158 Route 39 South
Sherman, Connecticut 06784
Reduced from $599,900
- Beds
- 3
- Baths
- 3
- SqFt
- 2,724
- Acres
- 1.84
- Year Built
- 1990
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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. Owner is a licensed agent.
Key Facts
- City/Town
- Sherman
- Neighborhood
- N/A
- Property / Style
- Single Family · Contemporary,Split Level
- Year Built
- 1990
- Days on Market
- 48 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
Active Listings
34
5 under contract
Median List Price
$998,500
34 active listings
Median Closed Price
$775,000
45 sales
Median Days on Market
86
34 active listings
Median $ / Sq Ft
$335
34 active listings
Sale-to-List Ratio
97.8%
45 sales
How this home compares
List Price
$579,000
vs $998,500 median
42.0% below median
Price / Sq Ft
$213
vs $335 median
36.4% below median
Days on Market
48 days
vs 86 days median
38 days fresher than median
Based on 34 active and 45 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of October 15, 2026.
Location
158 Route 39 South, Sherman, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$3,207
- Property Taxes$396
- Insurance$193
- 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
- 48
- MLS #
- 24202669
- MLS Status
- Active
Similar Properties
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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 12:30 AM UTC.