2 Grassy Plains Road
Westport, Connecticut 06880
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,881
- Acres
- 1.11
- Year Built
- 1955
- Neighborhood
- Old Hill
- 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
*SELLERS ARE AKSING FOR HIGHEST AND BEST OFFERS BY 4PM MONDAY JUNE 1ST*Set on a beautifully landscaped, bucolic acre at the top of a quiet cul-de-sac in Westport's coveted Old Hill neighborhood, this charming cottage-style ranch home offers the perfect blend of modern convenience, and luxurious Westport lifestyle. Move-in ready and beautifully maintained it's thoughtful layout is ideal for both everyday living and gracious entertaining. Light pours in through picture windows, French doors, and skylights giving a bright airy feel throughout. At the heart of the home is a stunning chef's kitchen equipped with high-end stainless steel appliances. The open dining area is perfect for feasts with family. Sliders leading to multiple decks make indoor-outdoor living seamless. Relax in the inviting living room with a cozy fireplace, or entertain outdoors on the expansive deck overlooking lush lawns. Retreat to the primary suite that boasts a newly renovated spa-like bath. Two additional bedrooms & full bath complete this level. The lower level offers a family room, perfect for movie nights, as well as office built-ins to WFH. A playroom/rec space, plus a fourth bedroom and full bath, make an ideal setup for guests, in-laws, or au pair. Step outside to your resort-like oasis featuring a stunning, sun-drenched saltwater pool and cabana with bar & Sonos - summer entertaining perfection! Energy efficient with Tesla Solar Roof, newer mechanicals and a generator give peace of mind.
Key Facts
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.79M
71 active listings
Median Closed Price
$2.42M
303 sales
Median Days on Market
56
71 active listings
Median $ / Sq Ft
$821
71 active listings
Sale-to-List Ratio
100.0%
303 sales
How this home compares
List Price
$1.70M
vs $4.79M median
64.6% below median
Price / Sq Ft
$590
vs $821 median
28.1% below median
Days on Market
62 days
vs 56 days median
6 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
2 Grassy Plains Road, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$8,663
- Property Taxes$586
- Insurance$566
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1955
- New Construction
- No/Resale
- Living Area
- 2,881 sq ft
- Below Grade
- 1,032 sq ft
Schools
- Elementary
- Kings Highway
- High
- Staples
Interior
- Heating
- Hot Water
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Gas CooktopWall OvenRange HoodRefrigeratorFreezerSubzeroDishwasherWasherDryerWine Chiller
- Basement
- FullSump PumpStorageFully FinishedGarage AccessInterior AccessWalk-out
- In-Law Apartment
- PossibleLower Level
Exterior & Lot
- Lot Size
- 1.11 acres
- Zoning
- AAA
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- In Ground Pool
- Construction
- ShingleStone
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- PorchCabanaDeckHot Tub
- Lot Description
- Fence - Full
Listing & Financials
- Property Taxes
- $7,029 / Annually
- Days on Market
- 62
- MLS #
- 24176436
- MLS Status
- Under Contract
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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 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 3:55 PM UTC.