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.
For sale
$749,000
55 Sleepy Hill Road, Southbury, CT 06488
5beds
3,415sqft
Single Family Residence
Built in 1984
4.37 Acres Lot
$731,100 Zestimate®
$219/sqft
$-- HOA
What's special
- 6 days |
- 851 |
- 67 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Phoebe V. Finch (617)645-3907,
William Pitt Sotheby's Int'l 203-245-6700
Source: Smart MLS,MLS#: 24184424
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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: $219/sqft
- Tax assessed value: $460,450
- Annual tax amount: $11,143
- Date on market: 6/17/2026
Estimated market value
$731,100
$695,000 - $768,000
$4,027/mo
Price history
| Date | Event | Price |
|---|---|---|
| 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 | $211,600 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06488
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
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- New Haven County
- Southbury
- 06488
- 55 Sleepy Hill Road
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