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Explore homes for sale in Martha's Vineyard.

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Find charming homes for sale in downtown Martha’s Vineyard. Enjoy the vibrant island lifestyle with these centrally located properties.

Downtown

Downtown Homes for Sale, Martha’s Vineyard | MV Seacoast

Perfect opportunity to own a Beautiful Beach Cottage with access to Lagoon. Totally renovated in 2019. It has been designed for relaxed living and memorable entertaining. There are 3 seating areas on the deck, to enjoy dining outside, experiencing incredible waterviews and lovely sky reflections of sunsets. Beautifully landscaped, with seasonal flowers, and Butterfly flowering bushes. Easement to the boardwalk to reach the beach, swim, kayak, canoe, and sunbathe. Two story Beach Cottage, first floor kitchen leads to the dining, living and sun room, Queen bedroom and a full bath. Second floor features three bedrooms. Master Queen en-suite with water view, Guest Bunk bedroom and Twin bedroom which share full bath. Wood floors, water views throughout, new outdoor shower. In the morning enjoy what mother nature has in store for you. The cry of gulls,deer running on the beach, it is just solitude. Property is being sold with 2 unbuildable lots. You will never have to worry about losing your view. This is a property worth seeing. Leases are in place for 2024 to be transferred to Buyer at closing. Showings only on Sunday from 12:00pm until 2:30pm during the rental season.

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34 Windemere Road

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Live the beautiful Island Life with this gorgeous condo at an affordable price. This is a delightful one and a half bedroom seasonal condo ( sleeps 6) available for your families use. When you’re not here, the management team will rent and take care of everything for you. Amenities are amazing. There’s a beautiful pool, spacious outdoor area with lots of seating, fire pits, play area &  barbecues.  Right next to the popular Nomads restaurant and walking distance to two ocean beaches, bike paths and buses to towns.
Brokers must accompany clients.

21 Island Inn Road 35G

New Construction To Be Built at Lagoon Ridge ~ The Homes at Lagoon Ridge is a subdivision of stylish, new construction properties to be built by M. Duffany Builders. The Naushon home design is an elegant 2 bedroom, 3 full and 1 half bath home with over 2500 square feet of fine craftsmanship. The curb appeal will immediately charm you with its welcoming wrap-around porch. Just off the foyer, the spacious Great Room is open to the kitchen and dining area, offering an ideal space to entertain large groups of friends and family. The smart kitchen design includes stainless steel Bosch appliances, spacious 42” tall wall cabinets, quartz countertops, and Kohler fixtures. The main floor has 9’ ceilings and oak hardwood floors throughout. French doors in the dining room open to a sunny side deck that flows onto an attached covered rear porch. For privacy, the main level guest bedroom and en suite bathroom are on the opposite side of the foyer. The spacious primary bedroom suite, on the second level, will be your serene and private retreat. The en suite primary bathroom includes a Kohler soaking tub, a tiled walk-in shower with a glass door enclosure, and a double vanity. A full bath and separate laundry room complete this lovely space. Enjoy the spacious backyard from your deck or covered porch, which can easily accommodate a pool and a two-car detached garage, offered as an optional upgrade, creating the perfect Vineyard dream. *Optional builder and appliance package upgrades are available. *Renderings are for illustrative purposes only. Construction details are governed by builder specifications and final construction agreement with Builder.

35 Double Ox Road

This 3 + acre Lower Makonikey lot with mature trees is a short distance away from a deeded private association beach. A quiet friendly community with protective covenants. The lot has been surveyed and a building envelope has been established. To date no testing or septic design has been performed.

00 Kennebago Avenue - 65-E-1

Edgartown opportunity—Finish off the seller's vision or create your own masterpiece! With over an acre of land, there is plenty of room to expand. Only two miles from lively downtown Edgartown, you get the privacy, beauty, and feel of the up-island without the commute. The lot can support a house, guest house, garage, and pool. Please no drive-bys.

4 Dubud Lane

11 Greenhouse Lane...an incredible opportunity to own in this sought after private enclave with deeded private south shore beach and pond access close by...this charming vintage cape enjoys views over wetlands out to the Atlantic beyond! Three bedrooms, two baths, living room with fireplace, dining area, updated kitchen, screened porch and outside shower. The owners have taken full advantage of this beautiful site, with a patio for entertaining and a dipping pool. A spacious shed has great storage for kayaks, paddle boards, surfboards and much more. Beautifully landscaped and ready for you to enjoy summer in Chilmark with additional beach access to Lucy Vincent and Squibnocket. An added bonus is the 240v ChargePoint at the driveway.

