Jen O'Hanlon

HUGE PRICE CUT! Aquinnah Retreat, set on a private 1.1-acre lot! This beautiful single-family home was lovingly built & cared for by one family, offering peaceful surroundings & beautiful ocean views, now, move-in ready for new owners to relax & put their own personal touch to. The wrap-around de...

• $1,575,000

  Price

• 3

  Beds

• 4

  Baths

• 2,308

  Sq.Ft.

Charming Edgartown Village GemNestled in the heart of Edgartown Village, this single-level jewel box home blends classic island charm with modern comfort. Set on a lot that can accommodate up to four bedrooms, the property currently features two bedrooms and two full baths, offering a flexible fo...

• $2,700,000

  Price

• 2

  Beds

• 2

  Baths

• 1,112

  Sq.Ft.

Move-In Ready Raised Ranch - Just 1 Mile from Circuit Ave, Harbor Shops, Restaurants & Ferry Terminal!Tucked away on a private side road, a rare find in this price range is ready for you to move in and make it your own! Whether you're looking for a year-round residence or a charming summer cottag...

• $982,000

  Price

• 3

  Beds

• 1

  Bath

• 980

  Sq.Ft.

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 w...

• $3,350,000

  Price

• 3

  Beds

• 3

  Baths

• 2,686

  Sq.Ft.

Thoughtfully designed post-and-beam home that blends character with modern comfort and flexible living in Tower Ridge. The open-concept main floor features spacious gathering areas, while the finished basement offers a quiet retreat for work, relaxation, or play. The outdoor living space is just ...

• $1,700,000

  Price

• 3

  Beds

• 4

  Baths

• 2,558

  Sq.Ft.

Welcome to this beautifully updated and privately situated home in one of West Tisbury's most desirable associations. Residents enjoy exclusive access to tennis courts, walking trails, horse pastures and Tisbury Great Pond. Designed for both comfort and luxury, this spacious 4+ bedroom, 3 bathroo...

• $3,120,000

  Price

• 4

  Beds

• 3

  Baths

• 3,669

  Sq.Ft.

The Captain George Harding Home sits gracefully on the westerly side of iconic William Street overlooking Vineyard Haven village with distant views of the harbor. This immaculate and re-imagined Gothic Revival offers both timeless elegance and modern luxury. Completed in 2024, the comprehensive d...

• $4,295,000

  Price

• 4

  Beds

• 5

  Baths

• 2,792

  Sq.Ft.

MOVE-IN READY ISLAND HOME ON DOUBLE LOT WITH EXPANSION OPTIONS--Nestled in a highly desirable West Tisbury neighborhood, this 3-bedroom, 1-bath ranch offers the perfect blend of convenience, privacy, and access to some of Martha's Vineyard's most sought-after amenities.Set on a spacious and priva...

• $1,200,180

  Price

• 3

  Beds

• 1

  Bath

• 1,144

  Sq.Ft.

STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. The highlight? A heated salt water pool surrounded by expansive decking and outdoor gathering spaces--...

• $2,590,000

  Price

• 4

  Beds

• 4

  Baths

• 3,052

  Sq.Ft.

EXTRAORDINARY COASTAL RETREAT IN MINK MEADOWS -- Welcome to an idyllic haven on Martha's Vineyard, tucked within the exclusive West Chop area of Tisbury. This contemporary residence offers sweeping water views across a vibrant salt marsh and out to the sparkling expanse of Vineyard Sound, where s...

• $6,200,000

  Price

• 4

  Beds

• 4

  Baths

• 3,278

  Sq.Ft.

Turn-Key 5-Bedroom Home with Legal Apartment Near Edgartown Village --Set back from the road and less than a mile from Main Street, this spacious and stylish Edgartown property offers an ideal blend of privacy, comfort, and investment potential. The main home features four well-proportioned bedro...

• $1,795,000

  Price

• 5

  Beds

• 3

  Baths

• 2,704

  Sq.Ft.

This beautifully renovated Katama retreat combines refined design, luxurious amenities, and thoughtfully crafted spaces. The main house features three bedrooms, including a peaceful primary suite with private deck access, a second en-suite bedroom, and a cozy bunkroom. The octagonal living room, ...

• $3,300,000

  Price

• 4

  Beds

• 6

  Baths

• 3,793

  Sq.Ft.

Tucked away on one of the most sought-after streets in Oak Bluffs, Fairview on Greenleaf Avenue offers an extraordinary location steeped in history and charm. With unparalleled views stretching across Sunset Lake, Oak Bluffs Harbor, and Nantucket Sound, this property captures the essence of coast...

• $2,100,000

  Price

• 3

  Beds

• 2

  Baths

• 1,608

  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 ...

• $1,250,000

  Price

• 3

  Beds

• 3

  Baths

• 1,682

  Sq.Ft.

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

• $1,250,000

  Price

• 3

  Beds

• 3

  Baths

• 1,682

  Sq.Ft.

This spacious post-and-beam home offers over 3,700 square feet of living space, allowing an ideal getaway for family and friends to gather. Surrounded by woods, fields, streams, and ancient stone walls, the property is minutes from Philbin Beach, Gay Head Cliffs, the historic lighthouse, and shop...

