luxury real estate for sale Weston, United States

The first time on the market, this custom-built Easton Colonial has been lovingly maintained by its original owner and offers approximately 3 private acres, generous living space, and a highly adaptable floor plan designed to suit a variety of lifestyles. With numerous rooms that can easily serve as a home office, playroom, gym, guest quarters, or additional living space, this home offers exceptional flexibility. A standout feature is the first-floor bedroom with its own private entrance, handicap access, and ensuite bath suitable for a wheelchair. This also could be an ideal setup for extended family, an au pair, guests, or anyone seeking the convenience of a private suite. Adding to the home's appeal is a natural-gas-powered whole-house generator, providing year-round peace of mind. Surrounded by nature and adjacent to protected watershed land, the setting offers an exceptional sense of privacy. During the warmer months, enjoy the heated in-ground pool, perfect for relaxing, entertaining, and making the most of your private outdoor retreat. Ideally located with convenient access to Easton, Westport, and Fairfield, this property offers the best of both worlds: a peaceful, private setting with easy access to local schools, shopping, dining, beaches, recreation, and commuter routes. Part of an estate, the property is being sold in its present as-is condition. No seller property disclosures are available. Please note: This is an estate sale. The property is being sold as-is, and no property disclosures are available.

Nestled among 3.56 acres of beautiful woodlands, this classic four-bedroom Dutch Colonial offers an inviting blend of timeless character and comfortable living. Enjoy tranquility with easy access to all that Fairfield has to offer. There are hardwood floors throughout, a welcoming foyer, a large living room with fireplace, and sliding doors that lead to an amazing screened porch surrounded by nature, making it the perfect spot for your morning coffee. An updated kitchen and spacious dining room with doors leading to a private patio are perfect for entertaining. Completing the main level are an office and half-bath. Upstairs you will find four bedrooms, two bathrooms, and a large bonus room. The lower level has a recreation room and plenty of storage. Be sure not to miss the two-story barn on the property. It's perfect for the animal enthusiast or as extra space for creative projects and hobbies. It even has a second story that can be transformed into a home office-or just a cool place to hang out! This home is a must see; a real stunner.

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.

Approached by a winding drive at the end of a quiet cul-de-sac in Fairfield County's premier gated community, The Ridge, this distinguished Colonial Revival residence is privately sited atop a gentle knoll on two beautifully landscaped acres. Expansive lawns, mature plantings, and private terraces create a tranquil setting with exceptional privacy. Spanning four levels and approximately 7,300 square feet, the home is designed for both comfortable everyday living and grand-scale entertaining. A spectacular Great Room with fireplace flows into the light-filled Kitchen and dramatic 2-story Breakfast Room, with both spaces opening to the terrace for effortless indoor-outdoor living and al fresco dining. A grand 2-story Foyer, formal Dining Room, Mudroom, and home Office complete the main level. Accessed by front and back stairs, the second level offers a luxurious Primary Bedroom featuring a fireplace, spa-like Bath and walk-in closet, three additional en-suite Bedrooms and a large Bonus/Play Room. A sizeable third-floor Craft/Office/Multipurpose Room provides exceptional flexibility. The home's striking appeal continues in the finished walk out lower level with mirror walled Gym and impressive Party/Game Room with fireplace and fully equipped wet bar with wine cooler, ice maker, and double-drawer under-counter refrigerators. Ideally located along the Fairfield/Westport line, The Ridge offers a true Country Club lifestyle with a clubhouse, Pool, Tennis Courts, and Playground.

The former home of Richard Rodgers, composer of The Sound of Music, this 10.92 acre estate with a stunning modern residence was recently fully renovated and expanded, and offers curated one floor living. Generous main rooms are enhanced by lofty ceilings, skylights and walls of glass. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. Separate residential wings include 7 bedrooms and 7 full baths, each with a unique design. All property systems have been upgraded and integrated to work seamlessly .The barn pool house includes a full eat-in kitchen and lounge, bath ,and full gym steps from the pool. An office pavilion is set privately in a quiet garden area. The park like property is surrounded by high stone walls, a nature preserve, open land, a heated paddle tennis court, and an orchard. Live in ultimate style and easy elegance just a quick commute to NYC and airports. This private haven surrounded by a 155 acre nature preserve is minutes to Fairfield, Westport and Greenwich dining and shopping.

