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393 South Rolling Acres Road

Cheshire, Connecticut 06410

ACTIVE - NEW$499,900
Beds
4
Baths
2
SqFt
2,151
Acres
0.45
Year Built
1956
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

About This Home

Welcome Home to Cheshire! Discover the perfect blend of comfort, space, and convenience in this inviting 4-bedroom, 2-full-bath ranch, ideally situated in a desirable Cheshire location. Designed for easy one-level living, this home offers spacious rooms and wonderful spaces to gather, relax, and entertain. The eat-in kitchen features granite countertops, stainless steel appliances, and sliders that open to a large deck, making indoor-outdoor entertaining a breeze. The living room is warm and welcoming, featuring beautiful hardwood floors and a wood-burning fireplace. The generously sized primary bedroom offers a walk-in closet and a primary full bath, while three additional well-proportioned bedrooms feature hardwood flooring. The laundry room is off the kitchen. One of the home's standout features is the spacious great room, filled with natural light from skylights and an abundance of windows, this versatile space is perfect for entertaining, relaxing, or everyday enjoyment. A door leads directly to the expansive deck overlooking a private, fenced-in backyard with plenty of room for outdoor gatherings, recreation, and summer fun. Additional highlights include a new furnace (2025), central air , city water , city sewer. This home is conveniently located close to schools, shopping plazas, and everyday amenities. With its generous living space, inviting atmosphere, and desirable location, this Cheshire ranch is a wonderful place to call home.

Key Facts

City/Town
Cheshire
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1956
Days on Market
0 days
Beds
4
Baths
2 full
Living Area
2,151 sq ft
Lot Size
0.45 acres
Property Taxes
$8,656 / Annually

Market Snapshot

The Cheshire Market

Single Family · trailing 12 months

Median Days on Market

36

23 active listings

Median $ / Sq Ft

$297

23 active listings

Sale-to-List Ratio

103.0%

243 sales

How this home compares

List Price

$499,900

vs $675,000 median

25.9% below median

Price / Sq Ft

$232

vs $297 median

21.9% below median

Days on Market

0 days

vs 36 days median

36 days fresher than median

Based on 23 active and 243 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of November 12, 2026.

Location

393 South Rolling Acres Road, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,597

per month

  • Principal & Interest$2,709
  • Property Taxes$721
  • Insurance$167
  • 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
Ranch
Year Built
1956
New Construction
No/Resale
Living Area
2,151 sq ft

Schools

Elementary
Per Board of Ed
High
Cheshire

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central AirHeat Pump
Fireplaces
1
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullFull With Hatchway
Interior Features
Cable - Available

Exterior & Lot

Lot Size
0.45 acres
Zoning
R-20
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckGutters
Lot Description
Fence - FullLightly Wooded

Listing & Financials

Property Taxes
$8,656 / Annually
Days on Market
0
MLS #
24219558
MLS Status
Active

Similar Properties

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Listed By

Cheryl Rosadino

(203) 379-7087

Berkshire Hathaway NE Prop.

(203) 272-2828

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

The IDX display contains information sourced from SmartMLS, Inc. as of 11/12/2026. 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 11/12/2026 at 10:15 PM UTC.