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140 Sleepy Hill Road

Southbury, Connecticut 06488

PENDING$639,000

Reduced from $665,000

Beds
4
Baths
3
SqFt
2,116
Acres
2.50
Year Built
1984
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 FireplacePrice Reduced

About This Home

140 Sleepy Hill Road, Southbury, CT Nestled on 2.5 private acres in one of Southbury's desirable cul-de-sac neighborhoods, this beautifully maintained Colonial offers the perfect blend of privacy, comfort, and convenience. Featuring 4 bedrooms and 3 bathrooms across more than 2,100 square feet, the home is surrounded by mature landscaping and backs directly to protected Southbury Land Trust property, creating a peaceful natural setting. The main level showcases hardwood flooring, a formal living room, elegant dining room, and a spacious family room with a cozy fireplace. The updated kitchen features granite countertops and stainless steel appliances, ideal for everyday living and entertaining. A full bath on the main level adds flexibility for guests or multi-generational living. Upstairs, the remodeled primary suite offers a private retreat, accompanied by three additional bedrooms with hardwood floors and another full bath. Step outside to an oversized deck overlooking beautifully landscaped grounds and gardens, perfect for summer gatherings, morning coffee, or simply enjoying the tranquility of the surrounding nature. Conveniently located just minutes from Southbury's town center, shopping, dining, and I-84 access, this exceptional property combines the serenity of country living with easy access to everyday amenities.

Key Facts

City/Town
Southbury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1984
Days on Market
51 days
Beds
4
Baths
3 full
Living Area
2,116 sq ft
Lot Size
2.50 acres
Garage / Parking
2 garage
Property Taxes
$7,389 / Annually

Market Snapshot

The Southbury Market

Single Family · trailing 12 months

Median Days on Market

27

33 active listings

Median $ / Sq Ft

$287

33 active listings

Sale-to-List Ratio

100.0%

164 sales

How this home compares

List Price

$639,000

vs $645,000 median

In line with median

Price / Sq Ft

$302

vs $287 median

5.2% above median

Days on Market

51 days

vs 27 days median

24 days longer than median

Based on 33 active and 164 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of July 28, 2026.

Location

140 Sleepy Hill Road, Southbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,087

per month

  • Principal & Interest$3,258
  • Property Taxes$616
  • Insurance$213
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Southbury
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Colonial
Year Built
1984
New Construction
No/Resale
Living Area
2,116 sq ft

Schools

Elementary
Pomperaug
High
Pomperaug Regional High School

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Window Unit
Fireplaces
1
Laundry
Upper Level
Laundry Location
Top floor
Appliances
Electric CooktopElectric RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
Basement
FullUnfinished
In-Law Apartment
No
Interior Features
Auto Garage Door Opener

Exterior & Lot

Lot Size
2.50 acres
Zoning
R-60
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Clapboard
Color
Yellow
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedDeckGuttersLightingHot Tub
Lot Description
Professionally Landscaped

Listing & Financials

Property Taxes
$7,389 / Annually
Days on Market
51
MLS #
24181652
MLS Status
Under Contract

Similar Properties

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Listed By

Corissa Sainato

(203) 509-0638

Eagle Eye Realty PLLC

(860) 263-9102

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:15 AM UTC.