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201 Route 37 South

Sherman, Connecticut 06784

ACTIVE$1,495,000

Reduced from $1,599,500

Beds
6
Baths
5 | 1
SqFt
4,258
Acres
1.42
Year Built
1862
Matt Caiola

Matt Caiola

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WaterfrontPool2 FireplacesPrice Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$8,847

per 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

Similar Properties

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

Listed By

Cory Neumann

(203) 947-5803

Houlihan Lawrence

(203) 746-6565

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.