208 Route 37 Highway South
Sherman, Connecticut 06784
- Beds
- 2
- Baths
- 1
- SqFt
- 777
- Acres
- 1.32
- Year Built
- 1920
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
36
5 under contract
Median List Price
$996,500
36 active listings
Median Closed Price
$775,000
45 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per 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
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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.