55 Sleepy Hill Rd

Southbury, CT 06488

$749,000
Price
5
Beds
3,415 Sq. Ft.
$219 / Sq. Ft.
3,415
Sq. Ft.
$219
per Sq. Ft.
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Coming SoonOpen: 6/20 01:00PM - 03:00PM
Coming SoonOpen: 6/20 01:00PM - 03:00PM
Welcome to 55 Sleepy Hill Road!
Gorgeous stone wall and landscaping.
Lovely front entrance.
Living Room. Pretty double French Doors.
Dining Room. Flows easily from Living Room and Kitchen.
Kitchen. Big and open. An anchor to the home.
Sunroom. Overlooks the huge yard.
Great Room. Note the wetbar.
Powder Room.
1st Floor In-Law. Would also be a great WFG space.
In-Law Kitchen. Note private entrance.
In-Law Ful Bath.
Primary Bedroom. Impressive!
Primary Bathroom. Also has a stall shower.
Bedroom #2.
Bedroom #3.
Bedroom #4.
2nd Floor Full Bath and Laundry.
Lower Level Playroom. TONS of storage and closets.
This space also connects to the Workshop.
Big Back Deck (wood).
Side yard. So much area to play.
Garden area.
Elegant and set back driveway. So private!

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...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.
  1. Listed by Phoebe V Finch • William Pitt Sotheby's Int'l
    P: (617)-645-3907 C: (617)-645-3907 pschreiner@wpsir.com

Property Details for 55 Sleepy Hill Road

Basement Description
Full, Partially Finished
Direct Waterfront
No
Expected Active Date
06-20-2026
Garages Number
2
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Under House Garage
Swimming Pool
No

Open Houses

Saturday, Jun 20th1:00 PM - 3:00 PM
PublicView contact
LISTING UPDATED: 06/17/2026 01:57 PM

Property Details for 55 Sleepy Hill Road

StatusComing Soon
MLS #24184424
Days on Market-
Taxes$11,143 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1984
Lot Size4.37 AC / 190,357 SF
CountyNew Haven County
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Location

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch
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Building Information for 55 Sleepy Hill Road

Stories-Year Built1984Building Size-Lot Size4.37 AC / 190,357 SF

Payment Calculator

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$4,661 per month

30 year fixed, 6.36% Interest

Principal and Interest

$3,732

Property Taxes

$929

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 55 Sleepy Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Bullet Hill and take a right on Sleepy Hill. House is up on the left. Long, private driveway.
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Latitude: 41.457372
  • Longitude: -73.215112
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $11,143
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer
  • Attic Description: Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Laundry Room Info: Upper Level
  • Rooms Total: 10
Room 1
  • Room Entry Order: 1
  • Room Features: Wall/Wall Carpet
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: Wall/Wall Carpet
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 4
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 5
  • Listing Key: 54600EAC7BD9EB13E063E201100A0716
  • Room Entry Order: 3
  • Room Features: French Doors,Island,Tile Floor
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 6
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling,Wet Bar,Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Great Room
Room 7
  • Room Entry Order: 5
  • Room Features: Tile Floor
  • Room Level: Main
  • Room Type: Sun Room
Room 8
  • Room Entry Order: 6
  • Room Features: Bedroom Suite,Full Bath,Laundry Hookup,Wall/Wall Carpet,Tub w/Shower
  • Room Level: Main
  • Room Type: Bedroom
Room 9
  • Listing Key: 54600EAC7BD9EB13E063E201100A0716
  • Room Entry Order: 7
  • Room Features: 9 ft+ Ceilings,Vaulted Ceiling,Fireplace,Full Bath
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 10
  • Room Entry Order: 8
  • Room Features: Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Room 11
  • Room Entry Order: 9
  • Room Features: Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1984
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: First Floor, Separate Entry
  • In Law Apartment: Yes
  • Living Area SQFT Per Public Records: 3415
Lot Information
  • Lot Description: Lightly Wooded, Cleared, Professionally Landscaped, Rolling, Open Lot
  • Parcel Number: 1330841
  • Sq Ft Est Heated Above Grade: 3415.0
  • Sq Ft Total: 3415.0
  • Zoning: R-60
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 55 Sleepy Hill Road

DateEvent & SourcePriceAppreciation
May 30, 1997

Closed (Public Record)

Public Record #92440849

$296,250—
DateEvent & SourcePrice
05/30/1997

Closed (Public Record)

Public Record #92440849

$296,250

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 55 Sleepy Hill Road

Taxable ValueLand$119,640Additions$340,810Total$460,450
Tax Record2024$11,143 ($929 / month)
Home Facts
Beds5Baths3.5Total Finished SqFt3,415 SqFtAbove Grade Finished SqFt3,415 SqFtUnfinished Basement SqFt432 SqFtStories2Lot Size190,357 SqFtStyleSingle Family ResidenceYear Built1984Year Renovated1999ZoningR-60CountyNAUGATUCK VALLEYAPNSBUR M:36 B:46 L:S20Fireplace TypeHas Fireplace

Schools near 55 Sleepy Hill Road

This home is within Regional School District 15.
Rating
School
Type
Grades
Distance
Pomperaug School
Public - PK to 5
Rochambeau Middle School
Public - 6 to 8
Pomperaug Regional High School
Public - 9 to 12
Rating
School
Distance
Pomperaug School
PublicPK to 5

Rochambeau Middle School
Public6 to 8

Pomperaug Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 55 Sleepy Hill Road, Southbury, CT 06488

55 Sleepy Hill Road is a single family home Coming Soon in Southbury, CT 06488. This property is currently priced at $749,000. This listing's school district is Regional School District 15. Nearby schools include Pomperaug School, Rochambeau Middle School and Pomperaug Regional High School. 55 Sleepy Hill Road is a 5-bed, 4-bath, 3,415 sqft single family home built in 1984.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Phoebe V Finch

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.