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$749,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,415 Sq. Ft.
  • 2 Car Garage
  • Updated 16 hours ago
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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.

Full Property Details for 55 Sleepy Hill Rd

General

  • Price: $749,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24184424
  • Updated: Today (6/20/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 10
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Oven/Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Vaulted Ceiling, Fireplace, Full Bath, Upper
  • Bedroom 1: Bedroom - Bedroom Suite, Full Bath, Laundry Hookup, Wall/Wall Carpet, Tub w/Shower, Main
  • Bedroom 2: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 3: Bedroom - Wall/Wall Carpet, Upper
  • Bedroom 4: Bedroom - Wall/Wall Carpet, Upper

Other Rooms

  • Living Room: Living Room - Wall/Wall Carpet, Main
  • Great Room: Great Room - Vaulted Ceiling, Wet Bar, Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - French Doors, Island, Tile Floor, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Wall/Wall Carpet, Lower
  • Rec Room: Wall/Wall Carpet, Lower
  • Laundry: Upper Level
  • In-Law/Au Pair Suite: Yes

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Under House Garage

Location

  • County: New Haven
  • Driving Directions: Bullet Hill and take a right on Sleepy Hill. House is up on the left. Long, private driveway.

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,415
  • Above Ground: 3,415 Sq. Ft.
  • Year Built: 1984

Lot Features

  • Lot Size (Acres): 4.37
  • Zoning: R-60
  • Lot Description: Lightly Wooded, Cleared, Professionally Landscaped, Rolling, Open Lot

Financial Considerations

  • Assessment Amount: $460,450
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1330841

Listed by William Pitt Sotheby's Int'l, Phoebe Finch

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Listing agent

— 55 Sleepy Hill Rd —

  • Phoebe Finch

    William Pitt Sotheby's Int'l

Agent Contact: (617) 645-3907 Office Contact: (203) 245-6700

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 55 Sleepy Hill Rd

School District:Regional School District 15
NameGradesDistance
Pomperaug School
607 Main Street North, Southbury, CT 06488
K-52.7 mi
Rochambeau Middle School
100 Peter Road, Southbury, CT 06488
6-80.9 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-124.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 55 Sleepy Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/20/2026
Listed
$749,000
152.83%
MLS
5/30/1997
Sold
$296,250
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 55 Sleepy Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$11,143
3%
$460,450
—
2023
$10,867
5%
$460,450
—
2023
$10,360
1%
$460,450
29%
2022
$10,219
-2%
$356,800
—
2021
$10,454
—
$356,800
—
2020
$10,454
1%
$356,800
—
2019
$10,383
—
$356,800
—
2018
$10,347
-7%
$356,800
-6%
2017
$11,137
2%
$380,090
—
2016
$10,947
1%
$380,090
—
2015
$10,795
3%
$380,090
—
2014
$10,490
5%
$380,090
—
2011
$10,034
—
$380,090
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Phoebe Finch

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55 Sleepy Hill Road, Southbury, CT 06488 (MLS# 24184424) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 55 Sleepy Hill Road is currently listed for $749,000 and was received on June 20, 2026. Want to learn more about 55 Sleepy Hill Road? Do you have questions about finding other Single Family real estate for sale in Southbury? You can browse all Southbury real estate or contact a Coldwell Banker agent to request more information.

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