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25 Oak Avenue, Oak Bluffs
$1,950,000
2 Beds ⋅ 2 Baths ⋅ 73593599 MLS
Thought to have been moved from the Campgrounds to the Highlands in the early 1900's, the Mary E. Gilkes house has been transformed into a sophisticated and easy-living Island abode. The thoughtful, intentional design and execution of this renovation/addition pays homage to its Victorian roots while adding every modern amenity for year-round or summer use. Every detail has been carefully considered from the mahogany front porch with Vineyard-blue ceilings that typifies the Oak Bluffs cottage history, to the "bonus" room/loft, to infrastructure which meets HERS requirements for energy efficiency. There isn't an inch of wasted space in this little powerhouse and the property offers a wealth of possibilities for expansion. The location is quiet and bucolic, and just up the hill from Circuit Ave., with easy access to East Chop and Eastville Beach. Roll right off the ferry and bring your Vineyard vision to life in this enchanting home where history, style and modern comfort come together!

25 Oak Avenue, Oak Bluffs

Listing courtesy of Listing Agent: Lisa Stewart from Listing Office: Sandpiper Realty, Inc..

58 Munroe, Oak Bluffs
$20,500
3 Beds ⋅ 2 Baths ⋅ 73588852 MLS
RATE REFLECTS PRIME RATE AVAILABLE AUGUST 1-8, 2027. Charming coastal retreat in the heart of East Chop, quietly sited yet close to downtown Oak Bluffs harbor front, restaurants, shops and popular local beaches.This tranquil three bedroom, two full bathroom oasis highlighted by muted coastal decor imbue relaxed vacation vibes.First floor primary suite with King bed, walk-in closet and large private bathroom. Impressive double height main living space appointed by comfortable furnishings. Sliding glass doors seamlessly connect indoor/outdoor living. Luxurious stone kitchen, adjacent panty and dining counter create an immersive chef experience.Gather and enjoy meals in the full size formal dining space perfectly positioned adjacent to the kitchen enhanced by open living flow. Escape and unwind in the media lounge quietly positioned for private moments or special broadcasts. Central stairs lead to a hallway with two additional bedrooms. The Queen bedroom is adjacent to shared full bathrooms with shower and skylight. At the end of the hallway is another bedroom with two Double beds and walk-in closet. Outdoor ambiance amplified by lush private yard, expansive rear deck offering ample outdoor living and dining spaces, complete with outdoor shower off the back patio. Convenient climate control afford optimized customization throughout. This memorable house is the perfect home base for your trip to Oak Bluffs. Available for weekly rentals for summer 2027 and four-night long weekend bookings spring/fall. Price reflects prime weekly rate inclusive of fees and taxes. Rates vary weekly, rate includes all estimated tax and fees.Inquire for availability.

58 Munroe, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.

20 Hidden Cove, Oak Bluffs
$1,595,000
4 Beds ⋅ 3 Baths ⋅ 73577547 MLS
Set within the sought-after Hidden Cove community, a 65-acre private enclave with direct access to Sengekontacket Pond, this contemporary retreat offers an exceptional Martha’s Vineyard lifestyle. Residents enjoy a private community boat dock, scenic walking trails, pickleball and tennis courts, all just moments from Oak Bluffs and Edgartown.Set on a private, wooded lot, the home blends classic Vineyard character with relaxed coastal living. Cedar siding, an expansive wood deck, screened porch, and outdoor shower create inviting spaces for everything from quiet mornings to long summer evenings and post-beach afternoons.Inside, the home unfolds around a striking two-sided gas and wood-burning fireplace, with large windows bringing the surrounding landscape indoors. Four bedrooms offer comfortable space for family and guests, while a finished lower level adds exceptional versatility — currently configured as a media room and home office, with an unfinished portion ready to become a private gym, wine cellar, or whatever you envision.With water access, exceptional community amenities, and a private setting close to the Island’s favorite towns, Hidden Cove offers a rare combination of active outdoor living, privacy, and quintessential Vineyard ease.

