27 & 30 North Bay Rd, Osterville, MA 02655

Off Market Oct 2020 for $5.5M

$7,662,524

Est. refi paymentEst. refi $17,733/mo

•

6,074

sq ft

27 & 30 North Bay Rd, Osterville, MA 02655

About this home

Waterfront property in Oyster Harbors comprised of two lots, one with house (#27) and another vacant across the street with water access and a deep-water dock with electric power (#30). The home has five bedrooms - a first floor master with twin en suite baths - and four upstairs bedrooms each with private bath; there are also two half baths. One of the upstairs bedrooms serves as a second master and has a separate sitting room and office. Open-concept common areas include a grand family room, a chef's kitchen, a breakfast nook, and a finished lower level. Oyster Harbors is a private, gated community with 24-hour security yet close to all major attractions, regional air travel, and island ferries.

Single-familyProperty Type

1984Year Built

2.04 acresLot Size

$1,262Est. Price/Sq.Ft.

2 car garageParking

Listed by Herb Pheeney • Oyster Real Estate

Bought with Kathleen Deerman • Robert Paul Properties, Inc.

Redfin checked: 2 minutes ago

•Source:CCIMLS #22004527

Redfin Estimate

$7,662,524

$2.2M since sold in October 2020$625K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 58.2% higher than the average sale price ($4.84M) of 6 comparable homes.

SOLD APR 16, 2026
$2,487,500
A
5 beds4.5 baths4,715 sq ft
98 Bunker Hill Rd, Osterville, MA 02655
SOLD DEC 3, 2025
$5,275,000
B
5 beds5.5 baths4,637 sq ft
245 North Bay Rd, Osterville, MA 02655
SOLD MAR 2, 2026
$4,400,000
C
5 beds6 baths6,768 sq ft
405 Bridge St, Osterville, MA 02655
SOLD APR 27, 2026
$2,200,000
D
4 beds5 baths6,294 sq ft
804 Main St, Cotuit, MA 02635
SOLD JUN 12, 2026
$6,900,000
E
6 beds5.5 baths8,713 sq ft
240 Baxters Neck Rd, Marstons Mills, MA 02648
SOLD JUL 29, 2026
$7,800,000
F
7 beds6 baths4,896 sq ft
255 Bayberry Way, Osterville, MA 02655

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Sell

$3,389,769

Est. take-home

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Est. cash available

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Rent

$4,625/mo

Redfin rental estimate

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Market trends in 02655, MA

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

96.4%

0.0% MoM

Median sale price

$1.5M

$321K MoM

Avg. days on market

19d

10 days MoM

Recently sold homes

1 MoM

New listings for sale

OPEN SAT, 11AM TO 12:30PM
$1,349,900
3 beds3 baths2,126 sq ft
30 Deerfield Rd, Osterville, MA 02655
OPEN SAT, 12PM TO 1PM
$999,000
2 beds2.5 baths1,564 sq ft
16 Second Ave #4, Osterville, MA 02655
EARLY ACCESS
$1,485,000
3 beds3 baths1,844 sq ft
23-27 Swift Ave, Osterville, MA 02655
$799,000
3 beds2 baths1,856 sq ft
329 Swift Ave, Osterville, MA 02655
$1,612,000
3 beds2 baths1,264 sq ft
137 Wianno Cir, Osterville, MA 02655
$629,000
3 beds1 bath1,156 sq ft
112 Osterville West Barnstable Rd, Osterville, MA 02655
See all

Provided by Redfin

Sale history for 27 & 30 North Bay Rd

Date

Event

Price

CCIMLS #22004527

Oct 30, 2020

Sold

$5,500,000

$905/sq ft

Aug 3, 2020

Pending

—

Jul 29, 2020

Contingent

—

Jul 18, 2020

Listing Removed

—

Jul 18, 2020

Listed

$5,800,000

$955/sq ft

CCIMLS #9903406

Oct 25, 1999

Sold

$2,772,000

$456/sq ft

May 8, 1999

Listed

$2,995,000

$493/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$31,501 (+7.8%)

$1,358,600 + $2,418,500

$3,777,100

2022

$29,214 (+0.7%)

$1,021,500 + $2,009,000

$3,030,500

2021

$29,002 (−6.5%)

$1,051,600 + $1,713,100

$2,764,700

2020

$31,024 (+8.5%)

$1,130,900 + $1,699,800

$2,830,700

2019

$28,591 (+6.9%)

$1,033,900 + $1,500,800

$2,534,700

2018

$26,734 (+7.6%)

$1,088,300 + $1,294,400

$2,382,700

2017

$24,849 (+6.4%)

