42 Straits Road
Chester, Connecticut 06412
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 2,882
- Acres
- 2.71
- Year Built
- 2003
- 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
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
Active Listings
9
5 under contract
Median List Price
$764,900
9 active listings
Median Closed Price
$550,000
39 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per 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
Homes with a close match in area, property type, and price.
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.