11 Fairwinds Dr, Osterville, MA 02655
OFF MARKET

11 Fairwinds Dr
Osterville, MA 02655

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

$2,633,300

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $14,785/mo*
Refinance Your Home

$2,633,300

Trulia Estimate
as of May 20, 2026
Est. Refi. Payment $14,785/mo*
Refinance Your Home
5 Beds
3.5 Baths
4,250 sqft
(on 1.04 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 11 Fairwinds Dr

DatePriceEventSource
09/12/2015$1,499,000ListingRemovedAgent Provided
06/10/2015$1,499,000Listed For SaleAgent Provided
09/30/2011$1,175,000Sold
CCIMLS #21007339
06/27/2011$1,295,000PriceChange
Agent Provided
02/26/2011$1,325,000PriceChange
Agent Provided
11/26/2010$1,375,000PriceChange
Agent Provided
10/29/2010$1,395,000PriceChange
Agent Provided
07/29/2010$1,449,000Listed For SaleAgent Provided
05/01/1996$122,500Sold
N/A
11/04/1994$330,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$17,111
Assessment$2,115,100
Home facts updated by county records

Comparable Sales for 11 Fairwinds Dr

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
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
77 Robbins Street, Osterville, MA
0.46
Single-Family Home
$1,349,000
05/08/26
4
2.5
2,976
162 Starboard Ln, Barnstable, MA
0.42
Single-Family Home
$2,210,000
10/08/25
4
3.5
2,710

Assigned Schools

These are the assigned schools for 11 Fairwinds Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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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11 Fairwinds Dr, Osterville, MA 02655 is a 5 bedroom, 3 bathroom, 4,250 sqft single-family home built in 2000. 11 Fairwinds Dr is located in Osterville, Osterville. This property is not currently available for sale. 11 Fairwinds Dr was last sold on Sep 30, 2011 for $1,175,000. The current Trulia Estimate for 11 Fairwinds Dr is $2,633,300.