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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

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

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

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

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

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

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

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

5 Stonehenge Rd, Weston
$760,000
5 Beds ⋅ 4 Baths ⋅ 24156384 MLS
Nestled in the heart of lower Weston, this sprawling five-bedroom Cape presents a rare opportunity to curate a bespoke estate tailored to your personal vision. The residence is anchored by a sun-drenched, eat-in kitchen and a formal dining room, where a magnificent picture window frames serene views of the expansive backyard and surrounding woods. Character abounds in the primary family room-complete with a classic fireplace, custom built-in bookcases, and a second picture window overlooking the scenic surroundings-while a dedicated study and a main-level bedroom with a full bath offer effortless living. For those seeking a versatile footprint, a secondary wing with its own private entrance provides the perfect setting for a sophisticated home office or a secluded in-law sanctuary. The upper level serves as a quiet retreat, featuring a primary suite complete with a full bath and walk-in closet, along with three additional well-appointed bedrooms. Beyond the interior, the grounds evoke the charm of a storied Fairfield County landscape; once a premier horse property, the acreage is defined by gentle meadows, historic Connecticut stone walls, and private woodland, complemented by a classic three-stall barn. This is more than a home; it is an invitation to transfigure a premier piece of Weston's countryside into an unparalleled modern masterpiece.

5 Stonehenge Rd, Weston

18 Cartbridge Rd, Weston
$757,000
3 Beds ⋅ 2 Baths ⋅ 24175778 MLS
Welcome to 18 Cartbridge Road! This beautifully stylish expanded Cape is flooded with natural light, it's warm & inviting throughout with over sized rooms. This home is located in lower Weston situated on an acre with beautiful gardens. The formal living room has a fireplace, hardwood floors, & it leads to a playroom/office. Just off of the living room is the formal dining room. The large family room has sliders which lead out to the deck & private flat yard. Just off of the kitchen is the breakfast nook with cathedral ceiling & lots of windows to accentuate the natural light. Additionally on the first floor is a bedroom & full bath. The upstairs has two bedrooms & an additional full bath. There are hardwood floors throughout this home. Outside a stone patio and play space. A Quintessential New England Cape! Property is being sold in "As-Is" Condition.

18 Cartbridge Rd, Weston

4 Colony Rd, Weston
$750,000
2 Beds ⋅ 2 Baths ⋅ 24133742 MLS
Step into comfort and style at 4 Colony Road in Weston, CT. This charming home located on coveted private cul de sac, boasts 1,689 square feet of living space that's perfect for relaxed day-to-day living or entertaining friends. Walk into a bright and airy living room that flows into a cozy dining area, great for hosting or just enjoying a meal. The kitchen is ready for your culinary adventures, offering a functional and stylish space to whip up your favorite dishes. With two spacious bedrooms, each with its own bathroom, you'll find a private and peaceful escape to unwind. Natural light fills every corner of this home, creating an inviting and warm atmosphere. It's the perfect spot to enjoy the tranquility of Weston while living in comfort and style.

4 Colony Rd, Weston

4 Scatacook Trl, Weston
$742,000
4 Beds ⋅ 2 Baths ⋅ 24180183 MLS
Located on a quiet cul-de-sac in convenient South Weston, this cherished one-owner home presents a wonderful opportunity to renovate, update, and create a home tailored to your vision. Offering 4 bedrooms and generous living spaces, the home is being sold as-is and provides the perfect canvas for buyers seeking value in a desirable location. The spacious eat-in kitchen features newer appliances and opens to comfortable living areas designed for everyday living and entertaining. A large dining room with sliders leads directly to the backyard, creating a seamless indoor-outdoor flow. The expansive living room offers abundant space for gathering with family and friends. A highlight of the home is the versatile bonus room above the garage, featuring vaulted ceilings and a wood-burning stove, making it ideal as a family room, home office, recreation room, or creative studio. Newer windows throughout much of the home provide added efficiency and natural light. Set on a level property, the outdoor space includes a walk-out patio and a separate barn with electricity for projects, tools, equipment, and seasonal storage. Main roof replaced in 2015 & garage roof replaced in 2022.Enjoy the privacy and tranquility of cul-de-sac living while benefiting from South Weston's convenient location near schools, shopping, commuting routes, and area amenities. With solid bones, flexible space, and endless potential, this is a rare opportunity to personalize a well-loved home and make it your own!

4 Scatacook Trl, Weston

42 Cannondale Rd, Weston
$700,000
3 Beds ⋅ 2 Baths ⋅ 24167250 MLS
Step into the dramatic charm of this 3 bedroom, 1 1/2 bath ranch, an architectural jewel nestled in lower Weston. The moment you cross the threshold, you are enveloped by an atmosphere of warmth & character. The expansive great room is defined by its stunning, soaring cathedral ceiling & a wall of floor-to-ceiling windows that perfectly frame the peaceful, captivating views of the stone patio & lush yard-a beautiful canvas of nature . An open-concept design unites the great room, dining space, & kitchen into a seamless flow of light & air. The kitchen, featuring granite countertops & clean, timeless lines, is a generous workspace where function meets utility. A truly versatile sun-drenched breakfast room offers a tranquil reprieve, ready to transform into an office or vibrant playroom as needed. Designed for easy, comfortable living, all bedrooms are on the main level, connected by rich hardwood flooring that flows throughout most of the home. Additional highlights include a detached barn (currently a two-car garage), which boasts a heated, finished second-level loft-a dedicated sanctuary ideal for a private gym, art studio, or home office. This property commands an unbeatable location in a friendly community, placing you mere minutes from schools, vibrant shopping & dining, with rapid access to the Metro-North train, RTE 7, & the Merritt PKWY, solidifying its status as the perfect equilibrium of private retreat and commuter convenience.

42 Cannondale Rd, Weston

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