Is a car needed in Osterville, Barnstable, MA?

As of early 2026, 91% of users say car is needed

Is parking easy in Osterville, Barnstable, MA?

As of early 2026, 83% of users say parking is easy

Is there wildlife in Osterville, Barnstable, MA?

As of early 2026, 78% of users say there's wildlife

Are yards well-kept in Osterville, Barnstable, MA?

As of early 2026, 76% of users say yards are well-kept

Is Osterville, Barnstable, MA quiet?

As of early 2026, 73% of users say it's quiet

Is Osterville, Barnstable, MA dog-friendly?

As of early 2026, 71% of users say it's dog friendly

Are neighbors friendly in Osterville, Barnstable, MA?

As of early 2026, 63% of users say neighbors are friendly

Does Osterville, Barnstable, MA show holiday spirit?

As of early 2026, 63% of users say there's holiday spirit

Do residents of Osterville, Barnstable, MA plan to stay at least 5 years?

As of early 2026, 59% of users say they plan to stay for at least 5 years

Would people walk alone at night in Osterville, Barnstable, MA?

As of early 2026, 57% of users say people would walk alone at night

Do kids play outside in Osterville, Barnstable, MA?

As of early 2026, 50% of users say kids play outside

Is Osterville, Barnstable, MA walkable to restaurants?

As of early 2026, 49% of users say it's walkable to restaurants

Are there community events in Osterville, Barnstable, MA?

As of early 2026, 40% of users say there are community events

Is Osterville, Barnstable, MA walkable to grocery stores?

As of early 2026, 38% of users say it's walkable to grocery stores

Does Osterville, Barnstable, MA have sidewalks?

As of early 2026, 27% of users say there are sidewalks

Are the streets well-lit in Osterville, Barnstable, MA?

As of early 2026, 25% of users say streets are well-lit

FOR SALE

0.38 ACRES

295 Westwind Circle
Osterville, MA 02655

Osterville

2 Beds
2 Baths
1,808 sqft (on 0.38 acres)

$649,000

Est. Mortgage $3,714/mo*

Get Pre-Qualified

$649,000

Est. Mortgage $3,714/mo*

Get Pre-Qualified

2 Beds

2 Baths

1,808 sqft

(on 0.38 acres)

We estimate this home will sell faster than 87% nearby.

Home Highlights

Parking

Garage

Climate Control

Heating only

Price/Sqft

$359

Listed

28 days ago

Local Information

Map ViewExplore the area around 295 Westwind Circle.
Schools2 Elementary Schools2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

About this House

Nestled in a neighborhood south of Route 28, this charming Osterville ranch offers the perfect blend of classic Cape Cod character & modern comfort. Before you even step inside, a private front patio welcomes you, the ideal spot for a pair of Adirondack chairs. The interior has been thoughtfully reimagined for contemporary living w/ a bright open concept layout. Upon entry, you're greeted by a sun-drenched dining area that sets an inviting tone w/ its cathedral ceilings, a skylight & sliders that lead out to a freshly painted deck. The kitchen offers a central island providing a natural gathering spot before transitioning into the living room. Anchored by a fireplace this central living space feels remarkably open & airy. The home features 2 bedrooms, including a primary en-suite. Brand-new carpeting flows throughout the entire home, paired w/ an abundance of storage space to keep everything perfectly organized. The living space extends to a walkout basement, providing a versatile layout that easily adapts to your specific needs. This lower level opens to a private, level yard. This Osterville gem is ready for you and its next chapter to begin.

We estimate this home will sell faster than 87% nearby.

Home Details for 295 Westwind Circle

Interior Features
Interior Details Basement: Interior Entry,FullNumber of Rooms: 4
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout Living Area: 1808 Square Feet
Appliances & Utilities Appliances: Gas Water Heater
Heating & Cooling Heating: Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Hot Water
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls Flooring: Other, Carpet
Levels, Entrance, & Accessibility Stories: 1Floors: Other, Carpet

Exterior Features
Exterior Home Features Roof: AsphaltFoundation: PouredNo Private Pool
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1Has a GarageParking Spaces: 1Parking: Garage
Frontage Road Frontage: PublicRoad Surface Type: PavedNot on Waterfront
Water & Sewer Sewer: Septic Tank

Days on Market
Cumulative Days on Market: 12Days on Market: 28

Property Information
Year Built Year Built: 1985
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building Construction Materials: Clapboard, Shingle SidingNot a New ConstructionNot Attached PropertyDoes Not Include Home Warranty
Property Information Condition: ActualParcel Number: OSTE M:0121 B:0011 L:0047

Price & Status
Price List Price: $649,000Price Per Sqft: $359

Active Status
MLS Status: Active

Location
Direction & Address City: Osterville
School Information Elementary School District: BarnstableJr High / Middle School District: BarnstableHigh School District: Barnstable

Agent Information
Listing Agent Listing ID: 22603216

Building
Building Area Building Area: 1808 Square Feet

HOA
No HOA

Lot Information
Lot Area: 0.38 acres

Listing Info
Special Conditions: None

Miscellaneous
BasementMls Number: 22603216Showing Requirements: Call Listing Agent, Yard Sign

Last check for updates: about 17 hours ago

Listing courtesy of Cindy Crawford, (508) 737-1481

Compass Massachusetts, LLC

Ryan Benoit, (508) 776-0233

Kinlin Grover Compass

Source: CCIMLS, MLS#22603216

Also Listed on MLS PIN, MLS PIN, CCIMLS.

