18 Winfield Way

Osterville, MA 02655

$2,999,000
Price
3
Beds
3,055 Sq. Ft.
$982 / Sq. Ft.
3,055
Sq. Ft.
$982
per Sq. Ft.
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Location
Front of Home
Exterior
Kitchen
Kitchen
Kitchen
Dining Area
Living Room
Living Room
Living Room
Living Room
Bedroom
Full Bath
Office
Family Room (Unheated)
Family Room (Unheated)
Garage
Garage
Mud Room
Hallway
Hallway
Bedroom
Bedroom
Full Bath
Full Bath
Bedroom
Bedroom
Bonus Room
Full Bath (unheated)
Exterior
Yard
Ariel
Ariel
Ariel
Ariel
Ariel
Ariel
Ariel
Ariel
42-web-or-mls-_DSC5358
43-web-or-mls-_DSC5359
44-web-or-mls-_DSC5360
45-web-or-mls-_DSC5361

Description

Nestled near downtown Osterville with picturesque views and access to West Bay, this inviting home offers the perfect blend of location, charm, and opportunity. Tucked away on a private lane, this 3-bedroom, 3 full bath property presents a rare chance to own in one of Osterville's most sought-after areas. Set on a generous 0.87-acre lot, the home feels like your own private Cape Cod retreat. This beautiful property includes a footpath (easement) to West Bay to enjoy gorgeous sunsets all summer long....Nestled near downtown Osterville with picturesque views and access to West Bay, this inviting home offers the perfect blend of location, charm, and opportunity. Tucked away on a private lane, this 3-bedroom, 3 full bath property presents a rare chance to own in one of Osterville's most sought-after areas. Set on a generous 0.87-acre lot, the home feels like your own private Cape Cod retreat. This beautiful property includes a footpath (easement) to West Bay to enjoy gorgeous sunsets all summer long. Inside, you'll find timeless character throughout, including wide pine floors, custom built-ins, and a warm, nostalgic ambiance that captures the essence of classic Cape living. There is an attached oversized 2-car garage with an additional storage space for your kayaks and canoes. Whether you're looking to enjoy it as-is or bring your vision to life, this property is full of possibilities in an unbeatable setting.
  1. Listed by Nikki DeFrancesco • SilverStone Capeside Realty Group

Property Details for 18 Winfield Way

Village
Osterville
School District
Barnstable
Style
Cape
Waterview Type
Bay/Harbor
Waterfront
No
Waterview
Yes
Num Parking Spaces
3.00
FEMA 100 Yr Flood Plain
X

Open Houses

Saturday, Apr 4th11:00 AM - 1:00 PM
PublicView contact
LISTING UPDATED: 03/29/2026 07:21 PM

Property Details for 18 Winfield Way

StatusActive
MLS #22600993
Days on Market6
Taxes$22,271 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Single Family Residence
Year Built1953
Lot Size0.87 AC / 37,897 SF
CountyBarnstable County
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Location

Listing Courtesy of SilverStone Capeside Realty Group, Nikki DeFrancesco
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Building Information for 18 Winfield Way

Stories2Year Built1953Building Size-Lot Size0.87 AC / 37,897 SF

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$16,410 per month

30 year fixed, 6.11% Interest

Principal and Interest

$14,555

Property Taxes

$1,856

HOA Dues

$0

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Property Information for 18 Winfield Way

