3-bed, 2-bath single-family home in Osterville

Active$795,000

MLS® Listing#22604019 · Single Family Residence · Listed Aug 14, 2026

111 Westwind Circle, Osterville, MA 02655

Barnstable County

Showing 5 of 39 photos

3Beds

2Baths

1,248Sq Ft

1985Year built

0.5Acre lot

1Garage

Description

Welcome to 111 W Wind Cir, a beautifully renovated single-family home nestled in the heart of Osterville, MA. This stunning 3-bedroom, 2-bathroom property has been thoughtfully updated and offers comfortable living across 1,248 square feet of well-designed space. Step inside to find a bright and airy layout with six inviting rooms, perfect for relaxing or entertaining. The newly renovated kitchen boasts modern updates and plenty of space to cook and gather. Both bathrooms have been tastefully updated to offer a fresh, contemporary feel. Cozy up by the charming fireplace in the living area, creating a warm and welcoming ambiance throughout the seasons. Outside, enjoy the serene surroundings from your private deck - ideal for morning coffee, evening dinners, or simply unwinding in nature. The home offers the convenience of air conditioning to keep you comfortable year-round. A walk out basement offers exceptional additional living space and is tastefully finished. Parking will never be a concern with an included garage and additional parking spaces. Whether you're looking for a full-time residence or a seasonal retreat, this property offers both comfort and practicality in a fant

Full description online — scan the code for the complete listing.

Property information

Property type: Residential
Sub-type: Single Family Residence
Year built: 1985
Living area: 1,248 Sq Ft
Lot size: 0.5 acres
Garage spaces: 1
Annual taxes (2026): $3,833
HOA fee: None
Price / Sq Ft: $637
Days on market: 44

Features

Appliances: Dishwasher · Gas Range · Refrigerator · Water Heater
Cooling: Central Air
Heating: Natural Gas
Flooring: Hardwood · Tile · Carpet
Parking: Direct Access · Garage Door Opener · Driveway · Paved
Patio: Deck
Lot: On Golf Course · Near Golf Course
Roof: Asphalt
Construction: Clapboard · Shingle Siding
Exterior: Outdoor Shower

$795,000List price

3Beds

2Baths

1,248Sq Ft

1985Year built

0.50Acre lot

1Garage

6 weeks agoOn market

$795,000

111 Westwind Circle

Osterville, MA 02655

Active

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EXIT Cape RealtyCotuit, MACall

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Description

Property Information

Property type: Residential
Sub-type: Single Family Residence
Style: Ranch
Year built: 1985
Living area: 1,248 Sq Ft
Lot size: 0.50 acres
Garage spaces: 1
Zoning: RC
Days on market: 44
MLS^® Listing#: 22604019

Property Features

Exterior: Outdoor Shower
Appliances: Dishwasher · Gas Range · Refrigerator · Water Heater
Cooling: Central Air
Heating: Natural Gas
Flooring: Hardwood · Tile · Carpet
Basement: Finished · Full
Parking: Direct Access · Garage Door Opener · Driveway · Paved · Attached
Patio: Deck
Lot features: On Golf Course · Near Golf Course
Construction: Clapboard · Shingle Siding
Roof: Asphalt
Sewer: Septic Tank
Water source: Public

Financial Details

HOA: None
Annual taxes: $3,833Tax year 2026
Assessed value: $563,700
Parcel number: OSTE M:0121 B:0011 L:0036

Directions

Rte 28 to south on Old East Osterville Rd to right on West Wind Circle

Listing Courtesy: Compass Massachusetts, LLC - 508-776-1971

Presented by: W&W Boston/Cape Cod Connection

The data relating to real estate for sale on this site comes from the Broker Reciprocity of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than the brokerage firm owning this website are marked with the IDX Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor the brokerage firm owning this website shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. 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.

Last Updated: 2026-08-14T00:00:00.000Z

Osterville Market Statistics

How this home compares to 38 active listings in Osterville, MA

	Osterville median	This listing
Median listing price	$2,687,500	$795,000
Median days on market	111	44
Median Sq Ft	2,903	1,248
Median price / Sq Ft	$804	$637

Market statistics compiled from active EXIT Realty® and MLS listings in Osterville, MA.

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Explore commute times from 111 Westwind Circle, Osterville, MA 02655.

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Similar Home Values

Comparable nearby listings and their asking prices.

Address	Price	Beds	Baths	Sq Ft
111 Westwind, Barnstable, MA	$795,000	3	2	1,248
114 King Arthur Drive, Osterville, MA	$724,000	3	2	1,426
114 King Arthur Dr, Barnstable, MA	$724,000	3	2	1,426
5 Briar Patch Road, Osterville, MA	$875,000	3	2	1,497

Connect with a Local Real Estate Expert

Caio Silva
REALTOR
EXIT Cape Realty
Sharon Barrows
REALTOR
EXIT Cape Realty
Lisa Eaton
REALTOR
EXIT Cape Realty
Anthony Bartolomei
REALTOR
EXIT Cape Realty
Heather Brigham
Sales Representative
EXIT Cape Realty
Dave Harris
Franchisee, Broker of Record
EXIT Cape Realty

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. 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, leasing or renting 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, leasing or renting. MLS Property Information Network, Inc. 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. Copyright ©2026 MLS Property Information Network, Inc. All Rights Reserved.

Description

Property Information

Property Features

Financial Details

Directions

Osterville Market Statistics

Commute Calculator

More homes to consider

111 WestwindBarnstable, MA 02655#73565006

114 King Arthur DriveOsterville, MA 02655#22602806

114 King Arthur DrBarnstable, MA 02601#73534191

5 Briar Patch RoadOsterville, MA 02655#22600998

23 & 27 Swift AvenueOsterville, MA 02655#22604426

Similar Home Values

Connect with a Local Real Estate Expert

Caio Silva

Sharon Barrows

Lisa Eaton

Anthony Bartolomei

Heather Brigham

Dave Harris

Osterville Market Statistics

More homes to consider

111 WestwindBarnstable, MA 02655#73565006

114 King Arthur DriveOsterville, MA 02655#22602806

114 King Arthur DrBarnstable, MA 02601#73534191

5 Briar Patch RoadOsterville, MA 02655#22600998

23 & 27 Swift AvenueOsterville, MA 02655#22604426

Similar Home Values