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55 Sleepy Hill Road

Southbury, CT 06488
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Bed 5

Bed

Bath 4

Bath

SqFt3,415

Sqft

Acres4.37

Acres(Lot)

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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Detail Ic Property Details

Property Type : Residential

Price : $749,000

AD Id : 85014887

MLS Id : 24184424

Beds : 5

Lot Size : 4.37 Acres

Living Area Size : 3,415

Year Built : 1984

Garage : 2

County : New Haven

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Feature Features

  • Bedroom Information

    Total beds: 5

    Bathroom Information

    Total Baths: 4 Full Baths: 3 Half Baths: 1

    Room Information

    Rooms Total: 10 Has Basement: Yes Basement: Full, Partially Finished
  • Roofing Information

    Asphalt
  • Interior Features

    In-Law Floorplan Roof: Asphalt Appliances: Dishwasher, Dryer, Freezer, Microwave, Range, Oven, Refrigerator, Washer
  • Heating & Cooling

    Has Heating: Yes Heating: Oil, Forced Air Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 1984 Building Area Total: 3415 Construction Materials: Frame, Clapboard Private Pool: No

  • Lot Information

    Lot Size Acres: 4.37 Lot Description: Cleared, Rolling Slope

  • Listing Price Information

    Listing Price: $749000

  • Tax Information

    Parcel Number: 1330841 Annual Tax: $11143

  • Garage Information

    Has Garage: Yes Garage Space: 2

  • School Information

    Elementary School: Per Board of Ed
    Junior High School:
    Senior High School: Per Board of Ed
  • Location Information

    Direction: Bullet Hill and take a right on Sleepy Hill. House is up on the left. Long, private driveway. WaterSource: Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
105 Quaker Farms Road, Southbury, CT, 06488 $595,000 4 2 1,981 1,981 SqFt
148 Homestead Road, Southbury, CT, 06488 $639,900 4 3 2,477 2,477 SqFt
163 W View Road, Southbury, CT, 06488 $675,000 3 3 2,160 2,160 SqFt
934 Jeremy Swamp Road, Southbury, CT, 06488 $549,000 3 2 1,296 1,296 SqFt
201 Skyview Drive, Southbury, CT, 06488 $649,000 3 3 1,958 1,958 SqFt
846 Southford Road, Southbury, CT, 06488 $775,000 3 3 2,257 2,257 SqFt
40 Oleson Drive, Southbury, CT, 06488 $549,000 5 2 1,500 1,500 SqFt
1489 Georges Hill Road, Southbury, CT, 06488 $450,000 4 2 1,408 1,408 SqFt
1049 Kettletown Road, Southbury, CT, 06488 $585,000 3 2 1,209 1,209 SqFt
472 Community House Road, Southbury, CT, 06488 $399,900 3 2 1,426 1,426 SqFt

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 06/17/2026 @ 18:32

MLS: 24184424 LISTED BY: Phoebe Finch, William Pitt Sotheby's Int'l SOURCE: SmartMLS

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