Summary
Location and General Information
  • Directions to Property: Eel River Road to Winfield Lane. First house on right. GPS Directions are 18 Winfield Lane Barnstable.
  • Convenient To:Conservation Area: Yes
  • Convenient To:Golf Course: Yes
  • Convenient To:Marina: Yes
  • Convenient To:Shopping: Yes
  • Convenient To:Convenient to Water Body 1: West Bay
  • Location Description:South of Route 28: Yes
  • Region: Mid-Cape
  • County: Barnstable
  • City Postal ID: 02655
  • Street Number: 18
  • MLSAreaMajor: Barnstable
Parking
  • Garage: Yes
  • Garage Description:Attached: Yes
  • Parking Description:Off-Street: Yes
  • Parking Description:Unpaved Driveway: Yes
  • Carport: No
  • Garage Spaces: 2.00
Taxes and HOA Information
  • Tax Year: 2025
  • Annual Assoc Fee: $0
  • Annual Taxes: $22,271
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Property
Lot Information
  • Zoning: R
  • Tax ID: OSTE M:116 L:103
  • Lot Size Source: Field Card
  • TopographyLot Desc:View: Yes
  • Land Use: 101 - Residential, single family
  • Lot Size Square Feet: 37897
  • Sqft Total: 3055
  • Field Card SqFt: 3055
  • Lot Size Units: Acres
  • Living Area: 3055.0
  • General Property Info:Leased Land: No
Property and Assessments
  • Total Assessment: $2,752,900
  • Land Assessments: $2,177,700
  • Building Assessments: $575,200
  • Other Assessments: $0
  • Renovated: No
  • Flood Ins Required: Not Verified
  • Lead Base Paint: Unknown
  • Year Round: Yes
  • Landlord Pays:Sewer: Private Sewerage
  • Year Built Desc:Actual: Yes
  • Property Type: Residential, Single Family Residence
  • Property Subtypes: Single Family Residence
  • Year Built Numeric: 1953
  • Construction Materials: Shingle
  • Property Type: Residential
  • Property Attached: No
  • Senior Community: No
Utilities
  • Cooling: None
  • Fuel Type:Electric: Circuit Breakers
  • Fuel Type:Natural Gas: Yes
  • Hot Water:Tank: Yes
  • Hot Water Source:Natural Gas: Yes
  • Sewer:Private Sewer: Yes
  • Water:Town Water: Yes
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Exterior Features: Other, Private Yard
  • Miles to Beach: .1 - .3
  • Private Dock: No
  • Foundation: Block
  • Roof Description: Asphalt
  • Siding Description:Shingle: Yes
  • Waterfront Description: West
  • Private Pool YN: No
  • General Property Info:Mi. to Beach Comments: Deeded neighborhood path to West Bay
Interior Features
  • Basement Description:Interior Access: Yes
  • Basement Description:Partial: Yes
  • Floors: Wood
  • Heating: Forced Air, Natural Gas
  • Interior Features: Eat-in Kitchen, Mud Room, Attic Storage
  • Basement: Yes
  • Fireplace: Yes
  • Sep Living Qtrs Info: Beds: 0
  • Total Rooms: 7
  • Baths Total: 3
  • Baths Full: 3
  • Baths Half: 0
  • Bedrooms Total: 3
  • Total Floor Plans Count: 4
  • RoomsTotal: 7
  • Bathrooms Total (Decimal): 3.00
  • Bathrooms Total (Notational): 3.00
  • Cooling: No
  • Fireplace Features: Living Room
  • Fireplaces Total: 1
  • Heating: Yes
  • Stories: 2
  • Laundry Features: First Floor
  • General Property Info:Stories: 2
Living Room
  • Living Room: Yes
  • Living Room:Living Room Length: 17'8
  • Living Room:Living Room Width: 30'
  • Living Room:Living Room Level: First Floor
  • Living Room:Flooring: Wood
Kitchen
  • Kitchen: Yes
  • KitchenDining Combo:Yes: Yes
  • Kitchen:Kitchen Length: 14'5
  • Kitchen:Kitchen Width: 15'11
  • Kitchen:Kitchen Level: First Floor
  • Kitchen:Flooring: Vinyl
Master Bedroom
  • Master Bedroom: Yes
  • Master Bedroom: Master Bedroom Length: 19'5
  • Master Bedroom: Master Bedroom Width: 18'2
  • Master Bedroom Level: Second Floor
  • Master Bedroom: Closet: Yes
Bedroom 2
  • Bedroom 2: Yes
  • Bedroom 2:Bedroom 2 Length: 13'5
  • Bedroom 2:Bedroom 2 Width: 12'5
  • Bedroom 2:Bedroom 2 Level: First Floor
  • Bedroom 2:Flooring: Wood
  • Bedroom 2: Closet: Yes
Bedroom 3
  • Bedroom 3: Yes
  • Bedroom 3:Bedroom 3 Length: 15'6
  • Bedroom 3:Bedroom 3 Width: 18'2
  • Bedroom 3:Bedroom 3 Level: Second Floor
  • Bedroom 3:Flooring: Wood
  • Bedroom 3: Closet: Yes
Foyer
  • Foyer: Yes
  • Foyer:Flooring: Wood
Other Room 1
  • Other Room 1:Room Type: Family Room
  • Other Room 1:Width: 23'5
  • Other Room 1:Length: 20'2
  • Other Room 1:Level: First Floor
Other Room 2
  • Other Room 2:Room Type: Home Office
  • Other Room 2:Level: First Floor
Other Room 3
  • Other Room 3:Room Type: Studio
  • Other Room 3:Width: 17'7
  • Other Room 3:Length: 8'11
  • Other Room 3:Level: Second Floor

Property History for 18 Winfield Way

DateEvent & SourcePriceAppreciation
Mar 26, 2026

Listed (Active)

MLS PIN #73492325

$2,999,000—
Mar 25, 2026

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22600993

$2,999,000—
DateEvent & SourcePrice
03/26/2026

Listed (Active)

MLS PIN #73492325

$2,999,000
03/25/2026

Listed (Active)

Cape Cod & Islands Multiple Listing Service #22600993

$2,999,000

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

Public Records for 18 Winfield Way

Taxable ValueLand$2,177,700Additions$575,200Total$2,752,900
Tax Record2025$22,271 ($1,856 / month)
Home Facts
Beds3Baths2Total Finished SqFt3,055 SqFtAbove Grade Finished SqFt3,055 SqFtStories2Lot Size37,897 SqFtStyleSingle Family ResidenceYear Built1953ZoningRCountyBARNSTABLEAPNOSTE M:116 L:103

Schools near 18 Winfield Way

This home is within Barnstable School District.
Rating
School
Type
Grades
Distance
West Villages Elementary School
Public - K to 3
Barnstable United Elementary School
Public - 4 to 5
Barnstable Intermediate School
Public - 6 to 7
Barnstable High School
Public - 8 to 12
Rating
School
Distance
West Villages Elementary School
PublicK to 3

Barnstable United Elementary School
Public4 to 5

Barnstable Intermediate School
Public6 to 7

Barnstable High School
Public8 to 12

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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More information about 18 Winfield Way, Osterville, MA 02655

18 Winfield Way is a single family home for sale in Osterville, MA 02655. This property was listed for sale on March 25, 2026 by SilverStone Capeside Realty Group, it's currently listed at $2,999,000. This listing's school district is Barnstable School District. Nearby schools include West Villages Elementary School, Barnstable United Elementary School and Barnstable Intermediate School. 18 Winfield Way is a 3-bed, 3-bath, 3,055 sqft single family home built in 1953.

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.

Listing Courtesy of SilverStone Capeside Realty Group, Nikki DeFrancesco

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Compass includes, at minimum, the name of the listing agent and broker attribution assigned by the listing broker. Neither the listing firm nor Compass shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. The Broker providing this data believes it to be correct but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.