20 Hidden Cove, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

61 Canonicus Ave, Oak Bluffs
$2,200,000
3 Beds ⋅ 3 Baths ⋅ 73576858 MLS
Location, location, location: This 1999 home with all the comforts of the 21st Century is nestled on a landscaped lot within mellow surroundings. And yet … it’s located within mere moments of town, beach, bike path, bus line, parks, recreation, Farm Pond and a Land Bank trail. The situation hardly gets better. The 3BR/2.5BA house features a deep wraparound farmer’s porch, Brazilian cherry floors, an open and flexible layout, recent kitchen and bath updates, a generous 2nd floor bonus room and an attached single-car garage. The poured basement stands ready for your finishing whims. Kick back in your sunny backyard or on your shady porch with the distant peek of Nantucket Sound. Songbirds will serenade you from towering maples and oaks. Pinkletinks will chime in from Farm Pond. It’s no wonder that this abode has been loved – by vacation tenants as well as the owner. Note: This property lies within the jurisdiction of the Cottage City Historic District and Copeland District of the Town of Oak Bluffs. Passed Title 5.

61 Canonicus Ave, Oak Bluffs

Listing courtesy of Listing Agent: Kristin Buck from Listing Office: Donnelly + Co..

68 Front Street, Oak Bluffs
$1,755,000
3 Beds ⋅ 3 Baths ⋅ 73576389 MLS
Located on a quiet street in Oak Bluffs, this beautifully expanded Cape offers generous living spaces, along with an additional 700+ square feet of newly finished recreation space above the two-car garage, complete with a private entrance and second-floor deck. The inviting first floor is designed for comfortable living and entertaining, featuring a spacious kitchen with a center island and abundant counter space. The adjacent dining room provides a warm gathering space with a wood stove, while glass doors open to a wood deck and bluestone patio for easy indoor-outdoor living. Multiple sitting areas, a living room with a gas fireplace, and a private office offer plenty of room to relax, gather, or work. Upstairs, two guest bedrooms share a recently updated bathroom, while the spacious primary suite features a walk-in closet and a large, light-filled bath with a soaking tub and tiled shower. Radiant-heated floors in the primary bedroom and bathroom provide an added level of comfort. Additional amenities include a two-car garage, versatile recreation space, second-floor deck, and half basketball court. Conveniently located near Downtown Oak Bluffs and Farm Neck Golf Club, this home offers an ideal setting for enjoying all that Martha’s Vineyard has to offer.

68 Front Street, Oak Bluffs

Listing courtesy of Listing Agent: Alyssa Halisky from Listing Office: Wallace & Co. Sotheby's International Realty.

267 Barnes Road, Oak Bluffs
$4,395,000
3 Beds ⋅ 6 Baths ⋅ 73572956 MLS
Set along 163 feet of Lagoon frontage with its own sandy beach, 267 Barnes Road offers a fresh, contemporary take on waterfront living in Oak Bluffs. Set on 1.25 acres, the 4,046-square-foot home balances privacy with comfortable spaces for entertaining or relaxing. Oversized windows bring Lagoon views into nearly every room. The main level features soaring ceilings, a wood-burning fireplace, wet bar, and an eat-in kitchen opening to a sunny patio. A separate two-room wing with full bath and private deck offers flexible space for an office, den, studio, or guest accommodations. Upstairs, the primary suite includes a fireplace, walk-in closets, ensuite bath, and Lagoon-facing deck. Two additional ensuite bedrooms open to a wraparound deck and 3-season porch. The refinished 2,000-square-foot walk-out lower level includes a full bath, laundry, and space for a gym, media room, or additional living area. Offered fully furnished, this waterfront retreat is ready to enjoy. Whether you are hosting a full house or savoring a quiet weekend, the Lagoon becomes your backdrop: sunrise coffees, afternoon swims, and sunset gatherings right at the water’s edge.

