135 Wallingford Road
Cheshire, Connecticut 06410
- Beds
- 3
- Baths
- 1
- SqFt
- 1,400
- Acres
- 0.44
- Year Built
- 1920
- 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
Opportunity meets location in Cheshire! Situated on just under a half acre corner lot with its very own brook running through the property, this 1920 Colonial offers charm, character, and the opportunity to make it your own. With approximately 1,400 square feet, 3 bedrooms, and 1 full bathroom, this home is ready for its next chapter. Bring your imagination and explore the possibilities! Update the kitchen with new cabinetry, countertops, and appliances, refresh the flooring, introduce modern lighting, or simply start with fresh paint and cosmetic improvements. Whether you envision preserving its vintage charm or creating a more contemporary feel, there's plenty of potential to personalize this home over time. The traditional layout provides a starting point for your ideas, while the unfinished basement offers additional storage and utility space. Outside, the corner lot offers opportunities for gardening, landscaping, and outdoor enjoyment, with the brook adding a distinctive natural feature. Conveniently located near Cheshire Academy, shopping, restaurants, and everyday amenities. If you've been looking for a property where you can build equity through thoughtful improvements rather than paying for someone else's renovations, this could be the opportunity you've been waiting for! Bring your vision and make this Cheshire Colonial your own. Sale is subject to probate approval.
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1920
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 1 full
- Living Area
- 1,400 sq ft
- Lot Size
- 0.44 acres
- Property Taxes
- $6,513 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
23
47 under contract
Median List Price
$675,000
23 active listings
Median Closed Price
$585,000
243 sales
Median Days on Market
33
23 active listings
Median $ / Sq Ft
$297
23 active listings
Sale-to-List Ratio
103.0%
243 sales
How this home compares
List Price
$315,000
vs $675,000 median
53.3% below median
Price / Sq Ft
$225
vs $297 median
24.2% below median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 23 active and 243 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of October 29, 2026.
Location
135 Wallingford Road, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$1,731
- Property Taxes$543
- Insurance$105
- 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
- Colonial
- Year Built
- 1920
- New Construction
- No/Resale
- Living Area
- 1,400 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardHot Water
- Heat Fuel
- Oil
- Cooling
- None
- Appliances
- None
- Basement
- FullUnfinished
Exterior & Lot
- Lot Size
- 0.44 acres
- Zoning
- R-20
- Waterfront
- Direct waterfront
- Waterfront Details
- BrookWalk to WaterAccess
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- Yes
- Construction
- WoodOther
- Color
- White
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- ShedPorch
- Lot Description
- Corner LotTreed
Listing & Financials
- Property Taxes
- $6,513 / Annually
- Days on Market
- 0
- MLS #
- 24216381
- MLS Status
- Coming Soon
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 10/29/2026. 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 10/29/2026 at 1:05 AM UTC.