$1,088,300 + $1,221,100

$2,309,400

2015

$23,350

$1,051,500 + $1,100,600

$2,152,100

Tax history for 27 & 30 North Bay Rd

Year

Property tax

Land + Additions

Assessment*

2023

$31,501 (+7.8%)

$1,358,600 + $2,418,500

$3,777,100

2022

$29,214 (+0.7%)

$1,021,500 + $2,009,000

$3,030,500

2021

$29,002 (−6.5%)

$1,051,600 + $1,713,100

$2,764,700

2020

$31,024 (+8.5%)

$1,130,900 + $1,699,800

$2,830,700

2019

$28,591 (+6.9%)

$1,033,900 + $1,500,800

$2,534,700

2018

$26,734 (+7.6%)

$1,088,300 + $1,294,400

$2,382,700

2017

$24,849 (+6.4%)

$1,088,300 + $1,221,100

$2,309,400

2015

$23,350

$1,051,500 + $1,100,600

$2,152,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

1.1 Acres

Year renovated

—

Sq. Ft.

6,074

Year built

1984

Style

Single Family Residential

County

Barnstable County

APN

2231495

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Mar 6, 2023.

Property details

Parking

Garage Infromation
Has Garage
Garage Spaces: 2

Interior

Master Bedroom Information
Master Bedroom Level: First

Bathroom Information
# of Bathrooms (Full): 5
# of Bathrooms (1/2): 2

Basement Information
Basement: Finished, Interior Entry

Other Room Information
Total Rooms : 13

Interior Features
Flooring: Hardwood, Carpet

Exterior

Exterior Features
Exterior Features: Outdoor Shower
Construction Materials: Shingle Siding
Roof: Wood, Shingle
Foundation Details: Poured

Pool Information
Pool Features: Heated, In Ground
Has Private Pool

Property Information
Property Sub Type: Single Family Residence
Property Condition: Updated/Remodeled, Actual

Lot Information
Lot Features: South of Route 28
Lot Size Source: Assessor
Has Waterfront
Water Body Name: North Bay
Waterfront Features: Bay, Salt, Deep Water Access
Road Frontage Type: Private Road
Road Responsibility: Assoc Maintained
Zoning: RF-1

Building Information
Year Built: 1984

Utilities

Heating & Cooling
Has Heating
Has Cooling
Cooling: Central Air

Utility Information
Sewer: Septic Tank, Septic Tank

Location

School Information
Elementary School District: Barnstable
Middle Or Junior School District: Barnstable
High School District: Barnstable

Location Information
Directions: Immediately after entering Oyster Harbors gate, take first right onto North Bay Road. Property with house is on the left (#27). Vacant lot with deep-water dock is across the street (#30).

Public facts

Beds: 6
Baths: 4.5
Sq. Ft.: 6,074
Stories: 2.0
Lot Size: 1.1 acres
Style: Single Family Residential
Year Built: 1984
Year Renovated: —
County: Barnstable County
APN: 2231495

Home facts updated by county records on Mar 6, 2023

Around this home

Schools

Barnstable United Elementary School

Public 4-5 • Assigned • 2.8mi

3/10

Barnstable High School

Public 8-12 • Assigned • 5.1mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk 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, 17 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

In this area, properties receive around 8.8 hours in June and 4.5 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.5 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$7.28M – $8.81M

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Nearby similar homes

OPEN SAT, 11AM TO 12:30PM

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30 Deerfield Rd, Osterville, MA 02655

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New listings for sale in 02655

OPEN SAT, 11AM TO 12:30PM

$1,349,900

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30 Deerfield Rd, Osterville, MA 02655

OPEN SAT, 12PM TO 1PM

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EARLY ACCESS

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23-27 Swift Ave, Osterville, MA 02655

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Home values near 27 & 30 North Bay Rd

Data from public records.

Address	Redfin Estimate
9 N Bay Road, Osterville, MA 5 Beds \| 5.5 Baths \| 4473 Sq. Ft.	$3,752,433
49 N Bay Road, Osterville, MA 7 Beds \| 6 Baths \| 5960 Sq. Ft.	$5,940,224

Address	Redfin Estimate
92 N Bay Road, Osterville, MA 6 Beds \| 6.5 Baths \| 6482 Sq. Ft.	$8,373,886
92 N Bay Road, Osterville, MA 6 Beds \| 6.5 Baths \| 6482 Sq. Ft.	$7,744,716

Address	Redfin Estimate
72 N Bay Road, Osterville, MA 3 Beds \| 2.5 Baths \| 2082 Sq. Ft.	$4,688,725
50 Oakdale Path, Osterville, MA 4 Beds \| 5.5 Baths \| 4823 Sq. Ft.	$4,968,804

Property information provided by CCIMLS when last listed in 2020. This data may not match . Learn more.

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