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158 Route 39 Road South

Sherman, Connecticut 06784

ACTIVE - NEW$599,900
Beds
3
Baths
3
SqFt
2,724
Acres
1.84
Year Built
1990
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Exceptional Opportunity in Southern Sherman! Tucked away on a scenic 1.84-acre parcel, this spacious 2,700 square foot custom-built home offers incredible upside for end users, builders, and investors alike. Bring your vision to life-all of the major items are already in place. Featuring a newer roof, top-of-the-line European Buderus boiler, hot water heater, Roth double-wall oil tank, and a premium well system with pump, pressure tank, and water treatment system. Hardwood oak floors and quality Andersen windows throughout. The interior highlights include an open concept layout with a dramatic two-story living room anchored by a fireplace, an expansive front-to-back living and dining space, and a versatile floor plan offering 3 to 4 bedrooms with flexible home office/guest suite options. A massive full walkout lower level with soaring ceilings offers tremendous potential for additional finished area. Outside, a huge deck overlooks a beautiful lot with mature trees and seasonal lake views. Just minutes to Squantz Pond, Candlewood Lake, and commuter lines. A solid, well-built home with excellent core systems-simply bring your finishing touches and make it your own.

Key Facts

City/Town
Sherman
Neighborhood
N/A
Property / Style
Single Family · Contemporary,Split Level
Year Built
1990
Days on Market
0 days
Beds
3
Baths
3 full
Living Area
2,724 sq ft
Lot Size
1.84 acres
Garage / Parking
2 garage
Property Taxes
$4,756 / Annually

Market Snapshot

The Sherman Market

Single Family · trailing 12 months

Median Days on Market

84

28 active listings

Median $ / Sq Ft

$340

28 active listings

Sale-to-List Ratio

96.5%

41 sales

How this home compares

List Price

$599,900

vs $1.01M median

40.7% below median

Price / Sq Ft

$220

vs $340 median

35.3% below median

Days on Market

0 days

vs 84 days median

84 days fresher than median

Based on 28 active and 41 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of August 28, 2026.

Location

158 Route 39 Road South, Sherman, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,680

per month

  • Principal & Interest$3,084
  • Property Taxes$396
  • Insurance$200
  • 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
Contemporary,Split Level
Year Built
1990
New Construction
No/Resale
Living Area
2,724 sq ft

Schools

Elementary
Sherman
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Laundry
Main Level
Appliances
Cook TopWall OvenRefrigeratorDishwasherWasherDryer
Basement
FullUnfinishedFull With Walk-Out

Exterior & Lot

Lot Size
1.84 acres
Zoning
res
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
WoodStucco
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Deck
Lot Description
Rolling

Listing & Financials

Property Taxes
$4,756 / Annually
Days on Market
0
MLS #
24202669
MLS Status
Active

Similar Properties

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

Listed By

Joe Chemero

(203) 770-1720

Coldwell Banker Realty

(860) 354-4111

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

The IDX display contains information sourced from SmartMLS, Inc. as of 8/28/2026. 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 8/28/2026 at 8:31 AM UTC.