153 Woods Way Drive
Southbury, Connecticut 06488
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,820
- Acres
- 4.49
- Year Built
- 1989
- 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
Set at the end of a cul-de-sac on 4.49 private acres, this classic Colonial offers 2,820 square feet of comfortable living and the kind of wooded seclusion that's increasingly hard to find in Southbury. The heart of the home is a sun-filled family room with vaulted ceilings, a floor-to-ceiling brick fireplace, custom built-ins, and an arched Palladian window framing the trees. The kitchen anchors daily life with a generous breakfast bar, stainless appliances, and a bay-windowed dining nook that floods the space with light. Hardwood floors run throughout the main level, and a separate formal dining room and private office give you room to spread out. Upstairs, four bedrooms include a spacious primary with a walk-in closet and ensuite bath. Main-level laundry and a convenient half bath round out the layout. Additional highlights: a two-car under-house garage, pre-wired for back-up generator power, basement with interior and garage access, central air, oil hot-air heat, fireplace, attic storage, and a level, lightly wooded lot with garden area and mature plantings. Minutes to Southbury's shopping, library, parks, and golf, with top-rated Pomperaug schools and easy I-84 access.Schedule your showing today and see what privacy and space really look like.
Key Facts
- City/Town
- Southbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1989
- Days on Market
- 1 day
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,820 sq ft
- Lot Size
- 4.49 acres
- Garage / Parking
- 2 garage · 2 total
- Property Taxes
- $9,283 / Annually
Market Snapshot
The Southbury Market
Single Family · trailing 12 months
Active Listings
45
29 under contract
Median List Price
$799,000
45 active listings
Median Closed Price
$626,000
162 sales
Median Days on Market
58
45 active listings
Median $ / Sq Ft
$281
45 active listings
Sale-to-List Ratio
100.0%
162 sales
How this home compares
List Price
$650,000
vs $799,000 median
18.6% below median
Price / Sq Ft
$230
vs $281 median
18.1% below median
Days on Market
1 day
vs 58 days median
57 days fresher than median
Based on 45 active and 162 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of November 11, 2026.
Location
153 Woods Way Drive, Southbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$3,523
- Property Taxes$774
- Insurance$217
- 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
- 1989
- New Construction
- No/Resale
- Living Area
- 2,820 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
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullUnfinishedGarage AccessInterior AccessConcrete Floor
Exterior & Lot
- Lot Size
- 4.49 acres
- Zoning
- R-60
- Garage / Parking
- 2 garage spaces2 total parking spacesUnder House GarageDrivewayPrivatePavedUnpavedCrushed Stone
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Light Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckGuttersGarden Area
- Lot Description
- Lightly WoodedLevel LotOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $9,283 / Annually
- Days on Market
- 1
- MLS #
- 24215451
- MLS Status
- Coming Soon
Similar Properties
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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 11/11/2026. 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 11/11/2026 at 6:16 PM UTC.