394 Jerusalem Road
Windham, Connecticut 06280
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 2,836
- Acres
- 1.50
- Year Built
- 1765
- 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
Timeless New England charm meets modern-day opportunity in this impressive 5-bedroom, 3.5-bath antique Colonial, where historic character and spacious living come together on a picturesque setting. Rich in original details, this one-of-a-kind home showcases wide-plank hardwood floors, stunning decorative fireplaces with ornate mantels, oversized windows, and classic architectural craftsmanship throughout. The spacious country kitchen offers ample room for gathering and opens to multiple living and entertaining spaces, including a formal dining room, inviting family room, and generously sized bedrooms filled with natural light. A flexible floor plan provides endless possibilities for today's lifestyle, whether you're looking for space for a home office, guest quarters, or multi-generational living. Outside, the property continues to impress with a welcoming covered front porch, expansive yard, and an oversized detached 2-car garage/barn offering exceptional storage, workshop space, or hobby potential. Surrounded by mature trees and timeless New England scenery, this remarkable property delivers the perfect balance of privacy, history, and functionality. Whether you're drawn to the craftsmanship of a bygone era or looking for a home with room to grow, this exceptional antique Colonial is ready for its next chapter. Schedule your private showing today and experience the character and possibilities this unique property has to offer.
Key Facts
- City/Town
- Windham
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Antique
- Year Built
- 1765
- Days on Market
- 11 days
- Beds
- 5
- Baths
- 3 full · 1 half
- Living Area
- 2,836 sq ft
- Lot Size
- 1.50 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $6,477 / Annually
Market Snapshot
The Windham Market
Single Family · trailing 12 months
Active Listings
13
40 under contract
Median List Price
$299,900
13 active listings
Median Closed Price
$271,000
166 sales
Median Days on Market
19
13 active listings
Median $ / Sq Ft
$203
13 active listings
Sale-to-List Ratio
100.7%
166 sales
How this home compares
List Price
$399,900
vs $299,900 median
33.3% above median
Price / Sq Ft
$141
vs $203 median
30.5% below median
Days on Market
11 days
vs 19 days median
8 days fresher than median
Based on 13 active and 166 closed sales (trailing 12 mo) of single family in Windham. Source: SmartMLS · As of July 28, 2026.
Location
394 Jerusalem Road, Windham, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,039
- Property Taxes$540
- Insurance$133
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Windham
- Neighborhood
- N/A
- County
- Windham
Residence
- Property Type
- Single Family
- Style
- Colonial,Antique
- Year Built
- 1765
- New Construction
- No/Resale
- Living Area
- 2,836 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Windham
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Window Unit
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinished
Exterior & Lot
- Lot Size
- 1.50 acres
- Zoning
- R1
- Garage / Parking
- 2 garage spacesDetached GarageBarn
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Wood
- Roof
- Asphalt Shingle
- Foundation
- Stone
- Lot Description
- Corner LotLevel Lot
Listing & Financials
- Property Taxes
- $6,477 / Annually
- Days on Market
- 11
- MLS #
- 24192242
- MLS Status
- Active
Similar Properties
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Listed By
Amy Rio
Better Homes and Gardens Real Estate Executive Real Estate
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.