For sale

$3,450,000

Est. $20,161/mo —

•

2,424

sq ft

156 East Bay Rd, Osterville, MA 02655

About this home

Prime location on one of Cape Cod's most coveted roads, East Bay Road in Osterville. This beautiful home is rich with character, having been repurposed from a large carriage house. It boasts history and classic Cape Cod charm. Enter the home through the large living room and move into the kitchen equipped with a bright sunroom off to the right. An old horse stable has been fashioned into an office space that is located to the left of the kitchen, with an adjacent first-floor full bathroom. Upstairs are 4 bedrooms, two are en-suites. Downstairs a finished basement provides more living space and a laundry room and full bath. Outside, a detached 2-car garage provides space for your vehicles and a shed for storage. A beautiful fenced in side yard is ideal for summer gatherings, games or just relaxing. There is also an outdoor area out back for grilling and dining, as well as an outdoor shower, perfect after a day spent at the beach.

Single-familyProperty Type

1915Year Built

0.62 acresLot Size

$1,423Price/Sq.Ft.

2 garage spacesParking

Listed by Barbara Corcoran • William Raveis R.E. & Home Services

Listed by • William Raveis R.E. & Home Services

Listing updated: Jun 18, 2026 at 02:40pm

Redfin checked: 2 minutes ago

•Source:MLS PIN #73531877

Payment calculator

$20,161 per month

Principal and interest$18,131

Property taxes

$1,282

HOA dues

Home insurance

$748

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN FRI, 3PM TO 5PM
$999,900
3 beds2.5 baths2,251 sq ft
19 Elmcroft Way, Yarmouth Port, MA 02675
OPEN FRI, 3PM TO 4PM
$647,000
3 beds2 baths1,132 sq ft
220 North Main St, South Yarmouth, MA 02664
OPEN FRI, 5PM TO 6:30PM
$749,900
3 beds2 baths2,072 sq ft
114 Carriage Ln, Barnstable, MA 02630
OPEN SAT, 10AM TO 12PM3D WALKTHROUGH
$575,000
3 beds1 bath1,589 sq ft
21 Captain Small Rd, South Yarmouth, MA 02664
OPEN SAT, 10AM TO 12PM
$649,900
2 beds2 baths1,306 sq ft
29 Race Ln, Sandwich, MA 02563
OPEN SAT, 11AM TO 1PM
$799,000
2 beds3.5 baths2,450 sq ft
78 Gold Leaf, Mashpee, MA 02649
OPEN SAT, 11AM TO 1PM
$875,000
3 beds2 baths1,704 sq ft
192 Winding Cove Rd, Marstons Mills, MA 02648
OPEN SAT, 11AM TO 1PM
$750,000
3 beds3 baths1,267 sq ft
34 Commodore Ln, Marstons Mills, MA 02648
OPEN SAT, 11AM TO 1PM
$997,000
5 beds2 baths2,300 sq ft
63 Ellsworth Dr, East Falmouth, MA 02536
OPEN SAT, 11AM TO 12:30PM
$1,349,900
3 beds3 baths2,126 sq ft
30 Deerfield Rd, Osterville, MA 02655

Around this home

Schools

K - 12
Preschool & daycare

Barnstable United Elementary School

Public 4-5 • Assigned • 2.5mi

3/10

Barnstable High School

Public 8-12 • Assigned • 3.5mi

3/10

Provided by GreatSchools

About

Osterville

Osterville, located between Centerville and Cotuit, is a coastal and village-style Barnstable neighborhood with a harborfront setting and a walkable Main Street. The neighborhood’s character concentrates around Main Street at Wianno Avenue, where galleries, outfitters, coffee counters, and small specialty shops set a polished Cape rhythm. Armstrong-Kelley Park frames the village green with lawns and shade trees, while nearby docks and marinas keep salt air in the mix. Shingle-style and Cape Cod cottages sit along shell drives, with larger waterfront homes facing North Bay. The Osterville Historical Society and Museum anchors local history, and the Osterville Village Library adds a quiet civic note. Dowses Beach and Joshua’s Pond shape days around sand, sailing, and freshwater swims.

Provided by Walk Score and Local Logic

Offer insights

156 East Bay Rd · $3,450,000

Strong offer

$3.42M and above

75% chance or better to win

Why $3.42M+ is a strong offer

DAYS ON MARKET

The average home goes pending in 29 days.