Market trends in Barnstable

Last updated June 2026

Avg. sale price

$702K

$29.31KMoM

Sale-to-List Price

98.2%

0.1%MoM

Price per sq ft

$442

$11MoM

Available listings

366

23MoM

Price History for 295 Westwind Circle

Date	Price	Event	Source
07/01/2026	$649,000	Listed For Sale	CCIMLS #22603216

03/02/1995	$120,000	Sold	N/A
Recording Date 03/02/1995 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$4,245
Assessment	$524,700

Home facts updated by county records

Comparable Sales for 295 Westwind Circle

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
40 Gunstock Road, Osterville, MA	0.11	Single-Family Home	$690,000	09/16/25	3	2	1,830
55 Seth Goodspeed Way, Osterville, MA	0.22	Single-Family Home	$415,000	11/04/25	2	2	1,040
31 Galahad Circle, Osterville, MA	0.09	Single-Family Home	$540,000	04/15/26	3	3	1,940
17 Avalon Cir, Barnstable, MA	0.12	Single-Family Home	$611,500	11/06/25	3	1.5	1,316
17 Avalon Circle, Osterville, MA	0.12	Single-Family Home	$611,500	11/06/25	3	1.5	1,316
40 Gunstock Rd, Barnstable, MA	0.11	Single-Family Home	$690,000	09/16/25	3	2	1,330
31 Galahad Cir, Barnstable, MA	0.10	Single-Family Home	$540,000	04/15/26	4	3	1,940
64 Falling Leaf Ln, Barnstable, MA	0.44	Single-Family Home	$850,000	05/07/26	2	2	1,667
64 Falling Leaf Lane, Osterville, MA	0.44	Single-Family Home	$850,000	05/07/26	2	2	1,667
51 Falling Leaf Ln, Barnstable, MA	0.48	Single-Family Home	$975,000	07/02/26	2	2	2,010

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OFF MARKET
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 295 Westwind Circle.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Osterville

63 Homes For You
Buy: $600k - $12.3m

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Osterville

At least 22 Trulia users voted on each feature.

91 % Say car is needed
83 % Say parking is easy
78 % Say there's wildlife
76 % Say yards are well-kept
73 % Say it's quiet
71 % Say it's dog friendly
63 % Say neighbors are friendly
63 % Say there's holiday spirit
59 % Say they plan to stay for at least 5 years
57 % Say people would walk alone at night
50 % Say kids play outside
49 % Say it's walkable to restaurants
40 % Say there are community events
38 % Say it's walkable to grocery stores
27 % Say there are sidewalks
25 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Jacqueline Hicks
Resident
4mo ago
"This area lacks decent public transportation. Having a car is extremely helpful. The is the bus system but it isn’t that reliable and it doesn’t have lots of stops and routes so one has to walk a distance to get to path of bus"
0
Flag
Trulia User
Resident
4y ago
"moderate traffic at regular business hours, otherwise VERY easy travel, and safe drivers on the road "
0
Flag
Purplevelvet917
Resident
7y ago
"The bus goes by only once an hour each way. A car is helpful. Summer traffic make the commute slow so allow for extra time."
1
Flag
Joshtweaver
Resident
7y ago
"Very friendly upscale area with beautiful scenery. Great for a summer vacation. Very peaceful. Can get quiet at times so if you’re looking for excitement you may want to look elsewhere. "
14
Flag
Joshtweaver
Resident
7y ago
"Great area for kids to grow up or spend the summers in. Very friendly community feel. Safe to walk around in. "
0
Flag
Ashleighmaeb
Resident
7y ago
"An hour and a half drive back to Boston if your lucky. You can fly which is way more convenient but driving is the cheapest. It’s our summer home so we don’t care that much since we’re down all summer."
2
Flag
Hudson
Resident
8y ago
"I’ve lived in this neighborhood for over 3 years and love it. The neighbors are nice and there are lots of kids and young families."
0
Flag
bagleyheath
14y ago
"Ostervile, lovely place apart from the people. Rude arrogant, dont you know who I am? types where the rules of civilty only apply to others. If you are in the top 1% or aspire to be you'll love it."
1
Flag

LGBTQ Local Legal Protections

Cindy Crawford, Compass Massachusetts, LLC

Agent Phone: (508) 737-1481

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 CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, 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. This site was last updated 2022-04-05 08:58:10 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2022© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

295 Westwind Circle, Osterville, MA 02655 is a 2 bedroom, 2 bathroom, 1,808 sqft single-family home built in 1985. 295 Westwind Circle is located in Osterville, Osterville. This property is currently available for sale and was listed by CCIMLS on Jul 1, 2026. The MLS # for this home is MLS# 22603216.

295 Westwind Circle Osterville, MA 02655

$649,000

$649,000

Home Highlights

Local Information

About this House

Home Details for 295 Westwind Circle

Interior Features

Exterior Features

Days on Market

Property Information

Price & Status

Active Status

Location

Agent Information

Building

HOA

Lot Information

Listing Info

Miscellaneous

Market trends in Barnstable

Price History for 295 Westwind Circle

Similar Homes You May Like

New Listings near 295 Westwind Circle

Property Tax and Assessment

Comparable Sales for 295 Westwind Circle

Nearby homes

Additional Cost

Assigned Schools

Neighborhood Overview

What Locals Say about Osterville

LGBTQ Local Legal Protections

Housing

Employment

Public accommodations

295 Westwind Circle
Osterville, MA 02655