267 Barnes Road, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

59 Tuckernuck Ave, Oak Bluffs
$2,595,000
4 Beds ⋅ 3 Baths ⋅ 73553801 MLS
Located in the heart of downtown Oak Bluffs, this charming updated home seamlessly blends classic Vineyard character with bright, modern comfort. Greeting you from the street is an expansive wraparound porch framed by vibrant hydrangeas and a cozy second-floor balcony. Step inside to an inviting open layout featuring crisp white paneled walls, exposed painted ceiling beams, and warm hardwood floors that create an airy, light-filled atmosphere. Designed for relaxed coastal living, this partially insulated retreat offers effortless indoor-outdoor flow and functional updates throughout. Enjoy an unbeatable location directly across the street from the neighborhood playgroud and just a short, scenic walk to pristine beaches, local dining, and the ferry terminal. Whether you are seeking a summer sanctuary or an investment property, this home delivers classic island living at its best! Showings on Saturdays 1-3pm only beginning August 1.

59 Tuckernuck Ave, Oak Bluffs

Listing courtesy of Listing Agent: Jennifer DaSilva from Listing Office: Compass.

40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs
$1,495,000
3 Beds ⋅ 4 Baths ⋅ 73544610 MLS
Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a detached garage, and exclusive access to Hidden Cove's sought-after amenities, including a private boat launch. Just minutes from Oak Bluffs, Farm Neck Golf Club, beaches, and the bike path, this is a place where generations return to create the kind of Martha's Vineyard summers that never go out of style.

40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.

27 Double Ox Rd, Oak Bluffs
$3,400,000
3 Beds ⋅ 5 Baths ⋅ 73542323 MLS
Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living areas. Upstairs are two additional bedroom suites, a loft-style family room/office, dedicated laundry, and flexible bonus room ideal for guests, media, or recreation. A screened porch, covered outdoor living spaces, and attached two-car garage enhance both functionality and lifestyle. Built with high-end finishes and attention to detail throughout, this stunning new construction offering presents an opportunity to own a luxury retreat with easy access to Oak Bluffs' beaches, harbor, restaurants, shops, and all the attractions that make the Vineyard such a sought-after destination.

27 Double Ox Rd, Oak Bluffs

Listing courtesy of Listing Agent: Lesley Heidt from Listing Office: Sandpiper Realty, Inc..

7 Ploughshare Lane, Oak Bluffs
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 73527741 MLS
Nestled in a quiet cul-de-sac within the coveted Hidden Cove neighborhood, this delightful property offers an exceptional Island lifestyle. The association delivers rare water access via a private dock on Sengekontacket Pond, plus newly resurfaced tennis and pickleball courts. The open-concept layout flows seamlessly from the fireplaced living room and kitchen through the dining area to an expansive screened porch — ideal for entertaining on warm summer evenings. A welcoming front porch provides additional outdoor living space. The main level is completed by a gracious primary suite with a full bath and a convenient half bath. The walk-out lower level features two additional bedrooms, a full bath, and laundry. A one-car garage offers excellent storage for your car, kayaks, or beach gear. Perfectly positioned between Edgartown and Oak Bluffs. Additional bedrooms possible with septic upgrade per BOH

7 Ploughshare Lane, Oak Bluffs

Listing courtesy of Listing Agent: Emma Kennedy from Listing Office: Sandpiper Realty, Inc..

44 Tiffany Dr, Oak Bluffs
$2,595,000
4 Beds ⋅ 5 Baths ⋅ 73527128 MLS
Tucked away in a serene setting and set on a private 1.38-acres, this beautifully renovated 4BR/4.5BA Cape offers over 4,000 sq ft. of living space with pleanty of room for a backyard pool. The property has been thoughtfully renovated with two new kitchens, 4.5 new bathrooms, 4-bedrooms (two ensuite), and all new appliances and windows. Its floor plan is great for entertaining and flows family and guests from an oversized living room with fireplace into the dining room, gourmet kitchen and an inviting family room with cathedral ceiling and propane stove. First floor includes an ensuite bedroom and large screened in porch. The 1-bedroom apartment above the 2-car garage includes living/dining/kitchen area, washer/dryer, and heat/AC. The property includes a full basement, spacious rear patio and deck, outdoor shower and is large enough for an in-ground pool. Assessed value does not reflect extensive 2026 renovations. Furnishings in the photos have been virtually staged.