UNBEATABLE VALUE IN EASTON | LOWEST PRICED COLONIAL IN ASPETUCK VALLEY! Highly motivated sellers present your golden opportunity to gain instant equity in one of Easton's most coveted neighborhoods! Set on 3 tranquil, tree-lined acres at the end of a quiet cul-de-sac, this beautifully maintained Center Hall Colonial is ready for its next chapter. Why You'll Love It: Effortless Main Level: Seamless flow featuring formal living & dining spaces, a dedicated main-floor office/library, and a cozy family room with a focal fireplace. Bright Kitchen & Mudroom: Expansive eat-in kitchen soaked in natural light with peaceful backyard views and convenient everyday entry. Spacious Upper Level: Four generous bedrooms, including a primary suite with a full bath and walk-in closet, plus gleaming hardwood floors throughout. Smart Efficiency & Privacy: Solar panels keep your utility bills low, while 3 private acres offer an idyllic, serene backdrop. Exceptionally priced and packed with potential-bring your vision and be settled just in time for the holidays!

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 this quintessential New England colonial, lovingly cherished by the same owner for over four decades. Nestled on 2 flat, picturesque acres, this timeless home offers serene, private living while remaining centrally located. A sweeping circular driveway creates a warm arrival, while the sprawling, level backyard provides an ideal setting for outdoor entertaining, with room for a pool and pool house. Inside, traditional character shines with hardwood floors throughout. The main level is designed for both casual daily life and formal hosting. The heart of the home features an expansive eat-in kitchen anchored by a center island, ideal for morning coffee or casual gatherings. A formal living room centers around a fireplace, with classic French doors opening into the dining room. The main level also offers exceptional layout flexibility, including a light-filled office with French doors to a private flagstone patio, a cozy den, a family room with a second fireplace, and a practical mudroom with garage access to keep everyday life organized. Upstairs, 4 generous bedrooms include a primary with an oversized bathroom, the rare convenience of a true 2nd-floor laundry room, and a 2nd full bathroom with double sinks. For extra storage, a full walk-up attic provides additional space. Offering rare privacy, incredible space, and enduring quality in a prime location, this exceptional property presents a wonderful opportunity for its next owners to make it their own.

Nestled at the end of a peaceful cul-de-sac, in the highly sought-after Greenfield Hill neighborhood, 220 Stonewall Lane offers a rare opportunity to own a beautifully situated home on 2.07 acres. The expansive outdoor setting provides an inviting space perfect for entertaining or relaxing while enjoying the tranquil surroundings. When entering the thoughtfully planned main level, you are drawn to the large open space with a renovated modern eat-in kitchen, a sitting area with a wood-burning pizza oven, a Great Room with cathedral ceilings, a wood-burning fireplace, and an additional family room with views of the in-ground pool and lush landscaped grounds. Natural light flows throughout. Additional highlights include hardwood floors throughout, large decorative tiles, a formal living room with fireplace, a dining room, walk-up bonus room, laundry and access to the two-car garage. Upstairs, five well-appointed bedrooms include a private primary suite, creating a comfortable and functional area. The unfinished basement offers ample space for utilities, storage and possible recreational activities. Ideally located near Fairfield's beaches, Metro-North, recognized restaurants, and the Fairfield Theatre Company, this private property blends lifestyle, location, and appeal in one of Fairfield's most desirable areas.

Elegance need not announce itself. Here, it simply feels at home. Quietly elegant and impeccably detailed, this Colonial pairs timeless architecture with interiors that feel as welcoming as they are sophisticated. 6170 SQ FT unfold across four finished levels, crafted for effortless entertaining and comfortable everyday living. A gracious living room with an oversized window seat and inviting fireplace sets the tone, while the soaring family room - anchored by a dramatic stone fireplace and walls of architectural window s- offers scale without sacrificing warmth. The Chef's kitchen w/ ultra-lux appliances flows seamlessly into gathering spaces, where memorable dinners and meaningful moments naturally unfold. Rich millwork, refined finishes and three fireplaces lend warmth and character throughout, while a handsome mahogany library provides a distinguished retreat. Five en suite bedrooms offer comfort, including three generously proportioned suites with sitting areas, walk-in closets and luxurious baths-each worthy of being the primary suite. The finished lower level offers exceptional flexibility with recreation, fitness and guest space. Outside, stone terraces, mature gardens and sweeping level lawns create a private setting for alfresco dining, relaxed gatherings or peaceful retreat. Set on 1.75 landscaped acres in one of Wilton's most sought-after estate neighborhoods, this is a home of enduring beauty, crafted to be enjoyed for generations.