11 Greenhouse Lane

Sublime hillside site with old growth trees and walking easement to 16' of sandy lagoon pond beach.
This property is in the lagoon pond water shed and will require a NitROE denitrification component on the septic system. All information should be verified by the Vineyard Haven Building Department and Board of Health. Seller not able to close prior to October 31, 2024.

126 Border Road

EXISTING FIVE (5) LOT SUBDIVISION IN OAK BLUFFS.  Almost 5 Acres of wooded, level land within half a mile of Eastville Beach, Doug's Cove Preserve (4.6 acres of Land Bank Property) and less than a mile to Oak Bluffs Harbor.  NEW Shared Use Path runs along Eastville Avenue, when finished will link Vineyard Haven and Oak Bluffs for walking and cycling.  Septic permits in place for two lots.  Lot #1 - 147.2 (45,782sq.ft.) Permit in place for an APPROVED 6 Bedroom Septic System;  Lot #2 - 147.3 - (31,320sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #3 - 147.4 - (34,824sq.ft.) 6 Bedroom Septic System Designed and submitted, NOT YET approved; Lot #4 - (52,451sq.ft.)  6 Bedroom Septic System Designed, NOT YET submitted; Lot #5 - (45,074sq.ft.) - Permit in place, APPROVED for a 4 Bedroom Septic System.  Lot # 5 - May have access directly from Wapello Street.  Ten (10) Bedrooms have been approved.  Applications for an additional Twelve (12) Bedrooms are in process.  Lot#2 - Application for 6 bedrooms. Lot#3 - Application for 6 Bedrooms.  Lot #4 is undetermined at this point.  Access may be allowed via Sunset Road or Eastville Avenue.  Water is available via Sunset Road, at the property.  Electricity is on site.  Buyer is responsible for verifying any and all information on this property.

0 Eastville Avenue

Nestled in Vineyard Haven, 46 Red Buoy Lane is an exquisite and sophisticated home completed in 2022. This residence offers 4 bedrooms and 3.5 bathrooms and spans a generous 1,816 square feet. The property's unique offering of a one-bedroom apartment in the basement is noteworthy, providing an additional 597 square feet of living space.  
The main level boasts a thoughtfully designed floor plan featuring a gourmet kitchen, a spacious living area, and a dining space ideal for entertaining. The primary bedroom suite offers a private retreat with a luxurious en-suite bathroom.

With a 6-bedroom septic in place, the possibilities for expansion are endless. The generous lot size allows for the potential of a garage, guest house, and pool catering to your individual vision. 

Located in the sought-after Vineyard Haven, this home presents a rare opportunity to embrace a lifestyle of luxury and tranquility. The property is located within the Lagoon Watershed and does not require a septic system upgrade. The current system complies with the new town regulations. 24-hour notice is needed for all showings.

46 Red Buoy Lane

THE PRESERVE at THE WOODLANDS ~ OAK BLUFFS COVETED COMMUNITY of architecturally designed residences. Live in ONE of the most sought-after locations in Oak Bluffs that is conveniently located to town, beaches, harbor, ferry ports, and Farm Neck Golf & Tennis Club. This is a RARE OFFERING to purchase one of the last remaining building lots and develop a family compound. There are underground utilities and town water in place and each lot has been approved for up to six bedrooms per Oak Bluffs Board of Health. A peaceful and private setting abutting conservation land and trails for hiking, walking and biking! Don't wait to be part of this lifestyle!

22 Paddock Road

KATAMA CONDOMINIUM IN MEETINGHOUSE VILLAGE - A bright and sunny center unit with an open floor plan, vaulted ceilings, skylights, and windows that fill the space with natural light. This home is in excellent condition, showing the pride of ownership. The wide-open kitchen with a breakfast bar offers a wonderful space for cooking and entertaining. Accommodations include a first-floor bedroom with a full bath and a second-floor primary suite. Outside, you will find a private back deck, beautiful garden and open lawn. The newly appointed Association swimming pool is close by. Located in the highly desirable Katama area, this home sits less than two miles from South Beach and even closer to Edgartown Great Pond. This private community is a hidden gem, ideal for year-round living, a vacation home, or a rental investment.

