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Weston, CT Homes for Sale with Acreage

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  • /40

    $2,474,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 5 Baths
    • 4,013 Sq Ft

    30 Cavalry Rd, Westport, CT 06880

    *THE HOME IS NOW 4600 Sq FT( Seller has finished an additional Sq ft that was previously unfinished)** Prepare to be wowed by this stunningly reimagined 4-bedroom, 3 full and 2 half bath masterpiece, set on over 2 acres of private, picturesque grounds with plenty of room for a pool. This home is fully equipped with the latest in smart home technology. The open-concept floor plan centers around a

    Agent Photo

    Hyleri Katzenberg

    Compass Connecticut, LLC

    (475) 275-9243

    30 Cavalry Rd, Westport, CT 06880
  • /33

    $799,000

    • 5 Beds
    • 3 Baths
    • 2,788 Sq Ft

    1 Greenlea Ln, Weston, CT 06883

    This charming 5-bedroom, 3-full-bath home offers 2,788 sq. ft. of beautifully designed living space, set on a generous 2-acre corner lot. Perfect for entertaining, the home boasts a convenient location with easy access to everything Weston has to offer. Main floor, eat-in Kitchen, Dining Room, Living Room with fireplace, Three Bedrooms with hall Bath and Primary Bedroom with Bath, Laundry Room,

    Agent Photo

    Kevin O'Brien

    O'Brien Premier Properties

    (203) 632-9988

    1 Greenlea Ln, Weston, CT 06883
  • /37

    $2,100,000 Open Sun 1AM - 3PM

    • 6 Beds
    • 7 Baths
    • 6,342 Sq Ft

    3 Mayflower Ln, Weston, CT 06883

    Refreshed and gorgeous, 3 Mayflower Lane offers a perfect blend of modern sophistication and timeless charm. This beautiful home is set on over two idyllic acres, overlooking the Aspetuck Valley Country Club Golf Course. It has been meticulously maintained and upgraded, offering a fresh, contemporary feel while retaining its classic charm. Upon entering the grand foyer with double-height ceilings

    Kim Harizman Compass Connecticut, LLC

    3 Mayflower Ln, Weston, CT 06883
  • /37

    $1,450,000

    • 4 Beds
    • 2.5 Baths
    • 3,894 Sq Ft

    31 White Birch Rd, Weston, CT 06883

    Set back from the street in a desirable lower Weston location, this elegant colonial offers just under 4,000 sqft of beautifully finished living space. Classic in form with farmhouse-inspired details, the exterior showcases traditional siding, board-and-batten accents, dual front doors, and detailed window trim that lend timeless curb appeal. Inside, the home impresses with remarkable scale and

    Matthew Nuzie RE/MAX Right Choice

    31 White Birch Rd, Weston, CT 06883
  • /40

    $1,495,000

    • 5 Beds
    • 2.5 Baths
    • 3,888 Sq Ft

    4 Trails End Rd, Weston, CT 06883

    This beautifully renovated 5-bedroom Colonial in Lower Weston, Connecticut, exemplifies exceptional craftsmanship and attention to detail throughout. Set on a level, two-acre corner lot, the home offers both privacy and a tranquil setting. The modern kitchen features top-quality finishes and flows seamlessly into the family and dining rooms, overlooking a picturesque backyard. The living room,

    Bozena Tisch Coldwell Banker Realty

    4 Trails End Rd, Weston, CT 06883
  • /40

    $2,099,000

    • 5 Beds
    • 6 Baths
    • 6,684 Sq Ft

    6 Winthrop Hills, Weston, CT 06883

    Welcome to this Modern Colonial, a sanctuary where luxury, comfort & tranquility converge on a premier cul-de-sac, conveniently located to the Merritt Parkway, Weston Center & the campus of award-winning schools and downtown Westport plus beaches. With 5 BRs plus a potential 6th BR/au-pair or in-law suite, this refined retreat offers elegant living & impressive entertaining. The newly reimagined

