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88 Dundee Drive

Cheshire, Connecticut 06410

ACTIVE$561,885
Beds
4
Baths
2 | 1
SqFt
1,424
Acres
0.28
Year Built
1999
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Welcome to this beautifully maintained Colonial, ideally situated in a sought-after neighborhood featuring underground utilities and sidewalks. From the inviting front porch to the private backyard, this home offers timeless charm and exceptional value. The first floor features gleaming hardwood floors throughout, a spacious living room with a cozy fireplace, and a formal dining room with two classic built-in corner hutches. A sliding glass door opens to a tranquil, tree-shaded patio overlooking a beautifully landscaped backyard with privacy fencing-perfect for relaxing or entertaining. Upstairs, you'll find four generously sized bedrooms, each equipped with ceiling fans. Additional updates include a roof that's only six years old, a brand-new hot water heater and furnace, plus the peace of mind of a whole-house Kohler generator for year-round comfort and security. A unique buying opportunity: This property is currently subject to an Affordable Housing Restrictive Covenant that is scheduled to expire in approximately three years. The current list price reflects the maximum allowed for a CHFA-financed purchase and CHFA buyers must meet applicable CHFA income guidelines. Other option is 80 per cent of State of CT median income guidelines. Cash buyers are also eligible to purhase property within certain income restrictions. See Attachment for Restrictive Covenant. Some notice required for showing.

Key Facts

City/Town
Cheshire
Neighborhood
Moss Farm
Property / Style
Single Family · Colonial
Year Built
1999
Days on Market
15 days
Beds
4
Baths
2 full · 1 half
Living Area
1,424 sq ft
Lot Size
0.28 acres
Garage / Parking
2 garage
Property Taxes
$5,835 / Annually

Market Snapshot

The Cheshire Market

Single Family · trailing 12 months

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

$561,885

vs $642,000 median

12.5% below median

Price / Sq Ft

$395

vs $270 median

46.3% above median

Days on Market

15 days

vs 33 days median

18 days fresher 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

88 Dundee Drive, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,538

per month

  • Principal & Interest$2,865
  • Property Taxes$486
  • Insurance$187
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Cheshire
Neighborhood
Moss Farm
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1999
New Construction
No/Resale
Living Area
1,424 sq ft

Schools

Elementary
Barnum Elementary
High
Cheshire

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
Basement
FullUnfinished
Interior Features
Auto Garage Door OpenerCable - Available

Exterior & Lot

Lot Size
0.28 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
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
SidewalkPorchPatio
Lot Description
In SubdivisionLightly WoodedLevel Lot

Listing & Financials

Property Taxes
$5,835 / Annually
Days on Market
15
MLS #
24189652
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Roberta Havlick

(203) 435-5256

William Raveis Real Estate

(203) 272-0001

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 5:15 AM UTC.