249 Winslow Gray Rd

Off Market

249 Winslow Gray Rd

South Yarmouth MA 02673

520 sq. ft.

4792 sq. ft.

Single-Family

Last sold for $380,000

Serena LoPiccolo-Smith, last sold this property on 13 August 2026 after 111 days on market.

Overview

Imagine starting your day with a walk to the beach, coffee in hand as the sun rises, then returning home to a space that’s easy to enjoy and effortless to maintain. This 2-bedroom ranch offers comfortable single-level living with hardwood floors, a cozy fireplace, and a bright enclosed porch that expands your living space. Outside, the private, fenced backyard features a deck, garden area, outdoor shower, and an electrically equipped shed- perfect for entertaining, gardening, pets, or relaxing after a day by the water. Conveniently located with easy access to Route 6 and Route 28, shopping, dining, and both ocean and freshwater beaches, this home blends convenience with coastal charm. Whether you’re buying your first home, downsizing, or investing, this is your opportunity to own an affordable piece of Cape Cod. Seller is offering a $5,000 concession, providing a great opportunity to install mini-splits for added comfort.

Features

2 bedrooms

1 bathroom

2 carspaces

2 open car spaces

520 sq. ft. floor area

4792 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 2 bedroom single-family properties sold in South Yarmouth over the last 12 months, the estimated median property value of 249 Winslow Gray Rd is $550.5k.

Median value

$550.5k

Estimated value range

$370k - $689k

Median days on market

Estimated value trend

11%

increase over the last 12 months

Average days on market is based on recent, comparable sales in South Yarmouth. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 249 Winslow Gray Rd

2026

Sold

$380,000

13 Aug 2026 by Serena LoPiccolo-Smith, of Keller Williams Realty - Cape Cod and the Islands

2019

Sold

$184,900

28 Feb 2019 by Steven Putnam

2018

Sold

$184,900

16 Mar 2018 by Steven Putnam, of Today Real Estate, Inc.

Happy sellers in South Yarmouth

We have insufficient information to provide an overview of customer satisfaction for South Yarmouth. Viewing the agent profiles, reviews and sales for South Yarmouth can provide insights for this location.

Local market activity for 2 bedroom single-family properties in South Yarmouth

In the last 12 months, 42 two-bedroom single-family properties similar to 249 Winslow Gray Rd, have been sold.

This represents a 3% increase in two-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in South Yarmouth for a market analysis.

Jessica Larsen

at Keller Williams Realty - Cape Cod and the Islands

(10 reviews)

Get a market analysis

Van Martins

at Weichert, REALTORS? - Donahue Partners

(20 reviews)

Get a market analysis

Karen Lilly

at Property Cape Cod

(9 reviews)

Get a market analysis

Christopher Manning

at William Raveis Real Estate - Yarmouth Port

(46 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in South Yarmouth

Jessica Larsen

Jessica Larsen is a recommended agent for South Yarmouth. They have 1 local sale and collected 2 local reviews across the last 12 months.

5 (10 reviews)
2 Reviews in South Yarmouth
1 Sale in South Yarmouth

View profile

Van Martins

Van Martins is a recommended agent for South Yarmouth. They have collected 2 local reviews across the last 12 months.

5 (20 reviews)
2 Reviews in South Yarmouth

View profile

Karen Lilly

Karen Lilly is a recommended agent for South Yarmouth. They have 4 local sales and collected 1 local review across the last 12 months.

5 (9 reviews)
1 Review in South Yarmouth
4 Sales in South Yarmouth

View profile

Christopher Manning

Sellers who recommend Christopher Manning have praised them for being local expert, responsive, detail-oriented, clear communication, resourceful, great negotiation, and well-prepared