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38 Mountain Road

Cheshire, Connecticut 06410

PENDING$439,900
Beds
4
Baths
2
SqFt
1,704
Acres
0.46
Year Built
1955
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

Nicely maintained 4-bedroom, 2 full bath split-level home offering 1,488 sq. ft. of living space plus an additional 216 sq. ft. in the finished lower level with walk-out access. This home features hardwood flooring and a bright, inviting living room with a large bow window and a cozy brick-faced raised hearth fireplace with wood-burning insert. The spacious kitchen offers white cabinetry, stainless steel appliances and a convenient breakfast bar, opening to a dining room with access to a covered three-season porch-perfect for relaxing or entertaining. The upper level includes four bedrooms and two full baths, including a primary bedroom with en suite bath, along with two large hall closets providing excellent storage. The finished lower level offers flexible living space ideal for a family room, playroom, home office, or gym, with direct access to the two-car garage and laundry area. Additional highlights include a newer roof (2024) and a versatile layout that suits today's lifestyle. A wonderful opportunity to own a move-in ready home with great space inside and out! Come see the beauty of what the town of Cheshire offers with it's open space, Roaring Brook Falls, The Farmington Canal Heritage Trail, Parks & outdoor recreation. Offering several retail districts that feature a variety of shops and restaurants. Easy commuting with I-91, I-84, I-691, and Rt 15 (The Merritt Parkway) 30 minutes to New Haven and Hartford. Seller to find suitable housing.

Key Facts

City/Town
Cheshire
Neighborhood
N/A
Property / Style
Single Family · Split Level
Year Built
1955
Days on Market
124 days
Beds
4
Baths
2 full
Living Area
1,704 sq ft
Lot Size
0.46 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$6,670 / Annually

Market Snapshot

The Cheshire Market

Single Family · trailing 12 months

Median Days on Market

33

24 active listings

Median $ / Sq Ft

$270

24 active listings

Sale-to-List Ratio

101.6%

238 sales

How this home compares

List Price

$439,900

vs $642,000 median

31.5% below median

Price / Sq Ft

$258

vs $270 median

In line with median

Days on Market

124 days

vs 33 days median

91 days longer than median

Based on 24 active and 238 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of July 28, 2026.

Location

38 Mountain Road, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,946

per month

  • Principal & Interest$2,243
  • Property Taxes$556
  • Insurance$147
  • HOA$0

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

Location

City/Town
Cheshire
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Split Level
Year Built
1955
New Construction
No/Resale
Living Area
1,704 sq ft
Below Grade
216 sq ft

Schools

Elementary
Doolittle
High
Cheshire

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
In finished lower level
Appliances
Oven/RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
FullGarage AccessPartially FinishedWalk-outFull With Walk-Out
Interior Features
Auto Garage Door OpenerCable - Available

Exterior & Lot

Lot Size
0.46 acres
Zoning
R-20
Garage / Parking
2 garage spaces4 total parking spacesUnder House GaragePavedOff Street ParkingDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Color
Gray
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Porch-ScreenedPorch-EnclosedShedPorchGutters
Lot Description
Fence - PrivacyFence - FullFence - Chain LinkLevel Lot

Listing & Financials

Property Taxes
$6,670 / Annually
Days on Market
124
MLS #
24161844
MLS Status
Under Contract

Similar Properties

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

Listed By

Katie Smith

(203) 996-1712

Berkshire Hathaway NE Prop.

(203) 272-2828

Co-Listed By

Sally Bowman

Berkshire Hathaway NE Prop.

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 6:55 AM UTC.