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23 Circuit Avenue Extension Oak Bluffs MA 02557
Sold

Listing Id 44170

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.1488

Rare Opportunity with Endless Possibilities - Unmatched Harbor & Vineyard Sound Views. Location, Location, Location! A truly rare offering in the heart of Oak Bluffs, where properties like this seldom become available. Positioned directly across from the iconic Oak Bluffs Harbor, this property boasts unobstructed harbor views and sweeping vistas of Vineyard Sound-a setting that captures the very best of island living. From your front yard, watch ferries come and go, boats drift through the harbor, and enjoy the stunning backdrop of open water stretching toward Vineyard Sound. This is a property that puts you right in the middle of everything, while still offering the charm and character of a classic island home. Zoned B-2 Commercial, the opportunities are truly endless. Continue the legacy of a successful tourist-oriented business like the longtime Anderson Bike Rentals, create a new commercial venture, or reimagine the property as your personal dream home. Whether you renovate the existing structure or build from the ground up, you'll benefit from one of the most visible and vibrant locations in Oak Bluffs. Walk to everything-ferries, beaches, the marina, restaurants, movies, shopping, Ocean Park concerts, the OB fishing pier, and the beloved Oak Bluffs Fireworks. This is a must-see, legacy property with rare potential in a location that can't be beat. Very easy to show. Pre-approval or proof of funds required with all offers.

Listed by Ocean Park Realty Inc

Listing Sold by Ocean Park Realty

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$
%
$/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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80 North Summer Street Edgartown MA 02539
Sold

Listing Id 43105

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.12

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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16 Atlantic Avenue Oak Bluffs MA 02557
Sold

Listing Id 44455

  • Residential
  • Mls Status Closed
  • Bedrooms 6
  • Bathroom 2.5
  • Acreage 0.4971

Oak Bluffs | East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse and breathtaking bluff views, this timeless retreat invites you to embrace the slower pace of island life. The stately five-bedroom main residence is rich in character and nostalgic charm, thoughtfully updated to enhance comfort for year-round living. Tucked privately at the rear of the property, a separate one-bedroom guest house offers flexibility and modern conveniences ideal for today's lifestyle. Set on a generous, level parcel with an existing seven-bedroom septic system, the property presents exceptional opportunities for future expansion, customization, or the creation of a true multi-generational compound. Located in the heart of East Chop, a cherished community known for its neighborly spirit, you're just minutes from the harbor and vibrant downtown Oak Bluffs. A rare offering that honors tradition while embracing the possibilities ahead.

Listed by Katie Donahue and Rachel Serwa of Sandpiper Realty

Listing Sold by Studio Realty

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$
%
$/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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61 Causeway Road Vineyard Haven MA 02568
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Listing Id 43495

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 3.5
  • Acreage 0.95

Welcome to this fabulous property nestled just a short stroll from all the best of Vineyard Haven. Easily accessible and within close proximity to the ferry, downtown shops, restaurants, galleries, Owen Park Beach, and the MV Playhouse, the location is ideal. This beautifully designed home has been lovingly maintained and offers a wonderful balance of Vineyard charm and modern convenience. Designed across multi-levels of living spaces, the home provides a flexible layout that works beautifully for entertaining, relaxing, and hosting guests. The main floor welcomes you to an inviting living room filled with natural light and open to the dining area with direct access to the wrap-around deck, perfect for outdoor relaxation and dining al fresco. Cooking and entertaining will be a joy in the kitchen with beautiful quartz countertops, a KitchenAid Professional 6-burner gas range, and custom cabinetry and bar by Ryan Dillon Designs. An en-suite bedroom with a full bath completes this level. The second-floor features the primary suite with pleasant views of the pristine yard, a full bathroom with a double-sink vanity, walk-in shower, Jacuzzi tub, and a large walk-in closet. Another en-suite bedroom with a walk-in closet and the “Hydrangea” half bath are also on this level. A third-floor retreat offers flexible bonus space for an office, den, and overflow. The finished walk-out lower level offers even more additional space for gathering or guests, including a recreation room, and large laundry room. Outside, enjoy the meticulously landscaped grounds, irrigation, and an outdoor shower. For added convenience, there is a detached two-car garage that offers both storage and parking. This exceptional property is ready for immediate enjoyment. Come and experience your Vineyard retreat where you can hear the ferry horn from every room! The property is located in the Lagoon Watershed District.

Listed by Stephanie Roache of Donnelly + Co

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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5 Bold Meadow Circle Edgartown MA 02539
Sold

Listing Id 40429

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.81

Bold Meadow - Tucked away on a quiet cul-de-sac within the Bold Meadow community of fine homes, this contemporary four bedroom colonial sits upon .81 acres abutting the State Forrest with access to walking paths, bike paths to Edgartown village, Katama/South Beach and Morning Glory Farm. There is a first floor primary suite, a second floor bedroom en suite, with two additional bedrooms sharing a common bath. Recent upgrades include a remodeled kitchen, rear deck, and the addition of a light filled, spacious family room with a 'bonus room' above. The professionally landscaped yard is cleared and private. A/C, stainless appliances, hardwood floors, gas and wood burning fireplaces, a full unfinished basement, large garden shed and above ground Intec pool complete this offering.