Privately sited in the heart of Greenfield Hill, this updated home blends European-inspired architecture with the modern comforts today's luxury buyers value most. Rich in character, it offers soaring ceilings with exposed wood beams and skylights, wide-plank hardwood floors, custom built-ins, antique mantels, and repurposed antique doors throughout. The dramatic family room flows to a private office, wet bar, and chef's kitchen beneath an expansive skylight. The desirable first-floor primary suite has been transformed with a new spa bath, new gas fireplace, and atrium with a private entrance. Upstairs, a second primary suite features an en-suite bath, dressing room, fireplace, and private balcony. A renovated one-bedroom guest residence with new flooring, updated kitchen and bath, washer/dryer, and private entrance is ideal for extended family, guests, an au pair, or home office. Extensive improvements include a generator, water purification system, drainage system, irrigation, security system with cameras, restored and re-stained roof, renovated mudroom/laundry room, gardens with bluestone walkways and raised beds, and new front fencing. Expansive terraces overlook beautifully landscaped grounds with mature specimen trees and perennial gardens. Just minutes from town, beaches, train, restaurants, and Fairfield Country Day School, this exceptional Greenfield Hill property offers timeless character, privacy, and extensive improvements. Ready to enjoy from the day you arrive! Recent Improvements and Capital Investments Interior - Beautifully renovated first-floor primary bathroom New gas fireplace in the first-floor primary suite Completely renovated mudroom and laundry room New flooring in the guest residence Renovated guest kitchen and bathroom Mechanical and Infrastructure - Whole-house water purification system Whole-house generator New drainage system with sump pump New irrigation system New security system with cameras Exterior - Restored and re-stained roof New fenced garden with bluestone walkways and raised planting beds New fencing along the front of the property

Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends sophisticated style with effortless everyday living. A stunning custom kitchen appointed with premium Thermador appliances anchors the home, flowing seamlessly into beautifully designed living and entertaining spaces. Superior materials, custom millwork, and bespoke finishes define every room, while 6 ensuite bedrooms in the main residence provide exceptional comfort. Elevator-ready! Walk-up attic offers added possibilities. Outdoors, beautifully landscaped grounds create a private resort setting featuring a spectacular saltwater pool and spa. A separate 550-square-foot guest/pool house/ADU offers ideal accommodations for guests, wellness, or entertaining, while the expansive property provides ample room for a future tennis or sport court. A rare offering in one of Westport's most coveted and prestigious locations, it's just minutes from Westport's bustling downtown, sunny beaches, and award-winning schools. This remarkable estate combines thoughtful design and an unparalleled lifestyle defined by privacy, bespoke design and high-end amenities. Still time to customize. Floor plans available

Few homes define a town; this is one of them. Located in the highly coveted South Wilton neighborhood, this iconic Grand Dame, originally dating to the 1830s and beautifully reimagined and expanded during the Colonial Revival of the 1930s, has been masterfully transformed from the inside out. Every inch has been thoughtfully restored and elevated by a renowned preservationist / designer, honoring its extraordinary heritage while embracing the finest comforts of modern living. Rich in character and timeless elegance, the home showcases magnificent stone fireplaces, high ceilings, hand-hewn beams, wide-plank chestnut floors, beautifully preserved millwork, designer lighting, Farrow and Ball finishes, exquisitely renovated baths, and countless bespoke details that reflect an uncompromising commitment to craftsmanship. Bathed in natural light, the spectacular living spaces are both spacious and welcoming, with walls of windows framing picturesque views in every season. The exquisite eat-in chef's kitchen and butler's pantry, with high-end appliances, light fixtures, and Carrara marble, is magazine-worthy! The luxurious primary suite offers a private retreat, while five additional generously scaled and beautifully designed bedrooms, charming balconies, multiple perfect office spaces, and a spectacular versatile historic barn create exceptional flexibility and enduring appeal. Equally extraordinary are the grounds. An inviting covered porch extends seamlessly from the living room, while an expansive stone terrace wraps the rear of the home, creating unforgettable spaces for entertaining or quiet evenings overlooking sweeping, level lawns and meticulously curated landscaping. Perfectly positioned just moments from the heart of Wilton and minutes to Westport and New Canaan, this is far more than a beautifully renovated timeless residence. It is one of Wilton's most iconic properties-a rare offering where history, architectural beauty, and timeless design come together in spectacular fashion. An exceptional opportunity for its lucky next steward. Truly a one-of-a-kind estate.

