3 BEDROOM HOUSE + 1 BEDROOM APARTMENT! Discover a rare opportunity in a convenient Vineyard Haven neighborhood. This move-in ready property features a 3 BR, 1.5 BA main house plus a legal 1 BR, 1 BA accessory apartment, offering the perfect setup for multi-generational living or a high-demand rental to offset your mortgage. The main house features a stunning solarium or sunroom, a cheerful efficient kitchen, and a sweet living room anchored by a beautiful stone fireplace. The main house has been emptied out and awaits the new owner's touch (please refer to images showing digital staging). Both the main house and the apartment have been freshly painted throughout, radiating a clean and bright atmosphere. Situated on a spacious lot, the site is large enough to support a 5-bedroom septic system; a design is currently being finalized by Sourati Engineering (buyer to be financially responsible for the upgrade). Other features include oak floors, two decks for outdoor enjoyment, a vintage garden shed, and a full dry basement for additional storage.

Residential Property Image/jpeg #1

Residential Property Image/jpeg #2

Residential Property Image/jpeg #3

Residential Property Image/jpeg #4

Residential Property Image/jpeg #5

Residential Property Image/jpeg #6

Residential Property Image/jpeg #7

Residential Property Image/jpeg #8

Residential Property Image/jpeg #9

Residential Property Image/jpeg #10

Residential Property Image/jpeg #11

Residential Property Image/jpeg #12

Residential Property Image/jpeg #13

Residential Property Image/jpeg #14

Residential Property Image/jpeg #15

Residential Property Image/jpeg #16

Residential Property Image/jpeg #17

Residential Property Image/jpeg #18

Residential Property Image/jpeg #19

Residential Property Image/jpeg #20

Residential Property Image/jpeg #21

Residential Property Image/jpeg #22

Residential Property Image/jpeg #23

Residential Property Image/jpeg #24

Residential Property Image/jpeg #25

Residential Property Image/jpeg #26

22 Oklahoma Avenue

Association Fee

Association Fee Includes

Basement

Fireplace Features

Flooring

Foundation Types

Frontage Type

Heating

Interior Features

Link MLS Comments

Lot Features

Parking Features

Possible Use

Assessed Building Value

Assessed Land Value

Set on a serene 3.02-acre parcel in Chilmark, 45 Quenames Road offers privacy, charm, and excellent potential. In a sunny clearing among mature trees, the maintained 2-bedroom house features first-floor living, an open kitchen and living area, two spacious bedrooms, a full bath with shower, an enormous three-season screened porch, a large outdoor shower, kitchen gardens, and a potting area with utility sink. Well system updated in 2011. With strong rental income, currently generating $2,500 month to month year-round, and expansion potential, this outstanding value is located close to South Road, West Tisbury's village center, and Chilmark's iconic town beaches Squibnocket and Lucy Vincent. Town records indicate a 4 bedroom septic, passed Title V Inspection in December 2025. #45 is shown as Lot 1-B on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 47 Quenames Lot 1-C is also available.

45 Quenames Road

On a beautiful 3.02-acre parcel in Chilmark, 47 Quenames Road offers privacy, outstanding value, and excellent potential. The year-round 2-bedroom home features first-floor living, an open floorplan with living and dining space, a kitchen remodeled in 2023, two bedrooms, and a full bath with tub. A new roof (2023) and outdoor deck with bluestone patio area overlooks the lawn and the natural woodland setting. With strong rental income, currently generating $2,500 month to month year-round, and expansion opportunities subject to town approvals, the property is conveniently located near South Road, West Tisbury’s village center, and Chilmark’s iconic Lucy Vincent and Squibnocket Beaches. Passed Title V in December 2025 for 3 Bedrooms. #47 is shown as Lot 1-C on a new subdivision not yet reflected on the assessments and public records - approved survey is attached. 45 Quenames Lot 1-B is also available.

47 Quenames Road

A rare offering on iconic Ocean Park. This beautifully renovated Victorian cottage sits in the heart of historic Oak Bluffs with unencumbered views of Ocean Park and Vineyard Sound. Completely rebuilt in 2024, the 3-bedroom home blends classic Vineyard charm with modern comforts, featuring a welcoming wraparound porch, a beach-stone wood-burning fireplace, a new kitchen, updated baths, and stylish finishes throughout. New windows and doors throughout complete this extensive renovation.

