25 Osprey Ln, Chilmark, MA 02535
Property image
Property image
OFF MARKET

$7,494,600

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 3,777 sqft (on 3.81 acres)

25 Osprey Ln, Chilmark, MA 02535

Est. Refi. Payment $43,249/mo*
Refinance Your Home
Currently Off Market - Sold Oct 15, 2025 for $7,289,000

Home Value

Trulia Estimate
$7.5M
Since last month
Decreased$10K (-0.1%)
Since last year
Increased$300K (+4.2%)
Since last sale
Increased$185K (+2.5%)
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 +44% in the last 10 years
MonthEstimated value
2026
September 2026$7.47M
August 2026$7.48M
July 2026$7.44M
June 2026$7.41M
May 2026$7.43M
April 2026$7.36M
March 2026$7.41M
February 2026$7.4M
January 2026$7.33M
2025
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
308 South Road, Chilmark, MA
0.55
Single-Family Home
$6,500,000
09/18/26
4
4.5
3,490
6 Trails End, Chilmark, MA
0.57
Single-Family Home
$2,700,000
09/16/26
4
3
2,346
60 Meeting House Rd, Chilmark, MA
1.34
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
6 Tabor Hls, Chilmark, MA
1.29
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
3 Fulling Mill Rd, Chilmark, MA
0.94
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
300 North Road 18 Belhaven Way, Chilmark, MA
1.92
Single-Family Home
$2,800,000
08/27/26
4
3.5
2,515
18 Homeward Way, Chilmark, MA
1.73
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
300 North Rd, Chilmark, MA
1.92
Single-Family Home
$2,800,000
08/27/26
2
3
2,515
49 Gosnolds Way, Chilmark, MA
2.27
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044

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
5 Ocean View Farm Rd, Chilmark, MA 02535
0.28
$2,469,800
3
1.5
1,342
Off Market
22 Ocean View Farm Rd #B, Chilmark, MA 02535
0.37
$1,076,900
2
1.5
1,520
Off Market
7 Yardarm Ln, Chilmark, MA 02535
0.41
$2,694,100
2
2.5
1,836
Off Market
27 Ocean View Farm Rd, Chilmark, MA 02535
0.45
$3,015,200
4
3
2,450
Off Market
18 Allen Farm Rd, Chilmark, MA 02535
0.53
$2,250,000
1
1
726
For Sale
308 South Road, Chilmark, MA 02535
0.55
$6,500,000
4
4.5
3,490
Recently Sold
10 N Abels Hill Rd, Chilmark, MA 02535
0.55
$1,653,300
4
3
2,850
Off Market
6 Trails End, Chilmark, MA 02535
0.57
$2,700,000
4
3
2,346
Recently Sold
8 Wauwompauque Trl, Chilmark, MA 02535
0.64
$5,300,000
5
3.5
2,210
For Sale
31 Cross Rip Ln, Chilmark, MA 02535
0.67
$1,074,900
1
1
512
Off Market
21 & 25 Fulling Mill Rd, Chilmark, MA 02535
0.72
$2,175,000
4
3
1,918
For Sale

Local Information

  • Map ViewExplore the area around 25 Osprey Ln.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1988
3.81 acre lot
3,777 sqft
$1,984/sqft
HOA $33/mo

About this House

Spectacular views from one of the most sought after private enclaves on Chilmark's South Shore. This lovely home was built to take advantage of this magical location. Just steps to the shared dock on the shores of Upper Chilmark Pond and minutes to the extraordinary deeded Atlantic Beach front. The homeowners worked with world renowned architects, Crissman & Solomon, along with revolutionary landscape designers, Wolfgang Oehme and James van Sweden, to create a home that fits perfectly into the lovingly curated landscape with native plants that are a joy to behold whatever the season. The open living, dining, kitchen area overlooks the glorious gardens and lawn sloping down to Upper Chilmark Pond, over to the barrier beach, Atlantic Ocean, Squibnocket Point and Noman's Land beyond. Two additional living areas complement the three bedrooms and three baths allowing areas to enjoy the views from the privacy of each bedroom wing. The home has two offices, a studio and laundry room. The basement and one car garage have ample storage. There is a detached bedroom with full bath and separate living area for guests, as well as a shared dock on the pond and a spectacular sandy beach away from the crowds in a world of its own, just a short trip across the pond from this beautiful home. This is rare offering on Chilmark's south side, available for the first time in almost 40 years! Definitely a must see...this could be the one you have been waiting for...please call for a guided tour to experience the magic of this very special location! Please note, the recorded deed is $7,222,546 but said price does not include the membership interest in Barrier Beach LLC (which provides the right to use the beach, which interest must be sold with the house lot).
25 Osprey Ln, Chilmark, MA 02535 is a 4 bedroom, 5 bathroom, 3,777 sqft single-family home built in 1988. It last sold for $7,289,000 on Oct 15, 2025 (9% below the $7,975,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $7,494,600.
Last check for updates: about 1 hour ago
Listed by Deb Hancock
Hancock Real Estate
Bought with: Deb Hancock, Hancock Real Estate
Source: LINK, MLS#43313

