Skip to main content

48 Woodside Avenue

Westport, Connecticut 06880

ACTIVE$4,100,000
Beds
6
Baths
5 | 1
SqFt
6,244
Acres
0.50
Year Built
2026
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
Pool2-Car Garage1 FireplaceNew Construction

About This Home

A rare opportunity to own new construction in Westport's coveted Old Hill neighborhood, offering refined design, a swimming pool, and a walkable lifestyle near Post Road and downtown. Tucked within one of Westport's most sought-after enclaves, this newly constructed 6-bedroom, 5.5-bath home blends architectural sophistication with modern livability. Natural light, clean lines, and well-proportioned spaces create an environment that feels both elevated and effortlessly comfortable. At the center of the home, a beautifully designed kitchen opens to expansive living and dining areas, creating a seamless flow for both everyday living and entertaining. The layout flows easily with ample room for work-from-home, multi-generational living, and evolving lifestyle needs. A main-level suite with a full bath provides privacy and versatility-ideal for guests, a dedicated office, or an extended family. Every detail accentuates comfort, function, and understated luxury. A back yard patio with pool abutting a nature preserve offers privacy with open space and the ease of in-town living. Positioned near Nash Pond and close to local nature trails and amenities, the home also offers exceptional convenience-walkable to the Post Road and just minutes to downtown Westport, shopping, dining, and Metro-North train service to New York City. Luxury new construction in Old Hill, Westport, CT-where location, design, and lifestyle align in one of the town's most desirable settings.

Key Facts

City/Town
Westport
Neighborhood
Old Hill
Property / Style
Single Family · Colonial
Year Built
2026
Days on Market
74 days
Beds
6
Baths
5 full · 1 half
Living Area
6,244 sq ft
Lot Size
0.50 acres
Garage / Parking
2 garage
Property Taxes
$9,187 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

56

71 active listings

Median $ / Sq Ft

$820

71 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$4.10M

vs $4.60M median

10.9% below median

Price / Sq Ft

$657

vs $820 median

19.9% below median

Days on Market

74 days

vs 56 days median

18 days longer than median

Based on 71 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

48 Woodside Avenue, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$23,038

per month

  • Principal & Interest$20,905
  • Property Taxes$766
  • Insurance$1,367
  • HOA$0

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

Location

City/Town
Westport
Neighborhood
Old Hill
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2026
New Construction
Under Construction
Living Area
6,244 sq ft

Schools

Elementary
Kings Highway
High
Staples

Interior

Heating
Baseboard
Heat Fuel
Oil
Cooling
None
Fireplaces
1
Appliances
None
Basement
Full

Exterior & Lot

Lot Size
0.50 acres
Zoning
AA
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Pool
In Ground Pool
Construction
Wood
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
Some Wetlands

Listing & Financials

Property Taxes
$9,187 / Annually
Days on Market
74
MLS #
24164137
MLS Status
Active

Similar Properties

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

Listed By

Judy Michaelis

(203) 247-5000

Coldwell Banker Realty

(203) 227-8424

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. 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 7/27/2026 at 11:05 AM UTC.