157 Southwind Road
Waterbury, Connecticut 06708
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 3,018
- Acres
- 0.35
- Year Built
- 1965
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
119
100 under contract
Median List Price
$325,000
119 active listings
Median Closed Price
$310,000
610 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per 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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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.