Refine Search
Sort by
27 Rogues Rdg, Weston
$1,200,000
4 Beds ⋅ 4 Baths ⋅ 24114393 MLS
Bringing the Indoors and Outdoors Together with Mid-Century Rustic Elegance... Designed by renowned Broadway scenic designer Ralph Alswang-whose legacy includes nearly 100 productions and iconic venues such as the George Gershwin Theatre-this extraordinary Weston home reflects his theatrical eye for light, space, and natural beauty. Alswang, who also designed a handful of homes for notable figures like Paul Newman, infused this residence with character, creativity, and timeless craftsmanship. Thoughtfully sited on nearly 3 bucolic acres to capture natural light and serene views, the home spans over 2,900 sq. ft. and offers 4 bedrooms and 3 full baths. Floor-to-ceiling windows, gleaming restored radiant heated slate floors, and a spacious open layout create seamless transitions between indoor and outdoor living. A dramatic double-story entry opens into a versatile family room, while the chef's kitchen flows effortlessly into the dining and living areas-perfect for entertaining or quiet everyday moments. The primary suite features 9+ ft. tray ceilings, a spa-inspired bath with a deep soaking tub, double sinks, a separate shower, and a large walk-in closet. A second ensuite bedroom includes oversized closets and opens directly to a wraparound stone terrace-an ideal spot for a morning latte, evening glass of wine, or peaceful nights of stargazing. Two additional bedrooms share a generously sized hall bath.

27 Rogues Rdg, Weston

195 Steep Hill Rd, Weston
$1,170,000
5 Beds ⋅ 4 Baths ⋅ 24172499 MLS
Surrounded by nature and complete privacy, this unique home offers a peaceful retreat with exceptional indoor-outdoor living. A large, welcoming entry foyer features tile flooring and a skylight that fills the space with abundant natural light. Hardwood floors and custom windows are found throughout the home.The main level showcases a spacious living room with a wood-burning fireplace and walls of glass sliders that open to the pool & cabana. The eat-in kitchen with new marble countertops is open to the sunken den...creating the perfect setting for entertaining. The dining room is filled with natural light from solarium windows and features built-in window seating. The impressive two-story primary suite serves as a true sanctuary, complete with its own staircase leading up to a private loft with a wood-burning fireplace, perfect for a den or office. Dramatic floor-to-ceiling two-story windows and direct access to the pool and stone patio further elevate the space. Two additional bedrooms share a recently updated Jack & Jill bathroom. The lower level offers two more bedrooms, a full bath, and laundry area. An attached two-car garage adds convenience. Outside, enjoy your own private oasis in the fully fenced backyard featuring a gunite pool, expansive stone patio, and a cabana equipped with a kitchenette, second laundry, and full bath - ideal for entertaining or relaxing all summer long. Conveniently located to town, award-winning schools, dog park, Westport, Merritt Parkway.

195 Steep Hill Rd, Weston

78 River Rd, Weston
$1,150,000
3 Beds ⋅ 3 Baths ⋅ 24189056 MLS
The Weston Cottage-where timeless charm, remarkable history, and tranquil riverfront living come together. Nestled along the river on the coveted Weston/Westport border, this beautifully updated 3-bedroom, 2.5 bath home offers a rare opportunity to own a piece of Connecticut history. Famously known as the retreat of legendary actress Bette Davis, the cottage became the setting for the true story that inspired the hit play Me and Jezebel, after Davis unexpectedly stayed for 32 unforgettable days. Today, this captivating home blends historic character with modern comfort. The renovated kitchen features a Wolf range, Bosch column refrigerator, and inviting marble fireplace, while all three bathrooms have been tastefully updated. Fresh interior and exterior paint, new lighting, and custom built-ins completed in 2025 enhance the home's move-in-ready appeal. Wake to the soothing sounds of the river, enjoy peaceful outdoor living, and experience the privacy and beauty of this exceptional setting just minutes from the shopping, dining, beaches, and train station in Westport. Whether you're searching for a full-time residence or a weekend escape, The Weston Cottage offers an extraordinary lifestyle in one of Fairfield County's most desirable locations.

