43 Fairwinds Dr, Osterville, MA 02655
OFF MARKET

43 Fairwinds Dr
Osterville, MA 02655

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

$1,989,900

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $11,159/mo*
Refinance Your Home

$1,989,900

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $11,159/mo*
Refinance Your Home
4 Beds
3 Baths
3,928 sqft
(on 1.18 acres)

Local Information

Map showing home location
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-- mins to
Commute Destination

Description

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
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
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 43 Fairwinds Dr

Interior Features

Heating & Cooling
Heating: Other, GasAir ConditioningHeating Fuel: Other
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 History for 43 Fairwinds Dr

DatePriceEventSource
12/22/2011$815,000Sold
CCIMLS #21103462
10/21/2011$850,000PriceChange
Agent Provided
09/06/2011$895,000PriceChange
Agent Provided
06/03/2011$995,000PriceChange
Agent Provided
04/24/2011$1,095,000Listed For SaleAgent Provided
06/02/2003$900,000Sold
N/A
05/28/1999$142,500Sold
N/A
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Property Tax and Assessment

Year2025
Tax$12,389
Assessment$1,531,400
Home facts updated by county records

Comparable Sales for 43 Fairwinds Dr

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
162 Starboard Ln, Barnstable, MA
0.37
Single-Family Home
$2,210,000
10/08/25
4
3.5
2,710
77 Robbins Street, Osterville, MA
0.50
Single-Family Home
$1,349,000
05/08/26
4
2.5
2,976
435 Old Mill Rd, Barnstable, MA
0.41
Single-Family Home
$655,000
12/19/25
3
2
1,660
141 Parsley Lane, Osterville, MA
0.13
Single-Family Home
$1,025,000
07/08/25
2
2
1,868

Nearby homes

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Assigned Schools

These are the assigned schools for 43 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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Homes for sale near 43 Fairwinds Dr

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Off Market Homes Near 43 Fairwinds Dr

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Homes for rent near 43 Fairwinds Dr

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43 Fairwinds Dr, Osterville, MA 02655 is a 4 bedroom, 3 bathroom, 3,928 sqft single-family home built in 2000. 43 Fairwinds Dr is located in Osterville, Osterville. This property is not currently available for sale. 43 Fairwinds Dr was last sold on Dec 22, 2011 for $815,000. The current Trulia Estimate for 43 Fairwinds Dr is $1,989,900.