27 Forest Road
Weston, Connecticut 06883
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,772
- Acres
- 2.00
- Year Built
- 1952
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
34
17 under contract
Median List Price
$1.72M
34 active listings
Median Closed Price
$1.40M
129 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 20, 2026per 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
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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.