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111 North Water Street Edgartown MA 02539
Sold

MLS Number 43323

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 4.5
  • Acreage 0.5

HISTORIC CAPTAIN'S HOME WITH GUEST COTTAGE AND DEEP WATER PIER. Step into the heritage and heart of Edgartown Village with this iconic historic captain's home, dating to circa 1850 and thoughtfully reimagined in 2002 under the vision of renowned architect Patrick Ahearn. Perfectly positioned on a rare double-wide lot along highly-coveted North Water Street, this extraordinary property seamlessly blends classic Vineyard character with luxurious modern amenities. Sweeping harbor views greet you from nearly every angle of the bright, sun-washed living spaces, wrapped in windows that frame an awe-inspiring 180-degree panorama of Edgartown Harbor and its iconic lighthouse. The open-concept first floor creates an effortless flow between the living room, dining area, and an inviting eat-in kitchen, all finished with beautiful heart pine flooring, custom millwork, timeless paneling and a handpainted wall mural by well-known island artist, Margot Datz. French doors lead outside to an expansive 18x29-foot mahogany deck - a picture-perfect stage for al fresco dining, summer entertaining, or simply soaking in the serene waterside setting. There are a total of six bedrooms, including a spacious Owner's Suite on the second floor with exceptional harbor views and an en suite bathroom with double vanity and walk-in glass shower. The detached, charming guest house provides private accommodations for visitors, maintaining the same timeless coastal appeal. The lawn gently slopes to a sandy beach at the water's edge, complemented by perennial gardens, an arbor, and a deep-water pier for convenient boating access. Set among lush gardens and surrounded by Edgartown's most storied residences, this is a truly rare waterfront opportunity - where legacy, lifestyle, and location converge.

Listed by Wendy Harman of Compass | Point B

Listing Sold by C McManus Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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12 Guernsey Lane Edgartown MA 02539

Edgartown, MA12 Guernsey Lane

Sale Price$15,400,000

Sold

MLS Number 34675

  • Residential
  • Mls Status Closed
  • Village Katama
  • Bedrooms 6
  • Bathroom 7.5

This spectacular Edgartown harbor front compound was newly built in 2009 and offers 3 buildings with over 7,000 sq. ft. of classically designed living space offering great flexibility in use. The main residence offers a cathedral ceiling living room with fireplace and antique beams. The home has a very livable floor plan with great flow. The 1st floor also includes a large kitchen, dining room, office, den and screened porch. The second floor has 4 bedrooms with 4 baths, two of which have access to a water facing deck. All of the above offers tremendous views over Edgartown Harbor to Chappaquiddick and across Katama Bay to South Beach. There is also a lower level with media room, large living room, powder room and private entrance from the exterior. There is a 3-car carriage house with an additional 2 bedrooms, living room and kitchenette. The rear yard is beautifully landscaped with a large pool, Jacuzzi, grill area and spacious pool deck. Lastly, there's a pool house with bunk beds and separate laundry and a garden storage shed. The 2.1-acres of property offers expansive manicured lawns sloping down to over 120 ft. of harbor frontage, deep-water pier and mooring. This property is located down a quiet drive, 1 mile from town and represents one of the great Edgartown Harbor properties.

Listed by Gerrett Conover of Landvest MV

Listing Sold by Compass | Point B

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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8 Snail Road Chilmark MA 02535

Chilmark, MA8 Snail Road

Sale Price$15,000,000

Sold

MLS Number 42994

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 9.5

LUXURY PROPERTY AUCTION: BID 11-24 APRIL. Listed for $14M. Starting Bids Expected Between $4M-$7M. Perched high on a hill, this Martha's Vineyard estate offers unparalleled privacy and commanding views of the Atlantic Ocean and Chilmark Pond. Designed by renowned architect Rick Sundberg and crafted by master builder Andrew Flake, this three-parcel residence harmoniously blends contemporary amenities with classic Vineyard aesthetics. Upon entering, tall ceilings and oak flooring bathe the interiors in natural light, while expansive glass walls frame panoramic ocean vistas. The modern kitchen boasts cherry cabinets, granite countertops, and premium appliances from Sub-Zero, Miele, Wolf, and Scotsman. The primary suite serves as a luxurious retreat, featuring a private study with fireplace, two opulent baths, a deck, and heated floors throughout. A heated infinity pool offers elegant terrace views of the ocean, complemented by a large kitchen garden, fruit trees, and a half-basketball court. A detached three-bay garage and a two-bedroom guest cottage provide ample space for visitors. Private south shore beach rights, accessible by boat from Chilmark Pond, complete this extraordinary offering.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

