8 Fresh Pond Road, Oak Bluffs MA 02557

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 full 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.

Listing Courtesy of Keller Williams Realty

DETAILS

Mls Id
43345
Status
Active
Bedrooms
7
Full Baths
4
Half Baths
1
Appliances
Stove: 3 Stoves, Washer: Yes
Water Source
Town
Flooring
3
Year Built
2006
Exterior Features
Deck, Garden, Patio, Private Pool, Gym, Beach Access - Private, Beach Access - Public
Parking Features
Ample Parking
Sewer
Septic Tank
Heating
Gas/FHA
Basement
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.
Utilities
Cable
Lot Features
Yes - With Pool
Frontage
Pnd
Interior Features
AC,Disp,Ins,Irr,MiniSplit,OSh, Floor 1: 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., Floor 2: 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.
Furnished
Unfurnished
Zoning
R3
Listing Updated
Monday, October 13, 2025 at 7:51 PM