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

11 Fairwinds Dr
Osterville, MA 02655

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

$2,692,200

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $15,171/mo*
Refinance Your Home

$2,692,200

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $15,171/mo*
Refinance Your Home
5 Beds
3.5 Baths
4,250 sqft
(on 1.04 acres)

Home Value

Trulia Estimate
$2.69M
Since last month
Increased$67K (+2.5%)
Since last year
Increased$218K (+8.7%)
Since last sale
Increased$2M (+133%)
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 +101% in the last 10 years
MonthEstimated value
2026
August 2026$2.74M
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
0.11
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
50 Deerfield Rd, Barnstable, MA
0.17
Single-Family Home
$1,165,000
09/15/25
4
3
2,098
50 Deerfield Road, Osterville, MA
0.17
Single-Family Home
$1,165,000
09/15/25
4
3
2,098
25 Sturbridge Drive, Osterville, MA
0.19
Single-Family Home
$1,030,000
12/15/25
3
2.5
2,227
107 Parsley Ln, Barnstable, MA
0.15
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
107 Parsley Lane, Osterville, MA
0.15
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
162 Starboard Lane, Osterville, MA
0.42
Single-Family Home
$2,210,000
10/08/25
4
3.5
3,510
120 Robbins Street, Osterville, MA
0.38
Single-Family Home
$1,220,000
09/03/25
3
3.5
3,226
120 Robbins St, Barnstable, MA
0.38
Single-Family Home
$1,220,000
09/03/25
3
3.5
2,976

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
8 Nutmeg Ln, Barnstable, MA 02630
0.06
-
4
3.5
4,800
Off Market
8 Nutmeg Lane, Osterville, MA 02655
0.06
$3,988,500
4
3.5
4,800
Off Market
141 Parsley Lane, Osterville, MA 02655
0.08
$1,029,400
2
2
1,868
Off Market
89 Swift Avenue, Osterville, MA 02655
0.10
$1,075,000
4
2
2,674
Recently Sold
89 Swift Ave, Barnstable, MA 02630
0.11
$1,075,000
4
2
2,674
Recently Sold
25 Nutmeg Lane, Osterville, MA 02655
0.12
$1,826,700
3
2
1,776
Off Market
23 & 27 Swift Avenue, Osterville, MA 02655
0.11
$1,324,200
3
2.5
1,844
Off Market
23&27 SW Ift Ave, Osterville, MA 02655
0.11
-
3
2.5
1,844
Off Market
60 Deerfield Rd, Barnstable, MA 02630
0.14
-
4
3
3,080
Off Market
60 Deerfield Road, Osterville, MA 02655
0.14
$1,594,700
4
3
3,795
Off Market
117 Parsley Ln, Barnstable, MA 02630
0.12
$1,570,000
3
2
1,872
Recently Sold
117 Parsley Lane, Osterville, MA 02655
0.12
$1,570,000
3
2
1,872
Recently Sold

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

Property Type
Single-Family Home
Year Built
2000
Lot Size
1.04 acres
Living Area
4,250 sqft
Price/Sqft
$633
Parking
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. It is currently off market. The Trulia Estimate is $2,692,200, with a rent estimate of $6,823/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 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
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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

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Apartments for Rent

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Explore by feature - Pet Friendly

12 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

8 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

28 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

7 rentals with a pool in Osterville, MA

Explore by feature - Washer/dryer

33 rentals with a washer/dryer in Osterville, MA

Homes for sale near 11 Fairwinds Dr

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Off Market Homes Near 11 Fairwinds Dr

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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 $2,692,200.
  • 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 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 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.