Home Details for 25 Osprey Ln

Interior Features

Interior Details
Basement: A partial full basement with interior and exterior access, as well as crawl space is some sections.Number of Rooms: 9
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 5
Dimensions and Layout
Living Area: 3777 Square Feet
Appliances & Utilities
Utilities: CblAppliances: Stove: Yes, Washer: Yes
Heating & Cooling
Heating: GFHANo CoolingHas HeatingHeating Fuel: GFHA
Fireplace & Spa
Fireplace: one
Windows, Doors, Floors & Walls
Flooring: one
Levels, Entrance, & Accessibility
Floors: One
View
Has a ViewView: Pasture

Exterior Features

Exterior Home Features
Other Structures: Detached bedroom, bath and living area with attached one car garage.Exterior: WViews, Deck, Garden, Patio, DdBch, CovFoundation: Poured Concrete - Full basement with bulkhead and crawlspace on one endGarden
Parking & Garage
No CarportNo GarageNo Attached GarageParking: Yes
Frontage
WaterfrontWaterfront: WaterfrontFrontage Type: WaterfrontOn Waterfront
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1988
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence

Price & Status

Price
List Price: $7,975,000

Active Status

MLS Status: S

Media

Location

Direction & Address
City: Chilmark

Building

Building Area
Building Area: 3777 Square Feet

HOA

HOA Fee Includes: Approximate annual costs per share of Barrier Beach, LLC. Consists almost exclusively of taxes, insurance & accounting fees.Has an HOAHOA Fee: $400/Annually

Lot Information

Lot Area: 3.81 Acres

Offer

Listing Agreement Type: E

Miscellaneous

BasementMls Number: 43313

Price and Tax history

DateEventPrice
Oct 15, 2025
Source: LINK #43313
Sold
$7,289,000
Aug 30, 2025
Source: LINK #43313
Pending
$7,975,000
Aug 9, 2025
Source: LINK #43313
Contingent
$7,975,000
May 23, 2025
Source: LINK #43313
Listed For Sale
$7,975,000

Market trends in Chilmark

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
40
1MoM

Around this home

What Locals Say about Chilmark

At least 2 Trulia users voted on each feature.

  • 100 % Say there's wildlife

  • 100 % Say there are community events

  • 100 % Say car is needed

  • 100 % Say yards are well-kept

  • 78 % Say neighbors are friendly

  • 75 % Say it's dog friendly

  • 75 % Say people would walk alone at night

  • 67 % Say parking is easy

  • 67 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 43 % Say there's holiday spirit

  • 33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Elaine V.
    "I work and live here, and have been in Real estate here for over 20 years, I would recommend it to anyone who needs to feel a sense of community and enjoys nature. A wonderful place to live!!"
    0
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LGBTQ Local Legal Protections

© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-21 08:08:31 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.

Frequently asked questions about 25 Osprey Ln

  • What is 25 Osprey Ln estimated to be worth?
    Trulia's estimated value for 25 Osprey Ln in Chilmark, MA is $7,494,600.
  • What is the price history for 25 Osprey Ln?
    25 Osprey Ln in Chilmark, MA last sold for $7,289,000 in October 2025.
  • Is Chilmark a buyer's or seller's market?
    Chilmark is currently a buyer's market, based on recent for-sale activity.
  • What are the closest schools to 25 Osprey Ln?
    The closest schools to 25 Osprey Ln in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
  • How big is the lot at 25 Osprey Ln?
    The lot at 25 Osprey Ln in Chilmark, MA is about 3.8 acres.
  • Does 25 Osprey Ln have a garage?
    Yes, 25 Osprey Ln in Chilmark, MA has a garage.

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