Tom O'Hanlon

Nestled within the serene and scenic up-island area of West Tisbury, 26 Flint Hill Road offers a rare opportunity to own a piece of Martha's Vineyard's untouched natural beauty. This extraordinary 3.32-acre property boasts panoramic views of the iconic Land Bank-owned Arrowhead Farm on one side, ...

• $1,475,000

  Price

Let your imagination run wild with this peaceful, pastoral property centrally located between down and up-island. This main house and guest house are perfectly sited on just over 2 acres and are ready for your vision. The cape-style main house features a spacious wrap around deck and an open floo...

• $1,290,000

  Price

• 4

  Beds

• 3

  Baths

• 1,664

  Sq.Ft.

Experience the ultimate luxury lifestyle at this exquisite Martha's Vineyard estate, set on 9.5 acres in two adjoining parcels. Situated in a private location with commanding views of the Atlantic Ocean and Chilmark Pond, the property offers safety and serenity, perched on an elevated site well a...

• $18,500,000

  Price

• 6

  Beds

• 7

  Baths

• 7,710

  Sq.Ft.

OAK BLUFFS BEACHFRONT WITH DOCK -Completed in 2024, this fully renovated three-bedroom, two-bath cottage offers sweeping views of Vineyard Haven Harbor, with private dock and an additional abutting parcel for extra privacy and expanded water frontage. The home seamlessly blends modern upgrades wi...

• $2,900,000

  Price

• 3

  Beds

• 2

  Baths

• 1,196

  Sq.Ft.

Nestled in Oak Bluffs, tucked away in a quiet enclave, this delightful A-frame home boasts three cozy bedrooms and two bathrooms, perfect for year round living or a vacation retreat with friends and family. Surrounded by a lush, spacious lawn, the property offers ample outdoor space for relaxatio...

• $800,000

  Price

• 3

  Beds

• 2

  Baths

• 900

  Sq.Ft.

Interior photos coming soon!! Here is your opportunity to build your family compound in the heart of Katama! Located 1.5 miles from Downtown as well as South Beach and right near the bike path, this property offers easy access to all things Edgartown! Short Walk or Bike ride to Field Club as well...

• $1,795,000

  Price

• 2

  Beds

• 2

  Baths

• 912

  Sq.Ft.

Nestled in the heart of Edgartown, this historic residence offers a perfect blend of timeless charm and modern comforts. Enjoy a leisurely stroll to shops and dining, a front-row view of the 4th of July parade, and easy access to Fuller Street Beach.This two-story home features a well-appointed k...

• $2,500,000

  Price

• 4

  Beds

• 2

  Baths

• 1,704

  Sq.Ft.

ASSOCIATION POOL, TENNIS, LAKE TASHMOO BEACH, PLUS GOLF NEARBY! This meticulously maintained 2+ bedroom, 3 bathroom end unit condo in the prestigious Tashmoo Woods Association has it ALL! The updated kitchen, with granite countertops and high-end appliances, opens to a dining room with access to ...

• $1,450,000

  Price

• 2

  Beds

• 3

  Baths

• 1,682

  Sq.Ft.

A desirable location in Vineyard Haven and just steps away from Owen Little Beach on Vineyard Sound. This home offers privacy and endless possibilities while being close to Downtown Vineyard Haven shops, restaurants, harbor and ferry. The home features an inviting porch overlooking a spacious law...

• $1,232,500

  Price

• 3

  Beds

• 2

  Baths

• 1,308

  Sq.Ft.

Immersed in the picturesque setting of Oak Bluffs on Martha's Vineyard, Fairview on Greenleaf Avenue, one of only ten homes in this coveted location, harmoniously blends historical charm with coastal serenity. This cherished family home holds a special place in the hearts of its owners, with root...

• $2,490,000

  Price

• 3

  Beds

• 2

  Baths

• 1,608

  Sq.Ft.

Experience the ultimate luxury lifestyle at this exquisite Martha's Vineyard estate. Situated in a private location with commanding views of the Atlantic Ocean and Chilmark Pond, the property offers safety and serenity, perched on an elevated site well above the flood zone. Chilmark House, design...

• $15,650,000

  Price

• 6

  Beds

• 7

  Baths

• 7,160

  Sq.Ft.

Welcome to this enchanting Edgartown home that seamlessly blends timeless charm with modern updates, nestled on a quiet street. This house exudes a sense of old Vineyard charm making it a truly captivating haven for those seeking a unique home. As you approach the property, its welcoming front po...

• $3,000,000

  Price

• 4

  Beds

• 4

  Baths

• 2,006

  Sq.Ft.

