luxury houses for sale Weston, United States

This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With trails leading directly from the back door to a secluded pond and hiking paths, it serves as an ideal weekend retreat and a convenient alternative to the Vermont or Connecticut River Valley. Located only 70 minutes from Grand Central via the Westport train station, this home offers easy access to both the Connecticut coastline and deep woods.

3808 Redding Road presents a rare opportunity to step into one of Fairfield's most distinctive properties; where early American history and modern living come together. Originally dating to 1769 and fully rebuilt in 2008, the home was reimagined to preserve its architectural integrity while delivering an ease making it livable for today. Inside the tone is warm, grounded, and refined. Original beams and centuries-old floors remain at the core, while refreshed interiors and natural light bring a sense of clarity and renewal throughout. A rare three-fireplace hearth anchors the main living spaces, creating a natural center point for gathering. Four bedrooms and four and a half baths offer both comfort and flexibility, including a primary suite with a private balcony overlooking the property as it comes alive in the spring. The land is expansive, yet entirely manageable. Nearly eighteen acres unfold into open fields, budding orchards, and wooded edges - offering the option to embrace the full scale of the property or maintain a more modest footprint. Whether for gardening, recreation, or quiet enjoyment, the setting adapts easily. A historic barn, carriage house, and chicken coop add character and versatility. Privately set yet just minutes from town, this is a property that delivers both space and convenience. 3808 Redding Road offers a sense of history, a renewed perspective, and the flexibility to live as you choose.

Welcome to 66 Gate Stone Lane, a quintessential Connecticut estate in the heart of historic Greenfield Hill. A gated entrance introduces this private 3.8-acre property, ideally positioned at the end of a quiet cul-de-sac among other distinguished homes. A gracious stone path leads to a double-height foyer, setting the tone for the home's refined architectural details and thoughtfully updated interiors. The formal living room features a fireplace, custom built-ins, and French doors opening to an outdoor dining area. A wood-paneled library with parquet floors offers serene views of the garden pond, while the elegant dining room flows seamlessly into a warm and inviting family room with fireplace and direct access to the patio. The home has been extensively and thoughtfully renovated throughout, including a completely redesigned chef's kitchen featuring custom cabinetry, high-end finishes, and the addition of a striking fireplace-creating a true heart-of-the-home gathering space. New hardwood floors run throughout, complemented by updated powder rooms and a state-of-the-art water filtration system. Upstairs, the expansive primary suite has been fully reimagined, offering a luxurious bedroom retreat with built-ins and window seat, along with a spa-caliber bath finished to the highest standard. Three additional guest bedrooms and a versatile additional room with Palladian windows-ideal for office or play-complete the second level.

Surrounded by stone walls, this storied, spectacular and private 38.91-acre Greenfield Hill country compound has had a stunning top-level transformation, creating a one of a kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence was restored and expanded to incorporate 7 bedrooms and 7 full baths, all with views over the open, landscaped property. Lofty ceilings and walls of glass create magical interior spaces, a perfect setting for an art collector. Private wings radiating off the house center accommodate guests comfortably. A hidden theater and a stunning Moroccan lounge with bar are some of the special features of this extraordinary property. The barn-style pool house with full kitchen, bath and spacious gym, the pool, and a heated paddle tennis court are all easily accessible from the main residence. The updated stone gatehouse accommodates guests or staff. A two story office pavilion is tucked in a private garden area. The landscape offers open vistas, meadows and an orchard. There is potential for equestrian use. Live in ultimate style and easy elegance at this private retreat just a quick commute to NYC and airports. Fairfield and Westport town centers are in close vicinity. Enclosed behind a stone wall and surrounded by a 155 acre nature preserve, this is a uniquely private haven. Main residence 9129 sq ft. Barn 2400 sq ft., Guest House 2800 approx. Total 14,329 sq ft. Whole property generator. Solar and geothermal systems. Water filtration system. Two laundries. Slate roof. Heated parking. Dog washing station. Wine room. Orchard. This offering encompasses three lots: 4800 Congress St consists of main residence, 10.92 acres, office pavilion, pool/barn pool house and heated paddle court. 4900 Congress St consists of stone guesthouse on 25.87 acres with fields, meadows and pond. 5010 Congress St is open land: 2.12 acres with potential for barn or tennis courts and tennis pavilion. Equestrian use potential for entire property. All measurements approximate.

