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394 Jerusalem Road

Windham, Connecticut 06280

ACTIVE$399,900
Beds
5
Baths
3 | 1
SqFt
2,836
Acres
1.50
Year Built
1765
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage

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

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

Property + 5 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,712

per 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

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

Listed By

Amy Rio

(860) 916-6048

Better Homes and Gardens Real Estate Executive Real Estate

(860) 633-8800

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.