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Browse All Weston CT Historical Properties for Sale

46 Valley Forge Rd, Weston image
46 Valley Forge Rd, Weston $2,000,000

WOW! Gorgeous MID CENTURY MODERN nestled on over 300 feet of direct Saugatuck river frontage! Enter to sweeping views of the leafy bucolic scenes of nature through the wa...

  • 3 Beds
  • 5 Baths
  • 24200625 MLS
38 Ravenwood Dr, Weston image
38 Ravenwood Dr, Weston $679,900

Welcome to 38 Ravenwood Drive, a classic Cape Cod-style home set on a private 2-acre parcel in desirable Weston. Offering approximately 1,515 square feet of living space,...

  • 3 Beds
  • 2 Baths
  • 24205703 MLS
227 Newtown Tpke, Weston image
227 Newtown Tpke, Weston $1,595,000

Quintessential New England Colonial meets updated living at this gracious home. Set amid mature trees, stone walls and beautifully established gardens, this 4-bedroom, 3....

  • 4 Beds
  • 4 Baths
  • 24205730 MLS
261 Newtown Tpke, Weston image
261 Newtown Tpke, Weston $599,900

Welcome to an incredible opportunity in the highly desirable town of Weston! Set back from Newtown Turnpike on a secluded, level 1.33 acre lot, this exceptionally well ma...

  • 3 Beds
  • 2 Baths
  • 24205265 MLS
24 Good Hill Rd, Weston image
24 Good Hill Rd, Weston $1,100,000

Imagine a storybook Cape along a babbling brook, surrounded by overflowing hydrangeas and mature plantings... this inviting lower Weston home feels like a private English...

  • 3 Beds
  • 2 Baths
  • 24198647 MLS
274 Lyons Plain Rd, Weston image
274 Lyons Plain Rd, Weston $739,000

This is very special. $7,500 per month income! 3 Units! INVESTOR'S DREAM !! AN AMAZING OPPORTUNITY IN LOWER WESTON-DIRECT SAUGATUCK RIVER FRONT VIEWS - Beautiful ...

  • 4 Beds
  • 4 Baths
  • 24203031 MLS
181 Georgetown Rd, Weston image
181 Georgetown Rd, Weston $1,249,000 ▼

Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and tho...

  • 4 Beds
  • 4 Baths
  • 24201546 MLS
9 Autumn Ridge Rd, Weston image
9 Autumn Ridge Rd, Weston $1,415,000

An exceptional example of mid-century modern architecture, this sophisticated 4-bedroom retreat on a cul-de-sac in Weston was designed by renowned Westport architect Larr...

  • 4 Beds
  • 3 Baths
  • 24201457 MLS
62 Wells Hill Rd, Weston image
62 Wells Hill Rd, Weston $1,880,000

Mid-century modern, completely reimagined and taken down to the studs. Set on a private Lower Weston cul-de-sac near the Westport/Fairfield border, this striking 5-bedroo...

  • 5 Beds
  • 3 Baths
  • 24200916 MLS
4 Pilgrim Ln, Weston image
4 Pilgrim Ln, Weston $1,299,000

Just 1/2 mile from the Westport border on a prestigious Weston cul de sac sits this beautiful, spacious 4 bedroom family colonial. Expansive kitchen gleams with stainless...

  • 4 Beds
  • 3 Baths
  • 24200819 MLS
81 Trails End Rd, Weston image
81 Trails End Rd, Weston $1,549,900

**A Sun-Filled Weston Retreat with Exceptional Space, Style & Spectacular Grounds** Welcome to 81 Trails End Road, an impressive 12-room, 6-bedroom, 5-bath residence whe...

  • 6 Beds
  • 6 Baths
  • 24199857 MLS
15 Birch Hill Rd, Weston image
15 Birch Hill Rd, Weston $1,795,000

Discover a truly special country retreat where warmth, character & timeless New England charm come together. Tucked away at the end of a long private drive, this inviting...

  • 5 Beds
  • 5 Baths
  • 24197636 MLS
33 Birch Hill Rd, Weston image
33 Birch Hill Rd, Weston $1,000,000

Bring your creativity and vision to make this distinctive home your own. Ideally situated in lower Weston, just 1 mile from the award-winning Weston schools and minutes, ...

  • 3 Beds
  • 4 Baths
  • 24197884 MLS
48 Salem Rd, Weston image
48 Salem Rd, Weston $1,048,900

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 wi...

  • 4 Beds
  • 2 Baths
  • 24194975 MLS
267 Newtown Tpke, Weston image
267 Newtown Tpke, Weston $949,000 ▼

**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 ...

  • 3 Beds
  • 3 Baths
  • 24194502 MLS
103 Steep Hill Rd, Weston image
103 Steep Hill Rd, Weston $1,000,000

Welcome to this spacious 4-bedroom, 3-bath Colonial offering 2,700+ square feet of versatile living space in Lower Weston. Set on 2.3 private wooded acres, the home featu...