House, guest house and studio! Located just outside of town and close to beaches and harbor, this unique property includes a 4 bed/2.5 baths. Many nice features include an open living, dining and kitchen, fireplace set up for a wood stove, wood floors and a first floor primary with en-suite bath ...

• $1,500,000

  Price

• 5

  Beds

• 4

  Baths

• 2,329

  Sq.Ft.

SERENE RETREAT IN KATAMA - Discover your perfect vacation home in Island Grove, mere moments from the soft sands of South Beach and the charming streets of Edgartown. This residence is not just a home; it's a launchpad to the quintessential island lifestyle, with unrivaled access to local gems li...

• $1,900,000

  Price

• 3

  Beds

• 3

  Baths

• 2,162

  Sq.Ft.

Discover the charm of this welcoming 2-bedroom, 1-bathroom ranch, located just a short drive from the lively center of Oak Bluffs. Set on the corner of a quarter-acre lot, the property offers ample opportunity for expansion, allowing you to tailor it into your ideal summer getaway or a cozy year-...

• $720,000

  Price

• 2

  Beds

• 1

  Bath

• 816

  Sq.Ft.

Situated in a quiet neighborhood, this .25-acre lot offers a level and square space, perfect for building your island home. The location is ideal - just about two miles from the lively downtown of Oak Bluffs and less than a mile from the Lagoon Pond town landing for fantastic boating or kayaking....

• $465,000

  Price

Nestled in a coveted private enclave on Martha's Vineyard, this charming 4 bedroom, 2.5 bath Cape-style home offers an idyllic retreat on 1.65 acres. Experience exclusivity with deeded access to a serene private beach on Lake Tashmoo, a mere five-minute stroll away. Designed with an open layout, ...

• $1,800,000

  Price

• 4

  Beds

• 3

  Baths

• 2,044

  Sq.Ft.

A delightful neighborhood in the heart of Oak Bluffs. This land offering is located within close proximity to the various public access points to the sandy shoreline of Lagoon Pond. With engineering in place, embrace the unique opportunity to build your own custom residence. Whether you envision ...

• $409,000

  Price

WATER VIEWS from almost every room in this home. Mooring permit transferred with home sale (current waitlist 6 years) The full service "Safe Harbor Vineyard Haven Marina" is 1/4 Mile down the road (See website link). The potential is endless with this ranch boasting 5/4 bedrooms and 4 full bathro...

• $2,600,000

  Price

• 5

  Beds

• 4

  Baths

• 2,276

  Sq.Ft.

$50,000 credit from the seller at closing (for new septic). Nestled down a scenic country lane and just a leisurely bike ride away from the vibrant town center, this delightful Vineyard Haven cottage offers the perfect blend of convenience and tranquility. The idyllic retreat is not just a home; ...

• $820,000

  Price

• 2

  Beds

• 1

  Bath

• 962

  Sq.Ft.

Your Martha's Vineyard retreat! Anchored by the charm of a classical, New England-styled, Greek Revival residence. Relax in a tastefully crafted island home for all seasons, easy to maintain and use. Comfortable living on three floors, with mahogany-bunged yellow pine flooring throughout. Exposed...

• $1,625,000

  Price

• 3

  Beds

• 1

  Bath

• 1,560

  Sq.Ft.

Custom built two story Colonial located in central West Tisbury. This expansive home built by an island craftsman includes Black Locust trim, mix of Wide Pine, White Oak, Pink Elm and Brazilian Cherry solid hardwood floors and a floor to ceiling stone fireplace. Kitchen with center island, as wel...

• $1,795,000

  Price

• 5

  Beds

• 3

  Baths

• 3,026

  Sq.Ft.

This charming 3 room cottage has tons of potential and is sited in a sweet spot off South Rd. Chilmark near the public boat landing and town center. Oriented towards the sunsets with ample privacy, you can almost see the pond from the 2nd floor deck. Lived in for the past 20 years, this home is s...

• $1,050,000

  Price

• 1

  Beds

• 1

  Bath

• 816

  Sq.Ft.

Magnificent Impeccably-maintained Edgartown Estate. Rare 5-acre compound in the heart of Katama, surrounded by 17 acres of Sheriff’s Meadow conservation property and across from the Nature Conservancy’s Farm Institute. Sited and designed by architect Jack Kemper to provide both sanctuary and larg...

• $6,950,000

  Price

• 5

  Beds

• 8.5

  Baths

• 7,500

  Sq.Ft.

Enjoy single-level living in this charming ranch-style home located one mile from Oak Bluffs Harbor and Downtown and just down the road from Lagoon Pond. Relax on the private back patio, covered front porch or the wrap-around deck. Open concept living room and kitchen features granite countertops...

