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
-- mins to
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
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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 |
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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 |
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Year Built Year Built: 1988 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
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Price List Price: $7,975,000Price Per Sqft: $1,930/sqft |
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MLS Status: S |
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Direction & Address City: Chilmark |
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Building Area Building Area: 3777 Square Feet |
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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 |
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Lot Area: 3.81 Acres |
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Listing Agreement Type: E |
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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
| Date | Price | Event | Source |
|---|---|---|---|
| 10/15/2025 | $7,289,000 | Sold | LINK #43313 |
| 08/30/2025 | $7,975,000 | Pending | LINK #43313 |
| 08/09/2025 | $7,975,000 | Contingent | LINK #43313 |
| 05/23/2025 | $7,975,000 | Listed For Sale | LINK #43313 |
Market trends in Chilmark
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
31
4MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 25 Osprey Ln.
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.
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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.