• $2,750,000

  Price

• 4

  Beds

• 4

  Baths

• 3,723

  Sq.Ft.

Welcome to this elegant haven offering a serene and private setting nestled on a generous lot and gracefully buffered by the lush greens of the Edgartown Golf Course. Conveniently located approximately 2.5 miles from Edgartown Village and 1 mile from Morning Glory Farm.Upon entering, you are gree...

• $2,000,000

  Price

• 3

  Beds

• 4

  Baths

• 2,417

  Sq.Ft.

SOLD TURNKEY - Discover this newly built, farmhouse-style residence nestled in the highly desirable Tower Ridge Neighborhood, just moments from downtown Oak Bluffs, with easy access to all other island towns. Offered completely turn-key, this property comes fully furnished, allowing you to settle...

• $3,500,000

  Price

• 4

  Beds

• 4

  Baths

• 3,503

  Sq.Ft.

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

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...

• $15,650,000

  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 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.

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.

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.

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.

$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.

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.

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.

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.

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.

IMPECCABLY UPDATED & MAINTAINED BUNGALOW - Truly in move in condition, this home has been restored and renovated by both the current and previous owners. The location on State Road lends itself perfectly for an easy jaunt to Cronig's or Vineyard Haven's Main Street. This is a unique opportunity t...

• $855,000

  Price

• 3

  Beds

• 1.5

  Baths

• 958

  Sq.Ft.

HOME FOR THE HOLIDAYS - Move right into this meticulously maintained and recently updated Edgartown property. Bold Meadow is a well established neighborhood of approximately 50 homes. Owners enjoy a bucolic setting with tennis courts and access to miles of state forest trails, as well as the pave...

• $1,475,000

  Price

• 3

  Beds

• 3

  Baths

• 1,700

  Sq.Ft.

A PRIME KATAMA LOCATION - This property is positioned to take advantage of everything Katama has to offer. Surrounded by 180 acres of conservation land, you will enjoy views of the Atlantic ocean and the plains of Katama. The heart of the home includes an open concept on the second floor with sli...

• $2,650,000

  Price

• 3

  Beds

• 3

  Baths

• 1,932

  Sq.Ft.

CHARMING EDGARTOWN VILLAGE COTTAGE. This charming one-bedroom, one-bath cottage is a perfect pied-a-tier, located within walking distance to all the best of Edgartown Village. This home is sited on a conforming R-5 lot, is already connected to Town Water and Town Sewer and will support a future...

• $1,150,000

  Price

• 1

  Beds

• 1

  Bath

• 560

  Sq.Ft.

NOTE: SELLING PRICE REFLECTS VALUE OF THE LAND PURCHASE ONLY. A SEPARATE CONSTRUCTION CONTRACT FOR $2.275 MILLION WAS EXECUTED ALONG WITH THE PURCHASE. TOTAL PRICE: $3,025,000. PRE-CONSTRUCTION: ELEVATED STYLE IN SOUTHRIDGE. Construction plans are now underway for this stylish, coastal chic far...

• $750,000

  Price

• 4

  Beds

• 4.5

  Baths

• 2,700

  Sq.Ft.

Charm of yesteryear balanced with upgraded systems! This YEAR 'ROUND three bedroom cottage home offers a newer central heating system, vintage built -ins, a front and back staircase, brick fireplace and a surprising amount of room! Clever use of space, tons of windows and a high ceilinged additio...

• $855,000

  Price

• 3

  Beds

• 2

  Baths

• 1,135

  Sq.Ft.

PRISTINE EDGARTOWN COTTAGE WITH EXPANSION POTENTIAL - Located just 2 miles from the Village, this charming cottage has maintained all of its charm, while being transformed for today's lifestyle. Ready for immediate occupancy for year round living or start booking your 2022 rentals and enjoy this ...

• $929,000

  Price

• 2

  Beds

• 1.5

  Baths

• 1,126

  Sq.Ft.

EDGARTOWN VILLAGE DESIGN-BUILD OPPORTUNITY. Here's an exciting opportunity to create an in-town residence -- within walking distance to all the best of Edgartown Village. This conforming R-5 lot is already connected to Town Water and Town Sewer and will support a 4-bedroom residence plus an in-gr...

• $1,150,000

  Price

• 1

  Beds

• 560

  Sq.Ft.

PERFECT EDGARTOWN LOCATION - At less than 1.5 miles from town and across from Morning Glory Farm, you'll have easy access to the shops and restaurants of the village, as well as miles of paved bike paths and hiking trails through Sheriff's Meadow and the State Forest. The location also allows for...

• $4,175,000

  Price

• 4

  Beds

• 5

  Baths

• 5,697

  Sq.Ft.

This home with a swimming pool enjoys a commanding position atop Atwood Circle - an elegant enclave just a short distance from Edgartown's vibrant village center. The well-loved 7-bedroom home has the warmth of a vintage home but with many of the amenities expected by the modern buyer, including...

• $2,325,000

  Price

• 7

  Beds

• 5.5

  Baths

• 2,596

  Sq.Ft.