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29 Route 37 East

Sherman, Connecticut 06784

ACTIVE$1,999,950

Reduced from $2,490,000

Beds
10
Baths
7 | 1
SqFt
5,856
Acres
5.51
Year Built
1887
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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4 FireplacesPrice Reduced

About This Home

Exceptional Renovated 7 Bedroom Farmhouse with 3 Bedroom In-Law Apartment. Expansive Living & Unforgettable Views Bordering the 70 Acre Naromi Land Trust. Welcome to this Stunning, Fully Renovated Farmhouse with In-law Apartment, where Timeless Character meets Modern Comfort on a Grand Scale. Offering 10 spacious Bedrooms and 8 Beautifully Updated Bathrooms, this One-of-a-Kind Property is Perfectly Suited for Extended Living, Guest Accommodations, or Income Potential as a Bed & Breakfast. At the Heart of the Home is a Massive, Light-Filled Kitchen and Eat-in Area, thoughtfully Redesigned with New Cabinetry and Premium Bosch Appliances, Creating the Perfect Space for Entertaining and Everyday Living. A Generous Walk-in Pantry provides Exceptional Storage and Functionality. The Home Features Multiple Inviting Living Spaces, including a Warm and Welcoming Family Room and a separate Living Room, Ideal for both Relaxation and Hosting. Multiple Entrances throughout the Property offer Flexibility, Privacy, and Ease of Access. Extensive Upgrades ensure Peace of Mind and Modern Efficiency: 3 Laundry Areas, New Windows, Interior Doors, and Flooring throughout. Contemporary Light Fixtures. Central Heating and Cooling for Year-Round Comfort. Newer Oil Tanks. Massive Basement with Upgraded Foundation, Offering Incredible Storage or Future Expansion Potential. Brand New Septic!

Key Facts

City/Town
Sherman
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1887
Days on Market
144 days
Beds
10
Baths
7 full · 1 half
Living Area
5,856 sq ft
Lot Size
5.51 acres
Property Taxes
$7,280 / Annually

Market Snapshot

The Sherman Market

Single Family · trailing 12 months

Median Days on Market

107

27 active listings

Median $ / Sq Ft

$341

27 active listings

Sale-to-List Ratio

96.9%

47 sales

How this home compares

List Price

$2.00M

vs $999,000 median

2.0× the median

Price / Sq Ft

$342

vs $341 median

In line with median

Days on Market

144 days

vs 107 days median

37 days longer than median

Based on 27 active and 47 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of September 25, 2026.

Location

29 Route 37 East, Sherman, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,951

per month

  • Principal & Interest$10,677
  • Property Taxes$607
  • Insurance$667
  • 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
Colonial
Year Built
1887
New Construction
No/Resale
Living Area
5,856 sq ft

Schools

Elementary
Sherman
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
4
Laundry
Main LevelUpper Level
Laundry Location
3 - Main LevelUpper Level & In-law
Appliances
Gas CooktopWall OvenConvection OvenMicrowaveRefrigeratorDishwasherWasherDryerWine Chiller
Basement
FullUnfinished
In-Law Apartment
YesFirst FloorSeparate Entry

Exterior & Lot

Lot Size
5.51 acres
Zoning
Res
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Wood
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Farm LandDryLevel LotClearedOpen Lot

Listing & Financials

Property Taxes
$7,280 / Annually
Days on Market
144
MLS #
24172461
MLS Status
Active

Similar Properties

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

Listed By

Joseph Perun

Perun Properties

(203) 313-5197

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/25/2026. 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 9/25/2026 at 8:35 PM UTC.