17 Meetinghouse Village Way

Rare opportunity to build on Chilmark's south shore. This 1.4 acre parcel should allow for new construction of 3,100 square feet and 24 feet in height, by right, with building department approval. Views to the Atlantic Ocean and Chilmark Pond can be seen from the second floor. This parcel comes with a dock on the pond which provides access to a beautiful barrier beach on the Atlantic. Well in place, buyer responsible for new septic system.

2 Other House Road

You haven't missed the boat. And if you live here, you will never miss the boat.
This fully furnished, classic Vineyard-style home can be your home in time for spring.  
This beautifully restored 3-bedroom, 2-bath home has touches from the old Vineyard—a sun porch for napping or reading, a large yard with magnificant magnolia tree, and a detached garage for your Island car. You will never have to worry about steamship reservations again.
You're within walking distance of everything you need—markets with locally grown food, fish, and meats; coffee shops, restaurants, galleries, 
and you can walk to the Steamship Authority terminal.  
This Vineyard classic home is being sold fully furnished down to the lobster pot. All you need to bring is your swimsuit.

249 State Road

Spectacular, private beach lot located just off Moshup Trail. Gated entry, parking rights and a deeded 1/5 acre of beach on the Atlantic. This is not a buildable lot, no structures of any kind are permitted. Lot 7-5

00 Moshup Trail

Exceptional 8 bedroom home with attached artist/fitness barn studios. 
Each bedroom includes a en-suite bathroom.
The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

26 Curtis Lane

Unique opportunity to purchase two adjoining lots at 211 Upper Main Street and 26 Curtis Lane in Downtown Edgartown. 

211 Upper Main St., Edgartown is a 15 bedrooms, 18 full baths, 2 half baths building with two large artist/fitness studios attached. It is in the B1 Commercial zoning district. Each bedroom includes an en-suite bathroom. Spacious kitchen and dining area. The kitchen/dining area includes: 2 refrigerators and 4 freezer drawers, A 5-burner gas stove and oven, 2 dishwashers, 1 microwave. Spacious living room: including 2 sofas and 1 coffee table, finished basement (2,000 square feet), Basement includes: 10 washer/dryers, 1 television and DVD player, 2 small rehearsal rooms, Complimentary Wi-Fi, Outdoor deck with picnic tables.

26 Curtis Lane is an exceptional 8 bedroom home with attached artist/fitness barn studios. Each bedroom includes a en-suite bathroom. The kitchen/dining area includes: 3 refrigerators and 6 freezer drawers, a 5-burner gas stove and oven, dishwasher and microwave. Finished basement (1,000 square feet). Basement includes: 3 washer/dryer units. Outdoor deck with table, chairs and an outdoor grill.

Two more adjacent lots with parking and a yard are also available for purchase upon request.

211 Upper Main Street & 26 Curtis Lane

PRIME 5-ACRE LOT - R20 ZONE EDGARTOWN 
Introducing a rare opportunity to own a piece of the island (currently two parcels) close to all Edgartown has to offer. This spectacular level lot is situated along Edgartown Road and provides the perfect setting to create a private retreat or a potential subdivision. The property borders the Triangle area of Edgartown, with ease of access to public transportation routes. Ideally located just minutes from beautiful beaches, boutique shops, and world-class dining. Please note, that perc tests and utilities are the buyer's responsibility. Don't let this extraordinary opportunity to build slip away!

15 & 27 Pennywise Path

Ocean views - Nestled on a quiet corner lot, this classic beach house  offers a reverse floor plan and distant views of the Atlantic Ocean over the Katama Plain. It is only 1.5 miles to South Beach and just under 2 miles to the heart of Edgartown village. The upper level features the common living space including the dining area, kitchen, living room with fireplace, and large powder room. The lower level is where you find the more private spaces, including the primary bedroom suite plus an 2 additional bedrooms and full bathroom. For 30 years the property has been a generational meeting place for the owners, their family, and friends, and now they are passing the baton on to its future owners. Enjoy it “as is” or put your vision to work to create a brand new Katama beach house to make your own memories.

18 Katama Drive

GROVEDALE BUILD YOUR DREAM OPPORTUNITY - Along a quiet country lane and close to all Oak Bluffs has to offer, this level lot is located in a neighborhood of nicely landscaped homes. The pride of ownership is apparent in this locale. There are not many opportunites like this left on Martha's Vineyard.

