159 Main St, Osterville, MA 02655
OFF MARKET

159 Main St
Osterville, MA 02655

Osterville
  • 5 Beds
  • 7 Baths
  • 5,788 sqft (on 4 acres)

$10,297,900

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $55,981/mo*
Refinance Your Home

$10,297,900

Trulia Estimate
as of May 14, 2026
Est. Refi. Payment $55,981/mo*
Refinance Your Home
5 Beds
7 Baths
5,788 sqft
(on 4 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Outstanding waterfront estate privately sited on a 4 acre lot with gunite pool, pool house, state-of-the-art clay tennis court, deep water dock and boat house. Additional 2.16 acre parcel of land included with private sandy beach and light pier.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 159 Main St

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 17

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Wood

Property Information

Year Built
Year Built: 1955
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Lot Information

Lot Area: 4.00 acres

Price History for 159 Main St

DatePriceEventSource
09/15/2022$18,500,000Sold
CCIMLS #22200221
01/26/2022$18,500,000PendingCCIMLS #22200221
01/18/2022$18,500,000Listed For SaleCCIMLS #22200221
03/31/2014$7,000,000Sold
CCIMLS #21400346
03/07/2014$7,600,000Listed For SaleAgent Provided
01/30/2014$7,600,000ListingRemovedAgent Provided
01/15/2014$7,600,000Listed For SaleAgent Provided
01/15/1999$4,700,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$72,640
Assessment$8,979,000
Home facts updated by county records

Comparable Sales for 159 Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
749 S Main Street, Centerville, MA
0.48
Single-Family Home
$6,500,000
06/12/25
10
7
8,834
749 S Main St, Barnstable, MA
0.48
Single-Family Home
$6,500,000
06/12/25
10
7
8,834
162 Starboard Lane, Osterville, MA
0.37
Single-Family Home
$2,210,000
10/08/25
4
3.5
3,510
162 Starboard Ln, Barnstable, MA
0.37
Single-Family Home
$2,210,000
10/08/25
4
3.5
2,710
89 Swift Ave, Barnstable, MA
0.32
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
89 Swift Avenue, Osterville, MA
0.32
Single-Family Home
$1,075,000
03/16/26
4
2
2,674
281 Wianno Avenue, Osterville, MA
0.98
Single-Family Home
$4,200,000
08/08/25
7
5.5
4,375
281 Wianno Ave, Barnstable, MA
1.01
Single-Family Home
$4,200,000
08/08/25
7
5.5
4,375
25 Sturbridge Drive, Osterville, MA
0.39
Single-Family Home
$1,030,000
12/15/25
3
2.5
2,227
50 Deerfield Road, Osterville, MA
0.47
Single-Family Home
$1,165,000
09/15/25
4
3
2,098

Assigned Schools

These are the assigned schools for 159 Main St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Osterville
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Osterville

At least 22 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 83 % Say parking is easy

  • 78 % Say there's wildlife

  • 76 % Say yards are well-kept

  • 73 % Say it's quiet

  • 71 % Say it's dog friendly

  • 63 % Say neighbors are friendly

  • 63 % Say there's holiday spirit

  • 59 % Say they plan to stay for at least 5 years

  • 57 % Say people would walk alone at night

  • 50 % Say kids play outside

  • 49 % Say it's walkable to restaurants

  • 40 % Say there are community events

  • 38 % Say it's walkable to grocery stores

  • 27 % Say there are sidewalks

  • 25 % Say streets are well-lit

Learn more about our methodology.
  • Jacqueline Hicks
    "This area lacks decent public transportation. Having a car is extremely helpful. The is the bus system but it isn’t that reliable and it doesn’t have lots of stops and routes so one has to walk a distance to get to path of bus"
    0
    Flag
  • Trulia User
    "moderate traffic at regular business hours, otherwise VERY easy travel, and safe drivers on the road "
    0
    Flag
  • Purplevelvet917
    "The bus goes by only once an hour each way. A car is helpful. Summer traffic make the commute slow so allow for extra time."
    1
    Flag
  • Joshtweaver
    "Very friendly upscale area with beautiful scenery. Great for a summer vacation. Very peaceful. Can get quiet at times so if you’re looking for excitement you may want to look elsewhere. "
    14
    Flag
  • Joshtweaver
    "Great area for kids to grow up or spend the summers in. Very friendly community feel. Safe to walk around in. "
    0
    Flag
  • Ashleighmaeb
    "An hour and a half drive back to Boston if your lucky. You can fly which is way more convenient but driving is the cheapest. It’s our summer home so we don’t care that much since we’re down all summer."
    2
    Flag
  • Hudson
    "I’ve lived in this neighborhood for over 3 years and love it. The neighbors are nice and there are lots of kids and young families."
    0
    Flag
  • bagleyheath
    "Ostervile, lovely place apart from the people. Rude arrogant, dont you know who I am? types where the rules of civilty only apply to others. If you are in the top 1% or aspire to be you'll love it."
    1
    Flag

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Apartments for Rent

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Homes for sale near 159 Main St

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Homes for rent near 159 Main St

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Off Market Homes Near 159 Main St

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Explore by feature

159 Main St, Osterville, MA 02655 is a 5 bedroom, 7 bathroom, 5,788 sqft single-family home built in 1955. 159 Main St is located in Osterville, Osterville. This property is not currently available for sale. 159 Main St was last sold on Sep 15, 2022 for $18,500,000. The current Trulia Estimate for 159 Main St is $10,297,900.