78 River Rd, Weston

5 Newtown Tpke, Weston
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 24162524 MLS
This distinctive Lower Weston retreat with incredible Post & Beam Barn is truly one to experience. Tucked away on more than 3.5 acres of wooded serenity, the home offers striking architectural details including soaring ceilings, pegged hardwood floors, exposed wood beams, and three stone / brick fireplaces. Multiple levels of living space create a dynamic & flexible floor plan. The chef's kitchen is equipped for serious cooking, featuring a Viking range and hood, double ovens, and a Sub-Zero refrigerator. The showpiece of the property is the exceptional Post & Beam Barn - an impressive 1,140+ square-foot structure crafted by renowned Vermont Timber Frames in 1998. Perfect for a hobbyist, car collector, creative studio, home office, or anyone seeking a separate, inspiring space, the barn is heated by propane, cooled with a split system, and supported by a whole-house generator. It offers two levels plus a loft and cupola, half bath, and extensive built-ins. A rare opportunity with tremendous character & potential, this special property is being sold "as is."

5 Newtown Tpke, Weston

5 Walker Ln, Weston
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 24118797 MLS
Natural light, soaring ceilings, and a dramatic stone fireplace set the tone for this spacious contemporary on one of the best lots in a quiet cul de sac. The airy living room opens to a dining area and an updated kitchen with granite counters, stainless appliances, Sub-Zero refrigerator, large island, and a coffee bar. From the kitchen sliders you step onto a spacious deck for seamless indoor-outdoor living. The main level primary suite offers two walk-in closets, a full bath with double sinks, a soaking tub and separate shower, and its own entrance to the deck. Upstairs are three more bedrooms including one with its own full bath and walk-in closet, plus a reading nook and a shared hall bath. The walk-out lower level provides a versatile finished space ready to be whatever you wish, along with abundant storage. Outside enjoy a generous level yard, a cozy fire pit area, and mature landscaping. All this is just minutes from top-rated schools, the town center, and nature preserves, with easy access to Westport, the train, and NYC.

5 Walker Ln, Weston

11 Ravenwood Dr, Weston
$1,150,000
5 Beds ⋅ 3 Baths ⋅ 24125749 MLS
Welcome to 11 Ravenwood Drive, a 5-bedroom, 3-bath, 2,704 sq. ft. home that offers both privacy and modern comfort in the heart of Weston. Nestled on a peaceful lot, this home features several updates, including a whole-house generator and smart technology for lights, thermostats, fans, blinds and more - bringing convenience to everyday living. Inside, you'll find inviting spaces perfect for gathering with family and friends. The primary suite is a true retreat, offering a beautifully appointed spa-like bathroom with steam shower, radiant heat, soaking tub and more and a dream walk-in closet (converted from the 5th bedroom, easily reverted to full bedroom). Outdoors, two remote-controlled awnings extend your living space for effortless entertaining or quiet relaxation, while a saltwater hot tub provides year-round enjoyment. Practical upgrades include three propane tanks supporting the dryer, stove, and grill. Adding even more peace of mind, this home comes with a home warranty included, making it truly move-in ready. Enjoy the tranquility of a private setting while still being minutes to Weston's award-winning schools and town center.

11 Ravenwood Dr, Weston

18 Briar Oak Dr, Weston
$1,105,000
5 Beds ⋅ 4 Baths ⋅ 24186968 MLS
Nestled on 2.25 breathtaking hilltop acres, this is one of Lower Weston's beautiful building sites. Set in a picturesque, level meadow w/ mature trees, the property offers exceptional privacy on a coveted cul-de-sac just south of Weston Center, near the Historical Society, & minutes from the Merritt Parkway. Whether you choose to renovate the existing home or create the custom estate you've always envisioned, the possibilities are endless. The existing residence offers 5 beds, 4 baths, & timeless features including original oak hardwood floors. The spacious layout includes a living room w/ fireplace, formal dining room, kitchen, and a family room with a second fireplace and radiant heated floors. The primary suite features a private entrance & deck, while a second-floor laundry room adds everyday convenience. A versatile 5th bedroom on the main level includes a kitchenette & full bath, making it ideal as a guest suite, in-law apartment, home office, or pool changing room. Additional highlights include a welcoming front foyer with heated slate flooring, a full dry basement with laundry sink, two separate attics, & a heated 21/2-car garage complete with sink, work area, radiant heat, & generator hookup. Outside, a secluded 20' x 40' in-ground pool enjoys a sunny, private setting & offers the opportunity to be restored to its former glory. An extraordinary opportunity to own one of Lower Weston's premier properties & create your dream home in an idyllic setting. Sold As-Is

