393 South Rolling Acres Road
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2
- SqFt
- 2,151
- Acres
- 0.45
- Year Built
- 1956
- Property Type
- Single Family

Matt Caiola
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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
Active Listings
23
41 under contract
Median List Price
$675,000
23 active listings
Median Closed Price
$586,000
243 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per 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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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.