Move-in ready and freshly updated, this expansive 5,000+ sq ft Colonial is located in the prestigious Ridge of Greenfield Hill-a 24-hour guard-gated community situated on the border of Fairfield and Westport. The Ridge offers a resort-style lifestyle with amenities including a heated pool, lighted tennis courts, pickle ball, playground, and a private recreation center-all set among 96 luxury homes on manicured grounds. This sun-drenched five-bedroom, six-bathroom home has been freshly painted inside and out and features extensive millwork, gleaming hardwood floors, and floor-to-ceiling windows that flood the home with natural light. The open-concept layout is ideal for entertaining, centered around a fully renovated gourmet kitchen with high-end appliances, custom cabinetry, and a large island, flowing seamlessly into the great room and out to a spacious patio. Upstairs, generous bedrooms include a luxurious primary suite, while flexible living spaces throughout the home cater to modern lifestyles-perfect for hosting or working from home. The flat, private yard offers multiple outdoor entertaining areas and is complemented by a three-car garage. Enjoy privacy and elegance while being just minutes from the vibrant downtowns of Fairfield and Westport, as well as local beaches and train stations. This is luxury living with everyday convenience-completely turnkey and ready for it's new homeowners.

A thoughtfully restored (2012-2017) post-and-beam colonial is perched on a scenic rise with panoramic views of meticulously maintained grounds, combining timeless elegance with high-performance modern comfort and amenities. Details include original barn doors, reclaimed wide-plank floors, abundant natural light through skylights, and a gracious wrap-around veranda. First Floor: Features an inviting living room with exposed beams and a wood-burning fireplace. The heart of the home is a generous eat-in kitchen, boasting an expansive island, premium appliances, an integrated desk nook, and French doors connecting to outdoor spaces. A den includes a wet bar, wine storage, and handcrafted built-in cabinetry. Also on this level are two well-appointed bedrooms, a full bath, a powder room, and convenient first-floor laundry. Second Floor:The primary bedroom suite is a true retreat with a wood-burning fireplace, separate sitting area, a custom closet system, and a spa-like bathroom offering pastoral vistas. Two additional bedrooms, a second full bath, and upper-level laundry complete this floor. Lower Level: A newly converted, climate-controlled, recreational / play room. A separate detached barn offers multiple possibilities-workshop, studio, storage, or a future renovation project. Barn-featuring a restored roof and structural reinforcements-is as-is and stands ready for conversion, with architectural plans included in a sale

28 Drewbarrie Lane was designed and built as a forever home, this remarkable Easton property blends thoughtful architecture, exceptional craftsmanship, and energy-conscious design in a way rarely found in today's market. Set on a quiet and private property surrounded by nature, the home was carefully oriented to capture winter sunlight, maximize passive solar heating, and create a bright, inviting living environment throughout the year. From the moment you enter, you'll notice the warmth and comfort that define this home. Thick insulated concrete walls, triple-pane windows, radiant heated floors, and a Scandinavian masonry fireplace work together to create a remarkably stable indoor climate. Sunlight streams through the south-facing windows during the cooler months, while carefully designed roof overhangs help keep the home comfortable throughout summer. The floor plan was intentionally designed for both connection and privacy. Separate bedroom areas allow family members and guests to enjoy their own spaces, while the open kitchen, dining, and gathering areas naturally bring everyone together. For creatives, hobbyists, and entrepreneurs, the property offers exceptional flexibility. The expansive bonus room above the attached three-car garage served as a professional artist's studio, while the dedicated workshop below, with high ceilings and vehicle lift, provides outstanding space for projects, collections, or home-based business needs. Outdoor living is equally impressive. Summers are centered around the in-ground pool, expansive stone patio, pool house, detached storage barn, and additional covered parking structure. Whether hosting intimate family gatherings or celebrations with dozens of guests, the property was designed to accommodate memorable moments with ease. This home was built with extraordinary attention to longevity and performance. Insulated concrete form construction provides strength, sound isolation, energy efficiency, and resistance to pests and weather. Radiant heating systems, high-efficiency mechanicals, extensive insulation, CAT-5 wiring infrastructure, security system wiring, and future-ready utility planning reflect the owner's commitment to thoughtful design and lasting quality. 28 Drewbarrie Lane is more than a house, it is a carefully crafted home designed to be enjoyed in every season.

