Is a car needed in Osterville, Barnstable, MA?

As of early 2026, 91% of users say car is needed

Is parking easy in Osterville, Barnstable, MA?

As of early 2026, 83% of users say parking is easy

Is there wildlife in Osterville, Barnstable, MA?

As of early 2026, 78% of users say there's wildlife

Are yards well-kept in Osterville, Barnstable, MA?

As of early 2026, 76% of users say yards are well-kept

Is Osterville, Barnstable, MA quiet?

As of early 2026, 73% of users say it's quiet

Is Osterville, Barnstable, MA dog-friendly?

As of early 2026, 71% of users say it's dog friendly

Are neighbors friendly in Osterville, Barnstable, MA?

As of early 2026, 63% of users say neighbors are friendly

Does Osterville, Barnstable, MA show holiday spirit?

As of early 2026, 63% of users say there's holiday spirit

Do residents of Osterville, Barnstable, MA plan to stay at least 5 years?

As of early 2026, 59% of users say they plan to stay for at least 5 years

Would people walk alone at night in Osterville, Barnstable, MA?

As of early 2026, 57% of users say people would walk alone at night

Do kids play outside in Osterville, Barnstable, MA?

As of early 2026, 50% of users say kids play outside

Is Osterville, Barnstable, MA walkable to restaurants?

As of early 2026, 49% of users say it's walkable to restaurants

Are there community events in Osterville, Barnstable, MA?

As of early 2026, 40% of users say there are community events

Is Osterville, Barnstable, MA walkable to grocery stores?

As of early 2026, 38% of users say it's walkable to grocery stores

Does Osterville, Barnstable, MA have sidewalks?

As of early 2026, 27% of users say there are sidewalks

Are the streets well-lit in Osterville, Barnstable, MA?

As of early 2026, 25% of users say streets are well-lit

OFF MARKET

44 Fairwinds Dr
Osterville, MA 02655

Osterville

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

$2,217,600

Trulia Estimate

as of May 20, 2026

Est. Refi. Payment $12,462/mo*

Refinance Your Home

$2,217,600

Trulia Estimate

as of May 20, 2026

Est. Refi. Payment $12,462/mo*

Refinance Your Home

3 Beds

2.5 Baths

2,700 sqft

(on 1.12 acres)

Local Information

-- mins to

Commute Destination

Description

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

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

No Info

A/C

Heating & Cooling

HOA

None

Price/Sqft

No Info

Listed

No Info

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 History for 44 Fairwinds Dr

Date	Price	Event	Source
11/24/2020	$1,070,000	Sold	CCIMLS #22005944
Recording Date 11/24/2020 County Transfer Tax N/A Total Transfer Tax N/A
10/07/2020	$1,195,000	Pending	Agent Provided

09/08/2020	$1,195,000	Listed For Sale	Agent Provided

10/10/1995	$115,000	Sold	N/A
Recording Date 10/10/1995 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2025
Tax	$16,808
Assessment	$2,077,600

Home facts updated by county records

Comparable Sales for 44 Fairwinds Dr

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
141 Parsley Lane, Osterville, MA	0.15	Single-Family Home	$1,025,000	07/08/25	2	2	1,868
117 Parsley Ln, Barnstable, MA	0.19	Single-Family Home	$1,570,000	04/14/26	3	2	1,872
117 Parsley Lane, Osterville, MA	0.19	Single-Family Home	$1,570,000	04/14/26	3	2	1,872
53 Spice Ln, Barnstable, MA	0.29	Single-Family Home	$1,305,000	04/29/26	3	1.5	1,740
53 Spice Lane, Osterville, MA	0.29	Single-Family Home	$1,305,000	04/29/26	3	1.5	1,740

Additional Cost

Assigned Schools

These are the assigned schools for 44 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

57 Homes For You
Buy: $600k - $12.3m

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
Resident
2mo ago
"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
Resident
3y ago
"moderate traffic at regular business hours, otherwise VERY easy travel, and safe drivers on the road "
0
Flag
Purplevelvet917
Resident
6y ago
"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
Resident
6y ago
"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
Resident
6y ago
"Great area for kids to grow up or spend the summers in. Very friendly community feel. Safe to walk around in. "
0
Flag
Ashleighmaeb
Resident
7y ago
"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
Resident
7y ago
"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
14y ago
"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

