33 Old Oakwood Drive
Southbury, Connecticut 06488
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 4,530
- Acres
- 2.77
- Year Built
- 2002
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Welcome to this private four-bedroom Colonial, where thoughtful updates, generous living spaces, and endless opportunities of work, play, and unwinding come together to create a home that truly has it all. Nestled on a cul-de-sac, this home is privately set back from the road. A long driveway leads to this inviting residence where it offers ample parking with a bump out for additional parking. Step inside to discover beautiful, recently updated, American Chestnut hardwood floors throughout, complemented by elegant wainscotting in the formal living and dining room. Designed with both everyday living and entertaining in mind, the inviting kitchen features a large granite island, ample cabinets and stainless-steel appliances. The kitchen is spacious and has an open floor plan to the family room where there are beautiful transom windows that let in an abundance of light and a beautifully updated granite gas fireplace for those cozy nights. The first-floor dedicated office space was carefully designed when building this home and is the perfect flex space offering the balance of functionality and privacy off the rest of the home.
Key Facts
- City/Town
- Southbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2002
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 4,530 sq ft
- Lot Size
- 2.77 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $10,807 / Annually
Market Snapshot
The Southbury Market
Single Family · trailing 12 months
Active Listings
49
21 under contract
Median List Price
$799,000
49 active listings
Median Closed Price
$627,000
163 sales
Median Days on Market
51
49 active listings
Median $ / Sq Ft
$281
49 active listings
Sale-to-List Ratio
100.0%
163 sales
How this home compares
List Price
$799,000
vs $799,000 median
In line with median
Price / Sq Ft
$176
vs $281 median
37.4% below median
Days on Market
0 days
vs 51 days median
51 days fresher than median
Based on 49 active and 163 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of November 1, 2026.
Location
33 Old Oakwood Drive, Southbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$4,356
- Property Taxes$901
- Insurance$266
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Southbury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 2002
- New Construction
- No/Resale
- Living Area
- 4,530 sq ft
- Below Grade
- 1,300 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Upper Level
- Laundry Location
- Laundry Room
- Appliances
- Electric CooktopWall OvenMicrowaveRefrigeratorFreezerDisposal
- Basement
- FullHeatedFully FinishedFull With Walk-Out
- In-Law Apartment
- Possible
- Interior Features
- Auto Garage Door OpenerOpen Floor Plan
Exterior & Lot
- Lot Size
- 2.77 acres
- Zoning
- B-3D
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- Taupe
- Roof
- Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesSidewalkDeckGutters
- Lot Description
- SecludedLightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $10,807 / Annually
- Days on Market
- 0
- MLS #
- 24216979
- MLS Status
- Coming Soon
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/1/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 11/1/2026 at 6:50 PM UTC.