Set in one of Westport's most prestigious estate enclaves, this exceptional shingle-style residence defines luxury living with a rare emphasis on multi-generational comfort, timeless architecture, and impeccable craftsmanship. Designed and built by a renowned architect and builder for a Fortune 500 CEO, the home reflects uncompromising quality, enduring design, and gracious curb appeal that impresses. Seamless indoor-outdoor living defines the home, with sun-filled interiors, soaring 10-foot ceilings, and an expansive walkout lower level with fireplace, all opening to a resort-style pool, stone patios, fire pit, and covered porch with fireplace, providing an effortless setting for entertaining. Extensive bespoke millwork, six fireplaces, and refined architectural finishes enrich every space. The expansive, level, and private grounds, framed by mature landscaping and abutting the 39-acre Newman Preserve, offer serenity with rare walkability to top-rated schools and 8 minutes to Westport's lively downtown. A spectacular chef's kitchen features Thermador and Wolf appliances, dual islands, 2 dishwashers, walk-in pantry, and a fully equipped butler's pantry with wet bar. The primary suite offers a turreted sitting room, fireplace, and 2 walk-in closets. 6 ensuite bedrooms and a private suite over the garage provide flexibility for guests. Space for elevator! New cedar roof, new boiler, new wine cellar, and other upgrades complete this rare offering in a premier Westport location.

Welcome to 4 Cardinal Lane ~ a beautifully expanded and thoughtfully updated home set on two private, level acres in one of Westport's most desirable cul-de-sac neighborhoods. Originally built in 1964 and enhanced with a significant 2015 addition, this 4-bedroom, 3.5 bath residence offers over 4,100 square feet of versatile living space designed for both everyday comfort and effortless entertaining. The layout blends classic charm with modern functionality, featuring sun-filled living spaces, a wood-burning fireplace, an office and seamless flow throughout. The standout bungalow addition creates a one-of-a-kind experience, complete with a bar and direct access to the patio, perfect for hosting gatherings year-round. Upstairs, the primary suite offers a peaceful retreat with a walk-in closet and well-appointed bath, while three additional bedrooms provide flexibility for family and guests. A partially finished basement adds more usable space, including a dedicated gym area. Outside, the expansive backyard is a rare find offering endless potential for outdoor living, play, or future enhancements. The patio extends the home's entertaining footprint, creating an ideal setting for dining and relaxing. Just minutes from Westport's top-rated schools, beaches, golf course, tennis and pickle courts, town center, and train this is a unique opportunity to own a spacious, move-in ready home with exceptional indoor-outdoor living and standout entertaining spaces in a coveted setting.

A rare offering distinguished by architectural clarity, complete privacy, and a deeply personal design vision, set within one of Fairfield County's most sought-after locations. Jay Manuel, internationally recognized creative director and fashion icon, brings a distinctly refined point of view to his architecturally significant modern residence in Connecticut. Acquired in 2011, the home was thoughtfully completed and refined under his direction into a highly considered lifestyle environment, where design, performance, and atmosphere exist in complete alignment. Set on 2.75 acres of exceptional privacy, the sunlit European modern unfolds as a discreet compound, surrounded by mature landscape and a protected nature preserve. Designed for both intimate living and large-scale entertaining, the property features a heated saltwater pool and spa, multiple terraces, an outdoor kitchen, fire pit, and a tranquil Zen garden. The residence reflects a disciplined approach to modern living, integrating passive solar principles, advanced HVAC, and whole-property connectivity, all seamlessly embedded within its clean architectural language. Interiors are defined by soaring ceilings, walls of glass, and a Poliform kitchen with Miele appliances. A private primary suite with balcony, a dramatic glass mosaic wine cellar, and a separate 800 sf skylit studio for fitness or flexible use further articulates the home's sense of intention and versatility. Rare. Private. Architectural.