18 Briar Oak Dr, Weston

14 Saw Mill Rd, Weston
$1,050,000
4 Beds ⋅ 3 Baths ⋅ 24182765 MLS
14 Saw Mill Road offers the convenience of suburban metropolitan New York living while maintaining a quaint, calm retreat by design. You are greeted by a historic draw bridge within the private drive that leads to the professionally landscaped and beautifully cared for lot. This home sits on about 2 acres, with privacy and room to live inside and out all year round. This oversized ranch offers a perfect blend of comfort, style, and functionality. The main level offers a bright, open concept kitchen with high ceilings, and ample natural light throughout. A beautiful custom island that was added in 2023. The dining room and kitchen are integrated for hosting and families. There are 2 bedrooms and 2 full baths on the main floor, and the lower levels expands a walkout basement which includes a separate fenced off area, perfect for multigenerational living or a guest suite with 2 rooms and a bathroom. Thoughtful improvements were made on the main floor for ease of living. A playroom was added off the kitchen with custom built ins for additional charm and storage, French doors were added, and both downstairs bedrooms have been updated for additional office space or a workout room. With the unpredictable New England weather, you will be happy to know this home is equipped with a full house generator that runs off propane, a heated roof for ease of maintenance, gorgeous gardens in the front and back yard that bloom all year round. A stunning, space that combines character and charm.

14 Saw Mill Rd, Weston

104 Blue Spruce Cir, Weston
$1,050,000
4 Beds ⋅ 4 Baths ⋅ 24134970 MLS
This Chalet-Style Retreat offers the best of both worlds, privacy and serenity of a country residence paired with convenient access to local amenities and recreation. Here, outdoor adventure and small-town charm are just minutes away, Devil's Den Preserve, Bisceglie-Scribner Park, Morehouse Farm Park, and Lachat Town Farm for community events and farmers markets. Aspetuck Valley Country Club, Weston Racquet Club and Weston Field Club offers private membership facilities just minutes away, while Westport's beaches, boutiques and cultural attractions are within a short drive. Commuters will appreciate proximity to Train Stations, Merritt Parkway, Georgetown Village and Weston, Westport and Wilton's Town Center, home to local cafes, shops and dining. Located within the award-winning Weston School District, recognized for academic excellence and outstanding programs.

104 Blue Spruce Cir, Weston

123 Lyons Plain Rd, Weston
$1,049,000
3 Beds ⋅ 3 Baths ⋅ 24176959 MLS
Perched atop a private, sun-drenched hill in the heart of Lower Weston, 123 Lyons Plain Road is a masterclass in charm and character. This home strikes the rare balance between secluded retreat and total convenience, located just minutes from the vibrant shopping and dining of Westport, local beaches, and easy commuting via the Merritt Parkway or Metro-North. Once inside the home, the craftsmanship speaks for itself. The interior is bathed in natural light, showcasing architectural details like elegant coffered ceilings, original wide-plank wood floors, and rustic restored beams. At the center of it all, a dramatic stone fireplace anchors the living space, creating a warm and inviting atmosphere. The layout is designed for a seamless lifestyle. The kitchen flows naturally toward the stone terrace, making it easy to transition from indoor prep to alfresco dining. Whether you're enjoying a quiet morning coffee on the covered porch or hosting friends to take in the vibrant sunset views, the outdoor spaces are truly an extension of the home. For added flexibility, the walkout lower level provides a versatile footprint for a gym, laundry, and plenty of storage. Beyond the property, the town of Weston offers a unique community spirit, highlighted by its award-winning schools all conveniently situated on one central campus. 123 Lyons Plain Road isn't just a house; it's a beautifully curated lifestyle defined by craftsmanship, light, and an incredible sense of place.

123 Lyons Plain Rd, Weston

48 Salem Rd, Weston
$1,048,900
4 Beds ⋅ 2 Baths ⋅ 24194975 MLS
Charming Nantucket Farmhouse Cottage majestically sited on one of Weston's most beloved cul-de-sacs. This sun-drenched home offers NEARLY 3000sq.ft. of timeless appeal with a welcoming living room featuring a fireplace and classic paneling, seamlessly adjoining the updated eat-in kitchen. A spacious front-to-back family room, complete with a second fireplace, opens to an expansive deck, terrace, fenced play yard, sparkling in-ground pool, and whimsical screened porch-creating the perfect setting for summer entertaining, outdoor dining, and relaxed family living. Gleaming hardwood floors extend throughout the main and upper levels, where you'll find four bedrooms and two full baths. The impressive 1,111 sq. ft. walk-out lower level offers exceptional flexibility as an in-law apartment, nanny suite, private guest quarters, or fifth bedroom with a full bath. This versatile space also includes a game room, office/studio, and private entrance opening to beautifully landscaped lawns and gardens. Thoughtfully updated in 2020 with numerous improvements, this home beautifully blends classic cottage character with today's modern comforts. Ideally located just moments from Weston's award-winning schools and town center, with convenient access to Westport's vibrant Main Street, beaches, Metro-North train service, and the Merritt Parkway. Approximately 55 minutes to Manhattan.

