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$699,000 Sale Pending

  • For Sale
  • Pending
  • Duplex
  • 6 Beds
  • 2 Full Baths
  • 2,580 Sq. Ft.
  • 0.17 Acres
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6 Bedroom Duplex. Unique opportunity to purchase a large investment in a very convenient location which features 6 bedrooms. 3 level split cape design offers 3 floors and 10 rooms. Good condition but could use updating/refresh. Upper unit is 4 bedrooms and lower unit has 2 bedrooms with expansion possibilities through previous lower level stairwell that has been removed and closed. Both units have separate utilities paid by tenants. Current rents are under market to long term tenants. The year round income of $4,400/month of which $2,000 is from the two bedroom and $2,400 is from the 4 bedroom. Good tenants who are currently tenant at will. Buyer can Keep them in place or seller will assist in relocation prior to close. OR, Buyer could live in one side and rent the other in order to subsidize your costs. Good size bedrooms, living areas and kitchens, nice fenced yard, separate utilities, FHW/gas heat, nearly 2000 square feet of living area.Broker/Owner. New 6 bedroom Title V has been designed to meet new codes and will be installed prior to sale. Some notice is requested. Seller is cooperating with Buyer's Agents.

Full Property Details for 299 Winslow Gray Rd

General

  • Price: $699,000
  • Taxes: $2,951 (2024)
  • Status: Pending
  • Type: Duplex
  • Source: CCI
  • MLS ID: 22505845
  • Updated: 12/30/2025
  • Added to Site: 37 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: High Speed Internet, Hi-Speed Internet, HU Cable
  • Appliances: Gas Water Heater, Water Heater, Refrigerator, Gas Dryer
  • Flooring: Carpet

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 6

Other Rooms

  • Laundry: Washer Hook-up

Parking

  • Total Spaces: 5

Location

  • Area: Hyannis Park
  • County: Barnstable
  • Driving Directions: Buck island to Winslow Gray. Right on Winslow Gray, second house on the right.

Heating & Cooling

  • Cooling Type: Other

Utilities

  • Sewer: Septic Tank

Structural Information

  • Architectural Style: Tri-Level
  • Construction: Shingle Siding
  • Exterior Const.: Shingle Siding
  • Basement Desc.: Bulkhead Access, Partial, Full
  • Roof: Pitched, Shingle
  • Stories/Levels: 3
  • Square Feet: 2,580
  • Sq. Ft. Source: Estimated
  • Year Built: 1970
  • Property Condition: Approximate

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,405
  • Lot Size Source: Field Card
  • Frontage: Public
  • Street/Road Desc.: Paved
  • Zoning: R1

Financial Considerations

  • Price Per Sq. Ft.: $270
  • Assessment Amount: $399,800
  • Land Assmt: $126,400
  • Tax Amount: $2,951
  • Tax Year: 2024

Disclosures and Reports

  • Special Conditions: Broker-Agent/Owner
  • Property ID: YARM M:0049 B:00089 L:0000

Listed by Oceanside Realty Group, Nile A Morin

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Listing agent

— 299 Winslow Gray Rd —

  • Nile A Morin

    Oceanside Realty Group

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 299 Winslow Gray Rd

School District:Dennis-Yarmouth School District
NameGradesDistance
Marguerite E Small Elementary School
440 Higgins Crowell Rd, Yarmouth, MA 02673
PK-31.6 mi
Station Avenue Elementary School
276 Station Avenue, Yarmouth, MA 02664
K-31.6 mi
Dennis-Yarmouth Intermediate School
286 Station Avenue, Yarmouth, MA 02664
4-51.7 mi
Dennis-Yarmouth Regional High School
210 Station Avenue, Yarmouth, MA 02664
9-121.6 mi
Dennis-Yarmouth Middle School
286 Station Avenue, Yarmouth, MA 02664
6-81.7 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 299 Winslow Gray Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/12/2025
Listed
$699,000
64.47%
MLS
12/08/2021
Sold
$425,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 299 Winslow Gray Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,228
9%
$455,900
14%
2024
$2,951
-6%
$399,800
4%
2023
$3,130
-11%
$386,000
—
2022
$3,535
-6%
$385,100
-2%
2021
$3,765
32%
$393,800
39%
2020
$2,843
11%
$284,300
15%
2018
$2,554
10%
$248,200
7%
2017
$2,332
4%
$232,700
3%
2016
$2,246
-9%
$225,100
-8%
2015
$2,461
2%
$245,100
3%
2014
$2,422
—
$237,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 299 Winslow Gray Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Oceanside Realty Group, Nile A Morin

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299 Winslow Gray Road, Yarmouth, MA 02673 (MLS# 22505845) is a Duplex property with 6 bedrooms and 2 full bathrooms. 299 Winslow Gray Road is currently listed for $699,000 and was received on December 12, 2025. Want to learn more about 299 Winslow Gray Road? Do you have questions about finding other Duplex real estate for sale in West Yarmouth? You can browse all West Yarmouth real estate or contact a Coldwell Banker agent to request more information.

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