95 Windswept Way, Barnstable, MA 02630
Property image
Property image
OFF MARKET

$4,124,900

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,590 sqft (on 1 acre)

95 Windswept Way, Barnstable, MA 02630

Osterville
Est. Refi. Payment $24,149/mo*
Refinance Your Home

Home Value

Trulia Estimate
$4.13M
Since last month
Decreased$806K (-19.2%)
Since last year
Increased$166K (+5.1%)
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 +83% in the last 10 years
MonthEstimated value
2026
September 2026$3.39M
August 2026$4.12M
July 2026$4.19M
June 2026$4.06M
May 2026$3.01M
April 2026$3.2M
March 2026$5.31M
February 2026$4.21M
January 2026$2.91M
2025
2024
2023
2022
2021
2020

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
245 N Bay Rd, Barnstable, MA
0.63
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
245 North Bay Road, Osterville, MA
0.67
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
916 Main Street, Cotuit, MA
0.71
Single-Family Home
$4,950,000
03/27/26
5
3
2,808
355 Bridge Street, Osterville, MA
0.98
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
916 Main St, Barnstable, MA
0.72
Single-Family Home
$4,950,000
03/27/26
5
3
2,808
355 Bridge St, Barnstable, MA
0.99
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
60 Nickerson Dr, Barnstable, MA
0.77
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
60 Nickerson Drive, Cotuit, MA
0.77
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
804 Main St, Barnstable, MA
0.70
Single-Family Home
$2,200,000
04/27/26
4
5
6,294
804 Main Street, Cotuit, MA
0.71
Single-Family Home
$2,200,000
04/27/26
4
4.5
6,294

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
0 Windswept Way, Osterville, MA 02655
0.15
$8,700,800
-
-
-
Off Market
47 Sunset Poin, Barnstable, MA 02630
0.28
$18,500,000
7
10
10,104
For Sale
47 Sunset Point, Osterville, MA 02655
0.31
$18,500,000
7
10
10,104
For Sale
350 Windswept Way, Osterville, MA 02655
0.32
$5,975,000
5
5.5
5,924
Off Market
350 Windswept Way, Barnstable, MA 02630
0.32
$6,320,000
5
5.5
5,407
Off Market
179 Pineleigh Path, Osterville, MA 02655
0.32
$5,950,000
5
6.5
8,740
For Sale
440 Grand Island Drive, Osterville, MA 02655
0.35
$7,250,000
7
10
11,546
For Sale
207 Pineleigh Path, Barnstable, MA 02630
0.35
-
6
5
6,783
Off Market
207 Pineleigh Path, Osterville, MA 02655
0.36
$5,966,300
6
5
6,783
Off Market
320 Seapuit River Rd, Barnstable, MA 02630
0.47
-
6
6
5,478
Off Market
28 Little River Rd, Barnstable, MA 02630
0.47
-
Studio
1
880
Off Market
28 Little River Road, Cotuit, MA 02635
0.48
$1,455,500
Studio
1
880
Off Market

Local Information

  • Map ViewExplore the area around 95 Windswept Way.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1985
1 acre lot
3,590 sqft
$1,149/sqft

About this House

95 Windswept Way in exclusive Oyster Harbors, with gated 24/365 security, enjoys the prevailing southwest summer breeze reminiscent of olde Cape Cod. The shingle style Home was thoughtfully placed on an elevated, very private lot and designed by famed architect Don Hisaka. This bright, airy sun filled home is a wonderful retreat for family and friends. Graceful architectural features inside and out can't help but put a smile on the faces of young and old... This home has been enjoyed, lovingly maintained and updated over the years. Thoughtful layout lends itself to entertaining large groups, yet allows guests intimate spaces as well. Walls of windows and doors bring nature inside and provide smooth transition for everyone to enjoy the expansive yard, decks, patios & requisite summer barbecues! Separate guest wing feature 3 bedrooms & magnificent bath. Upstairs is the very private master bedroom suite. Did we mention Beach and boating access are a 9 iron away!? This home is aggressively priced, represents a great investment, and we promise a viewing will be well worth the investment of your time!
95 Windswept Way, Barnstable, MA 02630 is a 4 bedroom, 5 bathroom, 3,590 sqft single-family home in Osterville, built in 1985. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,124,900, with a rent estimate of $5,751/month.

Home Details for 95 Windswept Way

Property Information

Year Built
Year Built: 1985
Property Type / Style
Property Type: Single Family Home

Interior Features

Interior Details
Number of Rooms: 7
Appliances & Utilities
Dishwasher
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Parking & Garage
Parking Spaces: 2Parking: Off Street

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Feb 15, 2021
Source: William Raveis Real Estate, Mortgage & Insurance
ListingRemoved
Dec 26, 2020
Source: Agent Provided
Pending
$1,875,000
Oct 22, 2020
Source: Agent Provided
PriceChange
$1,875,000
Price decreased by 6%
Jun 29, 2020
Source: Agent Provided
Listed For Sale
$1,995,000

Market trends in Barnstable

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$682K
$3.33KMoM
Sale-to-List Price
98.5%
0.3%MoM
Price per sq ft
$464
$3MoM
Available listings
309
37MoM

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 95 Windswept Way

  • What is 95 Windswept Way estimated to be worth?
    Trulia's estimated value for 95 Windswept Way in Barnstable, MA is $4,124,900.
  • Is Barnstable a buyer's or seller's market?
    Barnstable is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Barnstable?
    The median sale price in Barnstable is $682K. That is down $3.33K from the prior month.
  • What do residents say about the Osterville neighborhood?
    Residents describe the Osterville neighborhood in Barnstable, MA as easy to park in, well-kept, and quiet. Most residents say you need a car. See recently sold homes in Osterville, Barnstable.
  • Does 95 Windswept Way have air conditioning?
    Yes, 95 Windswept Way in Barnstable, MA has air conditioning.
  • How big is the lot at 95 Windswept Way?
    The lot at 95 Windswept Way in Barnstable, MA is about 1 acre.

Explore by feature - Pet Friendly

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Off Market Homes Near 95 Windswept Way

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