34 Cross Road
Chaplin, Connecticut 06235
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 1,664
- Acres
- 2.01
- 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 to 34 Cross Road, a beautifully maintained home offering the perfect blend of comfort, privacy, and timeless New England appeal. Set on over 2 acres in a serene, wooded setting, this 3-bedroom, 2.5-bath residence offers an inviting layout designed for both everyday living and entertaining. The main level welcomes you with a charming front porch entry and features a spacious living room, eat-in kitchen, formal dining room, and convenient half bath. Just off the main living spaces, the screened-in porch creates a peaceful retreat for morning coffee, summer evenings, or entertaining guests while enjoying the privacy of the surrounding landscape. Upstairs, the private primary suite offers its own full bath, complemented by two additional bedrooms and a second full bath providing flexibility for family, guests or a home office. An attached two-car garage adds everyday convenience and valuable storage. Outside, the expansive 2+ acre parcel provides plenty of space to enjoy nature and the tranquility of a private, wooded setting. Thoughtfully maintained and ideally suited for those seeking space, privacy, and classic Connecticut charm, 34 Cross Road is a special opportunity to make Chaplin home. More pictures uploaded soon!
Key Facts
- City/Town
- Chaplin
- 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
- 1,664 sq ft
- Lot Size
- 2.01 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $6,580 / Annually
Market Snapshot
The Chaplin Market
Single Family · trailing 12 months
Active Listings
5
2 under contract
Median List Price
$389,000
5 active listings
Median Closed Price
$365,000
27 sales
Median Days on Market
59
5 active listings
Median $ / Sq Ft
$202
5 active listings
Sale-to-List Ratio
103.1%
27 sales
How this home compares
List Price
$425,000
vs $389,000 median
9.3% above median
Price / Sq Ft
$255
vs $202 median
26.2% above median
Days on Market
0 days
vs 59 days median
59 days fresher than median
Based on 5 active and 27 closed sales (trailing 12 mo) of single family in Chaplin. Source: SmartMLS · As of August 10, 2026.
Location
34 Cross Road, Chaplin, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$2,192
- Property Taxes$548
- Insurance$142
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chaplin
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2003
- New Construction
- No/Resale
- Living Area
- 1,664 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- BaseboardHot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullPartially Finished
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 2.01 acres
- Zoning
- RA
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-EnclosedShedPorch
- Lot Description
- Lightly Wooded
Listing & Financials
- Property Taxes
- $6,580 / Annually
- Days on Market
- 0
- MLS #
- 24198054
- MLS Status
- Coming Soon
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 8/10/2026. 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 8/10/2026 at 6:45 PM UTC.