Apartments for Rent

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PET FRIENDLY
$2,550 - $3,350/mo
Fees may apply
1-2 bd
1-2 ba
Residence at 850 | 850 Falmouth Rd #216,
Hyannis, MA 02601
$2,700/mo
Fees may apply
2 bd
2 ba
1815 Falmouth Rd #I-2,
Centerville, MA 02632
Contact for price
1-2 bd
1-2 ba
22 Richardson Rd #776f18ccb,
Barnstable, MA 02630
Contact for price
1-2 bd
1-2 ba
979 Falmouth Rd #f320a52c6,
Hyannis, MA 02601
$2,500/mo
Fees may apply
3 bd
1 ba
2632-2638 NW 18th Terrace Oakland Park #33311,
Centerville, MA 02632
See more homes for rent in
Osterville
Take a look

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Explore by feature

SPECIAL OFFER
PET FRIENDLY
$2,642 - $4,674/mo
Total price
Studio-3 bd
1-2 ba
Maris Cape Cod | 99 Wilkens Ln #3202,
Hyannis, MA 02601
NEW - 9 HRS AGO
SPECIAL OFFER
PET FRIENDLY
$2,504 - $3,990/mo
Total price
1-2 bd
1-2 ba
Everleigh Cape Cod Active Adult | 265 Communication Way #417,
Hyannis, MA 02601
SPECIAL OFFER
PET FRIENDLY
$2,550 - $3,350/mo
Fees may apply
1-2 bd
1-2 ba
Residence at 850 | 850 Falmouth Rd #216,
Hyannis, MA 02601
PET FRIENDLY
$2,150 - $2,225/mo
Total price
1 bd
1 ba
Barnstable Flats | 199 Barnstable Rd #A-05,
Hyannis, MA 02601
APPLY INSTANTLY
PET FRIENDLY
$4,000/mo
Total price
3 bd
2 ba
2,898 sqft
613 Skunknet Rd,
Centerville, MA 02632
PET FRIENDLY
$3,100/mo
Total price
3 bd
1.5 ba
1,087 sqft
68 Yarmouth Rd,
Hyannis, MA 02601
PET FRIENDLY
$2,350/mo
Fees may apply
2 bd
1 ba
820 sqft
69 Camp St #1,
Hyannis, MA 02601
PET FRIENDLY
$2,350/mo
Fees may apply
2 bd
1 ba
820 sqft
69 Camp St,
Hyannis, MA 02601
8 pet-friendly rentals in Osterville, MA

Homes for sale near 44 Fairwinds Dr

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0.91 ACRES
$1,785,000
3 bd
2.5 ba
2,048 sqft
162 Main Street,
Osterville, MA 02655
Property Cape Cod
0.91 ACRES
$1,785,000
3 bd
2.5 ba
2,048 sqft
162 Main St,
Barnstable, MA 02630
Kimberly Gazal Santos, Property Cape Cod
1.44 ACRES
$810,000
2 bd
2 ba
2,110 sqft
441 Old Mill Rd,
Barnstable, MA 02630
Diane Boudreau, Kinlin Grover Compass
OPEN SAT, 10-12PM
0.36 ACRES
$1,150,000
2 bd
2.5 ba
1,992 sqft
170 Sturbridge Drive,
Osterville, MA 02655
Kinlin Grover Compass
OPEN SAT, 10-12PM
0.36 ACRES
$1,150,000
2 bd
2.5 ba
1,992 sqft
170 Sturbridge Dr,
Barnstable, MA 02630
Karen Rezendes, Kinlin Grover Compass
0.4 ACRES
$924,900
3 bd
2.5 ba
2,050 sqft
177 Bayview Circle,
Osterville, MA 02655
Berkshire Hathaway HomeServices Robert Paul Properties
1.44 ACRES
$810,000
2 bd
2 ba
1,144 sqft
441 Old Mill Road,
Osterville, MA 02655
Kinlin Grover Compass
OFF MARKET
818 S Main St,
Barnstable, MA 02630
0.64 ACRES
$695,000
3 bd
1 ba
1,008 sqft
351 Swift Ave,
Barnstable, MA 02630
Kami Dimitrova, EXIT Cape Realty
0.64 ACRES
$695,000
3 bd
1 ba
1,009 sqft
351 Swift Avenue,
Osterville, MA 02655
EXIT Cape Realty
See more homes for sale in
Osterville
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Off Market Homes Near 44 Fairwinds Dr

