Residential > Multi-family
Active
06/02/2025
List Price
$7,750,000$671/ft²
440 Grand Island Dr
Osterville, MA 02655
- 7Beds
- 11Baths
- 11,546ft²Living Area
- 1.1acLot Size
- 1Pool
- 6Car
- 2013Year Built
- 129DOM
- 17Permits
440 Grand Island Dr, Osterville, MA 02655 is a 7 bed, 11 bath, 11,546 ft² multi-family home house built in 2013 on a 1.100 acre lot with 17 construction permits. This multi-family home is currently for sale for $7,750,000, and it was last sold in 2018 for $4,200,000.
MLS Description
The listing agent's description. Original Listing
Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch welcomes you into a dramatic foyer, setting the tone for the refined interiors that follow. The main living spaces unfold in a thoughtfully designed layout that flows from formal living and family rooms to an elegant dining area with each space inviting connection, comfort, and celebration. At the heart of the home, the chef's kitchen is both striking and functional, anchored by dual oversized islands clad in premium granite, and accompanied by a fireside sitting room that beckons lingering conversation. Adjacent, the spectacular sunroom redefines indoor-outdoor living with a custom crafted bar and casual seating area at one end and a full second kitchen with custom built-in grill and dining area at the other, all enclosed by retractable screens for effortless seasonal enjoyment. Tucked away on the main level, the primary suite offers a private sanctuary, with its own fireplace, luxurious spa-like bath, and refined home office. The comfort and sophistication continue on the second level with four generously proportioned en-suite bedrooms and an inviting sitting room. Designed for comfort and connection, the finished lower level offers a wine cellar, media room, game room, and fitness space. This lavish interior flows effortlessly to an equally impressive exterior, where lush landscaping surrounds a resort-style pool framed by expansive lounging areas-perfect for everything from quiet afternoons to grand entertaining. Completing this offering is a beautiful two-bedroom guest house providing privacy and comfort for visiting guests. Set within a prestigious gated enclave with coveted beach and dock rights, this remarkable estate is the perfect fusion of architectural sophistication and everyday warmth - an extraordinary offering in one of Cape Cod's most prestigious settings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.
Listing Agents
The listing agent for 440 Grand Island Dr is Robert B Kinlin.
RB
Robert B Kinlin
Berkshire Hathaway HomeServices Robert Paul Properties
Phone: (508) 863-4663
Permits
440 Grand Island Dr has 17 permit records.
Permit History
17
Permits
Current Ownership
Information about the current owner(s).
Taxes Billed
Taxes billed in 2025$56,455.00From latest Total Assessed Value0.81%Total Assessed Value$6,978,400=Land+
Assessed Value$2,222,100Additions
Assessed Value$4,756,300
In 2025, taxes billed for 440 Grand Island Dr were $56,455, which is 0.81% from latest Total Assessed Value of $6,978,400.
Property History
440 Grand Island Dr has undefined property events records (listings, deeds, permits, tax, foreclosure, loan).
Property Events
Environment
Environmental factors around 440 Grand Island Dr
Hazard Risks
Hurricane183Particulates107Weather104Lead103Nat'l Avg100Air Pollution96Carb Mono92Ozone92Wind68Hail47Earthquake46Tornado6
12 hazards (Carbon Monoxide, Earthquake Risk, Hail Index, Tornado Index, Hurricane Index, Air Pollution Index, Ozone Index, Wind Index, Weather Risk, Lead Index, Particulate Matter, National Average) are above the national average around 440 Grand Island Dr.
Walkability Index
7 /20
Most Walkable
20-18
Very Walkable
17-15
Somewhat Walkable
14-10
Car Dependent
9-0
440 Grand Island Dr has a walkability score of 7 out of 20, which means that it is in a car dependent area.
Temperature
Seasonal temperature sampled over multiple years
Winter
Average
Low
24°F
High
40°F
Summer
Average
Low
60°F
High
76°F
In the winter at 440 Grand Island Dr, temperatures range from 24.03°F to 39.62°F with an average of 31.83°F. In the summer, the temperature ranges from 59.87°F to 76.3°F with and average of 68.09°F.
School Information
Public/private schools serving 440 Grand Island Dr
Public Schools
Barnstable High School
Grades: 8-12
5.80 mi
C
Barnstable Intermediate School
Grades: 6-7
5.94 mi
C
West Villages Elementary School
Grades: KG-3
3.75 mi
Barnstable United Elementary School
Grades: 3-5
3.60 mi
D
* The school rating is based entirely on the test score performance of each school. It is based on a scale of A-F, A being best.
Nearby public schools serving 440 Grand Island Dr have ratings undefined, undefined, undefined, and undefined.
Neighborhood
This property is located in 02655.
Seasonal Housing units 02655
89%of housing is for seasonal rent.
Daytime Population for 02655
-12%of people during work hours.
Crime Index for 02655
90
90
The crime index in 02655 is 90, which is 0.9 times lower than national average.
Market Trends
Historical market data near 440 Grand Island Dr over selected time period.
