160 Pineleigh Path, Osterville, MA 02655
OFF MARKET

$5,210,300

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

160 Pineleigh Path, Osterville, MA 02655

Osterville
Est. Refi. Payment $31,755/mo*
Refinance Your Home
Currently Off Market - Sold Jun 15, 2000 for $2,300,000

Home Value

Trulia Estimate
$5.21M
Since last month
Increased$52K (+1%)
Since last year
Increased$266K (+5.3%)
Since last sale
Increased$3M (+129.5%)
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 +130% in the last 10 years
MonthEstimated value
2026
October 2026$5.28M
September 2026$5.21M
August 2026$5.23M
July 2026$5.21M
June 2026$5.27M
May 2026$5.2M
April 2026$5.07M
March 2026$5.04M
February 2026$4.95M
January 2026$4.93M
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
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
405 Bridge Street, Osterville, MA
0.72
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
804 Main Street, Cotuit, MA
1.07
Single-Family Home
$2,200,000
04/27/26
4
4.5
6,294
205 Little River Road, Cotuit, MA
1.08
Single-Family Home
$2,350,000
09/11/26
5
6.5
5,348
60 Nickerson Dr, Barnstable, MA
1.13
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
60 Nickerson Drive, Cotuit, MA
1.13
Single-Family Home
$2,150,000
06/16/26
4
5
3,073
30 Cockachoiset Lane, Osterville, MA
1.21
Single-Family Home
$3,900,000
09/02/26
4
4.5
4,241
1045 Main Street, Cotuit, MA
1.24
Single-Family Home
$4,495,000
05/08/26
5
5.5
3,820
165 Baxter Neck Road, Marstons Mills, MA
1.52
Single-Family Home
$2,795,000
06/02/26
4
3.5
4,500

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
160 Pineleigh Path, Barnstable, MA 02630
0.00
-
-
-
-
Off Market
180 Pineleigh Path, Osterville, MA 02655
0.03
-
-
-
-
Off Market
146 Pineleigh Path, Osterville, MA 02655
0.06
$4,586,900
6
5
5,127
Off Market
163 Pineleigh Path, Osterville, MA 02655
0.06
$3,473,600
4
3
3,750
Off Market
163 Pineleigh Path, Barnstable, MA 02630
0.06
-
-
-
-
Off Market
179 Pineleigh Path, Barnstable, MA 02630
0.06
-
-
-
-
Off Market
193 Pineleigh Path, Osterville, MA 02655
0.07
$3,925,400
6
6
5,145
Off Market
149 Pineleigh Path, Osterville, MA 02655
0.08
$3,877,700
4
4
3,080
Off Market
140 PINELEIGH PATH, OSTERVILLE, MA 02655
0.09
$3,262,600
4
4.5
3,909
Off Market
140 Pineleigh Path, Barnstable, MA 02630
0.09
-
-
-
-
Off Market
140 Pineleigh Path, Osterville, MA 02655
0.09
$2,988,000
4
3.5
3,111
Off Market
207 Pineleigh Path, Osterville, MA 02655
0.09
$5,947,200
6
5
6,783
Off Market
143 Pineleigh Path, Osterville, MA 02655
0.10
$4,746,400
5
4.5
5,339
Off Market
143 Pineleigh Path, Barnstable, MA 02630
0.10
-
-
-
-
Off Market
271 Pineleigh Path, Osterville, MA 02655
0.11
-
-
-
-
Off Market
271 Pineleigh Path, Barnstable, MA 02630
0.11
-
-
-
-
Off Market
123 Pineleigh Path, Osterville, MA 02655
0.12
$4,575,900
4
5
5,287
Off Market
123 Pineleigh Path, Barnstable, MA 02630
0.12
-
-
-
-
Off Market
95 Pineleigh Path, Osterville, MA 02655
0.16
$5,037,000
7
7
5,983
Off Market
95 Pineleigh Path, Barnstable, MA 02630
0.16
-
-
-
-
Off Market

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

Single-Family Home
Built in 1998
1.22 acre lot
4,508 sqft
$1,156/sqft

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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,210,300.

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 and Tax history

DateEventPrice
Aug 17, 2016
Source: Agent Provided
ListingRemoved
$2,795,000
Jan 15, 2016
Source: Agent Provided
Listed For Sale
$2,795,000
Jun 15, 2000
Source: N/A
Sold
$2,300,000
Oct 27, 1997
Source: N/A
Sold
$465,000

Market trends in Barnstable

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$682K
$3.33KMoM
Sale-to-List Price
98.5%
0.3%MoM
Price per sq ft
$464
$3MoM
Available listings
309
37MoM

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"
    1
    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 160 Pineleigh Path

  • What is 160 Pineleigh Path estimated to be worth?
    Trulia's estimated value for 160 Pineleigh Path in Osterville, MA is $5,210,300.
  • 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 $682K. That is down $3.33K 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.

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