  • 4 Beds
  • 3 Baths
  • 24188955 MLS
131 Georgetown Rd, Weston image
131 Georgetown Rd, Weston $1,065,258

"A rare retreat where nature, comfort, and craftsmanship come together in perfect harmony." Enter through electronic gates,experience quiet & calm & feel as though you'v...

  • 2 Beds
  • 2 Baths
  • 24191063 MLS
49 Blue Spruce Cir, Weston image
49 Blue Spruce Cir, Weston $899,000 ▼

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 squar...

  • 4 Beds
  • 4 Baths
  • 24115297 MLS
4 Hidden Hill Rd, Weston image
4 Hidden Hill Rd, Weston $1,299,000

This artistically inspired Lower Weston retreat comes with a separate guest house, saltwater pool and beautifully cultivated grounds enhanced by numerous specimen trees a...

  • 3 Beds
  • 4 Baths
  • 24189015 MLS
78 River Rd, Weston image
78 River Rd, Weston $1,100,000

The Weston Cottage-where timeless charm, remarkable history, and tranquil riverfront living come together. Nestled along the river on the coveted Weston/Westport border, ...

  • 3 Beds
  • 3 Baths
  • 24189056 MLS
235 Newtown Tpke, Weston image
235 Newtown Tpke, Weston $1,399,900

Set on 1.57 picturesque acres this beautifully reimagined farmhouse colonial pairs timeless New England character with a comprehensive top-to-bottom renovation. From the ...

  • 4 Beds
  • 3 Baths
  • 24189016 MLS
9 Fall Ridge Rd, Weston image
9 Fall Ridge Rd, Weston $1,599,000 ▼

This architecturally distinctive mid-century modern Deck House offers a rare lifestyle retreat on two serene acres in Lower Weston. Designed to embrace its surroundings, ...

  • 6 Beds
  • 6 Baths
  • 24178099 MLS
284 Georgetown Rd, Weston image
284 Georgetown Rd, Weston $2,445,000 ▼

Completed in 2025, this extensively renovated and expanded residence lives like new construction, offering exceptional craftsmanship, luxury finishes, and a thoughtfully ...

  • 5 Beds
  • 6 Baths
  • 24182562 MLS
457 Newtown Tpke, Weston image
457 Newtown Tpke, Weston $549,000 ▼

Set in a convenient Weston location, this adorable 2 bedroom ranch offers an inviting opportunity to enjoy one of Fairfield County's most desirable communities. Filled wi...

  • 2 Beds
  • 1 Baths
  • 24181661 MLS
159 Newtown Tpke, Weston image
159 Newtown Tpke, Weston $2,195,000

This exceptional 150-year-old antique estate in Lower Weston has been thoughtfully and stylishly reimagined, seamlessly blending timeless historic character with the luxu...

  • 5 Beds
  • 6 Baths
  • 24179349 MLS
22 Pent Rd, Weston image
22 Pent Rd, Weston $2,995,000 ▼

Extraordinary riverfront modern retreat set against a breathtaking backdrop of waterfall, woodland, and sweeping water views in one of Weston's most remarkable settings. ...

  • 4 Beds
  • 6 Baths
  • 24176936 MLS
119 Kettle Creek Rd, Weston image
119 Kettle Creek Rd, Weston $1,425,000 ▼

If you're hunting for a cookie-cutter new build, a rectangular box with a floor plan you could sketch blindfolded, keep scrolling. This is a 19th-century barn, thoughtful...

  • 4 Beds
  • 4 Baths
  • 24174353 MLS
214 Good Hill Rd, Weston image
214 Good Hill Rd, Weston $3,149,000 ▼

Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Reviv...

  • 7 Beds
  • 8 Baths
  • 24168594 MLS
32 Steep Hill Rd, Weston image
32 Steep Hill Rd, Weston $2,495,000 ▼

A RARE property. The 28- year owners lovingly restored their 18th century antique and expanded it to 6,050 SF of modern comfort on its 4 acres including a 11/4 ac. pond. ...

  • 6 Beds
  • 7 Baths
  • 24160708 MLS
17 Richmond Hill Rd, Weston image
17 Richmond Hill Rd, Weston $1,300,000 ▼

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 tower...

  • 3 Beds
  • 2 Baths
  • 24147378 MLS
4 Good Hill Rd, Weston image
4 Good Hill Rd, Weston $3,500,000

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 3.2...

  • 3 Beds
  • 3 Baths
  • 24133078 MLS
15 Mountain View Dr, Weston image
15 Mountain View Dr, Weston $1,149,000 ▼

Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive ou...

  • 4 Beds
  • 4 Baths
  • 24122214 MLS

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.

Weston Historical Real Estate

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Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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Michael Parsell
Trusted Realty Partners
(203) 880-9675
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Trusted Realty Partners, LLC

324 Elm Street, Suite 105B

Monroe, CT 06468

Broker: John Fontana REB.0794755

(203) 880-9675
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