166 West Wind Circle, Osterville, MA 02655
Property image
Property image
OFF MARKET

$899,900

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,248 sqft (on 0.54 acres)

166 West Wind Circle, Osterville, MA 02655

Osterville
Est. Refi. Payment $5,111/mo*
Refinance Your Home
Currently Off Market - Sold Jul 10, 2020 for $392,000

Home Value

Trulia Estimate
$900K
Since last month
Increased$82K (+10%)
Since last year
Increased$207K (+29.8%)
Since last sale
Increased$508K (+129.6%)
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 +33% in the last 10 years
MonthEstimated value
2026
August 2026$900K
August 2026$900K
July 2026$818K
June 2026$827K
May 2026$783K
April 2026$804K
March 2026$787K
February 2026$778K
January 2026$738K
2025

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
31 Jasons Lane, Osterville, MA
0.18
Single-Family Home
$575,000
07/30/26
3
3
1,348
31 Galahad Circle, Osterville, MA
0.31
Single-Family Home
$540,000
04/15/26
3
3
1,940
40 Gunstock Rd, Barnstable, MA
0.18
Single-Family Home
$690,000
09/16/25
3
2
1,330
153 Hickory Hill Circle, Osterville, MA
0.03
Single-Family Home
$835,000
07/21/26
4
2.5
2,585
31 Galahad Cir, Barnstable, MA
0.31
Single-Family Home
$540,000
04/15/26
4
3
1,940
33 Aspen Way, Osterville, MA
0.23
Single-Family Home
$660,000
10/03/25
3
1.5
1,276
40 Gunstock Road, Osterville, MA
0.18
Single-Family Home
$690,000
09/16/25
3
2
1,830
17 Avalon Circle, Osterville, MA
0.36
Single-Family Home
$611,500
11/06/25
3
1.5
1,316
17 Avalon Cir, Barnstable, MA
0.36
Single-Family Home
$611,500
11/06/25
3
1.5
1,316
369 Bumps River Road, Osterville, MA
0.46
Single-Family Home
$625,000
04/30/26
3
2
1,152

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
153 Hickory Hill Circle, Osterville, MA 02655
0.03
$835,000
4
2.5
2,585
Recently Sold
143 Hickory Hill Circle, Osterville, MA 02632
0.04
-
4
2.5
1,911
Off Market
175 Hickory Hill Cir, Osterville, MA 02655
0.05
$1,250,000
4
4
3,355
For Sale
111 Westwind Circle, Osterville, MA 02655
0.08
$795,000
3
2
1,248
For Sale
130 West Wind Circle, Osterville, MA 02655
0.08
$680,600
3
2
1,248
Off Market
130 Westwind Cir, Osterville, MA 02655
0.08
$721,900
5
2
1,248
Off Market
106 Hickory Hill Cir, Barnstable, MA 02630
0.10
$841,100
3
2
1,650
Off Market
54 Jason's Lane, Osterville, MA 02655
0.12
$616,700
2
1
936
Off Market
51 Poplar Dr, Barnstable, MA 02630
0.12
$880,000
3
2
1,592
Off Market
51 Poplar Drive, Osterville, MA 02655
0.12
$855,300
3
2
1,592
Off Market
29 Poplar Dr, Barnstable, MA 02630
0.13
-
4
2.5
2,500
Off Market

Local Information

  • Map ViewExplore the area around 166 West Wind Circle.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1985
Lot Size
0.54 acres
Living Area
1,248 sqft
Price/Sqft
$721
Parking
1 Car Garage

About this House

Hidden gem! Tucked away, south of Route 28, quiet corner lot, & Gunite Pool! 1-Floor living, cathedral Living Room with fireplace opens to Kitchen and Dining area, Laundry area, slider to large Deck overlooking private Yard and Pool. Master Bedroom with private bath, 2 additional Bedrooms. Central A/C on main floor. Finished walk-out Lower Level with Den, Living Room with slider to yard, Bonus Room and Full Bath! Solar panels on rear roof (owned) 2013, Roof 2005, Septic 2007, Pool Pump 2017...Great Value! Short Sale requiring 3rd party approval.
166 West Wind Circle, Osterville, MA 02655 is a 3 bedroom, 3 bathroom, 1,248 sqft single-family home in Osterville, built in 1985. It last sold for $392,000 on Jul 10, 2020 (2% below the $399,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $899,900, with a rent estimate of $4,594/month.
Last check for updates: about 12 hours ago
Listed by Chuck Tuttle, (508) 367-8800
Kinlin Grover Real Estate
Bought with: Heather I Wilson, Kinlin Grover Real Estate
Source: CCIMLS, MLS#21908623

Home Details for 166 West Wind Circle

Interior Features

Interior Details
Basement: Finished,Interior Entry,FullNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Master Bathroom, Kitchen, Living Room, Basement
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 1248 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Refrigerator, Electric Range, Gas Water HeaterDishwasherLaundry: First FloorRefrigerator
Heating & Cooling
Heating: Hot WaterHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningHas a Fireplace
Gas & Electric
Electric: Photovoltaics Seller Owned
Windows, Doors, Floors & Walls
Window: Skylight(s)Flooring: Other
Levels, Entrance, & Accessibility
Stories: 1Floors: Other

Exterior Features

Exterior Home Features
Roof: Asphalt PitchedPatio / Porch: DeckFoundation: PouredHas a Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Garage Attached, Open
Pool
Pool: Gunite, In GroundPool
Frontage
Road Frontage: PublicRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Septic Tank, Septic Tank
Finished Area
Finished Area (below surface): 800 Square Feet

Days on Market

Cumulative Days on Market: 132

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: Shingle SidingNot a New ConstructionNot Attached PropertyDoes Not Include Home Warranty
Property Information
Condition: ActualParcel Number: 121011015

Price & Status

Price
List Price: $399,900

Active Status

MLS Status: Closed

Location

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

Building

Building Area
Building Area: 1248 Square Feet

HOA

No HOA

Lot Information

Lot Area: 0.54 acres

Listing Info

Special Conditions: Short Sale

Offer

Listing Terms: FHA

Miscellaneous

BasementMls Number: 21908623Showing Requirements: Appointment Required, Yard Sign

Price and Tax history

DateEventPrice
Jul 10, 2020
Source: CCIMLS #21908623
Sold
$392,000

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

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.

Frequently asked questions about 166 West Wind Circle

  • What is 166 West Wind Circle estimated to be worth?
    Trulia's estimated value for 166 West Wind Circle in Osterville, MA is $899,900.
  • What is the price history for 166 West Wind Circle?
    166 West Wind Circle in Osterville, MA last sold for $392,000 in July 2020.
  • 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 166 West Wind Circle have air conditioning?
    Yes, 166 West Wind Circle in Osterville, MA has air conditioning.
  • Does 166 West Wind Circle have a pool?
    Yes, 166 West Wind Circle in Osterville, MA has a pool.

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