Nearby Properties on Grand Island Dr
- 74 Grand Island Dr, Osterville, MA 02655 is a 2,670 square foot, 6 bedroom, 3.25 bathroom, 0.6 acre property. It was built in 1938 and has an estimate of $1,829,146 with a price per ft² of $685.
- 20 Grand Island Dr, Osterville, MA 02655 is a 3,015 square foot, 6 bedroom, 4 bathroom, 0.74 acre property. It was built in 1939 and has an estimate of $1,934,751 with a price per ft² of $642.
- 2 Grand Island Dr, Osterville, MA 02655 is a 1,953 square foot, 2 bedroom, 2 bathroom, 1.48 acre property. It was built in 1939 and has an estimate of $2,405,378 with a price per ft² of $1,232.
- 441 Grand Island Dr, Osterville, MA 02655 is a 6,265 square foot, 4 bedroom, 6.25 bathroom, 1.18 acre property. It was built in 1987 and has an estimate of $3,459,224 with a price per ft² of $552.
- 473 Grand Island Dr, Osterville, MA 02655 is a 6,959 square foot, 6 bedroom, 6.25 bathroom, 0.96 acre property. It was built in 1991 and has an estimate of $3,546,377 with a price per ft² of $510.
- 340 Grand Island Dr, Osterville, MA 02655 is a 4,297 square foot, 5 bedroom, 4 bathroom, 1.14 acre property. It was built in 1960 and has an estimate of $2,162,694 with a price per ft² of $503.
- 460 Grand Island Dr, Osterville, MA 02655 is a 5,437 square foot, 5 bedroom, 6 bathroom, 1.31 acre property. It was built in 2001 and has an estimate of $3,570,177 with a price per ft² of $657.
- 292 Grand Island Dr, Osterville, MA 02655 is a 4,707 square foot, 5 bedroom, 6.25 bathroom, 1.26 acre property. It was built in 1983 and has an estimate of $3,171,591 with a price per ft² of $674.
- 514 Grand Island Dr, Osterville, MA 02655 is a 6,618 square foot, 6 bedroom, 8.25 bathroom, 1.61 acre property. It was built in 1985 and has an estimate of $3,790,810 with a price per ft² of $573.
- 534 Grand Island Dr, Osterville, MA 02655 is a 1.21 acre property.
- 541 Grand Island Dr, Osterville, MA 02655 is a 1.04 acre property.
- 44 Grand Island Dr, Osterville, MA 02655 is a 3,579 square foot, 5 bedroom, 4.25 bathroom, 0.96 acre property. It was built in 1993 and has an estimate of $2,488,500 with a price per ft² of $695.
- 631 Grand Island Dr, Osterville, MA 02655 is a 7,881 square foot, 5 bedroom, 9.75 bathroom, 1.09 acre property. It was built in 2005 and has an estimate of $3,725,636 with a price per ft² of $473.
- 525 Grand Island Dr, Osterville, MA 02655 is a 6,107 square foot, 5 bedroom, 6.25 bathroom, 1.04 acre property. It was built in 1995 and has an estimate of $3,473,560 with a price per ft² of $569.
- 170 Grand Island Dr, Osterville, MA 02655 is a 13.58 acre property.
- 578 Grand Island Dr, Osterville, MA 02655 is a 4,808 square foot, 5 bedroom, 7.5 bathroom, 1.21 acre property. It was built in 2019 and has an estimate of $3,530,924 with a price per ft² of $734.
- 94 Grand Island Dr, Osterville, MA 02655 is a 1 acre property.
- 556 Grand Island Dr, Osterville, MA 02655 is a 605 square foot, 1 bedroom, 1 bathroom, 1.21 acre property. It was built in 2017 and has an estimate of $1,930,040 with a price per ft² of $3,190.
- 505 Grand Island Dr, Osterville, MA 02655 is a 0.98 acre property.
- 110 Grand Island Dr, Osterville, MA 02655 is a 1.1 acre property.
- 320 Grand Island Dr, Osterville, MA 02655 is a 2,508 square foot, 3 bedroom, 3 bathroom, 1.31 acre property. It was built in 1930 and has an estimate of $2,796,974 with a price per ft² of $1,115.
- 498 Grand Island Dr, Osterville, MA 02655 is a 2,462 square foot, 5 bedroom, 3 bathroom, 0.74 acre property. It was built in 1926 and has an estimate of $1,520,000 with a price per ft² of $617.
- 280 Grand Island Dr, Osterville, MA 02655 is a 4,879 square foot, 4 bedroom, 6.25 bathroom, 0.71 acre property. It was built in 1989 and has an estimate of $3,476,365 with a price per ft² of $713.
- 145 Grand Island Dr, Osterville, MA 02655 is a 134.07 acre property.
- 611 Grand Island Dr, Osterville, MA 02655 is a 3,641 square foot, 4 bedroom, 5.25 bathroom, 1.01 acre property. It was built in 1995 and has an estimate of $2,246,630 with a price per ft² of $617.
- View more properties on Grand Island-Dr