201 Route 37 South
Sherman, Connecticut 06784
Reduced from $1,599,500
- Beds
- 6
- Baths
- 5 | 1
- SqFt
- 4,258
- Acres
- 1.42
- Year Built
- 1862
- Neighborhood
- Timber Trails
- Property Type
- Single Family

Matt Caiola
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About This Home
Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes it equally suited for fireside evenings or lively gatherings. At its center lies the kitchen, beautifully reimagined for today while honoring its past. Soapstone countertops, custom cabinetry, and high-end appliances meet the warmth of an original fireplace and the practicality of a walk-in laundry room. Beyond the doors, your private world awaits. A heated, in-ground saltwater Gunite pool with automatic cover and outdoor shower sits tucked among lush gardens and gentle breezes, home abuts valley pond adding a hush of serenity. Extensive upgrades have been completed, from new mechanical systems to refined details throughout, ensuring comfort in every season. With central air, steam/hot air heating, and a standby generator, every modern convenience is in place. For Sale and or Lease.
Key Facts
- City/Town
- Sherman
- Neighborhood
- Timber Trails
- Property / Style
- Single Family · Colonial
- Year Built
- 1862
- Days on Market
- 104 days
- Beds
- 6
- Baths
- 5 full · 1 half
- Living Area
- 4,258 sq ft
- Lot Size
- 1.42 acres
- Property Taxes
- $8,713 / Annually
Market Snapshot
The Sherman Market
Single Family · trailing 12 months
Active Listings
28
4 under contract
Median List Price
$1.05M
28 active listings
Median Closed Price
$675,000
43 sales
Median Days on Market
63
28 active listings
Median $ / Sq Ft
$340
28 active listings
Sale-to-List Ratio
96.5%
43 sales
How this home compares
List Price
$1.50M
vs $1.05M median
42.4% above median
Price / Sq Ft
$351
vs $340 median
In line with median
Days on Market
104 days
vs 63 days median
41 days longer than median
Based on 28 active and 43 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of July 30, 2026.
Location
201 Route 37 South, Sherman, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$7,623
- Property Taxes$726
- Insurance$498
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Sherman
- Neighborhood
- Timber Trails
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1862
- New Construction
- No/Resale
- Living Area
- 4,258 sq ft
Schools
- Elementary
- Sherman
- High
- Voucher
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Gas RangeRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinished
Exterior & Lot
- Lot Size
- 1.42 acres
- Zoning
- RES
- Waterfront
- Direct waterfront
- Waterfront Details
- PondView
- Water Source
- Private Water System
- Sewer
- Septic
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- ClapboardCedar
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- BlockStone
- Exterior Features
- Porch
- Lot Description
- SecludedLevel LotWater View
Listing & Financials
- Property Taxes
- $8,713 / Annually
- Days on Market
- 104
- MLS #
- 24167831
- 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 7/30/2026. 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 7/30/2026 at 9:20 PM UTC.