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157 Southwind Road

Waterbury, Connecticut 06708

ACTIVE - NEW$475,000
Beds
3
Baths
2 | 1
SqFt
3,018
Acres
0.35
Year Built
1965
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage1 Fireplace

About This Home

Step inside this beautifully updated 3-bedroom custom ranch, originally built as a builder's own home, offering desirable one-level living in a sought-after location with walking distance to the town of Middlebury! An inviting foyer leads to a fully renovated eat-in kitchen featuring newer stainless steel appliances and soft-close cabinetry. The dining area boasts cathedral ceilings and oversized windows overlooking the backyard. The expansive, fully wood-paneled living room features soaring ceilings, skylights, abundant natural light, and a large wood-burning fireplace. Three generously sized bedrooms include a spacious primary suite with private en-suite bath and ample closet space. The renovated lower level offers additional versatile living space. Enjoy the private backyard and outdoor entertaining with a newer custom above-ground pool, representing a seller investment of nearly $28,000! Additional features include an irrigation system and an $8,000 basement water filtration system. Recent updates include a roof approximately 3 years old, fresh paint throughout, updated garage doors, hot water heater, dishwasher, refrigerator, and garbage disposal. Hardwood flooring, vaulted ceilings, and abundant natural light complete this special home. Enjoy custom craftsmanship, one-level living, and an exceptional walk-to-town location. A wonderful opportunity in one of Middlebury's sought-after areas. MOVE QUICK!

Key Facts

City/Town
Waterbury
Neighborhood
N/A
Property / Style
Single Family · Ranch
Year Built
1965
Days on Market
0 days
Beds
3
Baths
2 full · 1 half
Living Area
3,018 sq ft
Lot Size
0.35 acres
Garage / Parking
2 garage
Property Taxes
$11,122 / Annually

Market Snapshot

The Waterbury Market

Single Family · trailing 12 months

Median Days on Market

36

119 active listings

Median $ / Sq Ft

$217

119 active listings

Sale-to-List Ratio

100.0%

610 sales

How this home compares

List Price

$475,000

vs $325,000 median

46.2% above median

Price / Sq Ft

$157

vs $217 median

27.6% below median

Days on Market

0 days

vs 36 days median

36 days fresher than median

Based on 119 active and 610 closed sales (trailing 12 mo) of single family in Waterbury. Source: SmartMLS · As of November 6, 2026.

Location

157 Southwind Road, Waterbury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,659

per month

  • Principal & Interest$2,574
  • Property Taxes$927
  • Insurance$158
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Waterbury
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Ranch
Year Built
1965
New Construction
No/Resale
Living Area
3,018 sq ft
Below Grade
600 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
basement
Appliances
Gas RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullFully Finished

Exterior & Lot

Lot Size
0.35 acres
Zoning
RS-12
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Cement Block
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Level Lot

Listing & Financials

Property Taxes
$11,122 / Annually
Days on Market
0
MLS #
24217911
MLS Status
Active

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Listed By

David Aurigemma

(860) 406-5044

Regency Real Estate, LLC

(860) 945-9868

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 11/6/2026. 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 11/6/2026 at 1:05 AM UTC.