Originally crafted in the Victorian era and thoughtfully restored for contemporary living, this home enjoys an unbeatable setting and is steps to beaches, ferries, restaurants, galleries, and all the conveniences of downtown Oak Bluffs.

Whether cherished as a year-round residence, summer retreat, or a high-demand rental, this Ocean Park home offers exceptional walkability and an unrivaled island lifestyle in one of Oak Bluffs’ most coveted locations.

*This listing is for Parcel One of the current Deed. Also, the assessed value is yet to be properly recorded. Seller is actively correcting this issue.

*Agent is related to Seller.

Residential Property Image/jpeg #27

Residential Property Image/jpeg #28

Residential Property Image/jpeg #29

Residential Property Image/jpeg #30

Residential Property Image/jpeg #31

Residential Property Image/jpeg #32

Residential Property Image/jpeg #33

Residential Property Image/jpeg #34

Residential Property Image/jpeg #35

Residential Property Image/jpeg #36

Residential Property Image/jpeg #37

33 Ocean Avenue

A unique development opportunity in the heart of the State Road commercial corridor. This 1.47-acre assemblage of four parcels, zoned B-2, represents the largest available site in the area and offers expansive, unwooded land ideal for commercial or mixed-use development (buyer to verify). The property is fully tenanted on month-to-month leases—including a single-family home and additional buildings—providing immediate cash flow with long-term upside.

317 State Road

Set on just over half an acre near downtown Oak Bluffs abutting permanently preserved acres by Land Bank - a rare find in central Oak Bluffs! This home blends classic Midcentury architectural character with abundant natural light from floor-to-ceiling windows and soaring post-and-beam ceilings creating a warm and inviting space. The interior features hardwood floors in the dramatic great room highlighted by an impressive wall of windows that fills the space with sunlight and frames serene views of protected pastoral land.
The open-concept kitchen, dining, and living areas are anchored by a striking fireplace, creating an inviting setting for gatherings. Just off the kitchen, a charming, screened porch offers a cozy three-season retreat, perfect for morning coffee or evening relaxation.

The main level includes three generous bedrooms and a full bath. while the walk-out basement provides a workshop area with sink and storage room. Outside, the property is thoughtfully landscaped with irrigation with mature rows of Arborvitae trees, giving it a private, park-like feel. A back patio and a detached office offer additional spaces to work, unwind, or take in the peaceful surroundings.
Conveniently located, this property is within walking distance of the Oak Bluffs School, the Tradewinds walking trail just across the street, bike paths, and public transit. Downtown Oak Bluffs and the beach are only minutes away- an ideal combination of privacy, convenience, and potential. This lot could provide potential options for future enhancements such as expanded living space, a garage, guest house/ADU… Building possibilities should be explored and reviewed in accordance with town bylaws.  Note: The property is being sold as-is, and the buyer will be responsible for replacing the existing septic system.

Residential Property Image/jpeg #38

Residential Property Image/jpeg #39

Residential Property Image/jpeg #40

Residential Property Image/jpeg #41

Residential Property Image/jpeg #42

Residential Property Image/jpeg #43

Residential Property Image/jpeg #44

Residential Property Image/jpeg #45

Residential Property Image/jpeg #46

Residential Property Image/jpeg #47

Residential Property Image/jpeg #48

Residential Property Image/jpeg #49

Residential Property Image/jpeg #50

Residential Property Image/jpeg #51

Residential Property Image/jpeg #52

Residential Property Image/jpeg #53

Residential Property Image/jpeg #54

Residential Property Image/jpeg #55

Residential Property Image/jpeg #56

Residential Property Image/jpeg #57

Residential Property Image/jpeg #58

Residential Property Image/jpeg #59

101 Tradewinds Road

NEWLY BUILT 4-BEDROOM HOME WITH POOL – 10-Minute WALK TO TOWN,
Enjoy modern living in this beautifully furnished, recently built 4-bedroom home featuring a heated saltwater pool and a stylish 20' x 30' entertainment barn—all just a short walk to downtown Edgartown.The home offers two floors of bright, elegant living space with 3.5 beautifully designed bathrooms, an open kitchen and family room, a dining area overlooking the pool, and two laundry areas for added convenience. The sleeping arrangements include an upstairs primary suite with a king bed and an ensuite bathroom with both a tub and a shower. Also upstairs are a front bedroom with two twin beds and a middle bedroom with full-size bunk beds and a trundle. The first-floor guest suite provides added privacy with a queen bed and an ensuite bathroom.

