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 $3,728/mo*

Get Pre-Qualified

$649,000

Est. Mortgage $3,728/mo*

Get Pre-Qualified

2 Beds

2 Baths

1,808 sqft

(on 0.38 acres)

We estimate this home will sell faster than 86% 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 86% 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 2 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

Similar Homes You May Like

Skip to last item

1 ACRE
$650,000
3 bd
2 ba
1,442 sqft
20 Shannon Way,
Centerville, MA 02632
Kinlin Grover Compass
OPEN SUN, 12-1:30PM
1.29 ACRES
$759,000
4 bd
3 ba
1,568 sqft
66 Squaw'S Path,
East Wareham, MA 02538
Berkshire Hathaway HomeServices Robert Paul Properties
0.31 ACRES
$619,000
4 bd
2 ba
1,448 sqft
Address Not Disclosed,
Mashpee, MA 02649
Kinlin Grover Compass
0.6 ACRES
$675,000
3 bd
2 ba
1,778 sqft
42 Hamblin's Hayway,
Marstons Mills, MA 02648
Kinlin Grover Compass
0.56 ACRES
$739,000
3 bd
1.5 ba
1,416 sqft
122 Salt Rock Road,
Barnstable, MA 02630
Kinlin Grover Compass
0.57 ACRES
$800,000
3 bd
2 ba
1,542 sqft
52 Greenland Circle,
Yarmouth Port, MA 02675
Berkshire Hathaway HomeServices Robert Paul Properties
0.58 ACRES
$687,000
3 bd
2.5 ba
1,679 sqft
5 Kaycees Way,
West Yarmouth, MA 02673
Kinlin Grover Compass
OPEN SUN, 11-1PM
0.51 ACRES
$799,000
3 bd
2.5 ba
2,014 sqft
2 Fairway Circle,
Sandwich, MA 02563
Kinlin Grover Compass
0.31 ACRES
$750,000
3 bd
2 ba
1,542 sqft
50 Ancient Way,
Yarmouth Port, MA 02675
RE/MAX Executive Realty
2.17 ACRES
$815,000
4 bd
2 ba
1,792 sqft
83 Greenville Drive,
Forestdale, MA 02644
Keller Williams Realty
0.34 ACRES
$679,000
3 bd
2 ba
1,630 sqft
49 Powderhorn Way,
Centerville, MA 02632
LPT Realty
0.62 ACRES
$724,900
3 bd
2 ba
1,646 sqft
11 Deer Hollow Road,
Forestdale, MA 02644
Coastal Homes Realty Group LLC
0.38 ACRES
$664,000
3 bd
1.5 ba
1,440 sqft
195 Knotty Pine Lane,
Centerville, MA 02632
LPT Realty
OPEN SAT, 2-4PM
$765,000
4 bd
2.5 ba
2,529 sqft
6 Sylvan Way,
South Yarmouth, MA 02664
Chatelain Real Estate
0.67 ACRES
$699,000
3 bd
2 ba
1,547 sqft
10 Checkerberry Lane,
Forestdale, MA 02644
Redfin Corporation
OPEN SUN, 9:30-11AM
$675,000
3 bd
1 ba
1,116 sqft
129 Belmont Road,
West Harwich, MA 02671
Berkshire Hathaway HomeServices Robert Paul Properties
0.94 ACRES
$699,000
3 bd
2 ba
1,602 sqft
296 Meiggs Backus Road,
Sandwich, MA 02563
Lamacchia Realty, Inc.
$579,000
2 bd
2 ba
2,633 sqft
1 Sandview Terrace UNIT 1,
Mashpee, MA 02649
Compass Massachusetts, LLC
