285 Windswept Way
Osterville, MA 02655
- 5Beds
- 5Baths
- 4,727ft²Living Area
- 1acLot Size
- -Pool
- -Car
- 1999Year Built
- -DOM
- 6Permits
Property Valuations
Latest estimates for 285 Windswept Way based on TopHap automated valuation model (AVM).
TopHap Estimate
$4,454,181
$942/ft²
+$4M above Sold Price
Updated 5 months ago
Last Sold Price
$499,000
$106/ft²
26 years ago
285 Windswept Way is valued at $4,454,181 by TopHap AVM 5 months ago.
285 Windswept Way was last sold in 1998 for $499,000.
Permits
285 Windswept Way has 6 permit records.
Current Ownership
Information about the current owner(s).
Taxes Billed
Taxes billed in 2025$25,730.00From latest Total Assessed Value0.81%Total Assessed Value$3,180,500=Land+
Assessed Value$1,710,500Additions
Assessed Value$1,470,000
In 2025, taxes billed for 285 Windswept Way were $25,730, which is 0.81% from latest Total Assessed Value of $3,180,500.
Property History
285 Windswept Way has undefined property events records (listings, deeds, permits, tax, foreclosure, loan).
Environment
Environmental factors around 285 Windswept Way
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 285 Windswept Way.
Walkability Index
7 /20
Most Walkable
20-18
Very Walkable
17-15
Somewhat Walkable
14-10
Car Dependent
9-0
285 Windswept Way 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 285 Windswept Way, 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 285 Windswept Way
Public Schools
Nearby public schools serving 285 Windswept Way 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
The crime index in 02655 is 90, which is 0.9 times lower than national average.
Market Trends
Historical market data near 285 Windswept Way over selected time period.
Nearby Properties on Windswept Way
- 35 Windswept Way, Osterville, MA 02655 is a 5,726 square foot, 5 bedroom, 5.25 bathroom, 1 acre property. It was built in 1929 and has an estimate of $3,470,995 with a price per ft² of $606.
- 250 Windswept Way, Osterville, MA 02655 is a 4,739 square foot, 6 bedroom, 5.5 bathroom, 4.62 acre property. It was built in 1925 and has an estimate of $8,259,278 with a price per ft² of $1,743.
- 285 Windswept Way, Osterville, MA 02655 is a 4,727 square foot, 5 bedroom, 5.25 bathroom, 0.86 acre property. It was built in 1999 and has an estimate of $3,094,685 with a price per ft² of $655.
- 110 Windswept Way, Osterville, MA 02655 is a 1,449 square foot, 3 bedroom, 4.25 bathroom, 1.97 acre property. It was built in 1950 and has an estimate of $5,939,448 with a price per ft² of $4,099.
- 32 Windswept Way, Osterville, MA 02655 is a 6,622 square foot, 4 bedroom, 7.5 bathroom, 1.09 acre property. It was built in 2005 and has an estimate of $3,932,215 with a price per ft² of $594.
- 186 Windswept Way, Osterville, MA 02655 is a 5.87 acre property.
- 118 Windswept Way, Osterville, MA 02655 is a 5,767 square foot, 7 bedroom, 8.5 bathroom, 2.86 acre property. It was built in 1908 and has an estimate of $7,459,812 with a price per ft² of $1,294.
- 100 Windswept Way, Osterville, MA 02655 is a 5,575 square foot, 6 bedroom, 5 bathroom, 2.18 acre property. It was built in 1952 and has an estimate of $6,899,710 with a price per ft² of $1,238.
- 350 Windswept Way, Osterville, MA 02655 is a 5,407 square foot, 5 bedroom, 6.25 bathroom, 1 acre property. It was built in 2005 and has an estimate of $3,655,000 with a price per ft² of $676.
- 84 Windswept Way, Osterville, MA 02655 is a 5,862 square foot, 7 bedroom, 7 bathroom, 1.69 acre property. It was built in 1960 and has an estimate of $7,484,334 with a price per ft² of $1,277.
- 220 Windswept Way, Osterville, MA 02655 is a 1.8 acre property. It has an estimate of $6,744,563.
- 50 Windswept Way, Osterville, MA 02655 is a 2,630 square foot, 5 bedroom, 4 bathroom, 1.19 acre property. It was built in 1961 and has an estimate of $1,839,272 with a price per ft² of $699.
- 79 Windswept Way, Osterville, MA 02655 is a 1,504 square foot, 3 bedroom, 2 bathroom, 1 acre property. It was built in 1974 and has an estimate of $3,082,029 with a price per ft² of $2,049.
- 95 Windswept Way, Osterville, MA 02655 is a 3,590 square foot, 4 bedroom, 5.5 bathroom, 1 acre property. It was built in 1985 and has an estimate of $2,775,814 with a price per ft² of $773.
- 315 Windswept Way, Osterville, MA 02655 is a 4,832 square foot, 5 bedroom, 5.25 bathroom, 1.2 acre property. It was built in 1990 and has an estimate of $3,680,137 with a price per ft² of $762.
- 121 Windswept Way, Osterville, MA 02655 is a 1.34 acre property.
- 148 Windswept Way, Osterville, MA 02655 is a 1,822 square foot, 3 bedroom, 3.25 bathroom, 0.91 acre property. It was built in 1958 and has an estimate of $4,898,265 with a price per ft² of $2,688.
- 134 Windswept Way, Osterville, MA 02655 is a 6,258 square foot, 6 bedroom, 7.25 bathroom, 1.81 acre property. It was built in 1982 and has an estimate of $8,472,290 with a price per ft² of $1,354.
- 345 Windswept Way, Osterville, MA 02655 is a 6,104 square foot, 5 bedroom, 8 bathroom, 1.69 acre property. It was built in 2012 and has an estimate of $3,540,562 with a price per ft² of $580.