Listed by Sean Federowicz of Landmarks at TODAY Real Estate

Listing Sold by Compass | MV Team

$
$
%
$/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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43 Moshup Trail Aquinnah MA 02535

Aquinnah, MA43 Moshup Trail

Sale Price$2,425,000

Sold

Listing Id 37897

  • Residential
  • Mls Status Closed
  • Village South
  • Bedrooms 3
  • Bathroom 3.5

Waterviews and private beach in Aquinnah. Exceptional in every way, this 3,000 sq ft home is situated trail side overlooking the Atlantic ocean and Nomans. A stunning stone facade with granite sills leads you to the living level which offers a gourmet kitchen and open-planned living space. Expansive windows frame an unforgettable sweep of sparkling blue water which stretches from shore to Nomans. Last of its kind location. Deeded beach access to the Atlantic Ocean is just a bike ride away.

Listed by Natalie Conroy of Conroy & Company R.E.,Inc.

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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8 Drive Way Chilmark MA 02535

Chilmark, MA8 Drive Way

Sale Price$2,419,145

Sold

Listing Id 38298

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 2.5
  • Acreage 4.7

Middle Road Water View: This fabulous location, just off Middle Road, and not far from Beetlebung Corner, offers views of the lush countryside extending south to the blue waters of the south shore. The residence, designed by noted architect Milton Klein, has modern lines, a minimalist white interior with bleached bamboo floors, a wall of glass sliders with southern exposure and a high ceiling in the Great Room which encompasses living, dining and kitchen. The main level master suite has a separate office space and en suite bathroom. Off the Great Room is a large deck also leading to the screened porch which has access from the kitchen. The lower level floor plan has a family room with built in cabinets for storage and media, glass sliders out to deck and 2 outdoor showers, 3 guest bedrooms, a full bathroom plus powder room, closet laundry room, and utility room. The house is designed with plenty of built-in drawers and cabinets. The 4.7 acre site provides plenty of room for expansion. It is less than two miles to Lucy Vincent Beach and less than 1 mile to the Chilmark Store. Mini-Split A/C in Great Room and Master Bedroom. House heated by both Gas FHW and Electric, and also receives good solar gain from south side. See attached deed for covenants and view maintenance.

Listed by Patty Kendall of Kendall & Kendall

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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5 Ocean View Farm Road Chilmark MA 02535
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Listing Id 40967

  • Residential
  • Mls Status Closed
  • Bedrooms 3
  • Bathroom 1.5
  • Acreage 1.9

A summer house with views to Squibnocket and Aquinnah. Ocean views are seen from the first floor and the second floor and there's a glimpse of Chilmark Pond as well. According to Chilmark's zoning this parcel should support a new house of 3,225 square feet by right (larger with a special permit), with 24 feet in height. Current house is sited on highest point of the parcel. House is heated and air-conditioned with a heat pump. There are miles of crosstown walking trails at your doorstep from Ocean View Preserve to Fulling Mill, Peaked Hill and beyond. Lucy Vincent Beach is just 1.3 miles away. Please note: House is being sold "as is". Buyer needs to honor tenant lease through September 30, 2023.

Listed by Russell Maloney of Russell Maloney Real Estate

Listing Sold by Conroy & Company R.E.,Inc.

$
$
%
$/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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131 North Water Street Edgartown MA 02539
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MLS Number 40351

  • Condominium
  • Mls Status Closed
  • Bathroom 2
  • Bedrooms 2
  • Full Bath 2

UNPARALLELED LUXURY AWAITS AT THE HARBOR VIEW CAPTAIN'S COTTAGES - Near the end of North Water Street, overlooking Edgartown's picturesque harbor and steps from the iconic lighthouse, sits the most storied hotel on Martha's Vineyard. The legendary Harbor View Hotel has been a mainstay for all to gather for generations. Built in 1891 and after a top to bottom restoration in 2018 and extensive modernization again in 2021, this charming and sophisticated resort is offering the opportunity of fully managed residences with deeded ownership providing the splendor of Vineyard homeownership without the worry of maintenance and property management. Sprinkled across the property, the Harbor View Captain's Cottages provide all of the hotel's refined amenities. This all encompassing 2-Bedroom, 2-Bath second floor residence is located in the Captain Osborne Cottage and features fresh and inviting spaces with furnishings that evoke Vineyard style and life lived near the sea. There is even a private outdoor shower and deck right off the primary bedroom! Enjoy morning coffee on the front porch of your cottage enjoying the beautiful gardens, before a day lounging at the pool and cabanas. Have the Concierge book a tee time or pack a picnic for your afternoon relaxing with a book at Lighthouse Beach. Gather for sunset cocktails before dining at the hotel's award winning Bettini Restaurant, while the Chef prepares your favorite meal. Bicycle or stroll around Edgartown Village and enjoy the many art galleries, shops and restaurants surrounded by the beauty and historic charm of the village. Ownership at the Harbor View Captain's Cottages has been thoroughly contemplated to offer the finest service and unsurpassed experiences for Vineyard lovers of all ages. Owners enjoy a myriad of benefits including dining and beverage discounts at the hotel. There is also a fully managed rental program available for when owners are not in residence. The Harbor View Captain's Cottages offer easy and carefree second home ownership with the opportunity for idyllic in-town living.