44 Tiffany Dr, Oak Bluffs

Listing courtesy of Listing Agent: Perry Patterson from Listing Office: MV Luxury Homes LLC.

15 Tamarack Lane, Oak Bluffs
$4,600,000
6 Beds ⋅ 6 Baths ⋅ 73522816 MLS
Nestled within the idyllic and highly coveted setting of Farm Neck Golf Club, 15 Tamarack Lane offers a rare opportunity to own a stunning 3.7 acres in one of Martha’s Vineyard’s most exclusive communities. The property enjoys picturesque views over the 7th fairway and 8th tee box, across to Sengekontacket Pond, creating a peaceful backdrop of lush greens and distant water. The historic five-bedroom main residence, along with a separate one-bedroom carriage house, are rich in character and await a thoughtful renovation or reimagining. Ideally located near the clubhouse, restaurant, tennis courts, and pro shop, the property offers easy access to the Farm Neck lifestyle while remaining just minutes from town, the harbor, and ferry terminal. This is an extraordinary chance to secure a property within the esteemed Farm Neck Golf Club community. Included is a highly sought-after Farm Neck Club Stockholder Membership, enhancing both its prestige and value.

15 Tamarack Lane, Oak Bluffs

Listing courtesy of Listing Agent: Stephanie Roache from Listing Office: Donnelly + Co..

33 Vineyard Ave, Oak Bluffs
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 73511961 MLS
Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property encompassing 3B/2Ba in total featuring a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined finishes throughout. Open living flows to a gourmet kitchen with suede-finish stone counters, Bosch appliances, dining bar, and walk-in pantry. Upstairs offers two spacious bedrooms, a skylit bath with glass and stone shower, and a private balcony. Enjoy multiple outdoor spaces including a covered porch and side deck. The 1b/1ba ADU secondary suite provides a private entrance, parking, and utilities--ideal for guests or rental income. Featuring open living, oak floors, a stylish kitchen with stone counters and Bosch propane oven, plus a bedroom and full bath.

33 Vineyard Ave, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.

6 Brewster Ave, Oak Bluffs
$3,100,000
4 Beds ⋅ 3 Baths ⋅ 73472925 MLS
Enjoy sweeping water views from this beautifully updated East Chop Victorian, featuring a charming guest cottage. Renovated in 2010, the main home effortlessly blends historic character with modern comfort. The kitchen and bathrooms have been thoughtfully updated, enhancing functionality while preserving the home’s original charm. Tucked privately at the rear of the property, the guest cottage offers a peaceful retreat ideal for hosting family and friends or creating a flexible living space. Located in the heart of East Chop, a close-knit and distinguished community, this property is just moments from beaches, the lively harbor, and the vibrant shops and restaurants of downtown Oak Bluffs.

6 Brewster Ave, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

4 Canonicus Ave, Oak Bluffs
$5,225,000
6 Beds ⋅ 4 Baths ⋅ 73472922 MLS
Overlooking Nantucket Sound and just steps from the vibrant heart of downtown Oak Bluffs, this distinctive compound blends laid-back West Coast style with classic island charm. The light-filled four-bedroom main house has been thoughtfully updated with modern, year-round comforts. Privately set at the rear, the guest house known as The Nest offers a peaceful retreat with a private deck, outdoor shower, parking, and mini-split climate control; its upstairs bedroom enjoys views from Farm Pond to Nantucket Sound. Completing the property is the charming Lilac House, a fun open-concept bunk house with a full bath, water-view deck, and private outdoor shower. A wraparound porch captures sweeping ocean views, while beaches, shops, restaurants, Circuit Avenue, and the Harbor are moments away. An established rental history further enhances this rare opportunity in one of Oak Bluffs’ most iconic locations.