0 Concord Avenue

The Preserve at the Woodlands - A terrific opportunity to build in this beautiful and prestigious neighborhood in Oak Bluffs. The Preserve has matured into an enclave of significant residences and offers excellent privacy, with convenience to downtown, harbor and beaches. The orientation of this parcel is prime with southern exposure for backyard pool and patio, and it is abutting dedicated open space on two sides. The lot will support 6 bedrooms, has been perk tested and is ready for you to build your ultimate Vineyard compound.

34 Paddock Road

Panoramic Ocean Views can be enjoyed from each level of his thoughtfully built 4 BR home designed for easy Summer enjoyment or 4 Season living. It is wonderful in every way. It is built into the hill, so the first floor feels like a 2nd floor. Downstairs is a large open space to create a family room, or use it the way it is as a home gym/spa with state of the art equipment included. Energy efficient, private, easy access, plenty of outdoor space that has huge potential since the home takes up only 1/3d of the property. Enjoy complete privacy from neighbors or the road, nestled into a hillside where bird life abounds, yet convenient to dining at the Outermost Inn, Lighthouse and cliffs.

The home is lavishly laid out over 2 levels and provides over 3000 ft. of living space. A wall of glass on both levels for the enjoyment of the uniquely insteresting, forever protected vistas across a one of a kind beauty of the pristine fauna and flora of Aquinnah. There is nothing obstructing the views to the horizon with the Elizabeth Islands, and Menemsha hills. Watch the sailboats glide by and relax in style and comfort in this wonderful space. All Aquinnah Beaches are accessible within a short distance. Price has been drastically reduced by motivated Seller! House comes Turn Key for immediate use. Fully furnished and ready to go right now, or Enjoy your first Summer 2025 at this fabulous Vineyard Coastal home.

382 Lighthouse Road

Discover Your Up Island Retreat: Nestled in the heart of West Tisbury, this exceptional 5-bedroom, 3-bathroom, 2500-square-foot home awaits your personal touch to complete its remarkable transformation. Abutting a picturesque horse pasture, this property offers a tranquil escape from the daily hustle and bustle. A recent extensive gut renovation has laid the foundation for your creative vision, with much of the significant work already completed. Step outside onto the expansive mahogany wood deck (completed in 2021), a perfect space for entertaining, relaxing, and savoring the idyllic surroundings. Inside, the entire house showcases stunning Brazilian walnut hardwood flooring. New mechanical systems, upgraded electrical, and brand-new plumbing allow you to enjoy your new home worry-free. Additionally, the house has been fully spray-foamed, and a new roof was installed in 2021. Your dream kitchen awaits with a full set of brand-new Thermador kitchen appliances, still in their original packaging, ready for you to create culinary masterpieces. The spacious and well-designed kitchen layout will undoubtedly become the heart of your new home. When it's time to unwind and enjoy the natural beauty of the island, Lambert's Cove Beach is just a quick drive away. Known for its pristine shores and breathtaking sunsets, Lambert's Cove Beach provides the perfect backdrop for relaxation and recreation. Start imagining the endless possibilities that await in your new Up Island Retreat.

219 Oak Lane

Located in the heart of Oak Bluffs, this land offering abuts a protected Town park and is within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place for a 1 bedroom home, embrace the unique opportunity to build your own custom residence. Whether you envision a cozy cottage, a modern retreat, or a traditional island dwelling, the possibilities are endless.

0 Barnes Road

Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket Association, this four-bedroom, three-bathroom home offers stunning views of acres of conservation land, Sengekontacket Pond, and Nantucket Sound. Perched on a hillside, the house provides utmost privacy from all rooms while being just a short walk from the Association boat ramp and kayak storage.

The main level features a living area with a wood-burning fireplace, a spacious kitchen, and a screened-in porch with cathedral ceilings, perfect for dining while enjoying the beautiful views.

The primary suite is situated on the second floor and boasts French doors that open to a small deck, allowing you to take in the expansive scenery. The lower level includes three bedrooms, each with French doors leading to a lower deck, and they share a full bathroom. 

The Sengekontacket Association, established in 1971, encompasses 93 acres and provides a variety of amenities including tennis and pickleball courts, an Association Clubhouse situated on Wiggy’s Pond, and a boat ramp with kayak storage on Sengekontacket Pond. Homeowners can consult the Harbor Master for a mooring in Major’s Cove, where the Association dock is located.

Fully renovated in 2007, this property is ready for you to enjoy!

