237 Wallens Hill Road
Winchester, Connecticut 06098
Reduced from $599,000
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,628
- Acres
- 0.82
- Year Built
- 1994
- Neighborhood
- Wallen's Hill
- 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
Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal dining room, large family room, mudroom, and an impressive eat-in kitchen with quartz countertops, stainless steel appliances, built-in microwave, stainless hood system, and a large center island with seating for four. A standout feature is the dedicated entertaining room complete with a custom walnut bar, kegerator, and a 5-foot stainless steel hood system over a built-in grill and flat-top griddle. Upstairs, the primary suite offers his-and-her closets and a beautiful full bath, while two additional bedrooms share a full bath. The fourth bedroom could also be used as an office, is located in the lower level. Additional features include hardwood floors throughout most rooms, multi-zone heat, central air conditioning with separate zones for the main and upper levels, a hybrid hot water heater, and a generator transfer switch. Step outside to enjoy a 14-foot pavilion on a stamped concrete and paver patio with a built-in fire pit, and spacious open backyard. Conveniently located near the Farmington River and Peoples State Forest, with easy access to hiking, fishing, kayaking, and other outdoor recreation while remaining close to shopping, dining, and everyday conveniences.
Key Facts
- City/Town
- Winchester
- Neighborhood
- Wallen'S Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1994
- Days on Market
- 38 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,628 sq ft
- Lot Size
- 0.82 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $7,661 / Annually
Market Snapshot
The Winchester Market
Single Family · trailing 12 months
Active Listings
12
12 under contract
Median List Price
$524,900
12 active listings
Median Closed Price
$325,000
103 sales
Median Days on Market
39
12 active listings
Median $ / Sq Ft
$265
12 active listings
Sale-to-List Ratio
100.0%
103 sales
How this home compares
List Price
$579,900
vs $524,900 median
10.5% above median
Price / Sq Ft
$221
vs $265 median
16.6% below median
Days on Market
38 days
vs 39 days median
In line with median
Based on 12 active and 103 closed sales (trailing 12 mo) of single family in Winchester. Source: SmartMLS · As of July 28, 2026.
Location
237 Wallens Hill Road, Winchester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,957
- Property Taxes$638
- Insurance$193
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Winchester
- Neighborhood
- Wallen'S Hill
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1994
- New Construction
- No/Resale
- Living Area
- 2,628 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Gilbert
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Laundry
- Lower Level
- Appliances
- Gas CooktopGas RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullPartially Finished
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
Exterior & Lot
- Lot Size
- 0.82 acres
- Zoning
- RU-2
- Garage / Parking
- 2 garage spaces8 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedGuttersPatio
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $7,661 / Annually
- Days on Market
- 38
- MLS #
- 24185645
- MLS Status
- Active
Similar Properties
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Co-Listed By
Amy Sartirana
Northwest CT Realty
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 7:55 AM UTC.