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

44 Fairwinds Dr
Osterville, MA 02655

Osterville
  • 3 Beds
  • 2.5 Baths
  • 2,700 sqft (on 1.12 acres)

$2,210,900

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $12,507/mo*
Refinance Your Home

$2,210,900

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $12,507/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,700 sqft
(on 1.12 acres)

Home Value

Trulia Estimate
$2.21M
Since last month
Increased$6K (+0.3%)
Since last year
Increased$156K (+7.4%)
Since last sale
Increased$1M (+111.2%)
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 +104% in the last 10 years
MonthEstimated value
2026
August 2026$2.26M
July 2026$2.25M
June 2026$2.25M
May 2026$2.2M
April 2026$2.22M
March 2026$2.2M
February 2026$2.13M
January 2026$2.1M
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
0.07
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
89 Swift Ave, Barnstable, MA
0.07
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
25 Sturbridge Drive, Osterville, MA
0.12
Single-Family Home
$1,030,000
12/15/25
3
2.5
2,227
50 Deerfield Road, Osterville, MA
0.12
Single-Family Home
$1,165,000
09/15/25
4
3
2,098
50 Deerfield Rd, Barnstable, MA
0.12
Single-Family Home
$1,165,000
09/15/25
4
3
2,098
107 Parsley Ln, Barnstable, MA
0.21
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
170 Sturbridge Drive, Osterville, MA
0.17
Single-Family Home
$1,053,500
07/21/26
2
2.5
1,992
107 Parsley Lane, Osterville, MA
0.21
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
170 Sturbridge Dr, Barnstable, MA
0.17
Single-Family Home
$1,053,500
07/21/26
2
2.5
1,992
117 Parsley Ln, Barnstable, MA
0.19
Single-Family Home
$1,570,000
04/14/26
3
2
1,872

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
60 Deerfield Rd, Barnstable, MA 02630
0.08
-
4
3
3,080
Off Market
60 Deerfield Road, Osterville, MA 02655
0.09
$1,594,700
4
3
3,795
Off Market
65 Deerfield Road, Osterville, MA 02655
0.10
$1,041,000
3
2
2,061
Off Market
65 Deerfield Rd, Barnstable, MA 02630
0.10
$1,298,100
3
2
1,661
Off Market
89 Swift Avenue, Osterville, MA 02655
0.07
$1,075,000
4
2
2,674
Recently Sold
50 Deerfield Road, Osterville, MA 02655
0.12
$1,167,600
4
3
2,098
Off Market
89 Swift Ave, Barnstable, MA 02630
0.07
$1,075,000
4
2
2,674
Recently Sold
50 Deerfield Rd, Barnstable, MA 02630
0.12
-
4
3
2,098
Off Market
25 Sturbridge Drive, Osterville, MA 02655
0.12
$1,030,000
3
2.5
2,227
Recently Sold
25 Sturbridge Dr, Barnstable, MA 02630
0.12
$1,030,000
3
2.5
2,227
Recently Sold
30 Deerfield Rd, Osterville, MA 02655
0.16
$803,000
3
2
1,937
Recently Sold
31 Newport Ln, Barnstable, MA 02630
0.16
$1,454,300
3
2.5
1,762
Off Market

Local Information

  • Map ViewExplore the area around 44 Fairwinds Dr.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Lot Size
1.12 acres
Living Area
2,700 sqft
Price/Sqft
$819
Parking
Garage

About this House

Beautiful Custom Cape in the sought-after Fairwinds area of Osterville Sited on a 1.12 acre private parcel, this 7 RM, 3 BR, 2.5 Bath Light & Bright Home features an Open Floor Plan & Hardwood Floors throughout Spacious Living Room w/two story Ceiling, Gas Fpl., Built-Ins, Separate Dining Area & Slider to Private Deck & Yard Library w/Vaulted Beamed Ceiling, Gas Fpl., Built-Ins Eat-In Kitchen w/vaulted ceiling & island Primary Bedroom Suite w/Private Bath w/walk-in shower & jetted tub Welcoming Entry and Half Bath complete the 1st Level The 2nd Level offers two very spacious bedrooms, both with Vaulted Ceilings Full Bath w/Skylight and a large open balcony complete 2nd level Stroll to Dowses Beach, Osterville Main St. w/great shops and fine reataurants
44 Fairwinds Dr, Osterville, MA 02655 is a 3 bedroom, 3 bathroom, 2,700 sqft single-family home in Osterville, built in 1997. It last sold for $1,070,000 on Nov 24, 2020. It is currently off market. The Trulia Estimate is $2,210,900, with a rent estimate of $5,834/month.

Home Details for 44 Fairwinds Dr

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 7
Appliances & Utilities
MicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached, Off Street

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1.12 acres

Price and Tax history

DateEventPrice
Nov 24, 2020
Source: CCIMLS #22005944
Sold
$1,070,000
Oct 7, 2020
Source: Agent Provided
Pending
$1,195,000
Sep 8, 2020
Source: Agent Provided
Listed For Sale
$1,195,000
Oct 10, 1995
Source: N/A
Sold
$115,000

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

11 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

8 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

26 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

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Explore by feature - Washer/dryer

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Homes for sale near 44 Fairwinds Dr

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Off Market Homes Near 44 Fairwinds Dr

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Frequently asked questions about 44 Fairwinds Dr

  • What is 44 Fairwinds Dr estimated to be worth?
    Trulia's estimated value for 44 Fairwinds Dr in Osterville, MA is $2,210,900.
  • What is the price history for 44 Fairwinds Dr?
    44 Fairwinds Dr in Osterville, MA last sold for $1,070,000 in November 2020.
  • 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 44 Fairwinds Dr have air conditioning?
    Yes, 44 Fairwinds Dr in Osterville, MA has air conditioning.
  • How big is the lot at 44 Fairwinds Dr?
    The lot at 44 Fairwinds Dr in Osterville, MA is about 1.1 acres.