Extraordinary New Construction home on one of Westport's newest premier cul-de-sacs. Offering nearly 10,000 SF of impeccably finished living space, this exceptional home blends timeless elegance w/ modern luxury & showcases the finest craftsmanship throughout.Designed with an uncompromising attention to detail, features include exquisite millwork, stunning custom cabinetry, spectacular ceiling details & European windows that flood the interiors w/ natural light.The Chef's Kitchen is highlighted by natural stone countertops,a dramatic stone backsplash & custom stone hood, premium appliances with column refrigerator & freezer all set flush to the cabinets. Luxurious living and entertaining spaces flow seamlessly to the outdoor oasis featuring a sparkling pool, spa, & private 1.6 property w/an irrigation system Belgium block trimmed driveway The magnificent primary suite is a private retreat, complete w/ a custom rift oak cathedral ceiling & a covered balcony w/ glass & wood railings overlooking the property.The 2nd level features 5 BRs w/ensuite baths. The 6th BR Suite is privately in the LL where there is a large FR & Gym.Additional amenities include natural gas, city water, Visual Comfort luxury lighting throughout, integrated recessed lighting, & countless custom features that elevate every room.This is a rare opportunity to own a newly built, architecturally stunning estate where exceptional design and refined living come together beautifully. Ready for move in Summer 2026

Rarely does a new construction home and property like this come on the market in Westport. Set at the end of a cul-de-sac, in the coveted Long Lots neighborhood, this 2.3-acre, flat property offers a rare combination of privacy and convenience to town. The property features a resort-style, saltwater pool w/spa and automatic safety cover, expansive covered and open-air patios, and a fully equipped outdoor kitchen. There's still space to add a full sized Tennis Court and ADU to create a luxury compound! Built by award-winning Westport Family Homes, this thoughtfully designed 6 bed/8 bath home spans 9,062 square feet on 4 finished floors, showcasing exceptional craftsmanship and attention to detail. Soaring ceilings and an abundance of natural light. Main Level: Gracious Foyer, 2 Powder Rms, Formal Liv/Din Rms, private Office, Designer Kitchen w/Scullery for entertaining. Kitchen opens to large Great Rm w/FP and Outdoor Liv Rm. Second Level: Primary Ste w/FP, 2 walk in closets, spa inspired Bathrm and 4 other Bedrms. Third Level: Playroom w/Bathrm. Lower Level: Walk out to Pool w/ 6th Bedrm, full Bathroom, Family Rm w/Bar, Play/Media Room and large Gym. Full-house generator, oversized 3 car garage w/EV charging capability and room for 3 car lifts. The home is elevator-ready, enhancing convenience and long-term livability. Great for multi generational living. City Water, Natural Gas. This masterfully crafted home has a timeless floor plan and modern design.

Set on a private, serene two-acre lot surrounded by mature trees and lush landscaping, this spacious home offers a rare combination of comfortable living, flexibility, and additional income potential. Just steps from the main residence, a detached, self-contained legal cottage features one bedroom, one full bath, a kitchen, and a private deck-ideal for guests, extended family, a home office, or rental income. The main home features formal living and dining rooms, a family room, breakfast area, study, mudroom, powder room, and a guest bedroom with an en-suite bath and French doors opening to the rear deck. The well-appointed kitchen includes two sinks, two dishwashers, two ovens, a warming drawer, ice maker, wine refrigerator, and an additional refrigerator in the walk-in pantry. Upstairs, the primary suite offers two walk-in closets, a full en-suite bath, and doors opening to a private balcony with beautiful backyard views. A separate study, two additional bedrooms, and two full baths complete the second floor. The lower level provides a versatile bonus room. Additional highlights include an expansive deck, new roof, updated mechanicals, three-car garage, whole-house generator, and built-in speakers. Just steps from the Norwalk River Valley Trail and five minutes to town, train, and commuter routes.

