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153 Woods Way Drive

Southbury, Connecticut 06488

COMING SOON - NEW$650,000
Beds
4
Baths
2 | 1
SqFt
2,820
Acres
4.49
Year Built
1989
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 FireplaceVirtual Tour

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,514

per 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

Homes with a close match in area, property type, and price.

Listed By

Doug Peterson

(475) 274-2115

William Raveis Real Estate

(203) 453-0391

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.