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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.
$2,800,000
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 seller will escrow $50K towards a pool at closing depending on the offer. 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.
$1,850,000
4 Beds ⋅ 2 Baths ⋅ 73505800 MLS
Quintessential Waterview Farm! Built as a year-round home with the charm of the original cottages, this well-loved retreat awaits its next chapter. The sunny, open floor plan offers two bedrooms and a full bath on each level, with generous gathering spaces throughout. A skylit kitchen is tucked into a corner of the main living area, where a curved wall of glass opens to a deck and private yard. The sunken living room features a fireplace and stairs to a loft seating area. Built in 1978, the home is fully winterized with oil forced-air heat and a partial basement. The south facing half-acre lot abuts an 8-acre forever-wild meadow. A nearby path leads across wildflower fields to the association beach. Set between Farm Neck and Felix Neck, Waterview Farm offers 22 acres of common land, a sandy beach, dock, boat storage, and possible mooring—ready to enjoy now and enhance over time.

22 Old Harbor Lane, Oak Bluffs

Listing courtesy of Listing Agent: Lisa Stewart from Listing Office: Sandpiper Realty, Inc..
$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..
$20,000
4 Beds ⋅ 2 Baths ⋅ 72849934 MLS
THIS IS A WEEKLY SUMMER RENTAL ONLY.SEE WEB SITE FOR WEEKLY PRICING. Feel the ocean breezes from this classic waterfront home. There are four bedrooms, an open living room and dining room that open up to large deck overlooking beautiful views across the Lagoon. Walking path to private sandy beach. BOAT MOORING INCLUDED.

291 Barnes Rd Ob516, Oak Bluffs

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

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