Listing Sold by Wallace & Co. Sotheby's

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 South Water Street Edgartown MA 02539
Sold

MLS Number 40448

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 6.5
  • Acreage 0.67

This beautiful home lies on over a ½ of an acre of prime Edgartown harbor front land. It's the only house at the elbow of the harbor and has staggering views past the lighthouse and all the way into the harbor. The house was built in 1909 and was constructed on the original site of Governor Mayhew's summer residence, built in 1642. Governor Mayhew was one of the early settlers in Edgartown and chose this site as the finest lot on the harbor to build his home. The six-bedroom main house is in good condition and is highly situated with commanding views down a sloping grass hill, over Collins Beach, the central harbor and beyond to Chappaquiddick. The home features a large sun porch wrapping around the water side and the second-floor bedrooms access an expansive exterior deck. There is a one-bedroom apartment above a 2-car carriage house. All of the grounds are wonderfully landscaped offering the largest expanse of grass on the inner harbor. There is also a deep-water pier configured to host a number of boats. This is one of the harbor's finest properties located just 2 ½ blocks off of Main Street, and a must see for those seeking the very best.

Listed by Gerrett Conover of Landvest MV

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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20 & 26 Orr Lane Edgartown MA 02539

Edgartown, MA20 & 26 Orr Lane

Sale Price$15,000,000

Sold

MLS Number 37773

  • Residential
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 7
  • Bathroom 7.5

Located off a quiet lane, which ends at Eel Pond, this spectacular property is one of Edgartown's finest offerings. The property is protected by Sheriff's Meadow Conservation land on three sides. This creates the ultimate sense of privacy, and yet it is walking distance to Edgartown's shops and restaurants. The spectacular views look across an expansive lawn, conservation fields, Eel Pond, a barrier beach and out to Nantucket Sound. The 2.43 acre property includes a beautifully restored six bedroom, six and a half bath, 4,442 square foot home, with the finest attention to detail and amenities. The property also features a dramatic pool and hot tub, a one-bedroom pool house designed by Patrick Ahearn and a two-bedroom guest cottage over a two-car garage. Included in the offering is an additional water view building lot, creating flexibility for future expansion for a generational compound.

Listed by Thomas Leclair of Landvest MV

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Oyster Watcha Road Edgartown MA 02539
Sold

MLS Number 44158

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 5.5
  • Acreage 14.7

Located in one of Martha's Vineyard's most desirable enclaves, 30 Oyster Watcha Road offers over 4000 sq ft of living space with sweeping views of Oyster Pond across a wide wildflower meadow. It is a short drive or bike ride to the gated, private ocean beach. There are 4 bedrooms and 5 baths and a garage. The lot is almost 15 acres. There is almost one-third of a mile of pondfront beach. All lots in the Oyster Watcha Midlands Association are waterfront and are greater than 10 acres in size.

Listed by Mark Jenkins of Wallace & Co. Sotheby's

Listing Sold by Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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38 Cow Bay Road Edgartown MA 02539

Edgartown, MA38 Cow Bay Road

Sale Price$15,000,000

Sold

MLS Number 44281

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 7
  • Acreage 2.6

This traditionally styled 4-bedroom home lies on a 2.6-acre lot in the exclusive Cow Bay area of Edgartown. The home was built to the highest of standards and is in excellent condition. The living spaces include a gourmet kitchen with large island, open floor plan with family room, living room with fireplace and TV room/den. There is a ground floor bedroom, laundry and two powder rooms. The second floor has 3 bedrooms all with private baths and a office. Complimenting the property is a 2-car carriage house with 2-bedroom guest house above, a kids playroom, pool, pool house and storage shed. The grounds are perfectly manicured with ample parking, expansive fields filled with wildflowers and unobstructed views of Trapps Pond and the over 2,000 ft. of private white sandy beach. Cow Bay offers all of the beauty and serenity of up island while located only a mile from downtown Edgartown.

