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

$5,860,300

Trulia Estimate
  • 6 Beds
  • 5 Baths
  • 6,783 sqft (on 1 acre)

207 Pineleigh Path, Osterville, MA 02655

Osterville
Est. Refi. Payment $34,624/mo*
Refinance Your Home
Currently Off Market - Sold Aug 28, 2024 for $5,995,000

Home Value

Trulia Estimate
$5.86M
Since last month
Decreased$31K (-0.5%)
Since last year
Decreased$267K (-4.3%)
Since last sale
Decreased$76K (-1.3%)
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 +154% in the last 10 years
MonthEstimated value
2026
September 2026$5.92M
August 2026$5.95M
July 2026$6.1M
June 2026$6.09M
May 2026$5.98M
April 2026$5.99M
March 2026$6.07M
February 2026$6.22M
January 2026$6.21M
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 N Bay Rd, Barnstable, MA
0.72
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
245 North Bay Road, Osterville, MA
0.75
Single-Family Home
$5,275,000
12/03/25
5
5.5
4,637
405 Bridge Street, Osterville, MA
0.81
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
405 Bridge St, Barnstable, MA
0.82
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
355 Bridge Street, Osterville, MA
0.88
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
355 Bridge St, Barnstable, MA
0.88
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
916 Main Street, Cotuit, MA
0.98
Single-Family Home
$4,950,000
03/27/26
5
3
2,808
850 Sea View Ave, Barnstable, MA
1.15
Single-Family Home
$7,500,000
06/15/26
8
8
7,350
850 Sea View Avenue, Osterville, MA
1.15
Single-Family Home
$7,500,000
06/15/26
8
8
7,350
916 Main St, Barnstable, MA
0.99
Single-Family Home
$4,950,000
03/27/26
5
3
2,808

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
207 Pineleigh Path, Barnstable, MA 02630
0.00
-
6
5
6,783
Off Market
179 Pineleigh Path, Osterville, MA 02655
0.06
$5,950,000
5
6.5
8,740
For Sale
350 Windswept Way, Barnstable, MA 02630
0.15
$5,967,200
5
5.5
5,407
Off Market
350 Windswept Way, Osterville, MA 02655
0.15
$5,873,700
5
5.5
5,924
Off Market
440 Grand Island Drive, Osterville, MA 02655
0.16
$7,250,000
7
10
11,546
For Sale
320 Seapuit River Rd, Barnstable, MA 02630
0.23
-
6
6
5,478
Off Market
47 Sunset Poin, Barnstable, MA 02630
0.30
$18,500,000
7
10
10,104
For Sale
Lot 289 Seapuit River B Road, Osterville, MA 02655
0.28
$3,000,000
-
-
-
For Sale
320 Seapuit River Road, Osterville, MA 02655
0.33
$4,868,900
6
6
5,478
Off Market
Lot 288 Seapuit River A Road, Osterville, MA 02655
0.31
$3,100,000
-
-
-
For Sale
Lot 290 0 Indian Trail, Osterville, MA 02655
0.30
$3,125,000
-
-
-
For Sale

Local Information

  • Map ViewExplore the area around 207 Pineleigh Path.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2008
1 acre lot
6,783 sqft
$864/sqft
2 Car Garage
HOA $375/mo