Imagine a residence where every element has been considered for gracious living in stylish surroundings. This newly completed home by awardwinning Able Construction is set on a peaceful Coleytown estatearea street, framed by scenic land that enhances its sense of calm. A dramatic foyer with a woodaccented ceiling and millwork feature wall introduces interiors defined by creative decor, walls of glass, and exquisite lighting. The great room, anchored by a marble fireplace and French doors to the pool and patio, flows into the designer kitchen with a striking island, stone counters, custom cabinetry, Thermador appliances, and a beautiful and functional pantry. The dining room is a jewel, offering an elegant setting with illuminated shelving and views of the grounds. A quiet office and superb mudroom add daily convenience. A glasslined stair tower leads to sunfilled bedroom suites, beginning with the sublime primary suite set beyond double doors. An arched entry reveals a kingsized bedroom with balcony, two custom walkin closets, and a spalike bath with glass shower and distinctive vanity. The upper level also offers a laundry room with double washer and dryers and access to the finished thirdfloor bonus space. The lower level includes a fifth bedroom suite, recreation room, gym and media areas, and generous storage. Outside, the pool becomes the centerpiece for entertaining and relaxing at this designcentric showplace of style.

PLUS TWO ADDITIONAL VERSATILE ROOMS THAT SIGNIFICANTLY EXPAND THE HOME'S LIVABLE SPACE! Located in the highly sought-after Charcoal Hill neighborhood, this move-in ready home on 2+ private acres features 3 bedrooms and 3 full baths. Bordering a 7-acre Aspetuck Land Trust preserve on a quiet cul-de-sac, it offers serene privacy with easy access to town, the Merritt Parkway, and Coleytown schools. These flexible rooms are ideal for home offices, guest accommodations, a fitness studio, or other lifestyle needs, providing the adaptability today's buyers demand. The home's exceptional layout also includes a fully finished walk-out lower level with 8-foot ceilings, a large living room with fireplace, and a full bath-perfect for multi-generational living, extended guest stays, or entertaining. Together, the two additional rooms and finished lower level provide functionality, flexibility, and living space far beyond a traditional 3-bedroom home. The main level is anchored by a sprawling living room that flows into a chef's kitchen with premium Bertazzoni appliances and Kohler fixtures. Enjoy stunning sunset views from the primary bedroom, living areas, and dual decks. Architectural elegance is showcased through structural Marvin windows and handcrafted details throughout. Set on more than 2 private acres, this exceptional property offers a rare combination of space, privacy, versatility, and convenience.

Once in a lifetime, a home of this caliber becomes available. Sited on a cul-de-sac in a coveted neighborhood close to town, this exceptional residence pairs custom design with luxurious indoor-outdoor living areas enhanced with smart technology and supported by upgraded mechanicals. A gracious front-to-back foyer showcases elegant living and dining rooms. Everyday living and elevated entertaining are effortless with a new custom kitchen designed by Deane appointed with Simon Pearce pendants, premium appliances, wine frig, and a Zip tap for still and sparkling water. A sun filled eat-in area flows seamlessly into a coffered ceiling family room with fireplace and a covered porch-with flat screen TV, stone fireplace and Bromic heating. A richly paneled office, mudroom and second staircase complete the main level. Upstairs, five bedrooms include a serene primary suite with fireplace and sitting room, a private guest suite and an additional office. The outdoor experience is nothing short of a 5-star resort-with a saltwater Glengate pool, sun shelf, spa and a new outdoor kitchen fully equipped with a built-in grill, pizza oven, Traeger smoker, and refrigeration-all surrounded by stone terraces, lush landscaping, audio system and curated lighting. The lower level boasts a chalet-inspired retreat with recreation, fitness rooms, an infrared sauna, and bedroom suite with a flexible private entry. An exceptional offering for those seeking outstanding craftsmanship and luxury!

