18 Winfield Way Osterville, MA $ 2,999,000
18 Winfield Way
$ 2,999,000
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18 Winfield Way

Osterville, MA, 02655
$ 2,999,000
Bedrooms3 Baths3.0 Sq 3,055

Monthly Estimate*

$ 18,465

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Single Family Home for sale in Osterville, MA

for $2,999,000 with 3 bedrooms and 3 full baths. This 3,055 square foot home was built in 1953 on a lot size of 0.87.

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 deeded private neighborhood walkway 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.

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Single Family Active

Price

$ 2,999,000

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 22,271

Style

Cape Cod

Lot Size

0.87

Year Built

1953

Town/City

Osterville

County/Region

Barnstable

MLS | Web ID

22600993

Features
General
Sewer Private Sewer
Cooling None
Roof Asphalt
Appliances Gas Water Heater
Zoning R
Garage Spaces 2
Architectural Style Cape Cod
Construction Materials Shingle Siding
Year Built 1953
Stories Count 2
Township Barnstable
Property Subtype Single Family Residence
Tax Year 2025
County Barnstable
New Construction false
Property Type Residential
HOA false
Attached Garage true
Garage Y/N true
Total Rooms 7
Full Baths 3
Status Active
Directions Eel River Road to Winfield Lane. First house on right. GPS Directions are 18 Winfield Lane Barnstable.
City Osterville
High School District Barnstable
Lot Size Units Acres
Lot Size Square Feet 37897
Carport Y/N false
Property Attached Y/N false
Land Lease Y/N false
Tax Annual Amount 22271
Showing Instructions Call/ Text listing agent 774-271-1844
Home Warranty Y/N false
Property Condition Actual
Virtual Tour https://my.matterport.com/show/?m=TpaARCyioWD&brand=0&mls=1& https://my.matterport.com/show/?m=TpaARCyioWD&brand=0&mls=1&
Building Area Units Square Feet
Primary Bedroom Level Second
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District Barnstable
Elementary School District Barnstable
Tax Assessed Value 2752900
Waterview Y/N Bay/Harbor
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Interior
Interior Amenities Mud Room
Basement Interior Entry Partial
Flooring Vinyl Wood
Total Fireplaces 1
Kitchen Level First
Air Conditioning Y/N false
Heating Y/N true
Window Features Bay/Bow Windows
Fireplace Y/N true
Half Baths 0
Total Bedrooms 3
Living Room Level First
Below Grade Finished Area Unit Type Square Feet
Kitchen Features Kitchen
Total Baths 3
Living Room Features Built-in Features Living Room
Bedroom 3 Features Bedroom 3 Wet Bar Closet
Bedroom 2 Features Bedroom 2 Closet
Kitchen Area 229.465277777
Kitchen Description Flooring: Vinyl
Kitchen Length 14.416666666
Kitchen Width 15.916666666
Primary on Main 166.590277777
Second Bedroom Length 13.416666666
Second Bedroom Width 12.416666666
Bedroom 3 Area 281.583333333
Bedroom 3 Length 15.5
Bedroom 3 Width 18.166666666
Living Room Area 530
Living Room Length 17.666666666
Living Room Width 30
Primary Bedroom Area 352.736111111
Primary Bedroom Features Closet
Primary Bedroom Length 19.416666666
Primary Bedroom Width 18.166666666
Bedroom 3 Level Second
Second Bedroom Level First
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Exterior
Lot Features Conservation Area Near Golf Course Shopping Marina South of Route 28
Total Parking 3
Lot Size Area 0.87
Foundation Details Block
Building Area Total 3055
Lot Size Acres 0.87
Road Surface Type Dirt
Lot Size Source Field Card
Waterfront Y/N false
Road Frontage Type Dead End Street Private Road
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* Excluded Features
List By
Nikki DeFrancesco

Listing Agent

Silverstone Capeside Realty Group

Broker

nikki@silverstonerg.com

Email

Affordability Calculator

$20,321
Per Month
91%
9%
0%
Monthly Principal & Interest
$18,465
Monthly Property Taxes
$1,856
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4795841 Elementary School
4795840 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
3/26/2026$2,999,000 Listed Price

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18 Winfield Way, Osterville, MA, 02655 is a Single Family Home for sale at $2,999,000 with 3,055 sqft and a lot size of 0.87. 18 Winfield Way has 3 bedrooms, 3.0 baths, and was built in 1953. The property's zip code is 02655 which is in Osterville, MA