143 Pineleigh Path, Osterville, MA 02655
Property image
Property image
OFF MARKET

143 Pineleigh Path
Osterville, MA 02655

Osterville
  • 5 Beds
  • 4.5 Baths
  • 5,339 sqft (on 1 acre)

$4,845,900

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $27,348/mo*
Refinance Your Home

$4,845,900

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $27,348/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,339 sqft
(on 1 acre)

Local Information

  • Map ViewExplore the area around 143 Pineleigh Path.
  • 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 acre
Living Area
5,339 sqft
Price/Sqft
$908
Parking
Garage

About this House

This single-family home is located at 143 Pineleigh Path, Osterville, MA. 143 Pineleigh Path is in the Osterville neighborhood in Osterville, MA and in ZIP code 02655. This property has 5 bedrooms, 5 bathrooms and approximately 5,339 sqft of floor space. This property has a lot size of 1 acre and was built in 2000.
143 Pineleigh Path, Osterville, MA 02655 is a 5 bedroom, 5 bathroom, 5,339 sqft single-family home in Osterville, built in 2000. It last sold for $2,520,000 on Dec 21, 2018. It is currently off market. The Trulia Estimate is $4,845,900, with a rent estimate of $7,986/month.

Home Details for 143 Pineleigh Path

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Number of Rooms: 10

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: WoodPatioPorch
Parking & Garage
GarageParking Spaces: 6Parking: Garage Attached

Property Information

Year Built
Year Built: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1 acre

Building

Fitness & Sports
Tennis Court

Price History for 143 Pineleigh Path

DatePriceEventSource
06/18/2020$2,800,000ListingRemovedAgent Provided
03/18/2020$2,800,000Listed For SaleAgent Provided
12/21/2018$2,520,000Sold
CCIMLS #21801172
11/26/2018$2,550,000PendingAgent Provided
05/16/2018$2,550,000PriceChange
Agent Provided
03/01/2018$2,675,000Listed For SaleAgent Provided
11/27/2017$2,675,000ListingRemovedAgent Provided
02/28/2017$2,675,000Listed For SaleAgent Provided
12/12/2016$2,675,000ListingRemovedAgent Provided
03/17/2016$2,675,000Listed For SaleAgent Provided
12/15/2015$2,895,000ListingRemovedAgent Provided
03/20/2015$2,895,000Listed For SaleAgent Provided
03/13/2006$2,550,000Sold
N/A
08/28/2003$2,450,000Sold
N/A
01/28/2002$750,000Sold
N/A
12/17/1998$500,000Sold
N/A

Market trends in Barnstable

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$702K
$29.31KMoM
Sale-to-List Price
98.2%
0.1%MoM
Price per sq ft
$442
$11MoM
Available listings
366
23MoM
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Property Tax and Assessment

Year2025
Tax$37,895
Assessment$4,684,200
Home facts updated by county records

Comparable Sales for 143 Pineleigh Path

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
245 N Bay Rd, Barnstable, MA
0.59
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
245 North Bay Road, Osterville, MA
0.62
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
355 Bridge Street, Osterville, MA
0.79
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
355 Bridge St, Barnstable, MA
0.80
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
405 Bridge Street, Osterville, MA
0.73
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
405 Bridge St, Barnstable, MA
0.73
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
804 Main St, Barnstable, MA
0.98
Single-Family Home
$2,200,000
04/27/26
4
5
6,294
804 Main Street, Cotuit, MA
0.98
Single-Family Home
$2,200,000
04/27/26
4
4.5
6,294
60 Nickerson Drive, Cotuit, MA
1.04
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
60 Nickerson Dr, Barnstable, MA
1.04
Single-Family Home
$2,150,000
06/16/26
4
5
3,073

Nearby homes

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Assigned Schools

These are the assigned schools for 143 Pineleigh Path.
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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

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

8 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

9 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

24 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

6 rentals with a pool in Osterville, MA

Explore by feature - Washer/dryer

25 rentals with a washer/dryer in Osterville, MA

Homes for sale near 143 Pineleigh Path

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Off Market Homes Near 143 Pineleigh Path

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Frequently asked questions about 143 Pineleigh Path

  • What is 143 Pineleigh Path estimated to be worth?
    Trulia's estimated value for 143 Pineleigh Path in Osterville, MA is $4,845,900.
  • What is the price history for 143 Pineleigh Path?
    143 Pineleigh Path in Osterville, MA last sold for $2,520,000 in December 2018.
  • Is Osterville a buyer's or seller's market?
    Osterville is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Osterville?
    The median sale price in Osterville is $702K. That is up $29.31K from the prior month.
  • Does 143 Pineleigh Path have air conditioning?
    Yes, 143 Pineleigh Path in Osterville, MA has air conditioning.
  • How big is the lot at 143 Pineleigh Path?
    The lot at 143 Pineleigh Path in Osterville, MA is about 1 acre.