A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate, thoughtfully reimagined with an array of stunning features and superior craftsmanship. Sited on 2 private acres, this extraordinary property offers priceless panoramic views of a 7-acre nature preserve, affording permanent tranquility and a sense of wonder. The meticulous renovations center around a gracious farmhouse-style Colonial and spectacular post-and-beam Party Barn. Main residence features a gourmet chef's Kitchen with a single-piece, 14' Calacatta marble island, professional appliances, and dual Family Room fireplaces. Upstairs, the Primary Suite is highlighted by a custom marble-inlay bath floor, large walk-in shower + soaking tub, while the Living Room offers enhanced acoustics w/its tray ceiling for a superior piano experience. The property's exceptional appeal is anchored by the new Country Carpenters barn, connected by a breezeway w/barn doors that create an inviting welcome to backyard entertaining. This luxury 1BR barn is complete w/20-foot ceilings, heated floors, a full kitchen, and hinge-free retractable doors that seamlessly blend indoor/outdoor living. Resort-style amenities await outdoors with a Pebble Tec pool, waterfall hot tub & blue granite patio that remains cool underfoot on hot summer days. The entertainment porch features built-in heaters, a see-through fireplace, and an outdoor television. This is more than just a home, it's a legacy waiting to be claimed!

Set on a beautiful hilltop lot in the desirable Lake Hills neighborhood, this lovely home offers the perfect blend of comfort, privacy, and effortless entertaining space. The thoughtfully designed floor plan features expansive living and family rooms filled with natural light, creating inviting spaces for both everyday living and hosting guests. The newly renovated chef's kitchen is a true centerpiece, featuring double cooktops, double wall ovens, abundant workspace, and an ideal layout for cooking and gathering. Major recent upgrades include a new furnace, central air conditioning system, and hot water heater, providing peace of mind for years to come. Step outside to an extraordinary two-level deck designed for outdoor living at its finest. Complete with a covered area, this private backyard retreat is ideal for summer BBQs, dining al fresco, and entertaining on any scale while surrounded by total privacy. As part of the sought-after Lake Hills Association, residents enjoy deeded lake rights with access to multiple private beaches, swimming, swim lessons, kayaking, fishing, social events, and year-round recreation. Beach #4 is conveniently the closest lake access point to the home, offering a wonderful lifestyle enhancement just moments away. Ideally located near shopping, restaurants, and gourmet takeout along Black Rock Turnpike, easy access to the Merritt Parkway, this home combines tranquility and convenience in one of Fairfield's most desirable neighborhood

Nestled at the end of an exceptionally wide, tree-lined cul-de-sac on one of Westport's most picturesque streets, this timeless brick estate offers both elegance and privacy while remaining moments from town, beaches, and commuting conveniences. Set with a paver circular driveway and surrounded by mature landscaping, the property exudes warmth, scale, and classic sophistication at every turn. Designed for both grand entertaining and everyday living, the home features an extraordinary backyard anchored by a stunning pool and attached pool house, creating the ultimate resort-style setting. Inside, the thoughtfully designed floor plan includes a sought-after first-floor bedroom, expansive sun-filled living spaces, and seamless flow throughout. The dramatic family room showcases soaring 20-foot ceilings with striking wood beams, while the modern renovated kitchen beautifully blends contemporary style with everyday functionality. The second floor offers five spacious bedrooms along with an oversized playroom/flex space. A partially finished basement provides additional recreation room and storage possibilities. Zoned for highly desirable Long Lots Elementary and Bedford Middle School, this exceptional property combines timeless architecture, incredible outdoor living, and an unbeatable cul-de-sac location in the heart of Westport. Sturges Hwy to Daniel Court