48 Salem Rd, Weston

46 Old Farm Rd, Weston
$1,040,000
4 Beds ⋅ 3 Baths ⋅ 24127550 MLS
Tucked at the end of a quiet cul-de-sac, this 4-bedroom, 3-bath charming colonial delivers space, style, and flexibility. The heart of this home is the open kitchen/family room, with spacious island and cozy fireplace, perfect for casual living and entertaining. A bright sun porch invites you to relax year-round - the perfect spot for morning coffee or meals. The flexible, main level floor plan allows for a spacious formal dining room, home office, and/or formal living room - decide what works best for you. Upstairs, you'll find a versatile second-floor family room with fireplace - ideal as a media lounge, hangout spot, or playroom. All four bedrooms are generously sized, including a comfortable primary suite with its own bath. This thoughtfully designed home offers both open gathering areas and private retreats, making it easy to adapt to your lifestyle. The front porch creates beautiful curb-appeal, and the expansive level yard is inviting, giving you space for play, gardening, or relaxing in the private, peaceful setting. The large deck allows for lounging, grilling and entertaining. The built-in firepit creates the ultimate setting for get-togethers and cozy nights under the stars - smores anyone? Set in a neighborhood just minutes from shopping, dining, and conveniences, this home blends cul-de-sac tranquility with everyday ease. Walk the dog, ride your bike, take a run! This is the kind of home where you can settle in, spread out, and create lasting memories.

46 Old Farm Rd, Weston

131 Georgetown Rd, Weston
$1,035,000
2 Beds ⋅ 2 Baths ⋅ 24191063 MLS
"A rare retreat where nature, comfort, and craftsmanship come together in perfect harmony." Enter through electronic gates,experience quiet & calm & feel as though you've stepped into another world. This charming 2-bedroom,2-bath cottage welcomes you w/warmth, character & timeless appeal. Inside,you'll discover the results of thoughtful renovations & meticulous upgrades completed over the years. Aside from the main house--2 additional structures. Each room & outbuilding possess its own distinctive charm & function. Above the garage, a versatile 624+/- sq.ft. studio loft offers the perfect setting for either home/office/gym/studio or recreation room & is complete w/sauna,gas fireplace & abundant storage. The detached 204+/- sq.ft. studio office showcases soaring vaulted ceilings w/cedar & hemlock beams,rich pine floors,gas fireplace, baseboard heating & wrap around wood deck w/built-in seating-- overlooking a tranquil pond. The sun-filled kitchen features premium new appliances, custom cabinetry & new tile heated floors. The primary suite offers vaulted ceilings,revamped walk-in closet & private deck complete w/hot tub. The spacious primary bath is a spa-like retreat. Both rooms have access & views to the spacious backyard. Set on nearly 2 acres of beautifully landscaped grounds. Privately tucked away off Georgetown Road &bordering the protected open space of the Honey Hill Preserve. More than a home-it's a lifestyle.

131 Georgetown Rd, Weston

32 Calvin Rd, Weston
$998,000
3 Beds ⋅ 3 Baths ⋅ 24133411 MLS
LISTING IS OFF MARKET FOR THE HOLIDAYS. REACH OUT FOR MORE DETAILS.Step into a light-filled retreat where nature, comfort and creativity meet. Tucked on a private 2-acre lot just minutes from Weston town center and schools, this beautiful updated Cape offers warmth, serenity and timeless style. The first-floor primary suite, refinished floors, and flexible living spaces create an easy, inviting flow. The office has potential as a 4th bedroom with a full bath. A screened-in porch, three patios, and a spacious deck extend living outdoors, perfect for entertaining or relaxing in nature. Enjoy a hot tub, outdoor shower and fenced yard for pets. The lower-level family and music room adds creative charm and functionality. With approximately 3,000 sf of beautifully maintained space, this peaceful sanctuary offers convenient access to both Weston and Wilton.

