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

43 Fairwinds Dr
Osterville, MA 02655

Osterville
  • 4 Beds
  • 3 Baths
  • 3,928 sqft (on 1.18 acres)

$2,053,500

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $11,589/mo*
Refinance Your Home

$2,053,500

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $11,589/mo*
Refinance Your Home
4 Beds
3 Baths
3,928 sqft
(on 1.18 acres)

Home Value

Trulia Estimate
$2.05M
Since last month
Increased$44K (+2.2%)
Since last year
Increased$161K (+8.6%)
Since last sale
Increased$1M (+149.6%)
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 +124% in the last 10 years
MonthEstimated value
2026
August 2026$2.03M
July 2026$1.99M
June 2026$2.02M
May 2026$1.98M
April 2026$1.94M
March 2026$1.88M
February 2026$1.85M
January 2026$1.83M
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
0.05
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
89 Swift Ave, Barnstable, MA
0.05
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
25 Sturbridge Drive, Osterville, MA
0.17
Single-Family Home
$1,030,000
12/15/25
3
2.5
2,227
50 Deerfield Road, Osterville, MA
0.19
Single-Family Home
$1,165,000
09/15/25
4
3
2,098
50 Deerfield Rd, Barnstable, MA
0.19
Single-Family Home
$1,165,000
09/15/25
4
3
2,098
162 Starboard Lane, Osterville, MA
0.38
Single-Family Home
$2,210,000
10/08/25
4
3.5
3,510
107 Parsley Ln, Barnstable, MA
0.21
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
107 Parsley Lane, Osterville, MA
0.21
Single-Family Home
$1,700,000
07/28/26
3
2.5
2,240
162 Starboard Ln, Barnstable, MA
0.37
Single-Family Home
$2,210,000
10/08/25
4
3.5
2,710
170 Sturbridge Drive, Osterville, MA
0.24
Single-Family Home
$1,053,500
07/21/26
2
2.5
1,992

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
89 Swift Avenue, Osterville, MA 02655
0.05
$1,075,000
4
2
2,674
Recently Sold
89 Swift Ave, Barnstable, MA 02630
0.05
$1,075,000
4
2
2,674
Recently Sold
8 Nutmeg Ln, Barnstable, MA 02630
0.12
-
4
3.5
4,800
Off Market
23&27 SW Ift Ave, Osterville, MA 02655
0.09
-
3
2.5
1,844
Off Market
23 & 27 Swift Avenue, Osterville, MA 02655
0.09
$1,324,200
3
2.5
1,844
Off Market
8 Nutmeg Lane, Osterville, MA 02655
0.13
$4,022,200
4
3.5
4,800
Off Market
60 Deerfield Rd, Barnstable, MA 02630
0.15
-
4
3
3,080
Off Market
60 Deerfield Road, Osterville, MA 02655
0.16
$1,601,100
4
3
3,795
Off Market
141 Parsley Lane, Osterville, MA 02655
0.13
$1,029,400
2
2
1,868
Off Market
65 Deerfield Road, Osterville, MA 02655
0.17
$1,045,600
3
2
2,061
Off Market
65 Deerfield Rd, Barnstable, MA 02630
0.17
$1,298,100
3
2
1,661
Off Market
25 Sturbridge Drive, Osterville, MA 02655
0.17
$1,030,000
3
2.5
2,227
Recently Sold

Local Information

  • Map ViewExplore the area around 43 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
1.18 acres
Living Area
3,928 sqft
Price/Sqft
$523

About this House

REPRICED TO MARKET. Over 100K below assessed value! Custom Built Center Entry Colonial 1.18 acres in Osterville. This well designed home has everything needed for a comfortable, carefree lifestyle. Huge, eat-in, gourmet kitchen with granite countertops, breakfast island, desk area, wet bar, hardwood floors and pantry closet opens to spacious family room with vaulted ceiling and wood-burning fireplace. Both rooms have sliders to rear decks and backyard. Formal living and dining rooms. Master suite, private bath and sitting area, enormous walk-in closet. Three additional bedrooms plus a separate office/study. Lower level with entertainment, excercise and indoor hockey room. Farmer's porch. Central A/C, 6 zone FHA gas heat, irrigation, alarm, double car garage. Welcoming for all your family and friends Buyer to verify all informatioBrokered And Advertised By: Robert Paul Properties, Inc.Listing Agent: Kathleen Deerman
43 Fairwinds Dr, Osterville, MA 02655 is a 4 bedroom, 3 bathroom, 3,928 sqft single-family home in Osterville, built in 2000. It last sold for $815,000 on Dec 22, 2011. It is currently off market. The Trulia Estimate is $2,053,500, with a rent estimate of $6,766/month.

Home Details for 43 Fairwinds Dr

Interior Features

Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 8

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

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

Lot Information

Lot Area: 1.18 acres

Price and Tax history

DateEventPrice
Dec 22, 2011
Source: CCIMLS #21103462
Sold
$815,000
Oct 21, 2011
Source: Agent Provided
PriceChange
$850,000
Price decreased by 5%
Sep 6, 2011
Source: Agent Provided
PriceChange
$895,000
Price decreased by 10%
Jun 3, 2011
Source: Agent Provided
PriceChange
$995,000
Price decreased by 9%
Apr 24, 2011
Source: Agent Provided
Listed For Sale
$1,095,000

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

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 43 Fairwinds Dr

  • What is 43 Fairwinds Dr estimated to be worth?
    Trulia's estimated value for 43 Fairwinds Dr in Osterville, MA is $2,053,500.
  • What is the price history for 43 Fairwinds Dr?
    43 Fairwinds Dr in Osterville, MA last sold for $815,000 in December 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.
  • How big is the lot at 43 Fairwinds Dr?
    The lot at 43 Fairwinds Dr in Osterville, MA is about 1.2 acres.

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