    Alex Chingas Coldwell Banker Realty

    6 Winthrop Hills, Weston, CT 06883
  • /36

    $1,849,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 4,106 Sq Ft

    335 Georgetown Rd, Weston, CT 06883

    Discover the serenity of 335 Georgetown Road, where a grand, private approach leads you through exquisitely landscaped grounds adorned with lush foliage, natural stone, and vibrant blooms. This contemporary masterpiece is perched on 3.38 acres, featuring a professionally lit Tartan basketball court, expansive side deck and a secluded pool. The main floor primary suite has two generously sized

    Karen Hagen Compass Connecticut, LLC

    335 Georgetown Rd, Weston, CT 06883
  • /39

    $1,775,000

    • 5 Beds
    • 4.5 Baths
    • 5,645 Sq Ft

    225 Good Hill Rd, Weston, CT 06883

    This modern transitional Colonial at 225 Good Hill Road, Weston, CT 06883 offers 5 bedrooms, 4 full and 1 half baths, and an open-concept floor plan designed for natural light and seamless flow. The custom kitchen features white cabinetry, premium appliances, and a large center island opening to the sun-filled Great Room with a gas fireplace and French doors leading to two stone terraces. The

    Judy Michaelis Coldwell Banker Realty

    225 Good Hill Rd, Weston, CT 06883
  • /37

    $1,569,000

    • 5 Beds
    • 5.5 Baths
    • 3,579 Sq Ft

    145 Lyons Plain Rd, Weston, CT 06883

    Historic Elegance meets today's lifestyle in this 1845 Antique w/ 145' of scenic river frontage but not in the flood zone, in Lower Weston. A property rich in history, timeless charm & character is known as the Curtis Wood House. This beautifully restored & thoughtfully modernized home features 5BRS & 4.5 baths in the main house & a legal rental cottage (480 sf included in the SF) w/ a LR,

    Marilyn Heffers Coldwell Banker Realty

    145 Lyons Plain Rd, Weston, CT 06883
  • /14

    $1,500,000

    • 6 Beds
    • 9.5 Baths
    • 11,726 Sq Ft

    262 Lyons Plain Rd, Weston, CT 06883

    A Premier New England Property & Extraordinary Opportunity! Riversbend is a singular opportunity to own a one-of-a-kind stone and cedar shake New England Colonial located on a spectacular 1.7 acre property on the Saugatuck River. The Estate was home for 30 years to an international family who entertained many family & friends from around the world - heads of hotels & restaurants - and in great

    Rita Kirby William Pitt Sotheby's Int'l

    262 Lyons Plain Rd, Weston, CT 06883
  • /26

    $1,750,000

    • 5 Beds
    • 4 Baths
    • 4,056 Sq Ft

    31 Riverfield Dr, Weston, CT 06883

    The Ultimate Trifecta: Riverfront, Poolside, and Court with Exceptional Touches.This extraordinary estate is a masterpiece that marries nature's splendor with expert craftsmanship. A rare and private oasis, it offers a serene retreat where the river's gentle flow dictates the rhythm of life. Picture waking up to the soothing sounds of water, stepping out to witness the river's beauty unfold

    Betty Stroll William Raveis Real Estate

    31 Riverfield Dr, Weston, CT 06883
  • /34

    $965,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,529 Sq Ft

    23 Wilson Rd, Weston, CT 06883

    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

    Julia Broder Coldwell Banker Realty

    23 Wilson Rd, Weston, CT 06883
  • /40

    $1,199,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 4 Baths
    • 3,581 Sq Ft

    198 Steep Hill Rd, Weston, CT 06883

    This exceptional stone home, blending contemporary design with natural tranquility, sits on 2 private acres in Weston. Expertly engineered & beautifully constructed, the home welcomes you through a dramatic two-story foyer into a sun-filled living room with floor-to-cathedral windows, a custom two-sided fireplace, and sweeping woodland views. Open chef's kitchen features granite countertops,

    Elaine Schanzenbach William Raveis Real Estate

    198 Steep Hill Rd, Weston, CT 06883
  • /40

    $3,500,000

    • 3 Beds
    • 3 Baths
    • 8,500 Sq Ft

    4 Good Hill Rd, Weston, CT 06883

    Exquisite 1970 Renovated 3 Bedroom House with Renovated Barn and Private Art Museum in Weston, CT Nestled in the heart of Lower Weston, Connecticut, this exceptional 3.25 acre property offers a unique blend of historic charm and modern luxury. Situated on a meticulously landscaped estate, this renovated 3-bedroom house presents an unparalleled opportunity to experience gracious living alongside

