Open House 11/7 11am - 1pm
33 Old Oakwood Drive
Southbury, CT, 06488 $ 799,000
Bedrooms4 Baths2.1 Sq 4,530 Monthly Estimate*
$ 5,518
for $799,000 with 4 bedrooms and 2 full baths, 1 half bath. This 4,530 square foot home was built in 2002 on a lot size of 2.77.
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. The entertaining continues outdoors, where an updated Trex deck overlooks a private, level backyard with two distinctive deck areas, ideal for gatherings, relaxing, and making memories. Inside, the expansive finished basement provides even more versatile space for recreation, movie nights, game days, or hosting family and friends, complete with a walk-out basement. Upstairs, you'll find 4 generously sized bedrooms, including a spacious primary suite where you will find the updated American Chestnut hardwood floors featuring an updated bathroom that feels like a private retreat. Enjoy a spa-inspired atmosphere with a glass-enclosed walk-in shower, decorative tile accents, classic black fixtures, and a charming freestanding clawfoot soaking tub nestled beside a large window. The elegant, double sinks, white vanity and timeless black-and-white tile flooring complete this beautiful blend of classic character and modern style. With dedicated spaces for working from home, entertaining, and simply enjoying everyday life, this exceptional Colonial offers the privacy, flexibility, and comfort you've been looking for. Conveniently located near 84 and Pomperaug Highschool. A must-see home with room for every part of your lifestyle!
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Open House
11/7/2026 11:00 AM - 1:00 PM
33 Old Oakwood Drive Southbury, CT
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
Single Family Coming Soon
FeaturesGeneralZoning B-3D
Neighborhood N/A
County New Haven
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Coming Soon
Acres 2.77
Directions 84 Exit 16 Right on Rt 188 Strongtown Rd left on Judd Left on Tuttle Left on Old Oakwood Drive
High School Per Board of Ed
City Southbury
Elementary School Per Board of Ed
Sq Ft Total 4530
Year Built 2002
Style Colonial
Year Built Source Public Records
Energy Features Programmable Thermostat
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InteriorCooling System Central Air
Total Rooms 11
Basement Description Full Heated Fully Finished Full With Walk-Out
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ExteriorWater Source Private Well
Lot Description Secluded Lightly Wooded Level Lot
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* Excluded FeaturesList ByTracy WilsonListing Agent
twilson@lamacchiarealty.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $5,518
- Monthly Property Taxes
- $901
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 7.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Southbury, CT
Average List Price $803,356
Percent of Sale Price 1%
About Southbury, CT 19,982 Population
8% Since 2002
$ 84,270 Median Income
52.98 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 11/1/2026 | $799,000 | | Listed Price |