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.
Sold for $865,000
$865,000
299 West Flat Hill Road, Southbury, CT 06488
5beds
2,462sqft
Single Family Residence
Built in 1985
4.82 Acres Lot
$894,900 Zestimate®
$351/sqft
$4,387 Estimated rent
Home value
$894,900
$796,000 - $1.00M
$4,387/mo
Zestimate® history
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List your homeWhat's special
Expansive loft spaceLush five acresOversized two-stall barnRolling hillsHandicap accessible in-law
Zillow last checked:
Listing updated:
Listed by:
Michael Caporizzo 203-644-5228,
William Pitt Sotheby's Int'l 860-868-6600,
Erin Caporizzo 203-910-8288,
William Pitt Sotheby's Int'l
Bought with:
Christopher Crane, RES.0821028
Coldwell Banker Realty
Source: Smart MLS,MLS#: 24096319
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Ceiling Fan(s), Sliders
- Level: Main
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Level: Upper
Bedroom
- Features: Bedroom Suite
- Level: Upper
Dining room
- Features: Hardwood Floor
- Level: Main
Kitchen
- Level: Main
Living room
- Features: Hardwood Floor
- Level: Main
Heating
- Hot Water, Oil
Cooling
- Central Air, Ductless
Appliances
- Included: Electric Cooktop, Electric Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Tankless Water Heater
- Laundry: Main Level
Features
- Basement: Full
- Attic: Pull Down Stairs
- Number of fireplaces: 1
Interior area
- Total structure area: 2,462
- Total interior livable area: 2,462 sqft
- Finished area above ground: 2,462
Property
Parking
- Total spaces: 3
- Parking features: Detached, Garage Door Opener
- Garage spaces: 3
Accessibility
- Accessibility features: Accessible Bath, Accessible Approach with Ramp
Features
- Patio & porch: Deck, Patio
- Exterior features: Awning(s)
- Spa features: Heated
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Brook
Lot
- Size: 4.82 Acres
- Features: Level
Details
- Additional structures: Barn(s)
- Parcel number: 1333305
- Zoning: R-80
- Other equipment: Generator Ready
- Horse amenities: Paddocks
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1985
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available
Green energy
- Energy generation: Solar
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Lake, Park, Private School(s), Stables/Riding, Tennis Court(s)
Location
- Region: Southbury
- Subdivision: The Purchase
Price history
| Date | Event | Price |
|---|---|---|
| 9/29/2025 | Sold | $865,000-7.5%$351/sqft |
Source:  Smart MLS #24096319 Report a problem | ||
| 9/23/2025 | Pending sale | $935,000$380/sqft |
Source: Smart MLS #24096319 Report a problem | ||
| 5/16/2025 | Listed for sale | $935,000-5.3%$380/sqft |
Source: Smart MLS #24096319 Report a problem | ||
| 2/24/2025 | Listing removed | $987,500$401/sqft |
Source: Smart MLS #170626116 Report a problem | ||
| 11/19/2024 | Listed for sale | $987,500$401/sqft |
Source: Smart MLS #170626116 Report a problem | ||
| 9/17/2024 | Listing removed | $987,500-12.2%$401/sqft |
Source: Smart MLS #170626116 Report a problem | ||
| 7/20/2024 | Listed for sale | $1,125,000+373.7%$457/sqft |
Source: Smart MLS #170626116 Report a problem | ||
| 8/14/1992 | Sold | $237,500$96/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $9,569 +12% | $395,430 +9.3% |
| 2024 | $8,541 +4.9% | $361,910 |
| 2023 | $8,143 +1.8% | $361,910 +29.6% |
| 2022 | $7,998 -2.3% | $279,270 |
| 2021 | $8,183 +0% | $279,270 |
| 2020 | $8,183 +5.1% | $279,270 +4.3% |
| 2019 | $7,788 +11.3% | $267,640 +10.9% |
| 2018 | $7,000 -3.7% | $241,380 -2.7% |
| 2017 | $7,268 +3.2% | $248,050 |
| 2015 | $7,045 +2.9% | $248,050 |
| 2014 | $6,846 +4.5% | $248,050 |
| 2013 | $6,549 +6.9% | $248,050 -14.2% |
| 2012 | $6,126 -0.5% | $288,960 +0.4% |
| 2011 | $6,157 -0.5% | $287,720 |
| 2010 | $6,186 +2.9% | $287,720 |
| 2009 | $6,013 -1% | $287,720 |
| 2008 | $6,071 +4.8% | $287,720 +26.2% |
| 2007 | $5,793 +1.2% | $228,060 |
| 2006 | $5,724 +5% | $228,060 |
| 2005 | $5,451 +15.2% | $228,060 +1.3% |
| 2003 | $4,730 +43.6% | $225,230 +67.5% |
| 2001 | $3,295 | $134,500 |
Find assessor info on the county website
Neighborhood: 06488
Nearby schools
GreatSchools rating
- 8/10Gainfield Elementary SchoolGrades: PK-5Distance: 3.4 mi
- 7/10Rochambeau Middle SchoolGrades: 6-8Distance: 3.4 mi
- 8/10Pomperaug Regional High SchoolGrades: 9-12Distance: 6.8 mi
Schools provided by the listing agent
- High: Pomperaug
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- New Haven County
- Southbury
- 06488
- 299 West Flat Hill Road
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