SALE-TO-LIST

Most homes are selling 2% below list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bedroom

Living

Dining

Interior features
One fireplace
Bathroom features (general)
Six total rooms

Bedrooms
Master bedroom on second level
Bedroom 2 on second level
Bedroom 3 on second level
Bedroom 4 on second level

Bathrooms
Five full bathrooms
Primary/main bath on first level
Additional bath(s) on second level
Bathroom located in basement

Kitchen
Kitchen located on first level
Gas water heater

Laundry & utility
Laundry located in basement

Flooring
Carpet
Hardwood

Heating & cooling
Forced air heating

Sale and tax history for 156 East Bay Rd

Sale History
Tax History

Date

Event

Price

CCIMLS #22602593

Jun 3, 2026

Listed

$3,450,000

$1,423/sq ft

+55

Prime location on one of Cape Cod's most coveted roads, East Bay Road in Osterville. This beautiful home is rich with character, having been repurposed from a large carriage house. It boasts history and classic Cape Cod charm. Enter the home through the large living room and move into the kitchen equipped with a bright sunroom off to the right. An old horse stable has been fashioned into an office space that is located to the left of the kitchen, with an adjacent first-floor full bathroom. Upstairs are 4 bedrooms, two of which include ensuite bathrooms. Downstairs a finished basement provides more living space as well as a laundry room and a full bath. Outside, a detached 2-car garage provides space for your vehicles as well as a shed for storage. A beautiful fenced in side yard is ideal for summer gatherings, games or just relaxing. There is also an outdoor area out back for grilling and dining, as well as an outdoor shower, perfect after a day spent at the beach. Just minutes from Dowses Beach, the East Bay boat landing, and Osterville Main Street, this home embodies vintage Cape Cod charm and is ready for a future with somebody who will appreciate its beauty and character.

MLS PIN #73531877

May 28, 2026

Listed

$3,450,000

$1,423/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$14,183 (+12.4%)

$1,269,600 + $431,000

$1,700,600

2022

$12,620 (−5.8%)

$951,700 + $357,400

$1,309,100

2021

$13,393 (−1.8%)

$979,700 + $297,000

$1,276,700

2020

$13,645 (+6.9%)

$979,700 + $265,300

$1,245,000

2019

$12,767 (+0.6%)

$895,700 + $236,100

$1,131,800

2018

$12,689 (+4.5%)

$942,800 + $188,100

$1,130,900

2017

$12,144 (−2.6%)

$942,800 + $185,800

$1,128,600

2015

$12,463

$933,900 + $214,800

$1,148,700

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.62 Acres

Year renovated

—

Finished Sq. Ft.

2,424

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,424

Year built

1915

Style

Single Family Residential

County

Barnstable County

APN

2233393

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Climate risks

7/10 Flood Factor

Estimated 80%+ chance of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 88° expected this year, 19 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Osterville, MA • 02655

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

87/ 100

Very good sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.2 hrs

5 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 156 East Bay Rd

$3,321,321

$129K under list price of $3.45M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.1M to $3.5M.

SOLD AUG 12, 2026
$2,500,000 Last sold price
3 beds4 baths2,696 sq ft
146 Scudder Rd, Osterville, MA 02655
$496/sq ft
smaller lot
110 years newer
SOLD JUL 13, 2026
$2,000,000 Last sold price
3 beds2 baths1,194 sq ft
51 Wianno Cir, Osterville, MA 02655
$252/sq ft
larger lot
71 years newer
SOLD AUG 17, 2026
$3,475,000 Last sold price
4 beds4 baths4,364 sq ft
82 Crystal Lake Rd, Osterville, MA 02655
$627/sq ft
smaller lot
101 years newer
SOLD JUL 21, 2026
$1,053,500 Last sold price
2 beds2.5 baths1,992 sq ft
170 Sturbridge Dr, Osterville, MA 02655
$894/sq ft
smaller lot
78 years newer
SOLD APR 14, 2026
$1,570,000 Last sold price
3 beds2 baths1,872 sq ft
117 Parsley Ln, Osterville, MA 02655
$584/sq ft
smaller lot
55 years newer
SOLD JUL 29, 2026
$1,495,000 Last sold price
4 beds4 baths2,509 sq ft
25 Manor Way, Osterville, MA 02655
$827/sq ft
smaller lot
57 years newer

Rental earnings

Est. $4,107 per month, based on comparable rentals

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Nearby similar homes

OPEN SAT, 11AM TO 12:30PM

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New listings for sale in 02655

OPEN SAT, 11AM TO 12:30PM

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Details provided by MLS PIN and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

See this home in person

Nearby open houses (10)

Around this home

Schools

Offer insights

Property details

Sale and tax history for 156 East Bay Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 156 East Bay Rd

Early Access listings

Nearby similar homes

New listings for sale in 02655

More real estate resources