55 Sleepy Hill Road
Southbury, CT, 06488 $ 749,000
Bedrooms5 Baths3.1 Sq 3,415 Monthly Estimate*
$ 4,612
for $749,000 with 5 bedrooms and 3 full baths, 1 half bath. This 3,415 square foot home was built in 1984 on a lot size of 4.37.
Thoughtfully maintained and beautifully appointed, this elegant 5 bed, 3.5 bath Colonial offers 3,415 sqft of comfortable living space on a professionally landscaped cul-de-sac lot. Designed with both everyday living and entertaining in mind, this home features a wonderful floor plan with gracious formal and informal spaces throughout. The stunning Great Room showcases exposed beams, a wood-burning fireplace, and wet bar, while the sun-filled skylit Sunroom overlooks the expansive backyard and opens seamlessly to the kitchen. A classic Living Room and elegant Dining Room provide timeless appeal. A 1st floor In-Law with private entrance, full bath, and Kitchen offers exceptional flexibility for guests or multi-generational living. Upstairs, the impressive Primary features vaulted ceilings, a fireplace, three closets, and an Adirondack-inspired spa bath. Three add'l generously sized bedrooms, a full bath, and 2nd floor laundry complete the upper level. Additional highlights include a walk-up floored Attic, finished Playroom (not included in square footage), Workshop, and large open yard ideal for recreation and entertaining. Significant improvements include a new roof and 1,500-gallon septic system (2025), Andersen windows (2016), updated water heater and pressure tank, and twin 330-gallon oil tanks. Conveniently located close to schools, commuting routes, and everyday amenities, this is a home that combines timeless style, thoughtful updates, and exceptional functionality.
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FeaturesGeneralZoning R-60
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 4.37
Directions Bullet Hill and take a right on Sleepy Hill. House is up on the left. Long private driveway.
High School Per Board of Ed
City Southbury
Elementary School Per Board of Ed
Sq Ft Total 3415
DOM 0
Year Built 1984
Style Colonial
Year Built Source Public Records
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InteriorCooling System Central Air
Total Rooms 10
Basement Description Full Partially Finished
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ExteriorWater Source Private Well
Lot Description Lightly Wooded Cleared Professionally Landscaped Rolling Open Lot
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* Excluded FeaturesList ByPhoebe FinchListing Agent
William Pitt Sotheby's Int'lBroker
pschreiner@wpsir.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $4,612
- Monthly Property Taxes
- $929
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Southbury, CT
Average List Price $689,590
Percent of Sale Price 8%
About Southbury, CT 19,982 Population
8% Since 2002
$ 84,270 Median Income
52.98 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 6/17/2026 | $749,000 | | Listed Price |