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Island Wide Listings

OAK BLUFFS
Single Family Residence

8 Fresh Pond Road, Oak Bluffs, MA 02557

$4,695,000.00
Listed 24th March, 2026 for $4,695,000
LINK ID: 44237
STATUS: AVAILABLE
Bedrooms: 7
Baths: 4
Half Baths: 1
Rooms: 14
Living Space: 5320
Acreage: 1.5700
Water Frontage: Pnd

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Outdoor Spaces: Deck, Garden, Porch, Private Pool, Hot Tub, Beach Access - Private, Beach Access - Public
Features: Alarm, Central Alarm/C, Insulation, Irrigation, Outdoor Shower
Year Built: 2006
Second Dwelling: None
Zoning: R3
Water: Town
Sewer: Septic Tank
Lead Paint: Unknown
Foundation : Full Basement
Heat: GFHA
Fireplaces: 2
Yard Type: Yes - With Pool and Extensive Landscaping
Flooring: 3
Stove: Yes
Washer: Yes
TV: Cable

DESCRIPTION

The Ultimate Oak Bluffs Compound: A rare opportunity to own a stunning seven-bedroom estate, thoughtfully designed for both luxurious living and exceptional rental potential. This expansive property features a newly built pool, lush landscaping, and direct access to Fresh Pond—ideal for kayaking, paddleboarding, and swimming. Perfect for entertaining, the home showcases a dramatic great room, an expansive deck, a pergola with a fireplace, and an elevated gazebo overlooking meticulously manicured grounds. Versatility is at the heart of this unique compound. With three kitchens, the home easily accommodates use as a spacious single-family residence or as three separate living quarters—ideal for multi-generational living, hosting extended guests, or generating rental income. Additional highlights include a 10-bedroom septic system in place - allowing for future expansion, an oversized three car garage, and solar. Come experience the very best of Island living.

FIRST FLOOR DESCRIPTION
The first floor features a spacious living room, a dedicated office, a gym, a chef’s kitchen with a breakfast nook, a formal dining room, a half bathroom, and a mudroom.

SECOND FLOOR DESCRIPTION
The second floor includes the primary bedroom suite, complete with a fireplace, full bathroom, and walk-in closet. Two additional bedrooms and another full bathroom are also located on this level. Additionally, there is access to a separate second-floor apartment featuring a full kitchen, living room, two bedrooms, and a bathroom. The apartment also has its own private entrance.

BASEMENT DESCRIPTION
The newly completed lower level features both interior and exterior access. It includes a spacious living room with sliding doors leading to the outdoor patio a kitchen two bedrooms—one with direct patio access—a full bathroom and laundry area. An unfinished section of the basement provides ample storage space.

SECOND DWELLING
None

PARKING
Ample Parking
Martha's Vineyard - Island Wide Listings - Updated September 20, 2026
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ALISAN LOHAN-CONWAY PROPERTIES MARTHA'S VINEYARD
Martha's Vineyard Real Estate Sales and Rentals
PO Box 2670, Edgartown, MA 02539
Phone: 508.627.1858 Fax: 508.696.7648

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