The home includes two ensuite bathrooms, a shared upstairs bathroom between the secondary bedrooms, and a convenient main-floor powder room. The open family room, complete with a fireplace, 57" TV, and SONOS sound system, flows seamlessly into the fully equipped kitchen, which features a large island and pantry. The dining area seats eight to ten guests and offers a lovely view of the pool. Outside, a private backyard oasis awaits with a heated saltwater pool, outdoor shower, BBQ area, and a spacious entertainment barn outfitted with a ping pong table, cornhole, and relaxing hanging chairs. Offered fully furnished, excluding artwork, and boasting a strong rental history, this home invites you to experience the best of Edgartown living.

38 Pinehurst Road

Fresh, stylish, and fun best describe this inviting four-bedroom Edgartown home with a newly completed pool! Thoughtfully renovated from top to bottom, the interior offers warm, functional living spaces where every detail has been carefully considered. The same level of attention carries outdoors to a true backyard oasis, complete with a heated saltwater pool, multiple patios, a pergola, and an expansive lawn perfect for entertaining or relaxing. Connected to town sewer, the property is approved for up to seven bedrooms—offering exceptional flexibility for future expansion and added value. The location affords both privacy and convenience, with all downtown amenities and South Beach within easy reach. Whether for personal enjoyment or as an investment opportunity, this turn-key property checks all the boxes.

105 Whalers Walk

PRIME 0.5-ACRE BUILDING OPPORTUNITY WITH GRANDFATHERED GUEST HOUSE RIGHTS - 

Exceptional half-acre parcel offering a rare opportunity in a highly desirable location. This level, expansive lot provides an ideal foundation for a custom home, supported by ample frontage, favorable topography, and strong surrounding property values.

A key advantage of this property is its grandfathered right to construct a guest house, enabling valuable flexibility in site planning and future use. The parcel also benefits from proximity to the town sewer line, allowing a future dwelling to connect and support up to six bedrooms upon hookup—an increasingly significant asset for both residential and investment property potential.

Located just minutes from downtown Edgartown, the site offers easy access to boutique shops, acclaimed restaurants, and cultural amenities, while maintaining a private, tranquil setting.

A rare, high-quality offering well suited for those looking to bring a new vision to life on a versatile and well-positioned parcel. Reach out for more details or to schedule a showing.

44 Plantingfield Way

Post-and-beam style Edgartown home in a quiet, established neighborhood just minutes from downtown. This year-round home offers functional living spaces, a thoughtful layout, and generous outdoor areas ideal for relaxing or entertaining. Currently configured with a 3BR/1.5BA main house and 1BR/1BA accessory apartment over a one-car garage, this property affords multiple options for would-be buyers. The existing structures could be reconfigured and updated to meet a buyer's specific needs, while the large level lot also presents an excellent opportunity for those looking to start new and create a brand new, custom island retreat or private oasis complete with a pool. This property can be connected to town sewer and support up to six bedrooms with a grandfathered guest house. Located close to shops, restaurants, beaches, and the harbor, the home provides a perfect blend of convenience and privacy — ideal for year-round living, vacation use, or rental potential in one of Edgartown’s most sought-after areas.