32 Calvin Rd, Weston

212 Weston Rd, Weston
$995,000
4 Beds ⋅ 2 Baths ⋅ 24123471 MLS
RARE GEM IN LOWER WESTON - Minutes to Everything! Don't miss this extraordinary opportunity to own a piece of history in one of Connecticut's most sought-after locations, just moments from Westport and a quick .2 miles to Weston's renowned schools and charming town center. Welcome to "Walnut Hill", a distinguished 4-Bedroom, 2 Bath Antique Farmhouse with detached Guest Cottage, originally dating back to 1780 and officially recognized by the Connecticut Historical Commission as The David Adams House. This timeless residence beautifully blends historical charm with modern comforts, featuring original hardwood floors, hand hewn wood beams, and 2 grand, stone working fireplaces. Recently updated with a BRAND NEW septic system, the home offers spacious, MOVE-IN ready interiors, with many rooms freshly painted and ready to welcome you. Whether you prefer to preserve its classic character or reimagine with additional updates, the potential to create your "forever home" is limitless. Notable highlights include a stunning Family Room with soaring cathedral ceilings, a tranquil 3-season Porch - perfect for morning coffee or curling up with a good book, and updated 1BR Guest Cottage - could also serve as an Office or In-Law/Au-Pair Suite. Perched prominently atop a gentle knoll, this remarkable property spans 2+ acres of picturesque grounds, with a private, level backyard - perfect for plenty of outdoor fun, perennial gardens, mature trees, and quintessential New England serenity.

212 Weston Rd, Weston

8 Messex Ln, Weston
$985,900
4 Beds ⋅ 3 Baths ⋅ 24137694 MLS
Welcome to 8 Messex Lane, a classic Colonial perfectly positioned on a private cul-de-sac in sought-after Weston. Set on over 2 acres of beautiful, natural grounds, this 4-bedroom, 2.5-bath home offers an ideal blend of comfortable living spaces and outdoor beauty. The home's 3,208 square feet of heated living space provides generous room for everyday life and entertaining. Two cozy fireplaces add warmth and character throughout, while large windows capture abundant natural light. The thoughtful floor plan includes 9 well-proportioned rooms that flow effortlessly from one to the next. Outside, the property truly shines. A spacious deck overlooks the lovely yard and serves as the perfect vantage point for spectacular sunset views-ideal for morning coffee or evening gatherings. The expansive 2-acre lot offers privacy, room to play, and endless possibilities for outdoor enjoyment. The peaceful cul-de-sac location provides the tranquility of country living while maintaining convenient access to Weston's excellent schools, town center, and major commuting routes. This is Connecticut living at its finest-space, privacy, and natural beauty all in one exceptional package and comes with a fast electric car charger in the garage! This home awaits its next chapter. Come experience the perfect combination of location, land, and lifestyle at 8 Messex Lane.

8 Messex Ln, Weston

24 Nordholm Dr Unit 24, Weston
$975,000
2 Beds ⋅ 2 Baths ⋅ 24138727 MLS ⋅ River Estates Condominium - Pending Verification BLDG.
Welcome To 24 Nordholm A striking modern European-inspired design, this stunning river cottage draws inspiration from Scandinavian minimalism and the timeless forms of New England barns. Perched on the hillside of the Saugatuck River, the architecture is meticulously attuned to its natural topography, running parallel to the landscape and harmoniously blending with the grain of the land. The result is a seamless fusion of intentional design and contemporary elegance. This bungalow-style cottage offers sleek, modern lines in a thoughtfully compact approximately, 1,700 sq ft. (2 bedroom suites + office/media) layout that balances form and function. Designed as a full-time residence, weekend escape, or luxury country retreat, the home delivers comfort, sophistication, and nature-inspired living within a clean, contemporary footprint. New build commenced in 2022 hm., 2023-gar.to create a refined building envelope, as the home is plumbed to accommodate a future second story and designed for flexibility with potential to add 750 sq. ft., ideal for those seeking a property that can evolve with their lifestyle. The original home was removed, and an extraordinary newly constructed cottage was curated in its place. Set within a rare three-residential condominium enclave - a one-of-a-kind in Weston.

