55 Sleepy Hill Road, Southbury, Connecticut

$745,000

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5

Beds

3/1

Baths

3,415

Square feet

4.37

Acres

About 55 Sleepy Hill Road

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.

Features of 55 Sleepy Hill Road

MLS® # 24184424
Price $745,000
Bedrooms 5
Bathrooms 3/1
Full Baths 3
Half Baths 1
Square Footage 3,415
Acres 4.37
Type Single Family For Sale
Style Colonial
Status Closed

Community Information

Address 55 Sleepy Hill Road
Area N/A
City Southbury
County New Haven
State Connecticut
Zip Code 06488

Amenities

Parking Under House Garage
Garage Spaces 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Oven/Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer
Heating Hot Air, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 2

Exterior

Exterior Clapboard
Lot Description Lightly Wooded, Cleared, Professionally Landscaped, Rolling, Open Lot
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed June 17th, 2026
Days on Market 2
Zoning R-60
RE / Bank Owned No

Listing Details

OfficeWilliam Pitt Sotheby's Int'l

Listing Map

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