Downtown Oak Bluffs located in the Copeland District this Victorian home combines historic charm with modern comfort. Offering 6 spacious bedrooms and 3.5 bathrooms, this home provides ample living space for family and guests. Also making an ideal rental property Sleeping 12 comfortably just a block to the restaurants and shops of Circuit Ave. and a couple of blocks to the beach it's the perfect location for leaving your car behind and enjoy the best the Island has to offer at your doorstep.
 With a three-sided porch overlooking Hartford Park, one of the many grassy parks throughout the  historic Copeland district perfect for entertaining, dining al fresco or just relaxing outdoors on the many rocking chairs. Classic design details are paired with thoughtful updates, including heat and insulation creating a residence that is both inviting and functional all year round.
This property is ideal for those seeking a home with character, location, and enduring appeal.

34 Massasoit Avenue

Commercial Land Downtown Oak Bluffs on Circuit Avenue. Explore the many potentials this commercial land has to offer in the desirable location in the heart of Oak Bluffs.

0 Massasoit Avenue

Located on a cul-de-sac in a serene neighborhood, this classic Cape-style home sits on a generous 0.86-acre lot less than 1.5 miles from Main Street, Vineyard Haven. The location is ideal—close to restaurants, shopping, and the ferry, yet with enough land to accommodate the existing detached two-car garage and the potential for an Accessory Dwelling Unit. The three-bedroom home offers a comfortable and functional layout. The first floor features a spacious living room with a wood-burning fireplace, an adjacent dining room, and a fabulous three-season room off the kitchen, filled with an abundance of natural light. A bedroom and a full bath with laundry complete the main level. Upstairs, there are two generous bedrooms and a shared full bathroom. One bedroom includes a flexible bonus area suitable for a den, office, or overflow. The other bedroom enjoys an oversized walk-in closet. With classic Cape charm, hardwood floors, a full unfinished basement, and a detached two-car garage, this home presents an excellent opportunity in a desirable location. Located outside the Lagoon Pond Watershed, this property does not require a septic upgrade.

169 Clover Hill Drive

Experience refined coastal living in this impeccably renovated 2022 modern condominium nestled within the tranquil enclave of Meetinghouse Village. This sophisticated end-unit residence lives with the ease of new construction, offering bright, sun-washed interiors and an elevated design sensibility throughout.
Every detail has been meticulously upgraded — from the all-new appliances, lighting, and systems to the custom window treatments, energy-efficient tinting, and enhanced insulation that ensure quiet comfort year-round. The beautifully reimagined bathrooms and fully finished lower level add versatility and style, while three seamlessly integrated 50" smart TVs bring a touch of modern luxury to everyday living.
Outdoors, a newly crafted bluestone terrace with curated landscape lighting provides a serene private retreat, framed by the natural privacy of an additional side yard that borders the woods — a rare advantage for a condominium.
Residents of Meetinghouse Village enjoy a peaceful setting moments from downtown Edgartown’s fine dining, boutiques, and beaches, as well as access to a community pool and ample guest parking. Elegant, effortless, and move-in ready, this residence is perfectly suited for those seeking a polished year-round home or a sophisticated seasonal escape. 
24 hour notice for showings.

7 Meetinghouse Village Way

Experience sun-drenched living in one of Tashmoo Woods’ most desirable floor plans. This beautifully maintained 3-bedroom, 3-bath home offers full access to the coveted Tashmoo Woods amenities, including a pristine pool and pool house, multiple tennis courts, a children’s play area, a private launch on Lake Tashmoo, and a beautiful Association beach on the Sound. Inside, soaring ceilings and clerestory windows fill the living and dining areas with incredible natural light, creating an inviting, airy atmosphere. The eat-in kitchen features an entire wall of windows and glass doors that seamlessly blend indoor and outdoor living. The first-floor bedroom — currently enjoyed as a cozy study — sits next to a full bath, offering flexible options for guests or single-level living. Upstairs, the spacious primary suite boasts vaulted ceilings, an ensuite bath, and an enviable walk-in closet. A charming third bedroom with its own ensuite bath completes the upper level. Setting this unit apart, however, is the rare full, walk-out basement and here there is already a finished bonus room — ideal for a gym, home office or creative workspace. Of course, there is also a garage, an attached shed and the must-have outdoor shower.Could you add Offered TURNKEY for immediate enjoyment - this home is ready for its next chapter - whether as your year-round retreat or seasonal sanctuary.  Easy to Show.

