285 Windswept Way, Osterville, MA 02655
Property image
Property image
OFF MARKET

$3,782,600

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 4,727 sqft (on 1 acre)

285 Windswept Way, Osterville, MA 02655

Osterville
Est. Refi. Payment $21,827/mo*
Refinance Your Home
Currently Off Market - Sold Aug 5, 2013 for $1,400,000

Home Value

Trulia Estimate
$3.78M
Since last month
Decreased$62K (-1.6%)
Since last year
Increased$132K (+3.6%)
Since last sale
Increased$2M (+170.2%)
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 +91% in the last 10 years
MonthEstimated value
2026
August 2026$3.78M
August 2026$3.77M
July 2026$3.84M
June 2026$3.9M
May 2026$3.76M
April 2026$3.75M
March 2026$3.7M
February 2026$3.6M
January 2026$3.51M
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
245 N Bay Rd, Barnstable, MA
0.77
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
245 North Bay Road, Osterville, MA
0.80
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
804 Main St, Barnstable, MA
0.80
Single-Family Home
$2,200,000
04/27/26
4
5
6,294
804 Main Street, Cotuit, MA
0.81
Single-Family Home
$2,200,000
04/27/26
4
4.5
6,294
60 Nickerson Dr, Barnstable, MA
0.86
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
60 Nickerson Drive, Cotuit, MA
0.86
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
916 Main Street, Cotuit, MA
0.75
Single-Family Home
$4,950,000
03/27/26
5
3
2,808
355 Bridge Street, Osterville, MA
1.03
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
916 Main St, Barnstable, MA
0.76
Single-Family Home
$4,950,000
03/27/26
5
3
2,808
355 Bridge St, Barnstable, MA
1.04
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720

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
47 Sunset Poin, Barnstable, MA 02630
0.11
$18,500,000
7
10
10,104
For Sale
350 Windswept Way, Osterville, MA 02655
0.13
$5,975,000
5
5.5
5,924
Off Market
350 Windswept Way, Barnstable, MA 02630
0.14
$6,320,000
5
5.5
5,407
Off Market
47 Sunset Point, Osterville, MA 02655
0.15
$18,500,000
7
10
10,104
For Sale
440 Grand Island Drive, Osterville, MA 02655
0.16
$7,250,000
7
10
11,546
For Sale
179 Pineleigh Path, Osterville, MA 02655
0.23
$5,950,000
5
6.5
8,740
For Sale
207 Pineleigh Path, Barnstable, MA 02630
0.23
-
6
5
6,783
Off Market
207 Pineleigh Path, Osterville, MA 02655
0.23
$5,966,300
6
5
6,783
Off Market
0 Windswept Way, Osterville, MA 02655
0.29
$8,700,800
-
-
-
Off Market
320 Seapuit River Rd, Barnstable, MA 02630
0.27
-
6
6
5,478
Off Market
320 Seapuit River Road, Osterville, MA 02655
0.35
$4,933,700
6
6
5,478
Off Market
Lot 289 Seapuit River B Road, Osterville, MA 02655
0.50
$3,000,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 285 Windswept Way.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1999
1 acre lot
4,727 sqft
$800/sqft
Garage

About this House

Located in prestigious Oyster Harbors, this beautifully renovated five-bedroom residence overlooking the golf course, offers outstanding craftsmanship, customized details and wonderful natural surroundings creating an atmosphere of serenity in this private, gated community. The appeal of this home is found in the details; a magnificent great room with a raised river rock fireplace and vaulted ceiling opening to a stunning chef's kitchen with an oversized marble center island ideal for large family gatherings; elegant dining room; living room with custom fireplace; first floor master suite with luxurious bath; and delightful screened in porch with fireplace overlooking the gardens. The 2nd level features 3 en-suite bedrooms and a comfortable sitting room to relax. The suite over the garage is perfect for extended family or guests. There is also a finished lower level complete with a media room, game room and refined wine cellar. With many exterior upgrades such as new shingles, roof, wood shutters and blue stone porch, this beautiful one-acre lot offers multiple outdoor seating areas, gardens and golf course views. Pool plan is available in documents, under construction shortly. This completely turn-key home is ready for your family to discover its perfect Cape Cod property! Information herein is not guaranteed or warranted and should be verified by any person who is looking at this property to purchase.
285 Windswept Way, Osterville, MA 02655 is a 5 bedroom, 6 bathroom, 4,727 sqft single-family home in Osterville, built in 1999. It last sold for $1,400,000 on Aug 5, 2013. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,782,600, with a rent estimate of $7,491/month.

Home Details for 285 Windswept Way

Interior Features

Heating & Cooling
Heating: Forced Air, Gas, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Interior Details
Number of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Mud Room, Office, Pantry
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Shingle Not Wood
Parking & Garage
GarageParking Spaces: 5Parking: Garage Attached

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1 acre

Price and Tax history

DateEventPrice
Jan 21, 2021
Source: Robert Paul Properties
ListingRemoved
Aug 18, 2020
Source: Agent Provided
Listed For Sale
$3,400,000
May 31, 2015
Source: Agent Provided
ListingRemoved
$2,795,000
Feb 6, 2015
Source: Agent Provided
Listed For Sale
$2,795,000
Aug 5, 2013
Source: CCIMLS #21208347
Sold
$1,400,000

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 285 Windswept Way

  • What is 285 Windswept Way estimated to be worth?
    Trulia's estimated value for 285 Windswept Way in Osterville, MA is $3,782,600.
  • What is the price history for 285 Windswept Way?
    285 Windswept Way in Osterville, MA last sold for $1,400,000 in August 2013.
  • Is Osterville a buyer's or seller's market?
    Osterville is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Osterville?
    The median sale price in Osterville is $682K. That is down $3.33K from the prior month.
  • Does 285 Windswept Way have air conditioning?
    Yes, 285 Windswept Way in Osterville, MA has air conditioning.
  • Does 285 Windswept Way have laundry facilities?
    Yes, 285 Windswept Way in Osterville, MA has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 285 Windswept Way

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