30 Sengekontacket Road

Discover this private Katama retreat, perfectly situated on over 3 acres of forested and landscaped grounds. Located just a mile from Edgartown Great Pond and a little over 2 miles from both South Beach and Edgartown Village, this contemporary guesthouse offers the ultimate island escape. Built in 2018, it boasts a proven rental history and is outfitted with every modern amenity. With a 6-bedroom septic system already in place, there’s ample opportunity to expand by adding a main house or additional structures, pending necessary town approvals. Enjoy now while envisioning its full potential!

114 Meetinghouse Way

You’ll always feel like you’re on vacation at this four-bedroom, two and one half bath home sited perfectly on 2.4 acres to capture sweeping vistas of the Atlantic Ocean and Noman's Island. Built in 2006, this home features an open living room, dining room and stainless steel kitchen flooded with light from the wall of windows providing wide views to the Atlantic. Enjoy dining on the wrap around mahogany decking. Views are also seen from the large, first floor, primary bedroom with en-suite bath. Descend to the lower level, where three additional bedrooms await—two of which have water views. The larger of the three bedrooms has walk out access to a patio with an adjoining flower and vegetable garden. A large bathroom, laundry and utility room complete the lower level. The property is further enhanced by stone walls and mature landscaping, creating a picturesque setting. A workshop/studio with full basement, plumbing, electricity and a wood stove is located at the rear of the property. A new Land Bank/Sheriff's Meadow property currently under development will provide access to Squibnocket Pond and one of the most beautiful beaches on the island and is located just across the street.

4 Nomans Watch Road

PRIME 1.5 ACRE BUILDING LOT IN EDGARTOWN - Seize this opportunity to design and build your very own signature estate in Katama including the possibility of a Main House, Guest House, Garage, Pool, and more! This conforming, R-20 prime building parcel will support EIGHT BEDROOMS (8) with a standard Title 5 septic system. Nestled in an area of fine homes and ideally located on the edge of famed Katama, just 4 minutes to Main Street in Edgartown. PLEASE NOTE: Locus shown in first photo is approximate. Refer to attached documents for complete survey.

26 Mill Hill Road

Nestled in the heart of Edgartown, is this historic residence known as The Lightkeeper’s Inn. This property has five bedrooms, five baths and a separate one bedroom, one bath cottage, on .20 acre. Beautifully decorated in ole Vineyard style, the residence has the island feel of old time Martha’s Vineyard. This 5BD/5BA home sits in the heart of Edgartown close to the waterfront. Known as The Lightkeeper’s Inn, this historic Inn was said to be home to Henry Lyman Thomas, one of the last lightkeepers of the Edgartown Lighthouse.  The property is unique in that it offers onsite parking, which is a rarity on Martha’s Vineyard. Currently operated as an Inn, this property may be converted to a single family residence with the required proper permitting and approvals. It is conveniently located close to Edgartown Ferry, Edgartown Lighthouse, and minutes from N. Water Street, which offers shopping and restaurants.

25 Simpsons Lane

Located under a mile from downtown Oak Bluffs, this well-maintained 4-bedroom home includes a 3-bedroom main house and a 1-bedroom basement apartment. Recent upgrades include a new roof, Title V septic system, electric service, and town water connection. The first floor features a spacious living/dining area, kitchen, half bath, and a cozy den. Upstairs are 3 bedrooms and a full bath. The finished basement apartment offers an open kitchen/living area, 1 bedroom, and a full bath. Enjoy outdoor living with a large deck, front porch, a spacious backyard, an outdoor shower and a large shed. Ideal for year-round living or investment!

10 Kims Way

Waterfront home on Stonewall Pond. Nestled along the serene shores of Stonewall Pond, this waterfront home is located in one is Chilmark’s most idyllic locations. This remarkable property offers an unparalleled living experience with breathtaking Atlantic Ocean views and exclusive access to Stonewall Beach. Step inside and be greeted by a seamless fusion of elegance and comfort. The interior spaces are thoughtfully designed to maximize the views and large windows let in an abundance of natural light. With most of the living area on the first floor, the spacious layout features a large living room with stone fireplace, dining room with fireplace, home office, gourmet kitchen, and 3 spacious bedrooms. The second floor features a bedroom suite with breathtaking views of Stonewall Pond and the Atlantic Ocean beyond. This Chilmark location harmoniously combines natural beauty and modern conveniences. In addition to the immediate waterfront access, the surrounding area offers a wealth of activities including boating, fishing, kayaking and paddle boarding. Don't miss your chance to make this unparalleled waterfront retreat your own.