185 Sandpiper Lane 12

This spacious custom designed home is well sited to offer maximum privacy in the lush area of Long View.  A short bike ride to Lambert's Cove beach, it's also about a 20-minute walk down a quiet private road. The home lays out well for family and extended guests with a roomy living room boasting vaulted ceilings and large windows.   The house is designed to have an intimate relationship with the outdoors. A sunny dining area with French doors connects you to the deck and back yard.  The large spacious eat in kitchen has a wood stove and comfortable siting area and also a deck off of it that walks out to a brick barbeque, where you can chef up some great meals in the afternoon sun. Upstairs on one side is a huge ensuite primary bedroom with a walk out to a small deck on one side. There are 3 additional comfortably sized bedrooms with a shared bathroom also on the 2nd floor. A huge 1st floor laundry room could be converted into a bedroom if needed. A This home has fantastic wall space for art, and the oak floors radiate a wonderful warmth. While not designed as a rental, this home could generate solid rental income or be a wonderful place to call home.  Property runs along a scenic brook with wonderful diverse plants and birds. Possible ADU up to 900 square feet.  Septic design is for 5 bedrooms.

20 Brook Hollow Road

35 Mariner’s Way is sited on nearly a half acre lot and lies within walking distance to Edgartown Village shops, restaurants, galleries, and inns and Sheriff’s Meadow conservation land. This 4 bedroom, 2 ½ bath home features a large living room and formal dining room, chef’s kitchen with two ovens and wine room/pantry, and a spacious family room with a gas fireplace. There are two ensuite bedrooms found on each floor. A colorful children’s rec room is just downstairs which could also function as a media room. Step outside to wide front, back and side yards which provide plenty of room for a pool. Other features include hardwood flooring in most rooms, a two-car garage, patio with hot tub, and a large outdoor shower. This property is connected to both town water and sewer.

35 Mariners Way

Perched on 2.7 acres in one of Aquinnah’s most breathtaking settings, this beautifully sited coastal retreat offers sweeping views over the Atlantic and Noman’s Land from its elevated position. Designed to embrace the light and scenery, the main level features an open living/dining/kitchen area wrapped in walls of windows—an airy, sun-soaked space where ocean views take center stage. The adjoining wraparound mahogany deck extends the living space outdoors, perfect for morning coffee, sunset dinners, and everything in between.

The kitchen is anchored by Viking appliances, granite countertops, and warm wood floors, all overlooking the ocean. The spacious primary bedroom brings those same views right to your bedside, complete with an en-suite bath.

The lower level includes two additional bedrooms plus a generous flex room that opens directly to a gorgeous stone patio—an ideal den, overflow guest space, or home office with its own private outdoor area. A full bathroom, laundry room, and utility/storage spaces round out this floor.

The grounds are a standout: a manicured lawn, extensive custom stonework, garden beds, and multiple outdoor seating areas create a serene Vineyard setting. Tucked toward the rear of the property, the two-level workshop/studio—equipped with plumbing, electricity, and a wood stove—offers incredible potential for creative or practical use. With appropriate permitting and a future septic upgrade, buyers could explore the possibility of converting the studio into an accessory dwelling unit.

Directly across the street, the new Land Bank/Sheriff’s Meadow Squibnocket Pond Reservation provides access to one of the Island’s most spectacular stretches of shoreline. A 15–20 minute walk down the trail leads you to Squibnocket Pond and a pristine beach that feels like a private escape.

With its elevated ocean views, thoughtful layout, quality finishes, and incomparable proximity to conservation lands and water access, this is a rare opportunity to own a move-in-ready Aquinnah retreat that truly feels like vacation every day.

4 Nomans Watch Road

Featured Properties

22 Oklahoma Avenue

45 Quenames Road

47 Quenames Road

33 Ocean Avenue

317 State Road

101 Tradewinds Road

38 Pinehurst Road

105 Whalers Walk

44 Plantingfield Way

44 Plantingfield Way

34 Massasoit Avenue

0 Massasoit Avenue

169 Clover Hill Drive

7 Meetinghouse Village Way

185 Sandpiper Lane 12

20 Brook Hollow Road

35 Mariners Way

4 Nomans Watch Road