24 Nordholm Dr Unit 24, Weston

198 Steep Hill Rd, Weston
$960,000
5 Beds ⋅ 4 Baths ⋅ 24094159 MLS
Exceptional 5-BR stone home blending contemporary design w natural tranquility sits atop 2 private acres in Weston. Expertly engineered & beautifully constructed, this freshly painted home welcomes you through a dramatic 2-story foyer into a sun-filled living room with floor-to-ceiling windows, sweeping woodland views, and a custom 2-sided fireplace. Open chef's kitchen features granite countertops & island, custom cabinetry: Sub-Zero, Thermador stoves, Miele cappuccino station, warming oven, steamer. Large DR flows b/w LR and kitchen for perfect entertaining. Main level: 3 bedrooms, spacious primary suite w sitting room, spa bath, double vanity & custom staircase that winds to loft ideal reading/stargazing. Additional upstairs BRs feature full-length getaway lofts. Lower level incl 2 more BR, excellent for guests/au pair/office, full bath, wine cellar, sauna, game room & family w stone fireplace that opens to outdoor living area. Heated red barn, accessible from upper deck, perfect for exercise/yoga, office, studio, or meditation. Honeycombed by trails & two meandering rivers, Weston has largest nature preserve in Fairfield County, pairing abundant opportunities for hiking, cycling, fishing, & birding with easy access to NYC. Located in the desirable South Weston, minutes to Westport shopping. Its renowned school system w low ratio has been awarded CT Blue Ribbons for excellence. Community, sophistication, nature. It doesn't get any better than this!!!

198 Steep Hill Rd, Weston

267 Newtown Tpke, Weston
$950,000
3 Beds ⋅ 3 Baths ⋅ 24194502 MLS
**NEWLY PRICED** Tucked behind classic wood rail fencing and stone walls, this charming, beautifully updated Colonial offers turn-key living with a right-sized footprint in a private Weston setting. Thoughtful improvements include renovated baths, new windows, a new roof, new kitchen appliances and numerous additional updates-allowing the next owner to simply move in and enjoy. The welcoming floor plan makes smart use of every space, with formal living and dining rooms and French doors opening to an expansive wraparound deck for easy indoor-outdoor living. A sun-filled family room with vaulted ceilings adds an airy gathering space, while the well-appointed kitchen and powder room complete the main level. Upstairs, the primary suite features a custom walk-in closet and en suite bath, with two additional bedrooms and a full hall bath. The finished walk-out lower level, with its own entrance, adds valuable flexibility for a home office, playroom, fitness space or guests. Set on .83 private acres, the property strikes an ideal balance of privacy, outdoor space and lower-maintenance living, with a generous front yard, expansive back deck and peaceful babbling brook. Less than one mile from Weston's award-winning schools and convenient to major highways and NYC. Newly priced and truly move-in ready, this is a compelling opportunity to enjoy the privacy and lifestyle of Weston without the projects.

267 Newtown Tpke, Weston

50 Ravenwood Dr, Weston
$950,000
6 Beds ⋅ 3 Baths ⋅ 24178366 MLS
This exceptional 3,096 square foot home perfectly combines modern mechanical updates with prime convenience, located in Weston's top-rated school district with a bus stop right in front of the house. The sun-drenched main level boasts a dramatic open floor plan and soaring vaulted ceilings, creating an airy environment ideal for entertaining. Relax by one of the 3 cozy fireplaces on winter days, and enjoy the beautiful hardwood floors flowing throughout. This beautiful property features 6 spacious bedrooms and 3 full bathrooms, including a beautifully remodeled bathroom and laundry room on the lower level. Enjoy rare, premium convenience with a direct hookup to town water-a highly sought-after asset when most of Weston relies on private wells. Mechanics are completely worry-free with a brand-new HVAC system, new water heater, and a newly lined chimney. Solidly built and boasting a brilliant layout, this home is complete with reliable cell reception - providing the perfect foundation for Weston living at an incredible value in today's market.

50 Ravenwood Dr, Weston

17 Richmond Hill Rd, Weston
$950,000
3 Beds ⋅ 2 Baths ⋅ 24147378 MLS
The Oasis at Richmond Hill is a rare mid-century modern retreat nestled at the end of a quiet cul-de-sac in Weston. Set on 2 acres of landscaped grounds bordered by towering spruce, elms, and rhododendrons, this 1956 residence offers a seamless blend of architecture and nature. Inspired by the Harvard Five, its design features clean lines, warm materials, and walls of glass that frame the changing seasons. A dramatic stone fireplace anchors the main living space, while French doors from the granite-appointed kitchen open to a stone terrace overlooking tiered lawns and a gunite pool with cabana. A winding path leads through mature gardens to the pool, creating a private, resort-like setting perfect for entertaining. The home offers three bedrooms and two full baths, including a serene primary suite with en-suite bath, private deck, and tranquil views. Custom built-ins in the secondary rooms allow for flexible use as bedrooms, offices, or studios. Additional highlights include central air, updated systems, and a detached garage once used as an artist's studio. Located near nature preserves, walking trails, and Weston's beloved dog park, this property offers a rare opportunity to live within architecture - not just inside it.

