27 South Pond Circle
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,880
- Acres
- 0.61
- Year Built
- 1986
- 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
HIGHEST AND BEST BY 5/12/2026 NOON. Welcome to this classic Colonial located in the highly desirable South Pond subdivision, offering sidewalks, underground utilities, and a scenic neighborhood pond with benches. This spacious vinyl-sided home features beautiful hardwood floors, a flexible floor plan, and an ideal location close to schools, shopping, major highways, and the bus line. The beautifully updated kitchen features whitewashed cabinetry, quartz countertops, and an oversized island perfect for gathering and entertaining. Main level includes laundry, formal living and dining rooms, plus a first-floor family room with wood stove that can also function as a home office. Generous sized bedrooms, remodeled baths, and a stunning primary suite with walk-in closet, double sinks, separate tub, and oversized tiled walk-in shower. Finished lower-level rec. room adds additional living space. Enjoy central air, solar panels, a tiered deck, separate patio, and open level backyard perfect for outdoor entertaining. Exceptional layout and move-in ready condition make this home a standout opportunity.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1986
- Days on Market
- 81 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,880 sq ft
- Lot Size
- 0.61 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $10,642 / Annually
- HOA Fee
- $240 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$642,000
24 active listings
Median Closed Price
$553,750
238 sales
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
$675,000
vs $642,000 median
5.1% above median
Price / Sq Ft
$234
vs $270 median
13.3% below median
Days on Market
81 days
vs 33 days median
48 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
27 South Pond Circle, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,442
- Property Taxes$887
- Insurance$225
- HOA$20
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
- Colonial
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 2,880 sq ft
- Below Grade
- 600 sq ft
Schools
- Elementary
- Norton
- High
- Cheshire
Interior
- Heating
- Hot Air
- Heat Fuel
- OilSolar
- Cooling
- Ceiling FansCentral Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorWasherDryer
- Basement
- FullPartially FinishedFull With Hatchway
- Interior Features
- Auto Garage Door Opener
Exterior & Lot
- Lot Size
- 0.61 acres
- Zoning
- R-40
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl Siding
- Color
- Light green
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesSidewalkDeckHot TubPatio
- Lot Description
- In SubdivisionLevel LotOpen Lot
HOA / Association
- Fee
- $240 / Annually
Listing & Financials
- Property Taxes
- $10,642 / Annually
- Days on Market
- 81
- MLS #
- 24171642
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Lauren Seigel-Gross
RE/MAX RISE
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.