55 Sleepy Hill Road, Southbury, CT 06488 - Photo 1

1/1

$745,000

Sold
Closed
Single Family
5 Beds
3 Full Baths
1 Partial Bath
3,415 Sq. Ft.
2 Car Garage

1/1

Property Description

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

Full Property Details for 55 Sleepy Hill Rd

General

Sold For: $745,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24184424
Added to Site: 66 day(s) ago

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
Sold by Real Broker CT, LLC, Chantal O'Connell

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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

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NMLS#: 1598647

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Schools

Schools serving 55 Sleepy Hill Rd

School District:Regional School District 15

Name	Grades	Distance
Pomperaug School 607 Main Street North, Southbury, CT 06488	K-5	2.7 mi
Rochambeau Middle School 100 Peter Road, Southbury, CT 06488	6-8	0.9 mi
Pomperaug Regional High School 234 Judd Road, Southbury, CT 06488	9-12	4.1 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

Date

Details

Price

Change

Source

7/10/2026

Sold

$745,000

-0.53%

MLS

6/20/2026

Listed

$749,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

138 Minortown Rd, Woodbury, CT 06798 - Photo 1

Just Listed

$1,600,000

138 Minortown Rd Woodbury, CT 06798

Single Family
Active
Updated 5 days ago

4
Beds
3
Total Baths
3,122
Sq. Ft.

Listed by Re/Max Rise

39 Hard Hill Rd, Woodbury, CT 06798 - Photo 1

Just Listed

$695,000

Open House

39 Hard Hill Rd Woodbury, CT 06798

Single Family
Active
Updated 1 day ago

3
Beds
3
Total Baths
2,970
Sq. Ft.

Listed by William Pitt Sotheby's Int'l

8 Woods Way, Woodbury, CT 06798 - Photo 1

Just Listed

$309,000

8 Woods Way #8 Woodbury, CT 06798

Townhouse
Active
Updated 23 hours ago

3
Beds
3
Total Baths
1,467
Sq. Ft.

Listed by Berkshire Hathaway NE Prop.

47 Woods Way, Woodbury, CT 06798 - Photo 1

Just Listed

$299,900

Open House

47 Woods Way #47 Woodbury, CT 06798

Townhouse
Active
Updated 1 day ago

2
Beds
2
Total Baths
1,182
Sq. Ft.

Listed by BHGRE Gaetano Marra Homes

153 Old Sherman Hill Rd, Woodbury, CT 06798 - Photo 1

Price Reduced

-$50,100 (-6.68%)

$699,900

153 Old Sherman Hill Rd Woodbury, CT 06798

Single Family
Active
Updated 4 days ago

3
Beds
2
Total Baths
1,658
Sq. Ft.

Listed by Heather Weber (203) 232-5483

819 Main St N, Woodbury, CT 06798 - Photo 1

Price Reduced

-$125,000 (-7.94%)

$1,450,000

819 Main St N Woodbury, CT 06798

Single Family
Active
Updated 23 hours ago

3
Beds
3
Total Baths
2,992
Sq. Ft.

Listed by Klemm Real Estate Inc

40 Sherman Hill Rd, Woodbury, CT 06798 - Photo 1

Price Reduced

-$2,000 (-16.67%)

$10,000

40 Sherman Hill Rd Woodbury, CT 06798

Commercial Lease
Active

Listed by William Raveis Real Estate

24 Yale Ave, Middlebury, CT 06762 - Photo 1

Price Reduced

-$25,100 (-6.69%)

$349,900

24 Yale Ave Middlebury, CT 06762

Single Family
Active
Updated 3 days ago

3
Beds
2
Total Baths
1,469
Sq. Ft.

Listed by Ken Viele (203) 605-4251

201 Grey Rock Rd, Southbury, CT 06488 - Photo 1

Sold

$826,000

201 Grey Rock Rd Southbury, CT 06488

Single Family
Closed

4
Beds
4
Total Baths
4,023
Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by Eagle Eye Realty PLLC

192 N Georges Hill Rd, Southbury, CT 06488 - Photo 1

Sold

$800,000

192 N Georges Hill Rd Southbury, CT 06488

Single Family
Closed

4
Beds
3
Total Baths
2,679
Sq. Ft.

Listed by Around Town Real Estate LLC
Sold by William Raveis Real Estate

577 Lakeside Rd, Southbury, CT 06488 - Photo 1

Sold

$659,500

577 Lakeside Rd Southbury, CT 06488

Single Family
Closed

3
Beds
4
Total Baths
2,304
Sq. Ft.

Listed by Drakeley Real Estate, Inc.
Sold by Compass Connecticut, LLC

175 Hollow Swamp Rd, Southbury, CT 06488 - Photo 1

Sold

$820,000

175 Hollow Swamp Rd Southbury, CT 06488

Single Family
Closed

4
Beds
3
Total Baths
3,200
Sq. Ft.

Listed by Bob Warner
Sold by Preston Gray Real Estate

55 Sleepy Hill Road, Southbury, CT 06488 (MLS# 24184424) is a Single Family property that was sold at $745,000 on July 10, 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.

55 Sleepy Hill Rd Southbury, CT 06488