17 Richmond Hill Rd, Weston

22 Hill Farm Rd, Weston
$935,000
3 Beds ⋅ 3 Baths ⋅ 24144697 MLS
Perched atop 2.12 acres at the end of a quiet cul-de-sac, this fully renovated modern 3BR contemporary offers a rare blend of privacy, architectural drama, and seamless indoor-outdoor living. Set near Aspetuck Land Trust trails, the home blends refined design with serene surroundings. Enter into an open-concept main level featuring a long banquet-style dining area and a stunning great room with soaring ceilings, walls of glass, a stone fireplace, and a sculptural curved staircase that serves as a striking focal point. Just beyond the banquet dining area is a scullery-style working kitchen with premium appliances, including Sub-Zero, thoughtfully designed for effortless entertaining while keeping prep and clean-up discreetly tucked away. Rich dark walnut hardwood floors run throughout. The main level includes 3 bedrooms, each with access to a deck or patio. The spacious primary suite offers a gas fireplace, large custom walk-in closet, and a spa-like bath w/ soaking tub, standing shower, and smart toilet. Upstairs, a dramatic great room with double-height windows, a third fireplace, full bath, separate laundry room, and a sleek marble-clad designer kitchen provides exceptional flexibility for guests, entertaining, or multigenerational living. A truly rare and architecturally compelling home, this one-of-a-kind retreat captures the very best of privacy, design, and natural beauty in one of Weston's most coveted settings.

22 Hill Farm Rd, Weston

23 Wilson Rd, Weston
$935,000
3 Beds ⋅ 3 Baths ⋅ 24135551 MLS
Nestled on 2.99 private park-like acres in desirable Weston, this Timberpeg 1988 Post & Beam home is framed by exquisite mature specimen plantings. Timberpeg located in Claremont, New Hampshire, is considered the Artisan of Post and Beam design. This home blends rustic elegance w modern comfort. Solid beautiful wide plank floors w "ships" nails made specifically for this home. Great open floor plan, this home features exposed beams throughout and beautiful windows w fabulous natural light streaming into the home. Lge kitchen w exceptional counter space & breakfast bar, is adjacent to the open dining area. French Doors lead to the large wood deck, wonderful for grilling/dining/or relaxation. Primary suite on second level has walk-in closet, spa bath and storage. 2 more spacious bedrooms on the second level also have great closets. Two loft spaces above primary suite on 3rd floor are ideal for a private office/study or creative studio. This home has been beautifully maintained showcasing true pride of ownership. Move right in! More features:The flat usable backyard is a rare find in Weston inviting plenty of room for entertaining or playtime. Full House generator! Whether you're seeking a serene weekend escape or a full-time country retreat, this exceptional home offers the perfect balance of privacy, warmth and timeless New England.

23 Wilson Rd, Weston

29 Old Farm Rd, Weston
$903,000
3 Beds ⋅ 2 Baths ⋅ 24180148 MLS
B & F DUE MON. 4PM.If homeowners were graded on how they care for their homes, the owners of 29 Old Farm Rd would earn an A+. Thoughtfully updated and maintained, this inviting home offers the perfect balance of beauty, function, and worry-free living. Set on a landscaped, park-like property in a cul-de-sac neighborhood, the home enjoys an idyllic setting for walks & everyday enjoyment. Despite its peaceful surroundings, the location offers convenience to shops, restaurants, and trains, including Wire Mill Barbecue just a short stroll away. Upon entering, you are welcomed by an open, bright floor plan with hardwood floors, newer windows, oversized bay window, & dual sliders that enhance indoor-outdoor flow. The renovated kitchen serves as the heart of the home with white cabinetry, stainless steel appliances, island, & quartz countertops. The living room features a wood-burning fireplace and opens to a sunlit dining room with access to a stone patio with masonry walls and a garden with four raised beds. The upper level offers a primary suite with renovated bath, vaulted ceilings, steam shower, quartz vanity, and skylights. 2 additional bedrooms share a hall bath with double vanity and tub/shower. The lower level provides a home office/den & access to a pristine two-car garage with interlocking floor system. Major systems have been updated, including newer roof. Exceptional care, comfort, & effortless living in the sought-after town of Weston, known for its award-winning schoo

