25 Osprey Ln, Chilmark, MA 02535
Property image
Property image
SOLD
OCT 15, 2025

25 Osprey Ln
Chilmark, MA 02535

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

$7,289,000

Last Sold: Oct 15, 2025
9% below list $7.97M
$1,930/sqft
Est. Refi. Payment $39,892/mo*

$7,289,000

Last Sold: Oct 15, 2025
9% below list $7.97M
$1,930/sqft
Est. Refi. Payment $39,892/mo*
4 Beds
5 Baths
3,777 sqft
(on 3.81 acres)

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

Property Type
Single-Family Home
Year Built
1988
Lot Size
3.81 acres
Living Area
3,777 sqft
Price/Sqft
$1,930/sqft
HOA
$33/Monthly

Description

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). It is currently off market. The Trulia Estimate is $7,429,800, with a rent estimate of $7,924/month.

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: $7,975,000Price Per Sqft: $1,930/sqft

Active Status

MLS Status: S

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
Last check for updates: about 2 hours ago
Listed by Deb Hancock
Hancock Real Estate
Bought with: Deb Hancock, Hancock Real Estate
Source: LINK, MLS#43313

Price History for 25 Osprey Ln

DatePriceEventSource
10/15/2025$7,289,000Sold
LINK #43313
08/30/2025$7,975,000PendingLINK #43313
08/09/2025$7,975,000ContingentLINK #43313
05/23/2025$7,975,000Listed For SaleLINK #43313

Market trends in Chilmark

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
31
4
MoM
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Property Tax and Assessment

Year2025
Tax$17,244
Assessment$7,663,800
Home facts updated by county records

Comparable Sales for 25 Osprey Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1.34
Single-Family Home
$6,100,000
03/24/26
6
7
5,660
1.29
Single-Family Home
$2,100,000
11/25/25
4
3
2,544
1.71
Single-Family Home
$2,475,000
09/05/25
4
3.5
2,300
0.94
Single-Family Home
$1,775,000
11/07/25
3
2
1,728
1.73
Single-Family Home
$4,325,000
12/05/25
5
2.5
3,885
2.27
Single-Family Home
$4,850,000
12/05/25
5
3.5
4,044
2.59
Single-Family Home
$8,178,500
10/27/25
6
4.5
4,104
2.54
Single-Family Home
$3,710,000
03/12/26
3
5
3,171
2.41
Single-Family Home
$2,225,000
10/24/25
4
3
2,968

Nearby homes

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Assigned Schools

These are the assigned schools for 25 Osprey Ln.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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!!"

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Apartments for Rent

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Homes for sale near 25 Osprey Ln

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Off Market Homes Near 25 Osprey Ln

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© 2026 LINK, All Rights Reserved. Data last updated: 2026-07-23 09:49:42 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.