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$2,650,000
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.

$1,499,000
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..

$1,875,000
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.

$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..

$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.

$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..

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