    Kim Harizman Compass Connecticut, LLC

    4 Good Hill Rd, Weston, CT 06883
  • /40

    $829,000

    • 2 Beds
    • 2 Baths
    • 1,689 Sq Ft

    4 Colony Rd, Weston, CT 06883

    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,

    David Krasnoff Compass Connecticut, LLC

    4 Colony Rd, Weston, CT 06883
  • /85

    $3,795,000 Open Sat 11AM - 1PM

    • 7 Beds
    • 10 Baths
    • 11,075 Sq Ft

    214 Good Hill Rd, Weston, CT 06883

    Modern luxury meets historic charm on 5 private acres in lower Weston. Set at the end of a long, tree-lined drive, this reimagined Tudor Revival estate—once the retreat of Godspell creator John-Michael Tebelak—offers exceptional privacy and turnkey living. Renovated and expanded by architect Jack Franzen, the main home features 7 bedrooms, 8 full and 2 half baths, a dramatic two-story

    Eva Penson Sotheby's International Realty

    214 Good Hill Rd, Weston, CT 06883
  • /39

    $3,900,000

    • 6 Beds
    • 11 Baths
    • 10,634 Sq Ft

    76 Lords Hwy, Weston, CT 06883

    Prime Weston location! Set on 2.5 acres of glorious gardens and mature landscaping, this magnificent estate combines timeless sophistication with comfortable luxury. From the moment you step inside, the craftsmanship shines-rich walnut floors, exquisite millwork, and a beautiful coffered ceiling in the living room create an atmosphere of understated elegance. French doors open to two patios,

    Debi Orr Keller Williams Realty

    76 Lords Hwy, Weston, CT 06883
  • /40

    $999,999 Open Sat 10AM - 1PM

    • 5 Beds
    • 3 Baths
    • 2,220 Sq Ft

    191 Steep Hill Rd, Weston, CT 06883

    Discover a stunning blend of architectural charm and modern functionality at 191 Steep Hill Road, Weston, CT. This home features five spacious bedrooms and three bathrooms, set within a 2,220 sq ft interior. The living room impresses with 30-foot vaulted ceilings and a majestic two-story brick fireplace. French doors and a wrap-around deck enhance the indoor-outdoor flow, while additional

    David Krasnoff Compass Connecticut, LLC

    191 Steep Hill Rd, Weston, CT 06883
  • /21

    $449,000

    • Land
    • 2.04 Acres
    • $220,098 per Acre

    96 Georgetown Rd, Weston, CT 06883

    Discover the ideal site for your dream home with this exceptional 2.1-acre builder-ready lot. Set in a peaceful and private location, this property offers a unique opportunity to design a custom living space tailored to your lifestyle. Recent insights from The Wall Street Journal noted a shift in the housing market: "The premium that buyers normally pay for a brand new property have vanished. The

    Christine Poppy Compass Connecticut, LLC

    96 Georgetown Rd, Weston, CT 06883
  • /40

    $1,779,000

    • 5 Beds
    • 5.5 Baths
    • 7,611 Sq Ft

    28 Old Orchard Dr, Weston, CT 06883

    Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer.

    Barbara Bross Coldwell Banker Realty

    28 Old Orchard Dr, Weston, CT 06883
  • /11

    $2,500,000

    • Land
    • 27.55 Acres
    • $90,744 per Acre

    0 Old Easton Turnpike, Weston, CT 06883

    27+ acres of serene land along the Aspetuck River spreading between Weston and Fairfield. A rare opportunity to build your dream home and have seclusion while bordering Westport with all modern day conveniences and shopping. Close to Aspetuck Valley Country Club and golf course, The Patterson Club, Camp Aspetuck and the Connecticut Audubon Society. *All parcels sold together. *See attached

