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208 Route 37 Highway South

Sherman, Connecticut 06784

ACTIVE - NEW$338,000
Beds
2
Baths
1
SqFt
777
Acres
1.32
Year Built
1920
Matt Caiola

Matt Caiola

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1 Fireplace

About This Home

Built in the 1920s and wrapped in cedar shingles, this 2 bed 1 bath cottage was designed to harmonize with its surroundings. It sits right beside a protected land trust parcel, so your view stays green with privacy insured. Step onto the front deck and take in the mountain views with your morning coffee. Inside, the living room is cozy and full of character with custom built-ins and a wood burning stove for cold New England nights. The large eat-in kitchen is the heart of the home with a convenient laundry closet tucked to the side. Out back, a gravel patio and tiered backyard make a great spot for gardening, gathering, or a fire pit. A cabin/shed adds flexible space for a studio, workshop, or storage. The walkout basement has room to finish into a home gym or office. Charming, private, and full of potential! Located in Sherman just steps from the New Fairfield line, this is small-town Connecticut at its best. Residents enjoy access to Candlewood Lake through the Sherman Town Beach. Minutes to charming town center w/ community amenities, library & playhouse. Sherman is known for low taxes and K-8 school. And when you need more than country life offers, major shopping and routes in both CT & NY are only a short drive away. THIS IS ONE OF 2 HOMES FOR SALE NEXT DOOR TO EACH OTHER #210 & #208

Key Facts

City/Town
Sherman
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1920
Days on Market
0 days
Beds
2
Baths
1 full
Living Area
777 sq ft
Lot Size
1.32 acres
Garage / Parking
3 total
Property Taxes
$2,841 / Annually

Market Snapshot

The Sherman Market

Single Family · trailing 12 months

Median Days on Market

73

36 active listings

Median $ / Sq Ft

$340

36 active listings

Sale-to-List Ratio

97.8%

45 sales

How this home compares

List Price

$338,000

vs $996,500 median

66.1% below median

Price / Sq Ft

$435

vs $340 median

27.9% above median

Days on Market

0 days

vs 73 days median

73 days fresher than median

Based on 36 active and 45 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of October 15, 2026.

Location

208 Route 37 Highway South, Sherman, Connecticut

Property + 9 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,222

per month

  • Principal & Interest$1,872
  • Property Taxes$237
  • Insurance$113
  • HOA$0

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

Location

City/Town
Sherman
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Ranch
Year Built
1920
New Construction
No/Resale
Living Area
777 sq ft

Schools

Elementary
Sherman
High
Per Board of Ed

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Ceiling FansWall Unit
Fireplaces
1
Laundry
Main Level
Laundry Location
In closet off kitchen
Appliances
Oven/RangeRefrigeratorFreezerDishwasherWasherDryer
Basement
Crawl SpacePartialConcrete FloorPartial With Walk-Out

Exterior & Lot

Lot Size
1.32 acres
Zoning
residential
Garage / Parking
3 total parking spacesPavedDrivewayPaved
Waterfront Details
Beach Rights
Water Source
Private Well
Sewer
Septic
Construction
Shingle
Roof
Asphalt Shingle
Foundation
BlockConcrete
Lot Description
Lightly WoodedBorders Open SpaceSloping Lot

Listing & Financials

Property Taxes
$2,841 / Annually
Days on Market
0
MLS #
24214342
MLS Status
Active

Similar Properties

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Listed By

Donna Kennedy

(917) 669-2642

Compass Connecticut, LLC

(203) 290-2477

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/15/2026. 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 10/15/2026 at 2:25 PM UTC.