1.16 ACRES
$699,000
3 bd
2 ba
2,632 sqft
10 Marthas Way,
Barnstable, MA 02630
eXp Realty, LLC
0.34 ACRES
$695,000
3 bd
2 ba
1,892 sqft
17 Briggs Avenue,
Bourne, MA 02532
Coldwell Banker Realty
OPEN SAT, 10:30-12PM
0.41 ACRES
$764,000
3 bd
2 ba
1,426 sqft
114 King Arthur Drive,
Osterville, MA 02655
C. Case Realty, LLC
$949,000
3 bd
1 ba
960 sqft
21 Uncatena Road,
Mashpee, MA 02649
Berkshire Hathaway HomeServices Robert Paul Properties
0.29 ACRES
$799,000
4 bd
3 ba
2,169 sqft
9 E Harbor Circle,
East Falmouth, MA 02536
Keller Williams Realty
$450,000
2 bd
1.5 ba
1,506 sqft
374 Davisville Road Unit #4,
East Falmouth, MA 02536
Sotheby's International Realty
0.41 ACRES
$950,000
4 bd
2.5 ba
2,180 sqft
45 Sierra Way,
West Yarmouth, MA 02673
RE/MAX Executive Realty
0.47 ACRES
$564,900
2 bd
1 ba
1,514 sqft
545 Lincoln Rd Extension,
Hyannis, MA 02601
Sotheby's International Realty
$600,000
3 bd
1 ba
1,056 sqft
25 Deepwood Drive,
East Falmouth, MA 02536
Keller Williams Realty
0.35 ACRES
$649,000
2 bd
1 ba
2,214 sqft
14 Ahab Road,
Yarmouth Port, MA 02675
Kinlin Grover Compass
$350,000
2 bd
1.5 ba
920 sqft
12 Candlewood Lane APT 1-7,
Dennis Port, MA 02639
William Raveis Real Estate & Home Services
OPEN SAT, 11-12:30PM
0.28 ACRES
$529,000
3 bd
2 ba
1,512 sqft
311 Cotuit Road,
Mashpee, MA 02649
eXp Realty, LLC
0.97 ACRES
$775,000
3 bd
2.5 ba
1,456 sqft
100 Farmersville Road,
Sandwich, MA 02563
Kinlin Grover Compass
OPEN SAT, 10-11:30AM
1.05 ACRES
$759,900
3 bd
2 ba
1,848 sqft
303 Turtleback Road,
Marstons Mills, MA 02648
Kinlin Grover Compass
$385,000
2 bd
2 ba
1,080 sqft
300 Falmouth Road APT 9E,
Mashpee, MA 02649
Griffin Realty Group
$899,900
2 bd
2 ba
2,118 sqft
8 Lakeway Lane,
Harwich, MA 02645
Compass Massachusetts, LLC
0.67 ACRES
$705,000
3 bd
3 ba
1,934 sqft
620 Boxberry Hill Road,
East Falmouth, MA 02536
Kinlin Grover Compass
0.54 ACRES
$899,900
3 bd
2.5 ba
2,269 sqft
16 Widow Coombs Walk,
Sandwich, MA 02563
Sotheby's International Realty, Inc.
0.26 ACRES
$550,000
3 bd
1.5 ba
1,152 sqft
762 W Yarmouth Road,
Yarmouth Port, MA 02675
Seaport Village Realty
$599,000
3 bd
1.5 ba
1,100 sqft
5 Rosetta Street,
West Yarmouth, MA 02673
Redfin Corporation
OPEN SAT, 11-2PM
$749,000
2 bd
2.5 ba
1,440 sqft
480 Main Street UNIT 15,
Falmouth, MA 02540
Coastal Homes Realty Group LLC
$549,000
2 bd
2.5 ba
1,790 sqft
13 Laurel Hill Court UNIT 13,
Buzzards Bay, MA 02532
RE/MAX Executive Realty
See more homes for sale in
Osterville
Take a look

