for both everyday living and entertaining. Set on .70 acres, the backyard is a true surprise, featuring an expansive multi-level deck ideal for outdoor dining, entertaining, and relaxing. Beyond the property lies an additional 1.19 acres of protected open space, creating a beautiful natural backdrop and an unexpected sense of space. Timeless curb appeal, abundant living space, and an unbeatable in-town location make this a truly exceptional opportunity. Walk to downtown Darien, the train station, schools, restaurants, and the vibrant new Corbin District while enjoying all the comfort and flexibility of a move-in-ready home.

One-of-a-Kind Lakefront Retreat on Candlewood Lake - 14+ Acres of Pure Privacy & Panoramic Views. Perched high above Candlewood Lake on pristine woodland, this truly exceptional lake cottage offers an unmatched combination of direct waterfront access, total privacy, & sweeping 180-degree lake views. The home is a nature lover's dream. Meander down a private wooded trail & steps to your secluded dockside oasis. Lovingly maintained by its stewards, the home exudes warmth & charm. A wraparound deck provides multiple vantage points to soak in the breathtaking scenery. Inside, the layout is thoughtfully designed to highlight the views from nearly every room. The family room features walls of windows that bring the outdoors in. The dining room boasts a stunning stone fireplace & a large picture window overlooking the lake. The Kitchen, Laundry, a bedroom & full bath complete the main level. Upstairs, you'll find a Primary with its own full bath & private balcony. A second bedroom completes the upstairs, which enjoys its own balcony with the best views in the house! Recent upgrades include a newer roof, fresh paint, & updated mechanicals-this home is move-in ready. The offering includes the main home on 4.31 acres, a neighboring 3-acre parcel, and an additional 7.11 acre lot providing endless possibilities for expansion, or simply enjoying the untouched natural beauty. This is more than just a home-it's a lifestyle. There is truly nothing else like it on the market.

Live like you're on vacation all year round in Old Greenwich with spectacular 200 feet of waterfront with stunning views of Manhattan. Amazing vistas from every room of this 5 bedroom designer house. Sliding doors open to expansive deck, both covered and uncovered overlooking private pier with ramp to floating dock. Dine al fresco with stunningly beautiful sunsets, and enjoy sailing, boating, swimming and paddle boarding in Greenwich Cove. There is a wide lush lawn for entertaining, playing ball or croquet or hosting a wedding. Enjoy the private, exclusive Lucas Point beach and boatyard, close to Greenwich Point beach. At the end of a cul de sac, this home is a private retreat to enjoy. A short distance to the Old Greenwich village with shops and restaurants and the train station to NYC.

A rare opportunity to acquire Silvermine Farm, a fully integrated, professional-grade equestrian facility spanning two contiguous parcels at 80 & 90 Comstock Hill. Set on 7.06 level acres in a highly desirable Fairfield County location, the property supports a high-caliber training, boarding, or private equestrian operation. The facility includes one indoor ring (75' x 150') and two outdoor rings (200' x 300' and 150' x 100') with premium GGT footing, a ~35-stall main barn complemented by an additional 4 stalls at 90 Comstock Hill, multiple tack rooms, a heated wash stall, and well-designed turnout paddocks. A hay barn, office space, staff apartments and two homes further support daily operations. The property supports a range of uses, including training, boarding, and organized riding programs, with the flexibility to expand into private boarding, lesson programs, or a more tailored owner-driven approach. Its layout, infrastructure, and scale allow for the opportunity to shape the next chapter. Please contact listing agents for Equine Fact Sheet

TABER ACRES -This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 7.4 acres means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation, and have hiking trails, a bridge, and boardwalks! This is your chance to partner with an award-winning local design-build firm to create the home of your dreams! House plans shown are just a sample; this firm can do whatever fit your needs. Check out Sherman Building Design LLC on the web or on Instagram-extraordinary blend of superior craftsmanship and refined modern design. This is the only lot left in this small country 3 Lot subdivision; The sale price listed represents a land conveyance at 369K, and a building allowance starting at $500/ sf. Ease & proximity 5M-Metro North Train Station/4M-quaint small Town Center, Community Park w/Basketball, Tennis & Pickle Ball Courts, jogging path/Town Boat Slips/Kayak-Canoe Racks & Sandy Beach on CANDLEWOOD LAKE/2M to private golf club (The Club @ River Oaks) / 3.5M to Quaker Hill Country Club. 4M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/its 20M of trails. 60M to NYC-makes for a perfect weekend retreat or year round living. Welcome to Small Town USA! Builder available to meet and walk land.

Privately nestled on 1.76 exceptional acres in a coveted Westover setting, 450 Westover Road is a sophisticated retreat offering remarkable privacy, scale, and timeless appeal. Surrounded by mature landscaping and serene natural beauty, the property's expansive grounds create a rare sense of seclusion while remaining just moments from town, schools, and commuting routes. Sunlit interiors, expansive entertaining spaces, and oversized windows create an airy elegance throughout, while refined architectural details add warmth and character at every turn. The stunning primary suite is a true sanctuary, featuring soaring vaulted ceilings and dramatic arched windows that flood the space with natural light while overlooking the picturesque surroundings. Generously scaled bedrooms, renovated baths, and flexible living areas offer both comfort and versatility for today's lifestyle. Complementing the main residence is a separate accessory structure with rich wood interiors and entertaining space, perfectly suited as a private studio, wellness retreat, home office, or guest escape. An exceptional offering combining privacy, sophistication, and extraordinary land in one of the area's most sought-after locations.

Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes it equally suited for fireside evenings or lively gatherings. At its center lies the kitchen, beautifully reimagined for today while honoring its past. Soapstone countertops, custom cabinetry, and high-end appliances meet the warmth of an original fireplace and the practicality of a walk-in laundry room. Beyond the doors, your private world awaits. A heated, in-ground saltwater Gunite pool with automatic cover and outdoor shower sits tucked among lush gardens and gentle breezes, home abuts valley pond adding a hush of serenity. Extensive upgrades have been completed, from new mechanical systems to refined details throughout, ensuring comfort in every season. With central air, steam/hot air heating, and a standby generator, every modern convenience is in place. For Sale and or Lease.