19 Roosevelt Road
Westport, Connecticut 06880
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,762
- Acres
- 0.20
- Year Built
- 1920
- Neighborhood
- Compo Beach
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Active Listings
68
40 under contract
Median List Price
$4.80M
68 active listings
Median Closed Price
$2.42M
301 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per 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
Homes with a close match in area, property type, and price.
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.