Weston, CT Homes

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  $2,498,500

  • 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

  

  Hyleri Katzenberg

  Compass Connecticut, LLC

  (475) 275-9243

  30 Cavalry Rd, Westport, CT 06880
• Explore Weston

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  /20

  $2,200 per month plus fees

  • Studio
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  1Newtown Turnpike Unit Studio, Weston, CT 06883

  Property Id: 1735921A private entrance on the 2nd floor leads you to this beautifully renovated Studio. Enjoy living in peaceful serene, wooded environment. tudio is set inside a large cottage style house, featuring an open room concept with private use of a nicely remodeled kitchen. This nature inspired kitchen includes an induction cooktop, refrigerator, paired with beautiful warm teak

  1Newtown Turnpike Unit Studio, Weston, CT 06883
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  $3,350,000 Sold Oct 28, 2025

  • 9,597 Sq Ft
  • $349/SF
  • 17 Days On Market

  • 6 Beds
  • 9 Baths
  • Built 2007

  9 Banks Dr, Weston, CT 06883

  Exceptional Jack Franzen designed shingle style estate offering 9,000+ sq. ft. of refined living space on a private cul-de-sac in bucolic Weston. Nestled on 6.5+ acres abutting 33 acres of protected land, this rare property also includes a separate 3+ acre buildable lot-perfect for future expansion, a family compound, or simply to enjoy lasting privacy. The timeless layout showcases formal living

  Julie Vanderblue Higgins Group Real Estate

  9 Banks Dr, Weston, CT 06883
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  Est $2,980,480 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 7,910 Sq Ft

  10 Norfield Farm Ln, Weston, CT 06883

  10 Norfield Farm Ln, Weston, CT 06883
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  $875,000

  • 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,

  

  Kevin O'Brien

  O'Brien Premier Properties

  (203) 632-9988

  1 Greenlea Ln, Weston, CT 06883
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  /16

  $4,000 total monthly price

  • 4 Beds
  • 2 Baths
  • 960 Sq Ft
  • House for Rent

  515 Newtown Turnpike, Weston, CT 06883

  Public Remarks Attention Nature Lovers...Secluded and private 4 bedroom ranch surrounded by beautiful woods, wildlife and extensive watershed.Walk to Saugatuck Reservoir from your back yard.NEW ENGINEERED FLOOR ON SECOND FLOOR.Unique Layout makes it perfect for extended families or in home office. Updated spacious ranch style living with 2 bedrooms up and 2 downstairs. Full bath on each floor.

  Peter Sullivan Camelot Real Estate

  515 Newtown Turnpike, Weston, CT 06883
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  $2,950,000 Sold Oct 27, 2025

  • 4,347 Sq Ft
  • $679/SF
  • 56 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1952

  37 Cedar Hills, Weston, CT 06883

  Shortlisted for "Living Space - Americas" in The International Design & Architecture Awards 2025, this exceptional home with a gorgeous pool in a coveted Lower Weston location has garnered global attention. Fully reimagined by Shelley Morris, the published designer-owner, this showcase home feels like a retreat, while just 0.6 mile from Westport w/vibrant shopping, dining & amenities. Every

  Alex Chingas Coldwell Banker Realty

  37 Cedar Hills, Weston, CT 06883
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  Est $1,400,539 Not Listed For Sale

  78 Birch Hill Rd, Weston, CT 06883

  78 Birch Hill Rd, Weston, CT 06883
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  /31

  $610,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  12 Upper Parish Dr, Weston, CT 06883

  Welcome to this beautifully maintained raised ranch on 2.29 acres. The main level open-concept floor plan connects the living room, dining area, and kitchen. The main floor features three bedrooms and a full bathroom on the main floor, offering a perfect family living space. The finished lower level significantly expands the home's utility, featuring a cozy family room with a fireplace and

  

