Curious about this home?

Ask anything — no agents, no pressure

Try asking

About This Home

This 5-bedroom, 4-bathroom single family at 55 Sleepy Hill Road in Southbury, CT is listed for $749,000 ($219 per sqft). Built in 1984, the home offers 3,415 sqft of living space on a 4.37 acres lot.

Agent 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.

Key Features

  • Built in 1984
  • 4.37 acre lot
  • Fireplace

Property Details

3 full, 1 half
1984

Amenities

FireplaceA/C

Monthly Cost Estimate

$4,006/mo

20% down · 6.5% · 30 years

Principal$542
Interest$3,246
Insurance$218

Estimates only. Actual payments may vary.

Location

55 Sleepy Hill Road

Southbury, CT 06488

Property Details

Cooling

Central Air

Appliances

Oven/RangeMicrowaveRefrigeratorFreezerDishwasherWasherDryer

Questions & Answers

This 5-bedroom, 4-bathroom single family at 55 Sleepy Hill Road is listed at $749,000 ($219/sqft). The estimated monthly payment is $3,246 based on 20% down at 6.5% interest.

Key features include: Built in 1984, 4.37 acre lot, Fireplace.

This property is listed by Phoebe Finch and can be reached at 6176453907 or pschreiner@wpsir.com.

PF

Phoebe Finch

Agent at William Pitt Sotheby's Int'l

(617) 645-3907

Listed by William Pitt Sotheby's Int'l · View on Broker Site

MLS# 24184424· Source: listhub· Updated 4 days ago

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

55 Sleepy Hill Road, Southbury, CT 06488

Open this listing in: