8 Applewood Drive
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,900
- Acres
- 0.94
- Year Built
- 1963
- 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
Nestled in a quiet neighborhood on a private, flat lot bordered by a peaceful treeline, this rare oversized 1963 ranch combines mid-century build quality with meticulous, thoughtful updates. Upscale exterior stonework, a custom stone walkway, and a welcoming threshold set an elegant tone that continues throughout the entire residence. Inside, rich hardwood floors flow through gracious rooms thoughtfully laid out to separate the sleeping quarters from the main living spaces. Storage is unmatched with 17 closets, including two cedar closets in the foyer, while every room offers scenic views-including serene pond views from the living room. Designed for seamless indoor-outdoor entertaining, the family room connects through French doors to the home's true showstopper: an expansive sunroom with radiant heat floors, cathedral ceilings, and windows on three sides. Warm up by two fireplaces or gather outside on the 20x18 stone back patio. All bedrooms are generously sized, featuring walk-in closets in two of the rooms, while first-floor laundry provides authentic one-level living ease. A massive basement offers endless potential to expand your living space, with city sewer available in the street. Maintained with extraordinary care, this exceptional home presents a unique opportunity to become only its third owner. Easy highway access for commuting and 8 minutes to new Shops at Stone Bridge. Located in Highland Elementary School district which is a National Blue Ribbon Sch
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1963
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,900 sq ft
- Lot Size
- 0.94 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $9,613 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
25
40 under contract
Median List Price
$599,000
25 active listings
Median Closed Price
$570,000
257 sales
Median Days on Market
22
25 active listings
Median $ / Sq Ft
$287
25 active listings
Sale-to-List Ratio
102.3%
257 sales
How this home compares
List Price
$735,000
vs $599,000 median
22.7% above median
Price / Sq Ft
$253
vs $287 median
11.8% below median
Days on Market
0 days
vs 22 days median
22 days fresher than median
Based on 25 active and 257 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of September 25, 2026.
Location
8 Applewood Drive, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$3,924
- Property Taxes$801
- Insurance$245
- 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
- 1963
- New Construction
- No/Resale
- Living Area
- 2,900 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Cheshire
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Electric CooktopWall OvenRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinished
- Interior Features
- Auto Garage Door OpenerCable - Pre-wired
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 0.94 acres
- Zoning
- R-40
- Garage / Parking
- 2 garage spacesAttached Garage
- Water Source
- Public Water Connected
- Sewer
- Public Sewer In StreetSeptic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- GuttersLightingPatio
- Lot Description
- Lightly WoodedLevel LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $9,613 / Annually
- Days on Market
- 0
- MLS #
- 24209466
- MLS Status
- Coming Soon
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Kevin Kennedy
Coldwell Banker Realty
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/25/2026. 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 9/25/2026 at 10:05 PM UTC.