Skip to first item

New Listings near 295 Westwind Circle

Skip to last item

NEW
OPEN SAT, 11-1PM
COMING SOON
$595,000
3 bd
1.5 ba
1,076 sqft
53 Uncle Willies Way,
Hyannis, MA 02601
eXp Realty, LLC
0.54 ACRES
$899,900
3 bd
2.5 ba
2,269 sqft
16 Widow Coombs Walk,
Sandwich, MA 02563
Sotheby's International Realty, Inc.
OPEN THU, 4-5PM
$525,000
4 bd
1 ba
1,380 sqft
3 Yacht Club Road,
Centerville, MA 02632
Keller Williams Realty
1.16 ACRES
$699,000
3 bd
2 ba
2,632 sqft
10 Marthas Way,
Barnstable, MA 02630
eXp Realty, LLC
OPEN SAT, 11-12:30PM
0.28 ACRES
$529,000
3 bd
2 ba
1,512 sqft
311 Cotuit Road,
Mashpee, MA 02649
eXp Realty, LLC
NEW
OPEN SUN, 12-2PM
$675,000
2 bd
2.5 ba
2,259 sqft
20 Bishops Park #20,
Mashpee, MA 02649
Jennifer Knight, Century 21 Tassinari Gold
COMING SOON
0.48 ACRES
$620,000
3 bd
2 ba
1,248 sqft
23 Prudence Lane,
Cotuit, MA 02635
Keller Williams Realty
0.3 ACRES
$525,000
3 bd
2 ba
938 sqft
26 Adrena Ave,
Barnstable, MA 02630
William Hebenstreit, Craigville Realty, Inc.
NEW - 21 HRS AGO
0.32 ACRES
$625,000
2 bd
2 ba
1,157 sqft
804 Putnam Ave,
Barnstable, MA 02630
Ryan Mann, Sotheby's International Realty
NEW - 1 DAY AGO
0.46 ACRES
$625,000
2 bd
1.5 ba
1,157 sqft
804 Putnam Avenue,
Cotuit, MA 02635
Sotheby's International Realty
OPEN SAT, 10-11AM
0.26 ACRES
$380,000
2 bd
1 ba
480 sqft
153 Dunns Pond Road,
Hyannis, MA 02601
Property Cape Cod
OPEN SAT, 11-1PM
0.46 ACRES
$650,000
3 bd
2 ba
1,771 sqft
67 Old Fields Road,
Sandwich, MA 02563
MAC Realty
$539,000
3 bd
1 ba
1,164 sqft
32 Chadwick Avenue,
Hyannis, MA 02601
Kinlin Grover Compass
0.72 ACRES
$799,900
3 bd
2 ba
1,996 sqft
123 Asa Meigs Road,
Marstons Mills, MA 02648
Kinlin Grover Compass
OPEN SAT, 10-11AM
0.26 ACRES
$380,000
2 bd
1 ba
480 sqft
153 Dunns Pond Rd,
Barnstable, MA 02630
Dawn Andalft-Newman, Property Cape Cod
See more homes for sale in
Osterville
Take a look

Skip to first item

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

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
Est. $652,100
3 bd
2 ba
2,245 sqft
38 Westwind Cir,
Osterville, MA 02655
Kristen Ruggiero, RE/MAX Platinum
OFF MARKET
Est. $1,036,200
3 bd
2 ba
3,387 sqft
44 Avalon Circle,
Barnstable, MA 02630
SOLD
APR 15, 2026
$540,000
3 bd
3 ba
1,940 sqft
31 Galahad Circle,
Osterville, MA 02655
Today Real Estate
OFF MARKET
Est. $714,200
3 bd
2 ba
1,444 sqft
106 Bonnie Briar Drive,
Osterville, MA 02655
RE/MAX Spectrum of Osterville (INACTIVE)
SOLD
APR 15, 2026
$540,000
4 bd
3 ba
1,940 sqft
31 Galahad Cir,
Barnstable, MA 02630
Tanya Chadwick, Today Real Estate, Inc.
OFF MARKET
Est. $688,800
3 bd
2 ba
1,830 sqft
40 Gunstock Road,
Osterville, MA 02655
Today Real Estate
OFF MARKET
3 bd
1.5 ba
1,832 sqft
26 Captain Aldens Ln,
Barnstable, MA 02630
Courtney Tanguay, Coldwell Banker Realty
OFF MARKET
3 bd
2 ba
1,330 sqft
40 Gunstock Rd,
Barnstable, MA 02630
Kevin Eosco, Today Real Estate, Inc.
OFF MARKET
Est. $694,900
3 bd
2 ba
1,284 sqft
9 Gunstock Road,
Osterville, MA 02655
William Raveis Real Estate & Home Services
OFF MARKET
Est. $787,100
3 bd
2 ba
1,695 sqft
70 Bonnie Briar Drive,
Osterville, MA 02655
Kinlin Grover Real Estate
SOLD
NOV 6, 2025
$611,500
3 bd
1.5 ba
1,316 sqft
17 Avalon Cir,
Barnstable, MA 02630
John Fallon, LAER Realty Partners

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