227 Bridge St, Osterville, MA 02655
Property image
Property image
OFF MARKET

227 Bridge St
Osterville, MA 02655

Osterville
  • 9 Beds
  • 6.5 Baths
  • 3,315 sqft (on 3.73 acres)

$12,739,800

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $71,777/mo*
Refinance Your Home

$12,739,800

Trulia Estimate
as of Aug 2, 2026
Est. Refi. Payment $71,777/mo*
Refinance Your Home
9 Beds
6.5 Baths
3,315 sqft
(on 3.73 acres)

Local Information

  • Map ViewExplore the area around 227 Bridge St.
  • Schools2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1900
Lot Size
3.73 acres
Living Area
3,315 sqft
Price/Sqft
$3,843
Parking
Garage

About this House

Four distinctive dwellings set on 2 separate lots (198-1.28 ac & 227-2.45 ac) have provided the platform for many get togethers, both formal & informal, but more often than not have been the backdrop to the quiet serenity & immeasurable beauty this unique waterfront oasis has to offer.Imagine the splendor of a life lived as a steward of the harbor.This timeless family estate on Little Island in Osterville is set on nearly 4 acres w/2 deep water docks & a private beach.The main residence hosts 6 bedrooms complimented w/a separate 2 bedroom guest house, studio apartment & fully applianced boat house.From the properties vantage point, at the head of the inlet, watch as boats of varying shapes & sizes parade in & out of West Bay.The current stewards of this estate have welcomed many seafarers to their docks to tie up while they awaited the rise of the drawbridge into North Bay.They have shared refreshments at their refurbished antique shanty/boathouse & on their private sandy beach.
227 Bridge St, Osterville, MA 02655 is a 9 bedroom, 7 bathroom, 3,315 sqft single-family home in Osterville, built in 1900. It is currently off market. The Trulia Estimate is $12,739,800, with a rent estimate of $5,817/month.

Home Details for 227 Bridge St

Interior Features

Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile, Concrete, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 10Parking: Garage Detached

Property Information

Year Built
Year Built: 1900
Property Type / Style
Property Type: Single Family Home

Lot Information

Lot Area: 3.73 acres

Price History for 227 Bridge St

DatePriceEventSource
09/10/2024$12,250,000ListingRemovedCCIMLS #22300899
06/14/2024$12,250,000PriceChange
CCIMLS #22300899
03/17/2023$12,500,000Listed For SaleCCIMLS #22300899
01/19/2021ListingRemovedMLS PIN
01/03/2021$18,000,000PriceChange
Agent Provided
04/06/2020$19,500,000PriceChange
Agent Provided
09/26/2019$22,000,000PriceChange
Agent Provided
06/29/2019$25,000,000Listed For SaleAgent Provided

Market trends in Barnstable

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$702K
$29.31KMoM
Sale-to-List Price
98.2%
0.1%MoM
Price per sq ft
$442
$11MoM
Available listings
366
23MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$77,526
Assessment$9,582,900
Home facts updated by county records

Comparable Sales for 227 Bridge St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
255 Bayberry Way, Barnstable, MA
0.47
Single-Family Home
$7,800,000
07/29/26
7
6
4,896
255 Bayberry Way, Osterville, MA
0.48
Single-Family Home
$7,800,000
07/29/26
7
6
4,896
405 Bridge Street, Osterville, MA
0.37
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
355 Bridge Street, Osterville, MA
0.33
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
405 Bridge St, Barnstable, MA
0.37
Single-Family Home
$4,400,000
03/02/26
5
6
6,768
355 Bridge St, Barnstable, MA
0.34
Single-Family Home
$3,000,000
11/06/25
4
3.5
3,720
21 Cockachoisett Lane, Osterville, MA
0.28
Single-Family Home
$2,700,000
06/18/26
4
3.5
3,015
21 Cockachoiset Ln, Barnstable, MA
0.28
Single-Family Home
$2,700,000
06/18/26
4
3.5
3,015
545 Sea View Avenue, Osterville, MA
1.01
Single-Family Home
$10,500,000
09/16/25
6
5.5
3,859
545 Sea View Ave, Barnstable, MA
1.02
Single-Family Home
$10,500,000
09/16/25
6
5.5
3,859

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 227 Bridge 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

Sourced by Trulia users. 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

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

8 pet-friendly rentals in Osterville, MA

Explore by feature - Garage

9 rentals with a garage in Osterville, MA

Explore by feature - Air Conditioning

24 rentals with air conditioning in Osterville, MA

Explore by feature - Pool

Explore by feature - Washer/dryer

24 rentals with a washer/dryer in Osterville, MA

Homes for sale near 227 Bridge St

Skip to last item
Skip to first item

Off Market Homes Near 227 Bridge St

Skip to last item
Skip to first item