366 Winslow Gray Rd

1,155 Sq. Ft.
$432 / Sq. Ft.
1,155
Sq. Ft.
$432
per Sq. Ft.

Description

Charming 1790s Antique Cape. This 3bedroom, 2bath Antique Cape was moved to its current location in the mid 1990s and set on a new, full foundation—offering the best of historic character with modern stability. The spacious living room welcomes you with extra-wide pine plank flooring, exposed beams, a pine paneled fireplace wall, chair rail detailing, and classic 12 over 12 windows that fill the space with natural light. A dining room (or den) features built-ins, exposed beams, and matching wide...Charming 1790s Antique Cape. This 3bedroom, 2bath Antique Cape was moved to its current location in the mid 1990s and set on a new, full foundation—offering the best of historic character with modern stability. The spacious living room welcomes you with extra-wide pine plank flooring, exposed beams, a pine paneled fireplace wall, chair rail detailing, and classic 12 over 12 windows that fill the space with natural light. A dining room (or den) features built-ins, exposed beams, and matching wide plank floors, creating a warm and flexible gathering space. The kitchen, rich with character thanks to exposed brick and beams, wide plank flooring, skylight, dedicated pantry, copper lantern fixtures, built-ins, fabulous soapstone sink, and a charming alcove perfect for a breakfast nook or cozy reading corner. A hallway with multiple closets and a full bath—complete with clawfoot tub and wide plank floors—round out the first floor. Upstairs, you’ll find three inviting bedrooms, all with wide

Listing Agents

  1. Jan Rodrigues

    Jan Rodrigues

    Alternative Listing Agent

    Compass

    jan.rodrigues@compass.com

    P: (774)-836-0501

Property Details for 366 Winslow Gray Road

Town
Yarmouth
Area
MA-Yarmouth
Architectural Style
Cape, Antique
Style
Cape, Antique
Garage Spaces
0
Open Parking Spaces
2.00
Parking Spaces Total
2

Open Houses

Saturday, May 2nd11:00 AM - 1:00 PM
LISTING UPDATED: 04/28/2026 10:16 PM

Property Details for 366 Winslow Gray Road

StatusPrice Changed
MLS #73494522
Days on Market28
Taxes$2,578 / year
HOA Fees-
Property TypeSingle Family
MLS TypeSingle Family / Single Family Residence
Year Built1800
CountyBarnstable County
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Building Information for 366 Winslow Gray Road

Stories-Year Built1800Building Size-Lot Size0.23 AC / 10,019 SF

Payment Calculator

$2,728 per month

30 year fixed, 6.46% Interest

Principal and Interest

$2,513

Property Taxes

$215

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 366 Winslow Gray Road

General Details
Property Details
  • Building Area Units: Square Feet
  • Living Area: 1155.0
  • SqFt with Basement: No
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Water View: No
  • Year Built Details: Approximate
  • Year Built Source: Public Records
Features
Interior Features
  • Num of Baths: 2.0
  • Num of Full Baths: 2
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 2.00
  • Bathrooms Total Integer: 2
  • FireplaceYN: Yes
  • Fireplaces: 1
  • Flooring: Wood
  • Primary Bath: No
  • SpaYN: No
Exterior Features
  • Exterior Features: Porch - Enclosed
  • Lot Description: Corner Lot
  • Patio And Porch Features: Porch - Enclosed
  • Roof Material: Shingle
  • Waterfront Features: Ocean, 1 to 2 Mile To Beach, Beach Ownership(Public)
Parking Features
  • Covered Spaces: .00
  • Garage: No
Utilities
  • Cooling: None
  • Cooling: No
  • Heating: Baseboard, Natural Gas
  • Heating: Yes
  • Sewer: Inspection Required for Sale
  • Water: Public
Property Information
Property Info
  • Year Round: Yes
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Disclosures: Property to be sold in as-is condition. The D-box requires replacement,and the Title V inspection has not yet been completed.
Tax Information
  • Tax ID: M:0058 B:00388 L:0000,2418128
  • Assessments: $364,100
  • Book: 20868
  • Tax Year: 2025
  • Zoning: res
Building / Association Information
Living Characteristics
  • Beds Total: 3
Other Building Characteristics
  • Foundation: Concrete Perimeter
Complex & Association Information
  • Adult Community: No

Property History for 366 Winslow Gray Road

DateEvent & SourcePriceAppreciation
Apr 28, 2026

Price Change

MLS PIN #73494522

$499,000
Apr 1, 2026

Listed (Active)

MLS PIN #73494522

$525,000
Mar 27, 2026

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22601023

$525,000
DateEvent & SourcePrice
04/28/2026

Price Change

MLS PIN #73494522

$499,000
04/01/2026

Listed (Active)

MLS PIN #73494522

$525,000
03/27/2026

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22601023

$525,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 366 Winslow Gray Road

Taxable ValueLand$147,900Additions$216,200Total$364,100
Tax Record2025$2,578 ($215 / month)
Home Facts
Beds3Baths2Total Finished SqFt1,155 SqFtAbove Grade Finished SqFt1,155 SqFtStories1Lot Size10,019 SqFtStyleSingle Family ResidenceYear Built1800CountyBARNSTABLEAPNYARM M:0058 B:00388 L:0000

Schools near 366 Winslow Gray Road

This home is within Dennis-Yarmouth School District.
Rating
School
Type
Grades
Distance
Public - K to 3
Public - 8 to 12
Public - 6 to 7
Public - PK to 3
Rating
School
Distance
Station Avenue Elementary School
PublicK to 3

Dennis-Yarmouth Regional High School
Public8 to 12

Dennis-Yarmouth Middle School
Public6 to 7

Marguerite E Small Elementary School
PublicPK to 3

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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366 Winslow Gray Road is a single family home for sale in Yarmouth, MA 02673. This property was listed for sale on March 27, 2026 by Compass, it's currently listed at $499,000. It has been on the market for a total of 28 days and was last sold on March 30, 2006. This listing's school district is Dennis-Yarmouth School District. Nearby schools include Station Avenue Elementary School, Dennis-Yarmouth Regional High School and Dennis-Yarmouth Middle School. 366 Winslow Gray Road is a 3-bed, 2-bath, 1,155 sqft single family home built in 1800.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.