
Land with Home for Sale in Southbury, Connecticut
55 Sleepy Hill Rd, Southbury, CT 06488
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.
Location
- Street address
- 55 Sleepy Hill Rd
- County
- New Haven County
- Zip code
- 06488
- Elevation
- 581 feet
Directions
Bullet Hill and take a right on Sleepy Hill. House is up on the left. Long, private driveway.
Property details
- Acreage
- 4.37 acres
- Zoning
- R-60
- MLS #
- CTMLS 24184424
- Posted
Property taxes
- 2026
- $11,143
Details and features
Listing
- Type
- Residential
- Franchise
- Sotheby's International Realty
Lot
- Features
- Cleared, Lightly Wooded, Open Lot, Professionally Landscaped, Rolling
Structure
- Style
- Colonial
- Basement
- Full, Partially Finished
- Water
- Private
- Cooling
- Central Air
Interior
- Room Count
- 10
- Rooms
- Basement, Bathroom x 4, Bedroom x 5
- Fireplaces
- Yes
- Appliances
- Dishwasher, Dryer, Freezer, Microwave, Oven/Range, Refrigerator, Washer
Listing history
| Date | Event | Price | Change | Source |
|---|---|---|---|---|
| June 20, 2026 | New listing | $749,000 | — | CTMLS |







































