For sale

$3,450,000

Est. $21,092/mo —

•

3,924

sq ft

156 E 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 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.

Single-familyProperty Type

1915Year Built

0.62 acresLot Size

$879Price/Sq.Ft.

2 car garageParking

Listed by Barbara Corcoran • William Raveis Real Estate & Home Services

Listed by Kaitlyn Ramsey • William Raveis Real Estate & Home Services

Listing updated: Sep 16, 2026 at 01:25am

Redfin checked: 2 minutes ago

•Source:CCIMLS #22602593

Payment calculator

$21,092 per month

Principal and interest$19,063

Property taxes

$1,282

HOA dues

Home insurance

$748

Utilities

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Affordability tools

See this home in person

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN WED, 9AM TO 11AM
$518,000
4 beds1 bath1,132 sq ft
7 Emerald Way, Forestdale, MA 02644
OPEN SAT, 9AM TO 11AM
$415,000
3 beds1.5 baths1,344 sq ft
12 Sherwood Ln, Sandwich, MA 02563
OPEN SAT, 10AM TO 12PM
$549,444
2 beds1 bath936 sq ft
2 Spectacle Rd, East Sandwich, MA 02537
OPEN SAT, 10AM TO 12PM
$2,200,000
4 beds3 baths2,013 sq ft
205 South St, South Yarmouth, MA 02664
OPEN SAT, 10AM TO 1PM
$615,000
4 beds2.5 baths1,484 sq ft
14 Andersen Ave, East Sandwich, MA 02537
OPEN SAT, 10:30AM TO 12PM
$850,000
3 beds2 baths2,250 sq ft
1187 Osterville West Barnstable Rd, Marstons Mills, MA 02648
OPEN SAT, 11AM TO 1PM
$1,175,000
5 beds4.5 baths3,497 sq ft
2939 Main St, Barnstable, MA 02630
OPEN SAT, 11AM TO 1PM
$369,900
2 beds2 baths1,000 sq ft
222 Buck Island Rd Unit 6-2, West Yarmouth, MA 02673
OPEN SAT, 1PM TO 2:30PM
$849,900
2 beds1.5 baths1,055 sq ft
466 Old Mill Rd, Osterville, MA 02655
OPEN SUN, 11AM TO 12:30PM
$799,900
5 beds3 baths2,145 sq ft
5 Trenton St, West Yarmouth, MA 02673

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 E 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 32 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
Hardwood and carpet flooring
Patio

Bathrooms
5 full bathrooms

Laundry & utility
Water heater

Flooring
Hardwood
Carpet

Heating & cooling
Heating present
No central cooling

Sale and tax history for 156 E Bay Rd

Sale History
Tax History

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 E Bay Rd

$3,276,438

$174K under list price of $3.45M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $2.0M to $3.9M.

SOLD SEP 2, 2026
$3,900,000 Last sold price
4 beds4.5 baths4,241 sq ft
30 Cockachoiset Ln, Osterville, MA 02655
$41/sq ft
25 years older
SOLD AUG 12, 2026
$2,500,000 Last sold price
3 beds4 baths2,696 sq ft
146 Scudder Rd, Osterville, MA 02655
$48/sq ft
smaller lot
110 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
$83/sq ft
smaller lot
101 years newer
SOLD JUL 13, 2026
$2,000,000 Last sold price
3 beds2 baths1,194 sq ft
51 Wianno Cir, Osterville, MA 02655
$796/sq ft
larger lot
71 years newer
SOLD OCT 7, 2026
$2,850,000 Last sold price
3 beds3.5 baths4,608 sq ft
34 Farm Valley Rd, Osterville, MA 02655
$261/sq ft
81 years newer
finished basement
SOLD SEP 18, 2026
$3,075,000 Last sold price
10 beds7.5 baths6,905 sq ft
414 Eel, Osterville, MA 02655
$434/sq ft
larger lot
48 years newer

Rental earnings

Est. $3,898 per month, based on comparable rentals

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Make a winning offer with the help of a local agent

Ask a question

(617) 397-3327

Early Access listings

EARLY ACCESSCOMPASS COMING SOON

Contact for price

2 beds3 baths1,498 sq ft

79 Sheridan St #1, Jamaica Plain, MA 02130

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$579,900

2 beds2 baths1,512 sq ft

Undisclosed address, East Bridgewater, MA 02333

EARLY ACCESSCOMPASS COMING SOON

$995,000

3 beds3 baths3,249 sq ft

7 Dale Ter, Sandwich, MA 02563

EARLY ACCESSCOMPASS COMING SOON

$800,000

5 beds3 baths3,267 sq ft

36 Tufts Ave, Everett, MA 02149

EARLY ACCESSCOLDWELL BANKER REALTY COMING SOON

$975,000

5 beds2 baths2,067 sq ft

85 Franklin St, Allston, MA 02134

EARLY ACCESS

$880,000

3 beds2 baths1,898 sq ft

65 Emerald St, Quincy, MA 02169

Nearby similar homes

VIDEO TOUR

$1,895,000

4 beds2.5 baths2,636 sq ft

420 Starboard Ln, Osterville, MA 02655

VIDEO TOUR

$8,800,000

5 beds5 baths7,157 sq ft

25 Oyster Way, Osterville, MA 02655

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4 beds3 baths2,050 sq ft

72 Hathaway Rd Rd, Osterville, MA 02655

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3 beds2 baths1,248 sq ft

111 Westwind, Osterville, MA 02655

NEW CONSTRUCTIONVIDEO TOUR

$4,695,000

5 beds6 baths4,100 sq ft

22 Scudder Rd, Osterville, MA 02655

New listings for sale in 02655

$3,390,000

3 beds4.5 baths5,049 sq ft

140 Seapuit Rd, Osterville, MA 02655

$775,000

2 beds1.5 baths1,170 sq ft

15 South St, Osterville, MA 02655

$299,900

1 bed1 bath412 sq ft

3040 Falmouth Rd Apt G3, Osterville, MA 02655

VIDEO TOUR

$6,600,000

5 beds6.5 baths4,955 sq ft

434 Sea View Ave, Osterville, MA 02655

$795,000

2 beds1.5 baths1,170 sq ft

13 South St, Osterville, MA 02655

$975,000

3 beds2 baths1,706 sq ft

227 Bumps River Rd, Barnstable, MA 02630

$3,225,000

3 beds3 baths1,506 sq ft

32 Starboard Ln, Osterville, MA 02655

$975,000

3 beds2 baths1,706 sq ft

227 Bumps River Rd, Osterville, MA 02655

Details provided by CCIMLS 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

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Offer insights

Property details

Sale and tax history for 156 E Bay Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 156 E Bay Rd

Early Access listings

Nearby similar homes

New listings for sale in 02655

More real estate resources