Listed by Gerrett Conover of Landvest MV

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 R Temahigan Avenue Oak Bluffs MA 02557
Sold

MLS Number 40396

  • Residential
  • Mls Status Closed
  • Bedrooms 7
  • Bathroom 6
  • Acreage 1.397

Not listed in LINK.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23 Edgartown Bay Road Edgartown MA 02539
Sold

MLS Number 44264

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 4.5
  • Acreage 1.1

Not Listed in LINK - Property has staircase to beach and dock in Katama Bay.

Listed by LINK of LINK

Listing Sold by LINK

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Ask A QuestionMore Details

144 Plantingfield Way Edgartown MA 02539
Sold

MLS Number 42830

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 5
  • Acreage 1.5

Not listed in link

Listed by LINK of LINK

Listing Sold by

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Bayside North, Lot 1 Edgartown MA 02539
Sold

MLS Number 37736

  • Land
  • Mls Status Closed
  • Village Katama
  • Acreage 6.56

This property represents one of the finest opportunities on the Edgartown Waterfront. The 6.5-acres and 380+ feet of direct Katama Bay waterfront is accessed through 23 acres of pristine association land. The property has wonderful rolling pastures, rising from a tidal pond at the bays edge to a large building envelope that could afford a substantial main house, guest house and any number of accessory usages with up to 10 bedrooms. Expansive views stretch across Katama Bay to Chappaquiddick and the barrier beach. There is a substantial dock and the option to buy additional adjoining acreage. The association land could be improved and used for a range of recreational purposes. This very unique property offers tremendous flexibility to create an unparalleled compound in a beautiful and private setting, all located mid way between downtown Edgartown and South Beach.

Listed by Landvest MV

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Ask A QuestionMore Details

12 Caleb Pond Road Edgartown MA 02539

Edgartown, MA12 Caleb Pond Road

Sale Price$14,000,000

Sold

MLS Number 41522

  • Residential
  • Mls Status Closed
  • Bedrooms 5
  • Bathroom 4.5
  • Acreage 2.1

This stunning custom-built waterfront home has sweeping views of Edgartown Harbor. No details were overlooked when designing this unique Chappaquddick compound. Entering through ornate and creative stonework the pool, spa and patio areas are set away from the main house creating a separate space for entertaining or relaxing poolside. The well-appointed one0bedroom guest house is separated from the main house with a slate patio and outdoor stone fireplace. The expansive and sunny deck wraps around the main house with multiple sitting or dining areas. The views from this deck, and most rooms of the house are breathtaking. Once inside you will find an incredible use of rustic wood to give a warm and cozy feel to such a large space. The gourmet kitchen features top of the line appliances and a large center island. The adjacent living room has a stone fireplace and wall to wall windows to admire the view. The second floor bedrooms look out to the harbor and are designed with two queen suites and a bunkroom. The finished lower level has a ping-pong table and impressive home theatre. If you don't care to be indoors on summer vacation, take the walking path down to the private beach and deep-water dock. Enjoy a game of basketball across the meadow at the barn designed with 3 sides of sliding wood doors to let the outside in. A full fitness center with TV and kitchenette waits inside along with a gorgeous guest suite above. Cruise across the harbor to Main Street Edgartown with your own skiff or take the Chappy Ferry only 1/2 mile down the road. This is one special Chappaquiddick home.

Listed by Gerrett Conover of Landvest MV

Listing Sold by Landvest MV

$
$
%
$/month over payments
Federal 30-year interest rate: 6.52% last updated on Jun 11, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Ask A QuestionMore Details

Based on information submitted to LINKMV as of June 13, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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