18 Briar Oak Drive
Weston, Connecticut 06883
- Beds
- 5
- Baths
- 4
- SqFt
- 2,444
- Acres
- 2.25
- Year Built
- 1961
- 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
Nestled on 2.25 breathtaking hilltop acres, this is one of Lower Weston's beautiful building sites. Set in a picturesque, level meadow w/ mature trees, the property offers exceptional privacy on a coveted cul-de-sac just south of Weston Center, near the Historical Society, & minutes from the Merritt Parkway. Whether you choose to renovate the existing home or create the custom estate you've always envisioned, the possibilities are endless. The existing residence offers 5 beds, 4 baths, & timeless features including original oak hardwood floors. The spacious layout includes a living room w/ fireplace, formal dining room, kitchen, and a family room with a second fireplace and radiant heated floors. The primary suite features a private entrance & deck, while a second-floor laundry room adds everyday convenience. A versatile 5th bedroom on the main level includes a kitchenette & full bath, making it ideal as a guest suite, in-law apartment, home office, or pool changing room. Additional highlights include a welcoming front foyer with heated slate flooring, a full dry basement with laundry sink, two separate attics, & a heated 21/2-car garage complete with sink, work area, radiant heat, & generator hookup. Outside, a secluded 20' x 40' in-ground pool enjoys a sunny, private setting & offers the opportunity to be restored to its former glory. An extraordinary opportunity to own one of Lower Weston's premier properties & create your dream home in an idyllic setting. Sold As-Is
Key Facts
- City/Town
- Weston
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Split Level
- Year Built
- 1961
- Days on Market
- 18 days
- Beds
- 5
- Baths
- 4 full
- Living Area
- 2,444 sq ft
- Lot Size
- 2.25 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $12,435 / Annually
Market Snapshot
The Weston Market
Single Family · trailing 12 months
Active Listings
29
28 under contract
Median List Price
$1.40M
29 active listings
Median Closed Price
$1.38M
129 sales
Median Days on Market
48
29 active listings
Median $ / Sq Ft
$381
29 active listings
Sale-to-List Ratio
100.1%
129 sales
How this home compares
List Price
$899,000
vs $1.40M median
35.8% below median
Price / Sq Ft
$368
vs $381 median
In line with median
Days on Market
18 days
vs 48 days median
30 days fresher than median
Based on 29 active and 129 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of July 28, 2026.
Location
18 Briar Oak Drive, Weston, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,584
- Property Taxes$1,036
- Insurance$300
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Weston
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial,Split Level
- Year Built
- 1961
- New Construction
- No/Resale
- Living Area
- 2,444 sq ft
- Below Grade
- 376 sq ft
Schools
- Elementary
- Hurlbutt
- Middle
- Weston
- High
- Weston
Interior
- Heating
- BaseboardHot WaterRadiant
- Heat Fuel
- Oil
- Cooling
- Wall UnitWhole House FanWindow Unit
- Fireplaces
- 2
- Laundry
- Upper Level
- Appliances
- Electric CooktopOven/RangeDishwasherWasherElectric Dryer
- Basement
- FullHeatedSump PumpStorageInterior AccessPartially FinishedFull With Walk-Out
- In-Law Apartment
- PossibleSecond Floor
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 2.25 acres
- Zoning
- R
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivatePavedAsphalt
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- In Ground Pool
- Construction
- ShingleCedar
- Roof
- Asphalt Shingle
- Foundation
- BlockConcrete
- Exterior Features
- SidewalkTerracePorchDeckLightingStone WallPatio
- Lot Description
- Level LotOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $12,435 / Annually
- Days on Market
- 18
- MLS #
- 24186968
- MLS Status
- Under Contract - Continue to Show
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.