138 Westwind Cir, Osterville, MA 02655
Property image
Property image
OFF MARKET

$932,200

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 1,930 sqft (on 0.43 acres)

138 Westwind Cir, Osterville, MA 02655

Osterville
Est. Refi. Payment $5,277/mo*
Refinance Your Home
Currently Off Market - Sold May 19, 2022 for $785,000

Home Value

Trulia Estimate
$932K
Since last month
Decreased$11K (-1.2%)
Since last year
Increased$16K (+1.7%)
Since last sale
Increased$146K (+18.6%)
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 +142% in the last 10 years
MonthEstimated value
2026
August 2026$931K
August 2026$928K
July 2026$942K
June 2026$955K
May 2026$933K
April 2026$925K
March 2026$921K
February 2026$896K
January 2026$895K
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
153 Hickory Hill Circle, Osterville, MA
0.07
Single-Family Home
$835,000
07/21/26
4
2.5
2,585
40 Gunstock Road, Osterville, MA
0.21
Single-Family Home
$690,000
09/16/25
3
2
1,830
40 Gunstock Rd, Barnstable, MA
0.21
Single-Family Home
$690,000
09/16/25
3
2
1,330
31 Galahad Cir, Barnstable, MA
0.34
Single-Family Home
$540,000
04/15/26
4
3
1,940
6 Nathans Way, Barnstable, MA
0.34
Single-Family Home
$650,000
08/07/26
3
2
1,630
6 Nathans Way, Osterville, MA
0.35
Single-Family Home
$650,000
08/07/26
3
2
1,630
33 Aspen Way, Osterville, MA
0.24
Single-Family Home
$660,000
10/03/25
3
1.5
1,276
31 Galahad Circle, Osterville, MA
0.33
Single-Family Home
$540,000
04/15/26
3
3
1,940
17 Avalon Circle, Osterville, MA
0.38
Single-Family Home
$611,500
11/06/25
3
1.5
1,316
17 Avalon Cir, Barnstable, MA
0.38
Single-Family Home
$611,500
11/06/25
3
1.5
1,316

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
130 West Wind Circle, Osterville, MA 02655
0.04
$680,600
3
2
1,248
Off Market
130 Westwind Cir, Osterville, MA 02655
0.04
$721,900
5
2
1,248
Off Market
175 Hickory Hill Circle, Osterville, MA 02655
0.04
$1,250,000
3
3
3,355
For Sale
111 Westwind Circle, Osterville, MA 02655
0.07
$795,000
3
2
1,248
For Sale
166 West Wind Circle, Osterville, MA 02655
0.07
$899,900
3
3
1,248
Off Market
153 Hickory Hill Circle, Osterville, MA 02655
0.07
$835,000
4
2.5
2,585
Recently Sold
143 Hickory Hill Circle, Osterville, MA 02632
0.09
-
4
2.5
2,300
Off Market
51 Poplar Dr, Barnstable, MA 02630
0.14
$880,000
3
2
1,592
Off Market
51 Poplar Drive, Osterville, MA 02655
0.14
$859,100
3
2
1,592
Off Market
106 Hickory Hill Circle, Barnstable, MA 02630
0.16
$841,100
3
2
1,650
Off Market
29 Poplar Dr, Barnstable, MA 02630
0.17
-
4
2.5
2,500
Off Market
29 Poplar Drive, Osterville, MA 02655
0.17
$1,270,300
4
2.5
2,500
Off Market

Local Information

  • Map ViewExplore the area around 138 Westwind Cir.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1988
0.43 acre lot
1,930 sqft
$483/sqft
Garage

About this House

Osterville, beautiful private end lot in a neighborhood of lovely homes. Dowses Beach is only 8 minutes away! 5 minute drive to Osterville shops. This custom post and beam home is highlighted with exposed beams throughout and a fieldstone fireplace with beautiful gas insert. The first floor boasts handicapped accessible bathroom (with laundry), kitchen with terra-cotta tile floor, hardwood floors, bay window, and office/extra room (currently used as 4th bedroom). Upstairs there are 3 large bedrooms, one with access to the outside (easy to rent), plenty of closet space (one walk-in), a full bath, ceiling fans and skylights. Basement is fully finished (adds 700 sqft) and has a 1950's feel with bar and 4 retro bar stools, matching pool table (conveys), black and white tile floor, tin ceiling, bonus room (could be 5th bedroom!), and another extra room. So much fun to entertain! Out back there is a huge 500 sqft deck with retractable awning and custom 20’ bar overlooking a 16x32 saltwater in-ground pool (fenced in) with stamped concrete patio. The entire large back yard is fully fenced in for those 2 or 4 legged critters. Other outdoor features include a shed with indoor/outside shower and full in-ground irrigation system. Bring the guests and enjoy! Mentionable: new 50-gal water tank 2022, new furnace 2016, new roof 2012, large single car garage, and whole house alarm system. Don't let this one slip by...it's an amazing one-of-a-kind property!
138 Westwind Cir, Osterville, MA 02655 is a 4 bedroom, 2 bathroom, 1,930 sqft single-family home in Osterville, built in 1988. It last sold for $785,000 on May 19, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $932,200, with a rent estimate of $4,220/month.

Home Details for 138 Westwind Cir

Interior Features

Interior Details
BasementNumber of Rooms: 8Types of Rooms: Walk In Closet, Dining Room, Family Room, Office, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle, Wood, Cement ConcreteLawnSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Building

Levels, Entrance, & Accessibility
Disabled Access

Lot Information

Lot Area: 0.43 acres

Price and Tax history

DateEventPrice
May 19, 2022
Source: CCIMLS #22201189
Sold
$785,000
Apr 11, 2022
Source: CCIMLS #22201189
Pending
$799,000
Mar 25, 2022
Source: CCIMLS #22201189
Listed For Sale
$799,000
Oct 29, 2018
Source: CCIMLS #21806188
Sold
$425,000
Oct 8, 2018
Source: Agent Provided
Pending
$439,000

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 138 Westwind Cir

  • What is 138 Westwind Cir estimated to be worth?
    Trulia's estimated value for 138 Westwind Cir in Osterville, MA is $932,200.
  • What is the price history for 138 Westwind Cir?
    138 Westwind Cir in Osterville, MA last sold for $785,000 in May 2022.
  • 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.
  • Does 138 Westwind Cir have air conditioning?
    Yes, 138 Westwind Cir in Osterville, MA has air conditioning.
  • Does 138 Westwind Cir have a pool?
    Yes, 138 Westwind Cir in Osterville, MA has a pool.

Explore by feature - Pet Friendly

11 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

11 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

31 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

6 rentals with a pool in Osterville, MA

Explore by feature - Washer/dryer

40 rentals with a washer/dryer in Osterville, MA

Explore by feature - Outdoor Space

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 138 Westwind Cir

Skip to last item
Skip to first item

Homes for sale near 138 Westwind Cir

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item