4 Canonicus Ave, Oak Bluffs

Listing courtesy of Listing Agent: Katie Donahue & Rachel Serwa Group from Listing Office: Sandpiper Realty, Inc..

55 Samoset Ave, Oak Bluffs
$15,000
5 Beds ⋅ 3 Baths ⋅ 73209866 MLS
BOOK SUMMER 2027! Modernized 5 bed, 3 full bath Victorian in the heart of Downtown Oak Bluffs. Steps to restaurants, shopping, harbor, ferries and beaches. Accommodates 10 guests. Easy breezy outdoor living, dining, bluestone patio and BBQ grill. Relax on the covered porch surrounded by a lush flower garden or unwind in the outdoor shower. Updated stone and stainless kitchen. Formal dining for eight. A/C, WIFI and hardwood throughout. First floor bathroom and bedroom. Updated bathrooms. Fans and flatscreen TVs in each of the five-guest rooms. PRICES REFLECT PRIME SUMMER WEEKLY RATES. Weekly Prime Rates $12,000-15,000/wk. Available for 3-Night Weekend Fall/Spring. Tax, Cleaning and Deposit required. INQUIRE.

55 Samoset Ave, Oak Bluffs

Listing courtesy of Listing Agent: Allison Cameron Parry from Listing Office: Douglas Elliman Real Estate - Nantucket.

55 Samoset Ave  Ob503 Unit 1, Oak Bluffs
$20,000
5 Beds ⋅ 3 Baths ⋅ 73126946 MLS
THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Newly renovated, Great for Family Gatherings, Corporate Retreats, Central Air & Heat, very close to Circuit Ave and Beach, 5 Bedrooms, 3 full baths, galley kitchen, new appliances, dining room, family room, Flat Screen TV, FREE Wifi, washer & dryer, bay window breakfast nook, Oak and Pine wood flooring, outdoor shower, wrap around porch, blue stone patio, private cobblestone driveway, comfortable beds, pillows and mattresses encased in (non-vinyl) water and allergen proof protectors. COVID-19-conscious cleaning and disinfecting are done regularly. *Bathmats and kitchen towels are supplies.AVAILABLE ALL YEAR ROUND, CHECK THE CALENDAR FOR RATES.

55 Samoset Ave Ob503 Unit 1, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

5 Laurel Ave  Ob532, Oak Bluffs
$24,000
3 Beds ⋅ 2 Baths ⋅ 72849969 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Wonderful, fully redecorated Gingerbread house on East Chop, just minutes from the excitement of Oak Bluffs. There are three bedrooms and two full baths. The interior is clean and crisp, with beach cottage décor and beautiful bamboo floors. Entertainment options include high-speed wifi, Sonos, cable, HBO, Netflix and Hulu. Updated appliances and a fully equipped, modern kitchen complete this wonderful home. This is a perfect place to fully experience all the possibilities of Oak Bluffs. Circuit Avenue and town favorite Jetty Beach are each just 1/2 mile away. Enjoy expansive outdoor space: relax in a large, shaded backyard.

5 Laurel Ave Ob532, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

385 Barnes Rd Ob534, Oak Bluffs
$64,000
4 Beds ⋅ 7 Baths ⋅ 72850038 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $18,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with water views over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The first floor has a master bedroom with waterviews and private bath. There are two additional en suite bedrooms on the second floor with an open sitting area looking over the main floor living area out towards the water. The lower level is a great entertaining space with a pool table, poker table and kitchenette. The fourth bedroom is also on this level with a private bath. On the other side of the bedroom there is a small exercise room. Enjoy the outdoor heated pool or take a walk down to the small beach on the lagoon. The outdoor kitchen is non-functioning .

385 Barnes Rd Ob534, Oak Bluffs

Listing courtesy of Listing Agent: Karen M. Overtoom from Listing Office: Karen M. Overtoom R.E..

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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