44 Wakeley Road
Southbury, Connecticut 06488
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,720
- Acres
- 1.25
- Year Built
- 2003
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Set on a peaceful 1.25-acre lot, this 2,720 sq ft colonial blends classic charm with thoughtful updates. The welcoming two-story foyer opens to bright, spacious rooms with 9-foot ceilings and hardwood floors throughout the main level. The living room features a cozy fireplace, while the formal dining room offers a tray ceiling and elegant details perfect for gatherings. The eat-in kitchen is both stylish and functional, with quartz countertops, stainless steel appliances, a butcher block island and sliders leading to a private deck. The kitchen opens up to a large 23x19 great room with cathedral ceilings which provides the perfect space for relaxing or entertaining, Upstairs, the primary suite includes a walk-in closet and a beautifully updated bath with a double vanity and tiled shower, all 4 BRs have brand new carpeting. The partially finished lower level with walkout sliders is ready for your completion and adds even more flexibility and potential for more living space. Additional highlights include a central vacuum system, a brand-new roof, and a geothermal heating and cooling system that keeps energy costs exceptionally low-using less than one tank of oil in 11 years. The lawn will remain green with the sprinkler system. This home offers comfort, efficiency, and timeless appeal in one of Southbury's desirable neighborhoods.
Key Facts
- City/Town
- Southbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 2003
- Days on Market
- 47 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,720 sq ft
- Lot Size
- 1.25 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $7,161 / Annually
Market Snapshot
The Southbury Market
Single Family · trailing 12 months
Active Listings
33
35 under contract
Median List Price
$645,000
33 active listings
Median Closed Price
$632,500
164 sales
Median Days on Market
27
33 active listings
Median $ / Sq Ft
$287
33 active listings
Sale-to-List Ratio
100.0%
164 sales
How this home compares
List Price
$629,900
vs $645,000 median
In line with median
Price / Sq Ft
$232
vs $287 median
19.2% below median
Days on Market
47 days
vs 27 days median
20 days longer than median
Based on 33 active and 164 closed sales (trailing 12 mo) of single family in Southbury. Source: SmartMLS · As of July 28, 2026.
Location
44 Wakeley Road, Southbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,212
- Property Taxes$597
- Insurance$210
- 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
- 2003
- New Construction
- No/Resale
- Living Area
- 2,720 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Geothermal
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Oven/RangeRange HoodRefrigeratorDishwasher
- Basement
- FullPartially FinishedFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerCable - Available
Exterior & Lot
- Lot Size
- 1.25 acres
- Zoning
- R-30
- Garage / Parking
- 2 garage spacesUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- DeckUnderground Sprinkler
- Lot Description
- On Cul-De-Sac
Listing & Financials
- Property Taxes
- $7,161 / Annually
- Days on Market
- 47
- MLS #
- 24177681
- MLS Status
- Under Contract
- Financing
- FHA,VA,CHFA
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Joanne Combs
Dan Combs Real Estate
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:15 AM UTC.