Set in a peaceful Redding setting, 87 Giles Hill Road is a charming Cape with a thoughtful and inviting floor plan and exceptional outdoor spaces designed for both relaxation and entertaining. The home has a warm and welcoming feel, with hardwood floors throughout the main living areas, generous natural light, and a comfortable flow from room to room. Two bedrooms located upstairs offer private retreats separate from the main living spaces. Outside, the property truly shines. A custom heated Gunite pool with spa and waterfall creates a private backyard retreat, while the custom outdoor fireplace provides another inviting gathering space for entertaining or relaxing outdoors. The lower deck grilling area is also conveniently equipped with a direct propane connection. With propane heat, classic Cape character, versatile living spaces, and exceptional outdoor amenities, 87 Giles Hill Road offers a wonderful opportunity to enjoy the privacy, natural beauty, and relaxed lifestyle that make Redding such a special place to call home.

Incredible opportunity to build or completely renovate in one of Westport's most desirable locations. Situated on a picturesque 1-acre lot, 53 Cross Highway offers a prime canvas for builders, investors or buyers looking to bring a custom project to life. The property currently features a 1950s-era home, providing an excellent footprint for an extensive transformation or a complete luxury rebuild. Highly sought-after placement within the prestigious Coleytown school district. Located just minutes from downtown shopping, dining, the Merritt Parkway, and Compo Beach, this property delivers the ideal setting for a high-end Fairfield County lifestyle. Bring your architect and your vision to maximize the potential of this exceptional lot. House sold As-Is.

Charming Cape Cod home in Wilton, a desirable Mid Fairfield County community. Located along a scenic country road, yet mere minutes from the village center, top ranked Schools and popular Wilton Y campus....Not to mention commute roads; and 5 mins from Cannondale Metro North train! 315 Olmstead Hill embodies classic New England architecture paired with unbeatable convenience. This comfortably-sized Cape, with significant, quality additional space in the partially Finished Walk-Out Lower Level, offers maximum flexibility for a wide range of lifestyles and life situations. The lush half-acre Lot possesses the perfect balance of lawn/perennial beds and Nature with its gorgeous views. There are Full Bathrooms on each Level. Some Key Features and Benefits: The Living Room with Dining Area is sun-lit, and anchored by a cozy stone Fireplace--ideal for crisp New England evenings. The home's Layout is Open and Inviting, including the main level Primary, with Walk-In Closet; two Bright Bedrooms upstairs; the Bonus Finished Lower Level; the Mud Room/Breezeway, separating the Oversized 2 Vehicle Attached Garage from the living quarters. Seamless flow from the timelessly Updated Kitchen with newer high-end Appliances, past the Breakfast Bar, to the Dining Area and Living Room. 315 Olmstead Hill is an outstanding opportunity to acquire a Move-In Home, or to customize a Classic Home in a convenient, highly desirable Location!!

Set on a private, beautifully landscaped two-acre property, 14 Powder Horn Hill Road offers exceptional space, privacy and convenience just minutes from Wilton town center, shopping and the train. A stunning front porch creates a memorable first impression and opens to a grand entry foyer with a sweeping staircase. Inside, rich hardwood floors, generous room sizes, high ceilings and thoughtful architectural details create an elegant yet comfortable atmosphere. The spacious chef's kitchen features a large center island, Sub-Zero refrigeration and abundant workspace, flowing seamlessly into the inviting family room with coffered ceilings, a fireplace and French doors leading to the deck. Formal living and dining rooms provide ideal entertaining spaces, while a private library offers the perfect home office or quiet retreat. Upstairs, the expansive primary suite features a fireplace, luxurious bath and two exceptionally large walk-in closets. Four additional bedrooms and an oversized playroom room with a full bath offer outstanding flexibility for guests, recreation or media. The walk-out lower level is a true blank canvas, featuring impressive 9-foot ceilings, plumbing already in place for a future bathroom and endless potential to create a gym, home theater, game room, guest suite or additional living space. Outside, the flat, fenced backyard offers an ideal setting for entertaining, play and pets, with ample room for a future pool.