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.
Sold for $745,000
$745,000
55 Sleepy Hill Road, Southbury, CT 06488
5beds
3,415sqft
Single Family Residence
Built in 1984
4.37 Acres Lot
$732,100 Zestimate®
$218/sqft
$4,393 Estimated rent
Home value
$732,100
$666,000 - $805,000
$4,393/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Phoebe V. Finch (617)645-3907,
William Pitt Sotheby's Int'l 203-245-6700
Bought with:
Chantal O'Connell, RES.0831391
Real Broker CT, LLC
Source: Smart MLS,MLS#: 24184424
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: High Ceilings, Vaulted Ceiling(s), Fireplace, Full Bath
- Level: Upper
Bedroom
- Features: Bedroom Suite, Full Bath, Laundry Hookup, Wall/Wall Carpet, Tub w/Shower
- Level: Main
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Dining room
- Features: Hardwood Floor
- Level: Main
Great room
- Features: Vaulted Ceiling(s), Wet Bar, Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: French Doors, Kitchen Island, Tile Floor
- Level: Main
Living room
- Features: Wall/Wall Carpet
- Level: Main
Rec play room
- Features: Wall/Wall Carpet
- Level: Lower
Sun room
- Features: Tile Floor
- Level: Main
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Oven/Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Upper Level
Features
- In-Law Floorplan
- Basement: Full,Partially Finished
- Attic: Walk-up
- Number of fireplaces: 2
Interior area
- Total structure area: 3,415
- Total interior livable area: 3,415 sqft
- Finished area above ground: 3,415
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Lot
- Size: 4.37 Acres
- Features: Few Trees, Cleared, Landscaped, Rolling Slope, Open Lot
Details
- Parcel number: 1330841
- Zoning: R-60
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1984
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
HOA
- Has HOA: No
Location
- Region: Southbury
Financial & listing details
- Price per square foot: $218/sqft
- Tax assessed value: $460,450
- Annual tax amount: $11,143
- Date on market: 6/17/2026
Price history
| Date | Event | Price |
|---|---|---|
| 7/10/2026 | Sold | $745,000-0.5%$218/sqft |
Source:  Smart MLS #24184424 Report a problem | ||
| 7/8/2026 | Pending sale | $749,000$219/sqft |
Source: Smart MLS #24184424 Report a problem | ||
| 6/20/2026 | Listed for sale | $749,000+152.8%$219/sqft |
Source: Smart MLS #24184424 Report a problem | ||
| 5/30/1997 | Sold | $296,250$87/sqft |
Source: Smart MLS #96034903 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $11,143 +2.5% | $460,450 |
| 2024 | $10,867 +4.9% | $460,450 |
| 2023 | $10,360 +1.4% | $460,450 +29% |
| 2022 | $10,219 -2.2% | $356,800 |
| 2021 | $10,454 0% | $356,800 |
| 2020 | $10,454 +0.7% | $356,800 |
| 2019 | $10,383 +0.3% | $356,800 |
| 2018 | $10,347 -7.1% | $356,800 -6.1% |
| 2017 | $11,137 +3.2% | $380,090 |
| 2015 | $10,795 +2.9% | $380,090 |
| 2014 | $10,490 +4.5% | $380,090 |
| 2013 | $10,034 +21.1% | $380,090 -2.7% |
| 2012 | $8,285 -0.9% | $390,780 |
| 2011 | $8,363 -0.5% | $390,780 |
| 2010 | $8,402 +2.9% | $390,780 |
| 2009 | $8,167 -0.9% | $390,780 |
| 2008 | $8,245 +5.8% | $390,780 +27.4% |
| 2007 | $7,791 +1.2% | $306,730 |
| 2006 | $7,699 +5% | $306,730 |
| 2005 | $7,331 +13.8% | $306,730 |
| 2003 | $6,441 +24.2% | $306,730 +45% |
| 2001 | $5,184 | $211,600 |
Find assessor info on the county website
Neighborhood: 06488
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Nearby schools
GreatSchools rating
- 8/10Pomperaug SchoolGrades: PK-5Distance: 0.9 mi
- 7/10Rochambeau Middle SchoolGrades: 6-8Distance: 0.9 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 4.1 mi
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- Connecticut
- New Haven County
- Southbury
- 06488
- 55 Sleepy Hill Road
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