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8 Fresh Pond Road

$5,295,000

Sengy, Oak Bluffs, MA 02557

Recently Listed

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Single Family Residence in Sengy, Oak Bluffs

7 bedrooms

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4 bathrooms

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5320 SqFt

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1.57 acres

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MLS #43345

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.

Property highlights

Unfurnished

Deck

Garden

Patio

Private Pool

Gym

Private Beach

Public Beach

Septic Tank

Cable

Property Details

Association Fee:
Association Fee Includes:
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 patioa kitchentwo bedrooms—one with direct patio access—a full bathroomand laundry area. An unfinished section of the basement provides ample storage space.
Fireplace Features:
2
Flooring:
3
Foundation Types:
Frontage Type:
Pnd
Heating:
GFHA
Interior Features:
AC,Disp,Ins,Irr,MiniSplit,OShFloor 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.
Link MLS Comments:
County Rd to Fresh Pond Rd - #8 is at the end.
Lot Features:
Yes - With Pool
Parking Features:
Ample Parking
Possible Use:
Assessed Building Value:
2642500.00
Assessed Land Value:
1118600.00

Price History

May 30, 2025
$5,295,000

Tax Information

This property was most recently assessed in 2025. It has been assessed at a value of $3,761,100. The annual tax responsibility for this property is $18,994.

Contact an Agent
Phone number
(508) 696-7777

Property Location

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