  Brittany Strouse

  Coldwell Banker Realty

  (203) 945-1095

  12 Upper Parish Dr, Weston, CT 06883
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  /20

  $3,400 per month plus fees

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Condo for Rent

  2 Newtown Turnpike Unit ., Weston, CT 06883

  Property Id: 1332235This beautiful spacious rental is inside a large house, on the 2nd floor. It's a fully private unit with private entrance and 2 large bedrooms, 2 full bathrooms, living space, full kitchen, washer/dryer, and much more. This is not the entire house, it is an apartment in part of the house. Property Manager lives on site separately. A true hidden gem in the heart of

  2 Newtown Turnpike Unit ., Weston, CT 06883
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  $780,000 Sold Oct 24, 2025

  • 1,586 Sq Ft
  • $492/SF
  • 137 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1966

  7 Hillcrest Ln, Weston, CT 06883

  Tranquil Contemporary Retreat on 2.5 Acres in Weston. Tucked away in a peaceful natural setting, this beautifully updated contemporary home offers 2-3 bedrooms and 1,580 square feet of stylish, move-in-ready living space. Set on 2.5 serene acres, the home features gleaming hardwood floors, dramatic beamed and vaulted ceilings, and walls of glass that invite the outdoors in. The spacious living

  Yulka Markevich Iron Gates Realty

  7 Hillcrest Ln, Weston, CT 06883
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  Est $654,348 Not Listed For Sale

  83 Lords Hwy, Weston, CT 06883

  83 Lords Hwy, Weston, CT 06883
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  /30

  $524,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft

  20 Georgetown Rd, Weston, CT 06883

  Beautifully updated Colonial in an excellent location, close to downtown Weston! This 3-bedroom, 2-bath Colonial features a spacious living room, large kitchen with granite countertops, and a formal dining room with a full bath and separate laundry room. The second level has two bedrooms, a shared bathroom and office area. The expansive primary bedroom is located on the 3rd level with full-sized

  Jared Randall Redfin Corporation

  20 Georgetown Rd, Weston, CT 06883
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  $8,000 total monthly price

  • 3 Beds
  • 4.5 Baths
  • 4,025 Sq Ft
  • House for Rent

  58 Wells Hill Rd, Weston, CT 06883

  Do you love modern homes but the charm of wood beams? This 3/4 bedroom rental home is for you! This architecturally significant home is a wonderful former Westport barn that is now a light-filled modern home. The first floor's two-story open living area has a living room with fireplace, dining room, and kitchen, while also offering a library and full bath. Upstairs is the master bedroom suite

  Merry Hampton William Raveis Real Estate

  58 Wells Hill Rd, Weston, CT 06883
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  $2,900,000 Sold Oct 21, 2025

  • 4,962 Sq Ft
  • $584/SF
  • 33 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2016

  229 Good Hill Rd, Weston, CT 06883

  Hilltop Luxury with Unmatched Views, Privacy, and Sophistication Perched on a private hilltop, this architecturally designed masterpiece by Paul Harris and built by JD Rogers Development, offers a rare combination of seclusion, elegance & convenience. Just minutes from top-rated schools and the town center, this extraordinary home is a sanctuary where thoughtful design meets timeless comfort.

  Vickie Kelley Camelot Real Estate

  229 Good Hill Rd, Weston, CT 06883
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  Est $1,990,283 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,515 Sq Ft

  205 Davis Hill Rd, Weston, CT 06883

  205 Davis Hill Rd, Weston, CT 06883
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  /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
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  /10

  $6,700 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 5,321 Sq Ft
  • House for Rent

  18 Thorp Dr, Weston, CT 06883

  Light filled home on a quiet cul-de-sac. this sundrenched home offers an open floor plan with soaring ceilings and a desirable first floor primary suite and a dedicated home office on the main level. Upstairs, you'll find 3 additional bedrooms and 2 full baths. The finished walkout level adds flexibility for a playroom, gym, additional workspace. This home offers privacy and convenience.

