11 Fairwinds Dr, Osterville, MA 02655
Property image
Property image
OFF MARKET

$2,685,700

Trulia Estimate
  • 5 Beds
  • 3.5 Baths
  • 4,250 sqft (on 1.04 acres)

11 Fairwinds Dr, Osterville, MA 02655

Osterville
Est. Refi. Payment $15,662/mo*
Refinance Your Home
Currently Off Market - Sold Sep 30, 2011 for $1,175,000

Home Value

Trulia Estimate
$2.69M
Since last month
Decreased$3K (-0.1%)
Since last year
Increased$246K (+10%)
Since last sale
Increased$2M (+129.4%)
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 +98% in the last 10 years
MonthEstimated value
2026
November 2026$2.7M
October 2026$2.73M
September 2026$2.7M
August 2026$2.7M
July 2026$2.67M
June 2026$2.67M
May 2026$2.63M
April 2026$2.58M
March 2026$2.5M
February 2026$2.47M
January 2026$2.47M
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
89 Swift Avenue, Osterville, MA
0.10
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
89 Swift Ave, Barnstable, MA
0.10
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
25 Sturbridge Drive, Osterville, MA
0.19
Single-Family Home
$1,030,000
12/15/25
3
2.5
2,227
107 Parsley Lane, Osterville, MA
0.15
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
77 Robbins Street, Osterville, MA
0.46
Single-Family Home
$1,349,000
05/08/26
4
2.5
2,976
48 Bayview Circle, Osterville, MA
0.30
Single-Family Home
$1,168,500
05/08/26
3
2.5
1,775
170 Sturbridge Drive, Osterville, MA
0.21
Single-Family Home
$1,053,500
07/21/26
2
2.5
1,992
117 Parsley Lane, Osterville, MA
0.12
Single-Family Home
$1,570,000
04/14/26
3
2
1,872
53 Spice Lane, Osterville, MA
0.22
Single-Family Home
$1,305,000
04/29/26
3
1.5
1,740
30 Deerfield Rd, Osterville, MA
0.21
Single-Family Home
$803,000
02/06/26
3
3
2,126

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
11 Fairwinds Dr, Barnstable, MA 02630
0.00
-
-
-
-
Off Market
165 Parsley Ln, Osterville, MA 02655
0.05
$3,187,500
5
4
4,686
Off Market
165 Parsley Ln, Barnstable, MA 02630
0.05
-
-
-
-
Off Market
88 Cinnamon Ln, Osterville, MA 02655
0.05
$1,306,500
3
2.5
2,309
Off Market
88 Cinnamon Ln, Barnstable, MA 02630
0.05
-
-
-
-
Off Market
45 Fairwinds Dr, Osterville, MA 02655
0.05
$2,505,700
4
3.5
4,024
Off Market
45 Fairwinds Dr, Barnstable, MA 02630
0.05
-
-
-
-
Off Market
18 Fairwinds Dr, Osterville, MA 02655
0.05
$2,243,400
4
4
3,366
Off Market
18 Fairwinds Dr, Barnstable, MA 02630
0.05
-
-
-
-
Off Market
163 Parsley Ln, Osterville, MA 02655
0.06
$2,981,200
5
5
3,957
Off Market
163 Parsley Ln, Barnstable, MA 02630
0.06
-
-
-
-
Off Market
30 Fairwinds Dr, Osterville, MA 02655
0.06
$2,353,300
4
3.5
3,020
Off Market
30 Fairwinds Dr, Barnstable, MA 02630
0.06
-
-
-
-
Off Market
8 Nutmeg Ln, Barnstable, MA 02630
0.06
-
Studio
-
-
Off Market
8 Nutmeg Lane, Osterville, MA 02655
0.06
$3,900,700
4
3.5
4,800
Off Market
43 Fairwinds Dr, Osterville, MA 02655
0.07
$2,005,400
4
3
3,928
Off Market
43 Fairwinds Dr, Barnstable, MA 02630
0.07
-
-
-
-
Off Market
76 Cinnamon Ln, Osterville, MA 02655
0.07
$1,238,400
3
3
2,063
Off Market
76 Cinnamon Ln, Barnstable, MA 02630
0.07
-
-
-
-
Off Market
44 Fairwinds Dr, Osterville, MA 02655
0.07
$2,153,600
3
2.5
2,700
Off Market

Local Information

  • Map ViewExplore the area around 11 Fairwinds Dr.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2000
1.04 acre lot
4,250 sqft
$632/sqft
Garage

About this House

Recent renovations make this fully updated cul-de-sac home truly move-in ready. Upgrades include hardwood floors, marble baths, seamless glass showers, gourmet chef's kitchen, built-in bookcases, all new lighting fixtures & hardware, game room over 3-car garage, prof landscaping, irrigation, internal sound system, custom window treatments. Sturdy 2x6 construction, tray & vaulted ceilings, 1st floor Master, His & Her Walk-in closets, large separate office, four oversized bedrooms, 2nd upstairs Master, central vac, 4-zone hydroair, spacious family room with wet bar, large eat-in kitchen with skylights, double staircase to second floor, private patio & gardens in lush wooded setting and outdoor shower. Easy 1-mile walk to beaches, shops, restaurants. Luxurious living with modern amenities & exquisite details awaits your move to Osterville!
11 Fairwinds Dr, Osterville, MA 02655 is a 5 bedroom, 3 bathroom, 4,250 sqft single-family home in Osterville, built in 2000. It last sold for $1,175,000 on Sep 30, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,685,700, with a rent estimate of $5,022/month.

Home Details for 11 Fairwinds Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 11Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Mud Room, Office, Pantry, Recreation Room, Sun RoomWet BarCeiling Fan
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Shingle, WoodGardenLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2000Year Updated: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.04 acres

Additional Information

Intercom

Price and Tax history

DateEventPrice
Sep 12, 2015
Source: Agent Provided
ListingRemoved
$1,499,000
Jun 10, 2015
Source: Agent Provided
Listed For Sale
$1,499,000
Sep 30, 2011
Source: CCIMLS #21007339
Sold
$1,175,000
Jun 27, 2011
Source: Agent Provided
PriceChange
$1,295,000
Price decreased by 2%
Feb 26, 2011
Source: Agent Provided
PriceChange
$1,325,000
Price decreased by 4%

Market trends in Barnstable

Last updated October 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$675K
$2.17KMoM
Sale-to-List Price
98.6%
0.2%MoM
Price per sq ft
$457
$12MoM
Available listings
271
11MoM
Sourced by Trulia Market Trends

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"
    1
    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 11 Fairwinds Dr

  • What is 11 Fairwinds Dr estimated to be worth?
    Trulia's estimated value for 11 Fairwinds Dr in Osterville, MA is $2,685,700.
  • What is the price history for 11 Fairwinds Dr?
    11 Fairwinds Dr in Osterville, MA last sold for $1,175,000 in September 2011.
  • 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 $675K. That is down $2.17K from the prior month.
  • Does 11 Fairwinds Dr have air conditioning?
    Yes, 11 Fairwinds Dr in Osterville, MA has air conditioning.
  • Does 11 Fairwinds Dr have laundry facilities?
    Yes, 11 Fairwinds Dr in Osterville, MA has in-unit laundry.

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