160 Pineleigh Path, Osterville, MA 02655
OFF MARKET

160 Pineleigh Path
Osterville, MA 02655

Osterville
  • 4 Beds
  • 6 Baths
  • 4,508 sqft (on 1.22 acres)

$5,209,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $26,481/mo*
Refinance Your Home

$5,209,100

Trulia Estimate
as of Aug 10, 2026
Est. Refi. Payment $26,481/mo*
Refinance Your Home
4 Beds
6 Baths
4,508 sqft
(on 1.22 acres)

Local Information

  • Map ViewExplore the area around 160 Pineleigh Path.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1998
Lot Size
1.22 acres
Living Area
4,508 sqft
Price/Sqft
$1,156

About this House

Beautiful Cape style residence located in the private gated community of Oyster Harbors. This impeccably maintained home features 4 spacious bedrooms, a gourmet kitchen with casual dining and adjoining family room, formal living and dining rooms, first floor master suite and home office. The interior spaces are bathed in natural light and highlighted by wood floors, multiple fireplaces and golf course views. This home provides 4,508 square feet of living space and includes a fantastic lower level beautifully finished with family room, bar, and dual exercise rooms. A large deck overlooks the lush and private grounds encased with mature hydrangeas, an in-ground pool with well-equipped pool house and private putting green. This property is ideal for entertaining family and friends and offers deeded beach and docking rights. Information herein is not guaranteed or warranted and should be verified by any person who is looking at this property to purchase.
160 Pineleigh Path, Osterville, MA 02655 is a 4 bedroom, 7 bathroom, 4,508 sqft single-family home in Osterville, built in 1998. It last sold for $2,300,000 on Jun 15, 2000. It is currently off market. The Trulia Estimate is $5,209,100, with a rent estimate of $7,984/month.

Home Details for 160 Pineleigh Path

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 12

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood
Parking & Garage
Parking Spaces: 3

Property Information

Year Built
Year Built: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1.22 acres

Price History for 160 Pineleigh Path

DatePriceEventSource
08/17/2016$2,795,000ListingRemovedAgent Provided
01/15/2016$2,795,000Listed For SaleAgent Provided
06/15/2000$2,300,000Sold
N/A
10/27/1997$465,000Sold
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$32,577
Assessment$4,026,800
Home facts updated by county records

Comparable Sales for 160 Pineleigh Path

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
245 N Bay Rd, Barnstable, MA
0.65
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
245 North Bay Road, Osterville, MA
0.67
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
355 Bridge Street, Osterville, MA
0.78
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
355 Bridge St, Barnstable, MA
0.79
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
405 Bridge Street, Osterville, MA
0.72
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
405 Bridge St, Barnstable, MA
0.72
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
804 Main St, Barnstable, MA
1.07
Single-Family Home
$2,200,000
04/27/26
4
5
6,294
804 Main Street, Cotuit, MA
1.07
Single-Family Home
$2,200,000
04/27/26
4
4.5
6,294
780 Sea View Avenue, Osterville, MA
1.23
Single-Family Home
$3,400,000
10/03/25
4
4
5,460
60 Nickerson Drive, Cotuit, MA
1.13
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 160 Pineleigh Path.
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

LGBTQ Local Legal Protections

Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

9 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

23 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

Explore by feature - Washer/dryer

24 rentals with a washer/dryer in Osterville, MA

Homes for sale near 160 Pineleigh Path

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Off Market Homes Near 160 Pineleigh Path

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Frequently asked questions about 160 Pineleigh Path

  • What is 160 Pineleigh Path estimated to be worth?
    Trulia's estimated value for 160 Pineleigh Path in Osterville, MA is $5,209,100.
  • What is the price history for 160 Pineleigh Path?
    160 Pineleigh Path in Osterville, MA last sold for $2,300,000 in June 2000.
  • 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.
  • How big is the lot at 160 Pineleigh Path?
    The lot at 160 Pineleigh Path in Osterville, MA is about 1.2 acres.
  • Does 160 Pineleigh Path have parking?
    Yes, 160 Pineleigh Path in Osterville, MA has on-site parking.