  Georgia Wasserman Coldwell Banker Realty

  18 Thorp Dr, Weston, CT 06883
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  $2,000,000 Sold Oct 20, 2025

  • 7,804 Sq Ft
  • $256/SF
  • 103 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1994

  47 Tubbs Spring Dr, Weston, CT 06883

  This modern farmhouse offers year-round comfort and effortless entertaining! Set behind powered gates at the end of a quiet cul-de-sac, the 7,760 sq ft home borders the 37 acres of trails of the Grace Robinson Nature Sanctuary - yet is just minutes to Weston's award-winning schools and village center. Inside, the home is light-filled and inviting, featuring a flexible layout and spacious rooms. A

  Cyd Hamer William Pitt Sotheby's Int'l

  47 Tubbs Spring Dr, Weston, CT 06883
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  Est $869,923 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,996 Sq Ft

  479 Newtown Turnpike, Weston, CT 06883

  479 Newtown Turnpike, Weston, CT 06883
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  $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
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  /39

  $12,500 total monthly price

  • 5 Beds
  • 8 Baths
  • 7,470 Sq Ft
  • House for Rent

  5 Winthrop Hill, Weston, CT 06883

  Move-in before school starts! This stunning 7,000+ sq. ft Georgian colonial has been recently renovated from head to toe! This elegant light-filled residence with its open floor plan boasts 5 spacious ensuite bedrooms, high ceilings, hardwood floors, and several possible office spaces. Its flow is perfect for both entertaining and family life. The chef's eat-in kitchen is a true showstopper:

  Merry Hampton William Raveis Real Estate

  5 Winthrop Hill, Weston, CT 06883
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  $1,125,000 Sold Oct 16, 2025

  • 1,859 Sq Ft
  • $605/SF
  • 10 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1841

  47 Godfrey Rd W, Weston, CT 06883

  Once The Upper Parish Schoolhouse, now the most stylish renovated antique house in town! Beautifully reimagined in 2020, the main floor lives large with high ceilings, original beams, a gorgeous stone fireplace. The 1800's features are perfectly complemented by fresh white walls, polished hardwoods, as well as modern finishes like granite countertops, marble vanities and black hardware that are

  Jeannette Floto Compass Connecticut, LLC

  47 Godfrey Rd W, Weston, CT 06883
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  Est $1,221,661 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,040 Sq Ft

  5 Blue Spruce Cir, Weston, CT 06883

  5 Blue Spruce Cir, Weston, CT 06883
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  /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
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  /37

  $13,000 total monthly price

  • 4 Beds
  • 4.5 Baths
  • 6,244 Sq Ft
  • House for Rent

  9 Grey Fox Ln, Weston, CT 06883

  Tucked away on a quiet cul-de-sac off Osborn Farm Rd, this newer custom home offers 4 bedrooms, 4 full baths, and 1 half bath in a thoughtfully designed layout. The main floor features the spacious primary suite with a walk-in closet, spa-like bath, and access to a shared balcony overlooking the backyard. A second bedroom on the main level adds flexibility for guests or multigenerational living.

  Medina Kovaci William Raveis Real Estate

  9 Grey Fox Ln, Weston, CT 06883
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  $1,150,000 Sold Oct 14, 2025

  • 2,806 Sq Ft
  • $410/SF
  • 12 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1982

  14 Shinnecock Place, Weston, CT 06883

  This extraordinary country sanctuary, perfectly sited amid breathtaking natural surroundings, provides the ultimate in privacy and tranquility. You'll feel the stress of the day melt away as soon as you arrive at this retreat that borders acres of conservation land at the end of a peaceful cul-de-sac. This unique home unfolds across three levels of sunlit living spaces that are sure to surprise

  Randy Musiker Compass Connecticut, LLC

  14 Shinnecock Place, Weston, CT 06883
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  Est $925,368 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,425 Sq Ft

  31 Blue Spruce Cir, Weston, CT 06883

  31 Blue Spruce Cir, Weston, CT 06883
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  /36

  $1,849,000 Open Thu 11AM - 2PM

  • 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 primary suite offers a private deck, with direct pool