20 Eliot Avenue

Upon entering through the charming side door, you're welcomed into a beautifully screened sun porch – the perfect spot to relax and soak in the surroundings. This inviting space leads to a sprawling, light-filled chef’s kitchen, designed for both culinary creativity and social gatherings. Adjacent to the kitchen, a warm and welcoming living room awaits, featuring a convenient half bath and access to a cozy first-floor bedroom. Just to the right, you’ll discover a second ensuite bedroom, offering both comfort and privacy for guests or family.

From the hallway, a staircase leads to the upper level, where two additional, spacious bedrooms each come with their own well-appointed bathrooms, creating a serene and private retreat.

A second door off the living room opens to the lower level, where you’re greeted by a partially finished entertainment haven, complete with a pool table – an ideal space for relaxation and recreation. Further down the hall, to the left, is the media room, a cozy setting perfect for movie nights. Across from the media room, you’ll find a convenient half bath that leads into a laundry room with direct access to the backyard, blending functionality and convenience seamlessly.

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32 Norton Orchard Road

The Salt Shack merges historic preservation with modern updates in Menemsha. Designed by husband-and-wife luxury boutique design firm, Morgan Studio, the renovation of this 100-year-old ocean view cottage preserves its charm and historical integrity while incorporating contemporary design elements to enhance both comfort and aesthetics. Nestled behind Menemsha Pond, the cottage boasts a prime location for watching incredible sunsets over the pond to the ocean beyond and strolling into town for beach-going, fishing, boating, shopping, and dining. The layout and flow of the spaces feature captivating views from many vantages, and all new windows enhance natural light and views. The refined palette and materials reflect the natural surroundings and match the experience of Menemsha living. With modern forced air cooling and heating and a fully insulated structure, the property can be enjoyed year-round. Additionally, the ground level suite is the ideal complement to the two upper floors, providing a private retreat for family and friends. A turnkey ocean-view offering, the Salt Shack presents a rare opportunity to enjoy a stunning escape to the authentic fishing village of Menemsha.

10 Mollys Way

Ideal Tashmoo Woods Association, located adjacent to Mink Meadows Golf Course and minutes from downtown Vineyard Haven. This location offers private association beach on Vineyard Sound, access to Lake Tashmoo and association dock, heated pool, tennis courts, basketball court and playground, all on 100+ acres of association land. Well loved through the years, this unit is ideal for year-round living or as an investment opportunity. The first floor living room is full of windows, bringing natural light into the rooms. Open floor plan design connects the main living area with the cathedral ceiling and fireplace to the dining room, mini bar and eat-in kitchen. There is a separate den with French doors. The full bath is located across the hall from the den. Large refinished deck off the back. The second floor offers a primary suite with vaulted ceiling, spacious bath with Jacuzzi and large walk-in closet. A second floor balcony leads to the guest suite, with full bathroom, and offers views of the living and outdoor space on each side. This is a unique combination of location and amenities. Hiking trails through the property lead to both Lake Tashmoo and the north shore beach where you can enjoy amazing sunsets. Strong rental history.

200 Sandpiper Lane 11

Ideal Tashmoo Wood Association, located adjacent to Mink Meadows Golf Course and minutes from downtown Vineyard Haven. This location offers a private association beach on Vineyard Sound, access to Lake Tashmoo and association dock, heated pool, tennis courts, basketball court, and playground, all on 100+ acres of association land. Well-loved through the years, this unit is ideal for year-round living or as an investment opportunity. The first-floor living room is full of windows, bringing natural light into the rooms. Open floor plan design connects the main living area with the cathedral ceiling and fireplace to the dining room, mini bar and eat-in kitchen. There is a separate den with French doors. The full bath is located across the hall from the den. Large refinished deck off the back. The second floor offers a primary suite with vaulted ceiling, spacious bath with Jacuzzi, and large walk-in closet. A second-floor balcony leads to the guest suite, with full bathroom, and offers views of the living and outdoor space on each side. This is a unique combination of location and amenities. Hiking trails through the property lead to both Lake Tashmoo and the north shore beach where you can enjoy amazing sunsets. Strong rental history.

Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece of land.  One bedroom house situated on a 1/3 Acre, 14,810 sq.ft. level lot.  One side of the property is lush with vegetation and the opposite side is clear.  It is one lot in total and may not be subdivided. The existing house has been lived in year round. Only .6 of a mile to Oak Bluffs Harbor and .5 mile to the top of Circuit Avenue!  Title 5 Certification in place for existing one bedroom septic system.  Lot is in Zone II and will allow a total of two bedrooms with an advanced treatment system.  Land is large enough to have a house and guest house when meeting ZBA requirements or with new Massachusetts Accessory Dwelling Unit law.  A short stroll, just one house away, from Wesleyan Park.  Close to town, restaurants and all that Oak Bluffs has to offer!  Walk to the harbor!  This is a little gem, waiting to be polished!!  Property is being sold in "As is" condition. Easy to show!!

26 Winthrop Avenue

**Charming Vineyard Waterfront Cottage in Oak Bluffs**

Nestled in a peaceful cul-de-sac in Oak Bluffs, this newly renovated 2-bedroom, 1-bathroom cottage offers the perfect blend of traditional Vineyard charm and modern sensibility. With stunning panoramic views of Brush Pond, the Lagoon, and the iconic Drawbridge, this cozy retreat provides the ultimate setting for both relaxation and outdoor enjoyment.

Inside, natural light pours into the open-concept living, dining, and kitchen areas, creating a bright and airy space designed with comfort in mind. The spacious kitchen flows seamlessly into the dining area, where you can enjoy meals with a view or sip a morning coffee while taking in the serene landscape. The living room offers a cozy space to unwind, while large windows frame the breathtaking vistas and invite the outdoors in.

Step outside onto the surrounding patio, where you'll find plenty of seating to enjoy the tranquil surroundings. Adirondack chairs and patio furniture provide the perfect spots to watch the sunset over the water—an experience you won't want to miss. Lush greenery, vibrant flowers, and mature trees create an idyllic outdoor oasis.

Whether you’re seeking a peaceful retreat or a place to entertain, this Vineyard cottage offers it all. The combination of its charming interior, spectacular views, and serene outdoor spaces make it a true haven. Ideal for a vacation home or year-round residence, this property is a rare find in Oak Bluffs. Don't miss the chance to call this waterfront beauty your own! This property is a great income producer, with a very strong rental history.

66 Brush Pond Road

WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot.  According to the engineer who has percolated the lot, it will allow a 5 bedroom regular septic system.  The Board of Health have stated there are no Board of Health issues with this property and are deferring to the engineers opinion. Water and Electricity are all ready at the site.   There's also a small house on the property, built in 1900, and a dilapidated garage.  Property is being sold in 'As is" condition.  If BUYER chooses to remove the house and garage it will be at their expense.  Retaining the footprint of the garage has value as it could be rebuilt in place or possibly an ADU could be built on that footprint. Easy access to harbor, town, shops, restaurants, Oak Bluffs Ferry, Sunset Lake, Campground cottages, Oak Bluffs Library.  PRICED BELOW ASSESSED VALUE.

25 Oak Avenue

WALK TO THE HARBOR from this level 10,100 sq.ft. quarter acre lot set down a winding avenue off New York Avenue.  Currently there's a very cute Victorian Era two story cottage which could be renovated. If your preference is to build a new 5 Bedroom House instead, the Seller has already been through the lengthy process with the Martha's Vineyard Commission to receive approvals to knock down the house and has succeeding in obtaining that approval. According to the engineer who percolated the lot, the lot will allow a 5 bedroom regular septic system.  The Board of Health have stated there are no Board of Health issues with this property and are deferring to the engineer's opinion. Water and Electricity are already at the site. Property is being sold in 'As is" condition.  If BUYER chooses to remove the house and garage it will be at their expense.  Retaining the footprint of the garage has value as it's a preexisting non conforming location on the lot and therefore could be rebuilt in place or possibly an ADU could be built on that footprint. Easy access to harbor, town, shops, restaurants, Oak Bluffs Ferry, Sunset Lake, Campground cottages, Oak Bluffs Library.  Front porch for relaxing on a Summer evening.  Easy to show!  PRICED BELOW ASSESSED VALUE.