• $997,000

  Price

• 3

  Beds

• 2

  Baths

• 1,064

  Sq.Ft.

This charming Katama home with many recent improvements by the seller is perfectly located on a lovely side street off the left Fork to South Beach. You can be at South Beach in 5 minutes by car, or enjoy a bicycle ride to the beach on the nearby bike path. The house is nicely set back from the s...

• $3,250,000

  Price

• 4

  Beds

• 4

  Baths

• 2,407

  Sq.Ft.

* Seller would consider credit toward buyer closing costs to be used toward an interest rate buy down, paid points to reduce interest rate and Landbank Fee. Welcome to your enchanting farmhouse sanctuary in Island Grove! This serene retreat seamlessly harmonizes country charm with contemporary c...

• $2,250,000

  Price

• 3

  Beds

• 3

  Baths

• 2,162

  Sq.Ft.

Step Into History: Edgartown Village Home with Distinctive Heritage - This historic residence situated in the heart of the town offers a multitude of attractions. You can leisurely walk to the array of shops and dining establishments, enjoy the view of the 4th of July parade from the front porch,...

• $2,550,000

  Price

• 4

  Beds

• 2

  Baths

• 1,704

  Sq.Ft.

A DIAMOND IN ISLAND GROVE - Nestled amidst the enchanting beauty of Martha's Vineyard, discover a slice of paradise in the coveted Island Grove neighborhood located between Edgartown Village and Katama. Welcome to a truly exceptional retreat, where timeless elegance meets modern luxury. The resid...

• $2,250,000

  Price

• 3

  Beds

• 3

  Baths

• 1,875

  Sq.Ft.

Welcome to your West Chop Haven! Nestled in an established neighborhood, this 1980 home boasts a bright and inviting ambiance that will make you feel right at home. With three bedrooms, it is a perfect retreat for you and your loved ones. Step inside and be greeted by a delightful blend of contem...

• $1,050,000

  Price

• 3

  Beds

• 2

  Baths

• 1,140

  Sq.Ft.

Discover an exceptional opportunity in the desirable Mill Hill neighborhood. Tucked away behind a meticulously crafted custom gated driveway, this remarkable property presents 3 distinct living spaces, each with its own private entrance. Immerse yourself in the charm & versatility of this captiva...

• $3,400,000

  Price

• 4

  Beds

• 5

  Baths

• 2,498

  Sq.Ft.

Classic New England Cape lovingly maintained sits on 1/3 of an acre in a central Vineyard Haven neighborhood, convenient to downtown, Tisbury School, ferry & Tashmoo.This one owner home features hardwood floors throughout, first floor primary bedroom, cook’s kitchen with stainless appliances whic...

• $1,200,000

  Price

• 3

  Beds

• 3

  Baths

• 1,768

  Sq.Ft.

Coming Soon: Showings start July 9th. 3BR 2BA turn-key home is close to the ferry, shopping & restaurants that Tisbury has to offer. This Vintage 1930’s bungalow is truly an Island oasis. This home was updated in 2011 with new updates this spring. Enjoy coveted one floor living. The cozy kitchen...

• $1,200,000

  Price

• 3

  Beds

• 2

  Baths

• 1,230

  Sq.Ft.

Here's the perfect opportunity to make your Vineyard Dream come true. Check out this spectacular location tucked away in Edgartown. Steps away from Morning Glory Farm and a short ride into town and beaches. This home currently has two bedrooms with the potential of seven, with proper approvals an...

• $1,399,000

  Price

• 2

  Beds

• 2

  Baths

• 1,450

  Sq.Ft.

Introducing a charming home in Oak Bluffs, Martha's Vineyard, offering convenience and tranquility. Nestled in a sought-after location, just a stroll from the town center, this property features post and beam construction, vaulted ceilings, and an open concept design. The first floor includes a m...

• $1,250,000

  Price

• 3

  Beds

• 3

  Baths

• 2,135

  Sq.Ft.

RARE OPPORTUNITY to build your family compound on this acre and a half parcel in the private Witchwood association with association dock. With proper permitting, up to 8 bedrooms allowed. This is the first lot on Witchwood Lane, bordering Katama Road and the bike path leading to South Beach and D...

• $3,060,000

  Price

OAK BLUFFS BEACHFRONT AND DOCK- Spectacular frontage and views of Vineyard Haven Harbor are achieved from this classic three-bedroom, two-bath home. The charming cottage has been well maintained and offers a practical layout that will easily accommodate all who visit. However, not much time will ...

• $1,700,000

  Price

• 3

  Beds

• 2

  Baths

• 1,196

  Sq.Ft.