    Michael Ange Tromba Keller Williams Prestige Props

    0 Old Easton Turnpike, Weston, CT 06883
  • /6

    $1,995,000

    • Land
    • 27.55 Acres
    • $72,414 per Acre

    85-95 Old Easton Turnpike, Weston, CT 06883

    27+ acres of serene land along the Aspetuck River spreading between Weston and Fairfield. A rare opportunity to build your dream home and have seclusion while bordering Westport with all modern day conveniences and shopping. Close to Aspetuck Valley Country Club and golf course, The Patterson Club, Camp Aspetuck and the Connecticut Audubon Society. *All parcels sold together. *See attached

    Kim Tromba Keller Williams Realty

    85-95 Old Easton Turnpike, Weston, CT 06883
  • /2

    $833,300

    • 5 Beds
    • 3.5 Baths
    • 4,180 Sq Ft

    43 Valley Forge Rd, Weston, CT 06883

    NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1760, this home offers approximately 4180 square feet, five bedrooms, three full and one half bath, four fireplaces, partial basement and detached two car garage. This home sits on an approximate 261,360 sqft (6 acre) lot. This home has one accessory unit over garage/barn. "As is" cash only

    Sherry Price Realhome Services & Solutions

    43 Valley Forge Rd, Weston, CT 06883
  • /2

    $975,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,804 Sq Ft

    8 Messex Ln, Weston, CT 06883

    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

    Christine Oleynick Keller Williams Realty

    8 Messex Ln, Weston, CT 06883
  • /34

    $1,299,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3.5 Baths
    • 2,698 Sq Ft

    41 Calvin Rd, Wilton, CT 06897

    Imagine morning coffee with birdsong, and afternoons spent in your own lovely and private Backyard. If you have ever considered a move out of the city, this home offers the perfect blend of convenience, natural beauty, and sheer breathing space! Situated in coveted South Wilton, this 4 Bedroom, 3.5 Bath Classic Colonial provides both traditional New England charm and modern ambiance. The inviting

    Rob McCullough William Pitt Sotheby's Int'l

    41 Calvin Rd, Wilton, CT 06897
  • /30

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 1,664 Sq Ft

    80 Gilbert Hwy, Fairfield, CT 06824

    Through a pillared entrance sited privately from the road discover a tremendous opportunity to own a one of a kind Fairfield home with style, light & space for everyone inside & out. Reminiscent of a mid-century modern deck house, enhanced by vaulted ceilings in every main level room & newly refinished hardwood floors, you will be captivated by the open plan with abundant light throughout. Living

    Patricia Prenderville Higgins Group Real Estate

    80 Gilbert Hwy, Fairfield, CT 06824
  • /34

    $799,999

    • Land
    • 15.7 Acres
    • $50,955 per Acre

    90 Redding Rd, Easton, CT 06612

    Parklike, serene, rural, 15.7 acres of open land, mostly cleared and adjacent to the Aspetuck Country Club Golf Course. The Aspetuck River is between the property and the country club. Owner has cleared most of the acreage and built beautiful stone walls. This land is in a 100 year flood zone, and the setback from the Aspetuck River would be 200 feet. Buyer to do their due diligence. This is not

    Charlotte Cotton William Raveis Real Estate

    90 Redding Rd, Easton, CT 06612
  • /6

    $1,995,000

    • Land
    • 7 Acres
    • $285,000 per Acre

    1375 Westport Turnpike, Fairfield, CT 06824

    27+ acres of serene land along the Aspetuck River spreading between Fairfield and Weston. (7 acres in Fairfield). A rare opportunity to build your dream home and have seclusion while bordering Westport with all modern day conveniences and shopping. Close to Aspetuck Valley Country Club and golf course, The Patterson Club, Camp Aspetuck and the Connecticut Audubon Society. *All parcels sold

    Kim Tromba Keller Williams Realty

    1375 Westport Turnpike, Fairfield, CT 06824

Home Trends in Weston, CT

Housing Trends

Median Sale Price
$1,385,000
Median Single Family Sale Price
$1,399,500
Median Townhouse Sale Price
$1,414,500
Median 2 Bedroom Sale Price
$799,000
Average Price Per Sq Ft
$433
Number of Homes for Sale
23
Last 12 months Home Sales
139
Months of Supply
2.00
Median List Price
$1,385,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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