Listed by Kim Naylor of Compass | Point B

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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46 Bold Meadow Road Edgartown MA 02539
Sold

Listing Id 43855

  • Residential
  • Mls Status Closed
  • Bedrooms 4
  • Bathroom 3.5
  • Acreage 0.82

Welcome to 46 Bold Meadow, a beautifully crafted, move-in-ready 4-bedroom, 3.5-bathroom home nestled in Edgartown's desirable Bold Meadow neighborhood. This thoughtfully designed home showcases quality construction throughout, featuring well-appointed living spaces that balance comfort with functionality. The house features a beautiful front porch that opens into the hall, leading to a study and the living room. The living room has a brick fireplace, built-in bookcases, and hardwood floors throughout the house. The hall leads to a half bath with a washer and dryer, and the Kitchen, which was renovated in 2014. The Kitchen has beautiful counters, top-notch appliances, a wine fridge, a built-in gas range, and custom cabinets. The first floor features a primary with an ensuite bath, a sunporch offering a second dining room, and a cozy living space. The back of the house features a mud room and a two-car garage. Upstairs has two guest bedrooms with a shared bathroom and a second primary with an ensuite full bath. The house has an unfinished basement perfect for storage. The property includes access to the association tennis courts through the Bold Meadow association. The property abuts the Manuel F. Correllus State Forest, offering access to over 5,300 acres of protected forests and wildlife. This natural sanctuary provides endless opportunities for walking, biking along scenic trails, and enjoying the unique disc golf course. The expansive outdoor space, enhanced by the forest setting, creates an unparalleled sense of privacy and connection to nature. Whether you're seeking a year-round residence or a seasonal retreat, this property offers Martha's Vineyard living with the perfect balance between peaceful residential living and island convenience. Make this your next Vineyard home!

Listed by Julianna Flanders of Flanders Real Estate

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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20 Oliver Street Edgartown MA 02539

Edgartown, MA20 Oliver Street

Sale Price$2,400,000

Sold

MLS Number 36950

  • MultiFamily
  • Mls Status Closed
  • Village Downtown
  • Bedrooms 4
  • Bathroom 4.5

TWO GOOD TO BE TRUE: IN-TOWN PERFECTION. Sited on a quiet street in the heart of historic Edgartown Village, this charming and unique property is comprised of TWO beautifully renovated 2-bedroom residences offering the perfect opportunity for a smart rental investment property, multi-generational living and/or a built-in guest suite for visiting family and friends, as the two units can also be connected through a lock-off door. There is also a fully finished walk-out basement with private entrance. Tastefully renovated from top to bottom with a designer's eye, the property features beautiful hardwood floors, beautifully appointed kitchens and baths with stone countertops, custom tile work -- and so much more! The private and beautifully landscaped yard offers a private and serene oasis with a bluestone patio and outdoor gas fire pit sited beneath lovely shade trees. This property is absolutely charming and is truly a one-of-a-kind, special offering.

Listed by Wendy Harman of Compass | Point B

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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3 Jacobs Neck Road (South Lot 2) Edgartown MA 02539
Sold

MLS Number 43923

  • Land
  • Mls Status Closed
  • Acreage 7.08

Build your dream home or homes on the special 7.1 acre private wooded property surrounding a beautiful 4.5 acre meadow in the grand Boldwater Association (BWA) on the glorious Edgartown Great Pond with approx. 3,000 ft of private barrier beach. BWA is 40 homesites on 450 acres with 150 acres of conservation abutting another 1,500 acres of conservation and a few large estates - all convenient to town and airport. BWA amenities also include 2 tennis/pickleball courts and a boat launch which are both nearby. EDGARTOWN PLANNING BOARD APPROVED ON 10/22/25 A SUBDIVISION OF THE 14+ ACRES INTO TWO 7+ ACRE LOTS - North Lot 1 and South Lot 2. The lots can be purchased together for $4,950,000 or separately for $2,490,000. Both lots enjoy full BWA membership rights and privileges. The 2 lots will split ownership of the 4.5 acre meadow if sold separately. (see approved subdivision plan in DOCUMENTS)

Listed by Tea Lane Associates

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.

Virtual TourAsk A QuestionMore Details

Based on information submitted to LINKMV as of June 16, 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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