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19 Roosevelt Road

Westport, Connecticut 06880

ACTIVE - NEW$4,250,000
Beds
4
Baths
3 | 1
SqFt
2,762
Acres
0.20
Year Built
1920
Matt Caiola

Matt Caiola

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1 Fireplace

About This Home

Tucked along a tranquil lane, mere steps from the soft sands of Westport's coveted Compo Beach, 19 Roosevelt Road is coastal living at its most refined. This picture-perfect residence of four bedrooms and three and a half baths pairs timeless elegance with effortless comfort. It was reimagined from the studs up in 2019 and is fully FEMA-compliant, with two light-filled levels and every modern convenience. On the main level, a gracious living room sets the tone, framed by custom built-in bookcases and warmed by a gas fireplace. The chef's kitchen is the heart of the home. It has a generous center island, a Sub-Zero refrigerator, a Wolf gas range and a dedicated wine refrigerator. Beyond it, a sun-drenched dining area flows into a step-down family room wrapped in windows, opening directly to the patio for seamless indoor-outdoor living. A private den or home office and an elegant powder room complete the floor. Upstairs are four bedrooms. The serene primary suite has its own balcony overlooking the professionally designed grounds. Three additional bedrooms of generous proportion share two beautifully appointed baths. Outside, lush gardens unfold around two stone patios, an enchanting setting for alfresco dining and summer entertaining. The home also includes a whole-house generator, a security system and irrigation. A new roof (2019), natural gas, city water and sewer complete the picture. An exceptional offering moments from the shore, ready to be enjoyed in every season.

Key Facts

City/Town
Westport
Neighborhood
Compo Beach
Property / Style
Single Family · Colonial
Year Built
1920
Days on Market
0 days
Beds
4
Baths
3 full · 1 half
Living Area
2,762 sq ft
Lot Size
0.20 acres
Garage / Parking
4 total
Property Taxes
$30,251 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

35

68 active listings

Median $ / Sq Ft

$791

68 active listings

Sale-to-List Ratio

100.0%

301 sales

How this home compares

List Price

$4.25M

vs $4.80M median

11.5% below median

Price / Sq Ft

$1,539

vs $791 median

94.6% above median

Days on Market

0 days

vs 35 days median

35 days fresher than median

Based on 68 active and 301 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of October 15, 2026.

Location

19 Roosevelt Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$27,479

per month

  • Principal & Interest$23,541
  • Property Taxes$2,521
  • Insurance$1,417
  • HOA$0

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

Location

City/Town
Westport
Neighborhood
Compo Beach
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1920
New Construction
No/Resale
Living Area
2,762 sq ft

Schools

Elementary
Greens Farms
High
Staples

Interior

Heating
Zoned
Cooling
Central Air
Fireplaces
1
Laundry
Upper Level
Appliances
Oven/RangeRefrigeratorFreezerSubzeroDishwasherWasherDryer
Basement
Crawl SpaceHatchway Access
Interior Features
Audio SystemSecurity System
Additional Rooms
Laundry Room

Exterior & Lot

Lot Size
0.20 acres
Zoning
A
Garage / Parking
4 total parking spacesDrivewayPrivateCrushed Stone
Waterfront Details
Walk to WaterBeach RightsWater Community
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
Yes
Construction
Wood
Color
Grey
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedPorchUnderground SprinklerPatio
Lot Description
Fence - PrivacyLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$30,251 / Annually
Days on Market
0
MLS #
24213343
MLS Status
Active

Similar Properties

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Listed By

Miriam Luck

(203) 858-8568

Compass Connecticut, LLC

(203) 293-9715

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/15/2026. 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 10/15/2026 at 3:30 AM UTC.