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$865,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,462 Sq. Ft.
  • 3 Car Garage
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The second time since its construction, this home in the sought-after Purchase Brook area is for sale. Over the years, this home has hosted events and has entertained and charmed guests. Its lush five acres have been home to horses boarded in the oversized two-stall barn. The current homeowners have thoughtfully added to the original structure, adding five hundred square feet to what was originally a saltbox style. This investment created a space that has been versatile for the current owners, serving as a handicap accessible in-law, first floor primary, and even as a second living space; phase two of this renovation included an oversized three car detached garage with an expansive loft space - currently used as storage, but can easily be finished to accommodate whatever personal pursuits or passions the next steward may have. It is easy to understand how this area is the jewel of Southbury; the rolling hills, quiet streets, and convenience to Roxbury, Woodbury, and I-84 make this a place that is both a retreat and a practical location for everyday needs.

Full Property Details for 299 W Flat Hill Rd

General

  • Sold For: $865,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24096319
  • Added to Site: 248 day(s) ago

Interior

  • Number of Rooms: 8
  • Rooms/Areas: Laundry Room
  • Interior Features: Auto Garage Door Opener, Cable - Available, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Electric Cooktop, Electric Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Ceiling Fan, Sliders, Main
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom - Bedroom Suite, Upper
  • Bedroom 4: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen, Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Laundry: Main Level

Exterior

  • Exterior Features: Awnings, Barn, Deck, Hot Tub, Paddock, Patio

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking: Detached Garage

Location

  • County: New Haven
  • Neighborhood: The Purchase
  • Driving Directions: South Britain Road to East Flat Hill

School Information

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

Community

  • Community Name: The Purchase

Heating & Cooling

  • Cooling Type: Central Air, Split System
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Disability Access: Accessible Bath, Ramps
  • Square Feet: 2,462
  • Above Ground: 2,462 Sq. Ft.
  • Year Built: 1985

Lot Features

  • Lot Size (Acres): 4.82
  • Zoning: R-80
  • Lot Description: Level Lot, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Brook

Green Features

  • Energy Features: Active Solar, Passive Solar, Generator Ready

Financial Considerations

  • Assessment Amount: $395,430
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1333305

Meet the selling agent

Meet the selling agent
— 299 W Flat Hill Rd —

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 299 W Flat Hill Rd

School District:Regional School District 15
NameGradesDistance
Gainfield Elementary School
307 Old Field Road, Southbury, CT 06488
K-53.4 mi
Rochambeau Middle School
100 Peter Road, Southbury, CT 06488
6-83.4 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-126.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 299 W Flat Hill Rd

Date
Details
Price
Change
Source
9/29/2025
Sold
$865,000
-7.49%
MLS
5/15/2025
Listed
$935,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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299 West Flat Hill Road, Southbury, CT 06488 (MLS# 24096319) is a Single Family property that was sold at $865,000 on September 29, 2025. This property was sold by Chris Crane from our Newtown Office.Want to learn more about 299 West Flat 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.