Renovated in 2019, this sweet & petite cottage is located 2 blocks from Upper Main Street and just a short walk to all the activity of Edgartown Village. Recently connected to the town sewer, this lot will now permit up to 4 bedrooms with plenty of room to expand on the lot. A built-in pool would...

• $1,330,000

  Price

• 2

  Beds

• 1

  Bath

• 589

  Sq.Ft.

This commercial condo space is located in the heart of Oak Bluffs, conveniently situated near the harbor and bustling with plenty of foot traffic. The commercial condo is versatile, allowing for a wide range of uses, from retail to office space to service-oriented businesses. However, it cannot b...

• $500,000

  Price

• 1

  Bath

Sunny contemporary beach house with many recent improvements: roof, bath, siding. Still some updating to do so bring your ideas and imagination. Level 1/2 acre lot allows for 4 bedrooms so think expansion or maybe even a guest cottage. Large main level deck and a 2nd floor deck/balcony off on...

• $1,153,000

  Price

• 3

  Beds

• 2

  Baths

• 1,697

  Sq.Ft.

Nestled on Simpson's Lane, discover this classic Edgartown Colonial at the heart of the village. Walk to Fuller Street Beach, dine in excellent restaurants, and explore charming boutiques steps away. The open-concept first floor flows seamlessly from entry to kitchen, dining, and living areas. A ...

• $5,490,000

  Price

• 5

  Beds

• 4

  Baths

• 3,535

  Sq.Ft.

Love being in downtown Edgartown? Want to generate income when you can't be here? Welcome to Edgartown Commons - a seasonal, condo/hotel on Martha's Vineyard that offers a combination of private condo ownership and investment opportunity. Unit 16 is a unique second-floor unit located in the main ...

• $415,000

  Price

• 1

  Beds

• 1

  Bath

• 529

  Sq.Ft.

This gracious three-bedroom, 3 1/2 bath Colonial is sited at the top of a winding driveway in the midst of expansive lawns, gardens and treed acreage. It is tastefully screened with numerous flowering shrubs, plants and specimen trees. The floor plan is intelligently designed and offers one floor...

• $2,000,000

  Price

• 3

  Beds

• 4

  Baths

• 2,620

  Sq.Ft.

CLASSIC EXPANDED CAPE WITH SALTWATER POOL & DOCK SLIP - Quietly tucked away in the desirable Witchwood area of Katama surrounded by mature woods for total privacy. Combines great outdoor space around the pool area, with newly refreshed indoor spaces. First floor features a large Family Room with...

• $4,200,000

  Price

• 5

  Beds

• 3.5

  Baths

• 4,475

  Sq.Ft.

ROOM FOR A POOL! MOVE-IN-READY CUSTOM CAPE WITH FARMER'S PORCH AND ATTACHED GARAGE. Grandfathered FIVE BEDROOM per Edgartown Wastewater Dept. Three blocks from Edgartown Village. This well-maintained and thoughtfully renovated home is waiting for its next family. With an additional 1100sqft of ...

• $2,000,000

  Price

• 4

  Beds

• 4.5

  Baths

• 2,676

  Sq.Ft.

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 ...

• $15,400,000

  Price

• 6

  Beds

• 7.5

  Baths

• 6,346

  Sq.Ft.

Location is always key and this home allows easy access to South Beach, Farm stand, downtown Edgartown or up island. Large landscaped property allows room for garage and or expansion. Ability to connect to Town Sewer for up to 7 bedrooms. Open kitchen living area floor plan that leads to a 3 seas...

• $795,000

  Price

• 3

  Beds

• 2

  Baths

• 1,128

  Sq.Ft.

Look no further for the upcoming 2022 summer season than this four-bedroom, three-bath home in the heart of Katama! The open and functional layout makes entertaining a breeze, accented by a fully equipped chefs' kitchen and multiple living spaces. A detached garage, in addition to the ample stora...

• $3,050,000

  Price

• 4

  Beds

• 3

  Baths

• 2,955

  Sq.Ft.

This charming home is located near the bike path and less than 2 miles from town, yet tucked away down a country lane. With this prime location comes deeded access to the Lagoon Pond, which is perfect for kayaking, boating and swimming. There is also a walking path nearby that connects to 16 acre...

• $1,050,000

  Price

• 3

  Beds

• 2

  Baths

• 1,260

  Sq.Ft.

EXCELLENT OPPORTUNITY - Expanded ranch with full basement and large garage on a level 1/2 acre lot in Vineyard Haven. The property is being sold AS IS. OPEN HOUSE on Saturday, February 19, from 12-2pm. No showings prior to the open house.

• $905,000

  Price

• 3

  Beds

• 1.5

  Baths

• 1,534

  Sq.Ft.