281 Westwind Cir, Osterville, MA 02655
OFF MARKET

$656,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,260 sqft (on 0.36 acres)

281 Westwind Cir, Osterville, MA 02655

Osterville
Est. Refi. Payment $3,741/mo*
Refinance Your Home
Currently Off Market - Sold Aug 28, 2017 for $352,000

Home Value

Trulia Estimate
$657K
Since last month
Decreased$12K (-1.8%)
Since last year
Decreased$3K (-0.5%)
Since last sale
Increased$306K (+87%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +96% in the last 10 years
MonthEstimated value
2026
August 2026$658K
August 2026$658K
July 2026$671K
June 2026$674K
May 2026$667K
April 2026$658K
March 2026$651K
February 2026$640K
January 2026$638K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
40 Gunstock Rd, Barnstable, MA
0.10
Single-Family Home
$690,000
09/16/25
3
2
1,330
17 Avalon Circle, Osterville, MA
0.14
Single-Family Home
$611,500
11/06/25
3
1.5
1,316
17 Avalon Cir, Barnstable, MA
0.14
Single-Family Home
$611,500
11/06/25
3
1.5
1,316
40 Gunstock Road, Osterville, MA
0.09
Single-Family Home
$690,000
09/16/25
3
2
1,830
6 Nathans Way, Barnstable, MA
0.17
Single-Family Home
$650,000
08/07/26
3
2
1,630
6 Nathans Way, Osterville, MA
0.17
Single-Family Home
$650,000
08/07/26
3
2
1,630
55 Seth Goodspeed Way, Osterville, MA
0.24
Single-Family Home
$415,000
11/04/25
2
2
1,040
31 Jasons Lane, Osterville, MA
0.22
Single-Family Home
$575,000
07/30/26
3
3
1,348
31 Galahad Circle, Osterville, MA
0.11
Single-Family Home
$540,000
04/15/26
3
3
1,940
31 Galahad Cir, Barnstable, MA
0.11
Single-Family Home
$540,000
04/15/26
4
3
1,940

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
295 Westwind Circle, Osterville, MA 02655
0.02
$649,000
2
2
1,808
For Sale
38 Westwind Cir, Osterville, MA 02655
0.06
$668,700
3
2
2,245
Off Market
44 Avalon Circle, Barnstable, MA 02630
0.08
$1,003,700
3
2
3,387
Off Market
106 Bonnie Briar Drive, Osterville, MA 02655
0.04
$717,000
3
2
1,444
Off Market
31 Galahad Circle, Osterville, MA 02655
0.10
$540,000
3
3
1,940
Recently Sold
31 Galahad Cir, Barnstable, MA 02630
0.11
$540,000
4
3
1,940
Recently Sold
40 Gunstock Road, Osterville, MA 02655
0.09
$706,800
3
2
1,830
Off Market
9 Gunstock Road, Osterville, MA 02655
0.10
$688,800
3
2
1,284
Off Market
26 Captain Aldens Ln, Barnstable, MA 02630
0.15
-
3
1.5
1,832
Off Market
40 Gunstock Rd, Barnstable, MA 02630
0.10
-
3
2
1,330
Off Market
70 Bonnie Briar Drive, Osterville, MA 02655
0.11
$783,600
3
2
1,695
Off Market
17 Avalon Circle, Osterville, MA 02655
0.14
$622,700
3
1.5
1,316
Off Market

Local Information

  • Map ViewExplore the area around 281 Westwind Cir.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1985
0.36 acre lot
1,260 sqft
$521/sqft

About this House

Osterville, a carefully designed and well-built home (Theo Construction), in quiet, manicured, sought after planned neighborhood perfect for families, south of Rt 28. The yard is a tasteful combination of mature flowering shrubs and trees and a lush lawn. This well-maintained gem offers 3 bedrooms (master with private bath), open kitchen/dining room, generous living room with sunny bay window and fireplace, a super deck with awning and shade, plus an inviting finished walkout lower level with lots of natural light, and an attached garage. Newer vinyl windows, fresh outdoor shower. Ready to enjoy. Close to Osterville center, Dowses Beach etc. Room sizes are approximate.
281 Westwind Cir, Osterville, MA 02655 is a 3 bedroom, 2 bathroom, 1,260 sqft single-family home in Osterville, built in 1985. It last sold for $352,000 on Aug 28, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $656,800, with a rent estimate of $3,690/month.

Home Details for 281 Westwind Cir

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Interior Details
Number of Rooms: 6
Appliances & Utilities
DishwasherWasher

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Lot Information

Lot Area: 0.36 acres

Price and Tax history

DateEventPrice
Aug 28, 2017
Source: CCIMLS #21713738
Sold
$352,000
Jul 16, 2017
Source: Agent Provided
Pending
$359,900
Jul 11, 2017
Source: Agent Provided
Listed For Sale
$359,900
Aug 24, 2006
Source: N/A
Sold
$350,000

Market trends in Barnstable

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$681K
$20.33KMoM
Sale-to-List Price
98.2%
Price per sq ft
$461
$19MoM
Available listings
346
20MoM

Around this home

Neighborhood Overview

Osterville
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
    "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
    "moderate traffic at regular business hours, otherwise VERY easy travel, and safe drivers on the road "
    0
    Flag
  • Purplevelvet917
    "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
    "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
    "Great area for kids to grow up or spend the summers in. Very friendly community feel. Safe to walk around in. "
    0
    Flag
  • Ashleighmaeb
    "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
    "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
    "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

Frequently asked questions about 281 Westwind Cir

  • What is 281 Westwind Cir estimated to be worth?
    Trulia's estimated value for 281 Westwind Cir in Osterville, MA is $656,800.
  • What is the price history for 281 Westwind Cir?
    281 Westwind Cir in Osterville, MA last sold for $352,000 in August 2017.
  • Is Osterville a buyer's or seller's market?
    Osterville is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Osterville?
    The median sale price in Osterville is $681K. That is down $20.33K from the prior month.
  • How big is the lot at 281 Westwind Cir?
    The lot at 281 Westwind Cir in Osterville, MA is about 0.36 acres (15,681 sq ft).

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Off Market Homes Near 281 Westwind Cir

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