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65 Main Street South

Bethlehem, Connecticut 06751

COMING SOON - NEW$595,000
Beds
5
Baths
3
SqFt
2,272
Acres
0.50
Year Built
1870
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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1 Fireplace

About This Home

Historic little town of Bethlehem. An in town charmer just steps from the town green. Front row seats for the annual Christmas Town Festival and the 4th of July parade. Much admired, sunflower lined walkway in front of the house opens to the fenced yard w amazing perennials and seasonal festive decorating. This stewardship has taken this house to the next level w major improvements and upgrades. Beautiful bright and sunny new kitchen w a breakfast bar and a sitting area. A large wide hallway w leaded glass window encompass's a laundry room and leads to a first-floor primary BR. The living room and dining room have exposed beamed ceilings, brick fp and wide board flooring. Three good sized bedrooms, full bath and walk up attic on the second floor. Bonus is a one bedroom first floor in-law apartment in the back of the house, rental income, family or professional office - you choose! Back private decking overlooks a deep level yard w mature landscaping. Roof is 2 years young. This has been an ongoing project bringing this home to modern specifications w out losing the charm. Def worth a visit - enjoy year-round or a sweet weekend property. Close proximity to Litchfield, Washington and Woodbury. This rural town packs a punch with the famous Bethlehem Fair, the Garlic Festival, Hunters Pace and Long Meadow pond (kayak, fish, swim). Visit March Farms: farm store, PYO fruits and dance the night away w local bands in the fields. Numerous local organic provisions

Key Facts

City/Town
Bethlehem
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1870
Days on Market
1 day
Beds
5
Baths
3 full
Living Area
2,272 sq ft
Lot Size
0.50 acres
Garage / Parking
4 total
Property Taxes
$4,518 / Annually

Market Snapshot

The Bethlehem Market

Single Family · trailing 12 months

Median Days on Market

78

11 active listings

Median $ / Sq Ft

$279

11 active listings

Sale-to-List Ratio

98.5%

36 sales

How this home compares

List Price

$595,000

vs $699,900 median

15.0% below median

Price / Sq Ft

$262

vs $279 median

6.1% below median

Days on Market

1 day

vs 78 days median

77 days fresher than median

Based on 11 active and 36 closed sales (trailing 12 mo) of single family in Bethlehem. Source: SmartMLS · As of September 6, 2026.

Location

65 Main Street South, Bethlehem, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,650

per month

  • Principal & Interest$3,075
  • Property Taxes$377
  • Insurance$198
  • HOA$0

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

Location

City/Town
Bethlehem
Neighborhood
N/A
County
Litchfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1870
New Construction
No/Resale
Living Area
2,272 sq ft

Schools

Elementary
Bethlehem
High
Nonnewaug

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central AirDuctless
Fireplaces
1
Laundry
Main Level
Laundry Location
in large hall/ laundry room off kitchen
Appliances
Gas RangeOven/RangeRange HoodRefrigeratorDishwasherWasherDryer
Basement
Full
In-Law Apartment
YesFirst FloorSeparate Entry
Interior Features
Cable - Pre-wired

Exterior & Lot

Lot Size
0.50 acres
Zoning
R-1
Garage / Parking
4 total parking spacesPavedOff Street ParkingDrivewayPrivatePaved
Waterfront Details
Beach RightsAccess
Water Source
Private Well
Sewer
Septic
Construction
Clapboard
Color
blue
Roof
Asphalt Shingle
Foundation
Stone
Exterior Features
SidewalkShedDeckGarden AreaPatio
Lot Description
Fence - PartialLevel LotOpen Lot

Listing & Financials

Property Taxes
$4,518 / Annually
Days on Market
1
MLS #
24204738
MLS Status
Coming Soon

Similar Properties

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Listed By

Mary Ann Bennett

(203) 206-7048

Drakeley Real Estate, Inc.

(203) 263-4336

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/6/2026. 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 9/6/2026 at 8:05 AM UTC.