About this House

Stunning Oyster Harbors residence, with commanding curb appeal, situated on a beautifully manicured one-acre lot overlooking the Oyster Harbors Golf Course. This special property, offering 6,783 square feet of living space, blends refined elegance with inviting warmth creating an atmosphere of comfort that resonates with family and guests alike. Showcasing an open floor plan, the great room serves as the centerpiece of the home featuring two-story ceilings, built ins, wet bar, and a fireplace with a cozy seating area. Adjacent is a gourmet kitchen equipped with top-of-the-line appliances, custom cabinetry, soapstone countertops, and a large center island. The dining room is highlighted by an elegant custom curved window. A luxurious first-floor primary suite features a sitting area, a spa-like bathroom with high-end finishes, and two walk-in closets. Completing this level is a home office with fireplace and seating area, and expansive sunroom with cathedral ceiling and walls of windows. On the second floor, five additional bedrooms offer comfort and privacy, each generously sized and filled with natural light. Designed for entertainment, the finished lower level is complete with a game/media room and kitchenette. The lavish interior seamlessly transitions into a stunning exterior. Indulge in unparalleled luxury with a heated Gunite pool, a well-equipped outdoor kitchen, elegant firepits and an array of sumptuous lounging areas. This exquisite property blends flawless design with top-tier amenities, presenting unmatched spaces for relaxation and entertainment, offering the ultimate backdrop for a life of opulence and sophistication. Located in a private gated community, with beach and dock rights, this exceptional property will appeal to the most discerning of buyers.
Please note: Gross Square footage includes finished lower level.
The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.
207 Pineleigh Path, Osterville, MA 02655 is a 6 bedroom, 6 bathroom, 6,783 sqft single-family home in Osterville, built in 2008. It last sold for the $5,995,000 asking price on Aug 28, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,860,300.
Last check for updates: about 14 hours ago
Listed by Robert B Kinlin, (508) 420-1414
Berkshire Hathaway HomeServices Robert Paul Properties
Bought with: Robert B Kinlin, (508) 420-1414, Berkshire Hathaway HomeServices Robert Paul Properties
Source: CCIMLS, MLS#22403119

Home Details for 207 Pineleigh Path

Interior Features

Interior Details
Basement: FullNumber of Rooms: 12Wet Bar
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2
Appliances & Utilities
Appliances: Wine Cooler, Water HeaterLaundry: Electric Dryer Hookup,Washer Hookup
Heating & Cooling
Heating: OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Oil
Fireplace & Spa
Number of Fireplaces: 2
Windows, Doors, Floors & Walls
Flooring: Wood, Tile, Carpet
Levels, Entrance, & Accessibility
Stories: 2Floors: Wood, Tile, Carpet

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Deck, Patio
Parking & Garage
Number of Garage Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 5Parking: Direct Access,Garage Door Opener,Off Street
Frontage
Not on Waterfront

Days on Market

Cumulative Days on Market: 1

Property Information

Year Built
Year Built: 2008
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Shingle Siding
Property Information
Parcel Number: 071001010

Price & Status

Price
List Price: $5,995,000

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: OstervilleCommunity: Oyster Harbors

Building

Building Area
Building Area: 6783 Square Feet

Community

Community Features: Deeded Beach Rights

HOA

Has an HOAHOA Fee: $4,500/Annually

Lot Information

Lot Area: 1 Acres

Listing Info

Special Conditions: None

Miscellaneous

BasementMls Number: 22403119Attribution Contact: rkinlin@robertpaul.comShowing Requirements: Appointment Required, Call Listing Agent

Additional Information

HOA Amenities: Road Maintenance,Snow Removal,Beach Access,Boat Dock

Price and Tax history

DateEventPrice
Aug 28, 2024
Source: CCIMLS #22403119
Sold
$5,995,000
Jul 2, 2024
Source: CCIMLS #22403119
Pending
$5,995,000
Jul 1, 2024
Source: CCIMLS #22403119
Listed For Sale
$5,995,000

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"
    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

All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than CC&I Assoc. of REALTORS®, Inc. includes the name of the listing company. Neither the listing company nor CC&I Assoc. of REALTORS®, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. This site was last updated 2026-09-23 10:33:16 PDT. All properties are subject to prior sale, changes, or withdrawal. Copyright 2026© Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.

Frequently asked questions about 207 Pineleigh Path

  • What is 207 Pineleigh Path estimated to be worth?
    Trulia's estimated value for 207 Pineleigh Path in Osterville, MA is $5,860,300.
  • What is the price history for 207 Pineleigh Path?
    207 Pineleigh Path in Osterville, MA last sold for $5,995,000 in August 2024.
  • 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.
  • Does 207 Pineleigh Path have air conditioning?
    Yes, 207 Pineleigh Path in Osterville, MA has air conditioning.
  • Does 207 Pineleigh Path have laundry facilities?
    Yes, 207 Pineleigh Path in Osterville, MA has laundry facilities.

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