You will find this outstanding property at the end of a quiet country lane in West Tisbury nestled alongside hundreds of acres of conservation land and walking trails that extend all the way to Lamberts Cove Road. The setting is magical - 4 acres of rolling lawns with specimen trees and ponds. There are multiple structures to allow you to customize this compound to your personal needs. The main house was recently renovated by a top local contractor and the result is a rustic Vineyard vibe with a sophisticated twist. The cozy and comfortable kitchen and sitting room areas lead to the dramatic Great Room on the north end of the house - the 600 square foot space with its 26’-high ceilings is bathed in light thanks to the banks of windows and French doors.  There are two bedroom suites upstairs with views of the main pond, one of them with a sundeck. The third floor loft area has also been used as a bedroom and is the perfect spot to accommodate younger members of the family and their friends. The detached two-story guest quarters continue the Vineyard country chic theme with a delightful bedroom with veranda overlooking a separate area of the property from the main house. In addition to the main house and detached guest bedroom, there is a barn with a large finished room and loft as well as a secluded writing studio. A new garage completes the compound. Note: Four-bedroom septic in place. Property currently has 3 bedrooms plus 1 loft sleeping space. One more legal bedroom may be added. *Homeowner images of the landscape in season are available upon request.

157 Ben Chase Road

Exceptional Land Parcel in West Tisbury! Located on a dead end private paved road with swift proximity to Sepiessa and Tiah's Cove boat launch, Long Point Nature Preserve and quick access to Town Center. This tranquil land is a clean canvas for you to design your MV Dream Home to your specification with proper Town permitting. Pool and Pool House by special permit. Electric phone and cable utilities in place on the property. Enjoy Farmers Markets beaches kayaking and bike trails. Centrally located and convenient to Conservation Properties and all Vineyard Towns. Exclusive access to Lambert's Cove Beach for West Tisbury residents!!!

25 North Vine Lane

Private Atlantic Ocean beach lot located on the serene coastline of Aquinnah on Martha's Vineyard.  This exceptional beach lot offers a rare opportunity to own a piece of prime oceanfront. Located just off of Moshup Trail is private gated access to your own designated parking area. From there, a picturesque boardwalk meanders through native flora and opens onto a sandy path leading directly to the water's edge. The sandy ocean beach offers panoramic views of the Atlantic Ocean. Don't miss your chance to own a piece of Martha's Vineyard's coveted coastline.

Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, is this 4-bedroom home with a separate studio guest apartment, office, and heated 2-car garage with 10-ft doors. There is also an unfinished full basement. The living space is in excellent condition with a combination of hardwood, carpet, and tile floors. This light and bright home could be a reliable income producer or might be appropriate for the buyer who needs space for guests or employee housing. There is a 10.14 kilowatt rooftop solar array installed by South Mountain Company.

11 Bernard Way

WELCOME to this turn-key CHAPPY COMPOUND!  This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a WORKOUT & GAME BARN, a POOL, a VOLLEY BALL COURT and a TENNIS and PICKLEBALL COURT that has recently been resurfaced with the traditional US Open colors. The court is lined for tennis as well as two full pickleball courts with portable nets.  Game on!  All of this is set upon three acres of private, expansive land with distant WATER VIEWS! 

The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location!

This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping.

The Workout & Game Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. 

The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large.  

The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Workout & Game Barn.  The interplay between the Workout & Game Barn, Pool House, Pool and abutting Tennis and Pickleball Courts makes this Chappy Compound fun and playful! Strong Rental History.

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72 Chappaquiddick Avenue

East Chop - Tucked away on a quiet tree-lined street, you will find this contemporary three-bedroom home. A distinctive floor plan provides ample living spaces on all three levels. The expansive outdoor deck and large yard expand the living space and are the perfect places to enjoy the quiet setting. The unique layout and five-bedroom septic allows easy reconfiguration. A fantastic opportunity to call East Chop, a close-knit community only a short distance from the harbor and downtown Oak Bluffs, home!

33 Clay Avenue

Move-In Ready – CONSTRUCTION COMPLETE -

This 8-bedroom, 7.5-bath generational home, completed in 2025, is now fully furnished and move-in ready. The property includes a 6-bedroom, 5.5-bath main residence, seamlessly blending timeless elegance with modern comfort, along with a 1-bedroom, 1-bath guest house featuring its own kitchen, and a 2-car carriage house with a 1-bedroom, 1-bath living quarters.

The private backyard oasis is designed for relaxation and entertainment, boasting a 16' x 32' saltwater pool and spa complemented with a pool cabana. This thoughtfully curated property is being offered fully furnished, ensuring effortless enjoyment from day one.

While the window treatments for the main house are not pictured, they are included. Please note that the reported days on market reflect the construction and finishing period, and the certificates of occupancy have been issued. The property features a total gross square footage of 8,607 SF.

This is a once-in-a-lifetime opportunity to own a truly extraordinary property in one of Edgartown's most desirable locations.

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