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SOLD
MAY 19, 2026
$3,250,000
3 bd
3.5 ba
2,844 sqft
481 Lakeside Drive W,
Centerville, MA 02632
Premier Commercial
SOLD
MAY 15, 2026
$2,225,000
4 bd
4 ba
3,510 sqft
357 Lakeside Drive W,
Centerville, MA 02632
Sotheby's International Realty
SOLD
MAY 14, 2026
$2,700,000
3 bd
3 ba
3,055 sqft
18 Winfield Lane,
Osterville, MA 02655
SilverStone Capeside Realty Group
SOLD
MAY 14, 2026
$3,200,000
4 bd
4.5 ba
2,752 sqft
125 Wianno Circle,
Osterville, MA 02655
Sotheby's International Realty
SOLD
MAY 14, 2026
$3,200,000
4 bd
4.5 ba
2,752 sqft
125 Wianno Cir,
Barnstable, MA 02630
Ellen Valentgas, Sotheby's International Realty
SOLD
MAY 8, 2026
$1,349,000
4 bd
2.5 ba
2,976 sqft
77 Robbins Street,
Osterville, MA 02655
Berkshire Hathaway HomeServices Robert Paul Properties
SOLD
MAY 8, 2026
$1,168,500
3 bd
2.5 ba
1,775 sqft
48 Bayview Circle,
Osterville, MA 02655
Kinlin Grover Compass
SOLD
MAY 8, 2026
$1,168,500
3 bd
2.5 ba
1,775 sqft
48 Bayview Cir,
Barnstable, MA 02630
Falconio Jones Team, Kinlin Grover Compass
SOLD
APR 29, 2026
$1,305,000
3 bd
1.5 ba
1,740 sqft
53 Spice Lane,
Osterville, MA 02655
Compass Massachusetts, LLC
SOLD
APR 29, 2026
$1,305,000
3 bd
1.5 ba
1,740 sqft
53 Spice Ln,
Barnstable, MA 02630
Livia Freitas Monteforte, Compass
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Osterville
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Homes for rent near 44 Fairwinds Dr

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APPLY INSTANTLY
PET FRIENDLY
$5,500/mo
Total price
3 bd
3 ba
2,319 sqft
16 This Way,
Osterville, MA 02655
APPLY INSTANTLY
$3,700/mo
Total price
3 bd
1 ba
996 sqft
34 Tevyaw Rd,
Hyannis, MA 02601
APPLY INSTANTLY
$3,300/mo
Fees may apply
3 bd
2 ba
1,536 sqft
45 Vermeer Ct,
Osterville, MA 02655
APPLY INSTANTLY
$4,000/mo
Total price
3 bd
2.5 ba
2,050 sqft
21 Amanda Ct,
Cotuit, MA 02635
APPLY INSTANTLY
PET FRIENDLY
$4,000/mo
Total price
3 bd
2 ba
2,898 sqft
613 Skunknet Rd,
Centerville, MA 02632
$3,150/mo
Total price
2 bd
2 ba
1,040 sqft
Address Not Disclosed,
Osterville, MA 02655
APPLY INSTANTLY
$2,200/mo
Total price
3 bd
2 ba
1,248 sqft
71 Canterbury Cir,
Hyannis, MA 02601
APPLY INSTANTLY
PET FRIENDLY
FURNISHED
$2,800/mo
Total price
3 bd
2 ba
1,630 sqft
135 Highland Dr,
Centerville, MA 02632
$3,000/mo
Total price
3 bd
1.5 ba
1,402 sqft
Address Not Disclosed,
Hyannis, MA 02601
$4,500/mo
Fees may apply
4 bd
3 ba
2,400 sqft
251 Great Marsh Rd,
Barnstable, MA 02630
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Osterville
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44 Fairwinds Dr, Osterville, MA 02655 is a 3 bedroom, 3 bathroom, 2,700 sqft single-family home built in 1997. 44 Fairwinds Dr is located in Osterville, Osterville. This property is not currently available for sale. 44 Fairwinds Dr was last sold on Nov 24, 2020 for $1,070,000. The current Trulia Estimate for 44 Fairwinds Dr is $2,217,600.

44 Fairwinds Dr
Osterville, MA 02655

$2,217,600

$2,217,600

Local Information