140 Sleepy Hill Road
Southbury, Connecticut 06488
Reduced from $665,000
- Beds
- 4
- Baths
- 3
- SqFt
- 2,116
- Acres
- 2.50
- Year Built
- 1984
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
33
35 under contract
Median List Price
$645,000
33 active listings
Median Closed Price
$632,500
164 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
Homes with a close match in area, property type, and price.
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.