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42 Straits Road

Chester, Connecticut 06412

ACTIVE - NEW$699,000
Beds
3
Baths
2 | 1
SqFt
2,882
Acres
2.71
Year Built
2003
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

Welcome home this beautifully redesigned house set on over 2.5 acres in picturesque Chester, a quintessential New England town celebrated for its art, history, music, theater and exceptional dining. Completely renovated for today's lifestyle while retaining its warmth and character, this three-bedroom, 2.5-bath home offers beautifully refinished hardwood floors, 9-foot ceilings and thoughtfully designed living spaces throughout. The main level is ideal for entertaining, featuring an inviting living room with fireplace and sliders opening to a balcony/deck overlooking the property. The stunning new kitchen features quartz countertops, new cabinetry, a center island, new appliances, wine cooler and a charming dining nook. A spacious 17' x 13 room provides wonderful flexibility as a home office, or guest room. An updated half bath completes the main level. Upstairs, the primary suite offers a beautifully remodeled luxury bath and walk-in closet. Two additional bedrooms and a remodeled full bath complete the second floor. The finished lower level adds even more living space with an 11' x 21' family room, interior and direct garage access. The auxiliary generator has you covered for New England winters. Move-in ready and beautifully updated inside and out, this special property combines privacy, space and modern comfort with the charm of one of Connecticut's most desirable small towns. The home you've been waiting for-just in time for the holidays!

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
2003
Days on Market
0 days
Beds
3
Baths
2 full · 1 half
Living Area
2,882 sq ft
Lot Size
2.71 acres
Garage / Parking
2 garage · 6 total
Property Taxes
$9,035 / Annually

Market Snapshot

The Chester Market

Single Family · trailing 12 months

Median Days on Market

30

9 active listings

Median $ / Sq Ft

$287

9 active listings

Sale-to-List Ratio

100.0%

39 sales

How this home compares

List Price

$699,000

vs $764,900 median

8.6% below median

Price / Sq Ft

$243

vs $287 median

15.3% below median

Days on Market

0 days

vs 30 days median

30 days fresher than median

Based on 9 active and 39 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of October 7, 2026.

Location

42 Straits Road, Chester, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,812

per month

  • Principal & Interest$3,826
  • Property Taxes$753
  • Insurance$233
  • HOA$0

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

Location

City/Town
Chester
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Colonial
Year Built
2003
New Construction
No/Resale
Living Area
2,882 sq ft
Below Grade
814 sq ft

Schools

Elementary
Chester
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Laundry Location
Located between 1/2 bath and kitchen
Appliances
Gas CooktopOven/RangeMicrowaveRefrigeratorDishwasherWine Chiller
Basement
FullHeatedFully FinishedGarage AccessCooledInterior AccessFull With Walk-Out
In-Law Apartment
No

Exterior & Lot

Lot Size
2.71 acres
Zoning
R-2
Garage / Parking
2 garage spaces6 total parking spacesAttached GaragePavedDrivewayPrivatePaved
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Color
Blue
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Deck
Lot Description
Lightly WoodedTreedSloping Lot

Listing & Financials

Property Taxes
$9,035 / Annually
Days on Market
0
MLS #
24212291
MLS Status
Active
Financing
FHA,VA,CHFA

Similar Properties

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Listed By

Donna Genovese

(860) 280-4334

Great Estates, CT

(203) 200-7030

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 10/7/2026. 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 10/7/2026 at 1:25 AM UTC.