29 Old Farm Rd, Weston

8 Oak Ln, Weston
$868,000
4 Beds ⋅ 4 Baths ⋅ 24089673 MLS
80 K Price Reduction! Amazing Value! Oak Lane is a welcoming, tranquil retreat on a quiet cul de sac in the bucolic town of Weston. Set back, this home offers a private setting with lush, level lawns, lovely gardens/landscaping, a circular driveway, & alluring topography. This home combines the best features of colonial & contemporary elements with high, vaulted ceilings, skylights, open layout, wood beams, & wide oak-pegged hard wood floors. Truly a beautiful marriage of old & new! The 1st floor has a large, light-filled great room complete with a dramatic fireplace, & sliders to the huge deck. The white, spacious kitchen has an island, granite countertops & a wonderful eating area with sliders to the deck. The dining room is a great place to entertain & is adjacent to a sunny porch as well as the large, living room with a sizable storage closet. A 1st floor office & pristine powder room complete this level. The 2nd floor has an oversized ensuite primary bedroom with vaulted ceilings, skylights, & its own charming balcony overlooking the gorgeous grounds. It has generous closet space & a stylish, large bathroom with jacuzzi, double sinks & a separate shower. There are 3 additional spacious bedrooms all with ample closet space; one with its own private balcony. The full bathrm has a tub/shower combination & is immaculate. A fully finished lower level (with half bath & laundry) has built in custom cabinetry, terra cotta floors & is a great exercise, play or rec rm

8 Oak Ln, Weston

2 & 4 Old Weston Old Weston Rd, Weston
$800,000
5 Beds ⋅ 4 Baths ⋅ 24154425 MLS
Rare opportunity to own a historic 2-acre compound featuring a circa 1770 home (1223 SF), charming 1930s cottage (1048 SF), classic barn, and a rare surviving corn crib. An exceptional property rich in New England history & character! Step into the heart of the 1770 home where centuries-old craftsmanship is on full display. Massive hand-hewn beams stretch across the ceiling, beautifully preserved wide-plank floors run underfoot, and impressive open-hearth fireplaces with original woodwork & built-in cupboards anchor the rooms, reflecting the practical elegance of early American homes where a hearth served as the center of daily life. Natural light filters through multi-pane windows, highlighting the warm patina of aged timber w/ remarkable period details including beams, historic wood doors, traditional hardware. Complementing the main residence is a quintessential 1930s cottage filled with warmth & personality, featuring a vaulted 2 story ceiling living room w/ wood-burning fireplace, a loft offering extra living space, two bedrooms, 2 full baths, country kitchen w/vaulted ceiling , a bright sun-filled sitting rm w/skylight & walls of windows. Currently rented, but ideal as a guest house or studio. Surrounded by classic stone walls, oversized stone slab steps & walkways, plus a traditional barn and rare corn crib, this extraordinary property offers a truly one-of-a-kind New England opportunity. Room counts include cottage. Property runs on both sides of Old Weston Rd

2 & 4 Old Weston Old Weston Rd, Weston

49 Blue Spruce Cir, Weston
$770,000
4 Beds ⋅ 4 Baths ⋅ 24115297 MLS
Welcome to 49 Blue Spruce Circle, a sun-drenched contemporary colonial nestled on two picturesque acres of mature trees and vibrant flowering plants. Boasting 3,297 square feet of versatile living space, this 4-bedroom, 3.1-bath home features a unique, airy layout designed to maximize natural light at every turn. The heart of the home centers around an inviting, open floor plan that flows effortlessly to the expansive back deck-perfect for indoor-outdoor entertaining or enjoying peaceful woodland views. Relax on the sweet front porch, or retreat to the upper level, where you will find the private primary suite complete with a full bath and walk-in closet. Directly adjacent to the primary is a fantastic, light-filled studio loft, offering a creative sanctuary for an art studio, home office, or additional recreation space. Additional features include a fully finished 1,430sf walk-out basement providing endless possibilities for recreation, along with convenient interior access to the 2-car garage. While being Sold AS-IS, this exceptional 2 acre property with a fully fenced backyard represents an incredible opportunity to bring your personal touch and updates to a truly special Weston retreat.

49 Blue Spruce Cir, Weston

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!