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8 Applewood Drive

Cheshire, Connecticut 06410

COMING SOON - NEW$735,000
Beds
4
Baths
2 | 1
SqFt
2,900
Acres
0.94
Year Built
1963
Matt Caiola

Matt Caiola

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2-Car Garage2 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,970

per 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.

Listed By

Laureen Kennedy

(203) 671-1817

Coldwell Banker Realty

(203) 272-1633

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.