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27 Forest Road

Weston, Connecticut 06883

PENDING$1,285,000
Beds
4
Baths
3 | 1
SqFt
3,772
Acres
2.00
Year Built
1952
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Highest and Best Offers due Monday 5/22 at 5PM.At the end of a cul-de-sac lies this hidden Weston gem. This light and bright 4 BR, 3 1/2 bath home is on 2 acres and has wonderful entertaining spaces. Comfortable and welcoming with privacy and convenience. Fall in love with the large sun-filled Great Room with vaulted ceilings, gas log fireplace, dry bar with wine chiller, perfect for relaxing with family and friends. The eat-in kitchen has a large island and a cozy breakfast nook perfect for family dinners. A formal dining room and living room with fireplace complete the main level. The primary bedroom features a walk-in closet and an elegant and updated bath with Calacatta marble tile, jetted tub and shower. Three additional bedrooms with ample closets and a built-in study area. Working from home is not an issue here with a large and quiet office space or fun bonus room complete with wet bar. A flexible lower level offers a variety of options with built-ins, a wall of windows and walk out access to the backyard. For those who love to entertain guests or enjoy spending time outdoors, summer fun awaits on the large deck or on the two expansive stone patios. A built-in barbeque area with a gas grill and a gas fired Fontana Forni pizza oven is an entertainer’s dream. Get ready to host many memorable occasions in this serene and tranquil setting. Minutes to Weston's award-winning schools and close enough to Westport to meet friends for shopping or dining.

Key Facts

City/Town
Weston
Property / Style
Single Family · Colonial,Split Level
Year Built
1952
Days on Market
1200 days
Beds
4
Baths
3 full · 1 half
Living Area
3,772 sq ft
Lot Size
2.00 acres
Property Taxes
Not on file from MLS

Market Snapshot

The Weston Market

Single Family · trailing 12 months

Median Days on Market

56

34 active listings

Median $ / Sq Ft

$377

34 active listings

Sale-to-List Ratio

101.7%

129 sales

How this home compares

List Price

$1.28M

vs $1.72M median

25.4% below median

Price / Sq Ft

$341

vs $377 median

9.5% below median

Days on Market

1200 days

vs 56 days median

1144 days longer than median

Based on 34 active and 129 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of August 28, 2026.

Location

27 Forest Road, Weston, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$7,027

per month

  • Principal & Interest$6,599
  • Property Taxes$0
  • Insurance$428
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Weston
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial,Split Level
Year Built
1952
Living Area
3,772 sq ft

Schools

Elementary
Hurlbutt
Middle
Weston
High
Weston

Interior

Heating
Hot AirRadiantZoned
Cooling
Ceiling FansCentral AirZoned
Fireplaces
2
Laundry
Lower Level
Interior Features
Auto Garage Door OpenerCable - AvailableCentral VacuumSecurity System
Additional Rooms
Mud Room

Exterior & Lot

Lot Size
2.00 acres
Garage / Parking
Attached Garage
Waterfront Details
Not Applicable
Construction
ClapboardHardie Board
Roof
Fiberglass Shingle
Foundation
Block
Exterior Features
Covered DeckFrench DoorsGarden AreaGrillLightingPatioPorchShed
Lot Description
On Cul-De-SacBorders Open SpaceFence - PartialProfessionally Landscaped

HOA / Association

Amenities
None

Listing & Financials

Days on Market
1200
MLS #
170567087
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Polly Sykes

(203) 216-0621

Houlihan Lawrence

Co-Listed By

Taylor Tait

Houlihan Lawrence

Buyer's Agent

Gigi Murray

William Pitt Sotheby's Int'l

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 8/28/2026 at 2:20 AM UTC.