  Karen Hagen Compass Connecticut, LLC

  335 Georgetown Rd, Weston, CT 06883
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  $1,400,000 Sold Oct 09, 2025

  • 1,792 Sq Ft
  • $781/SF
  • 720 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1925

  176 Weston Rd, Weston, CT 06883

  Amazing opportunity to be the first developer in Weston’s newly created mixed-use district! This pioneering role gives one the creative freedom to establish a unique atmosphere for the Village District, setting the stage for future development and commercial growth. With a variety of commercial options allowable on the first level and apartments on the second level, these essential services will

  Sandra Calise Cenatiempo Settlers & Traders

  176 Weston Rd, Weston, CT 06883
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  Est $1,231,364 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,158 Sq Ft

  27 Blue Spruce Cir, Weston, CT 06883

  27 Blue Spruce Cir, Weston, CT 06883
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  /28

  $1,325,000

  • 4 Beds
  • 3 Baths
  • 1,686 Sq Ft

  111 & 115 Old Easton Turnpike, Weston, CT 06883

  2 SEPARATE, ADJACENT LOTS in lower Weston, one with an interior designer's personal home, thoughtfully renovated in 2024 with luxurious, high-end finishes rarely found in a classic ranch. Step inside to discover a brand-new quartz kitchen with custom cabinetry and millwork, a spa-inspired primary bathroom with double sinks, gorgeous tile and a walk-in shower, two additional beautifully renovated

  Joan Wright Compass Connecticut, LLC

  111 & 115 Old Easton Turnpike, Weston, CT 06883
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  $1,300,000 Sold Oct 07, 2025

  • 3,720 Sq Ft
  • $349/SF
  • 37 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1978

  42 Trails End Rd, Weston, CT 06883

  Ideally set on 3.62 acres of professionally manicured grounds in Weston, CT, this stunning 4/5 bdrm 2/2 bath colonial offers a blend of timeless architecture and modern upgrades. The corner lot features a circular driveway leading to a beautifully expansive yard, an idyllic setting for outdoor gatherings or quiet moments surrounded by nature's serenity. The property boasts a spacious multilevel

  Louise Bromberger The Riverside Realty Group

  42 Trails End Rd, Weston, CT 06883
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  Est $823,322 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  81 Blue Spruce Cir, Weston, CT 06883

  81 Blue Spruce Cir, Weston, CT 06883
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  /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
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  $915,000 Sold Oct 03, 2025

  • 2,756 Sq Ft
  • $332/SF
  • 40 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1974

  5 Woodland Way, Weston, CT 06883

  Come make 5 Woodland Way your new home! This 5 Bdrm Colonial is perfectly tucked away on a serene cul-de-sac just minutes from the Fairfield/Westport border. Blending classic charm with a comfortable open floor plan, this home offers a warm & inviting space for all to spread out. The spacious multi-purpose Living Rm spans the full length of the home perfect for hosting lively gatherings or

  Lisa Gallagher William Raveis Real Estate

  5 Woodland Way, Weston, CT 06883
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  Est $1,271,678 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 4,168 Sq Ft

  440 Newtown Turnpike, Weston, CT 06883

  440 Newtown Turnpike, Weston, CT 06883
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  /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
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  $859,000 Sold Oct 02, 2025

  • 2,317 Sq Ft
  • $371/SF
  • 25 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1951

  1 Graystone Ln, Weston, CT 06883

  Located on a quiet Lower Weston cul-de-sac, this 4-bedroom, 2.5-bath home offers generous living space, stylish updates, and a seamless indoor-outdoor connection. The first-floor primary suite is a true retreat with a large walk-in closet, updated en-suite bath, and sliding doors that open directly to the backyard. The living room features a wood-burning fireplace and its own backyard access,

  Benjamin Howell Coldwell Banker Realty

  1 Graystone Ln, Weston, CT 06883
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  Est $1,442,768 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,100 Sq Ft

  5 Good Hill Rd, Weston, CT 06883

  5 Good Hill Rd, Weston, CT 06883

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