OFF MARKET

Off Market Oct 2018 for $5.4M

$8,943,951

Est. refi paymentEst. refi $3,843/mo

•

5,715

sq ft

58 South Bay Rd, Osterville, MA 02655

About this home

Luxurious Waterfront Estate with southern exposure overlooking the soothing waters of West Bay. Enjoy the magnificent southern exposure as you watch the boats navigating to and from Nauticus, Crosby, and Oyster Harbors Yacht Clubs. The 5,700+ sf residence was designed by architect Tom Catalano (Boston) with the extensive interior craftsmanship custom finished by WoodMeister Master Builders (Boston, Nantucket, N.Y., and VT.) This captivating residence provides warm and inviting living areas for family and friends and features large impressive rooms with high ceilings, detailed custom millwork, a gourmet kitchen, 5-bedrooms, 3-full baths, 2-half baths, a home office, 2 fireplaces, a magnificent sun room overlooking the water, an expansive deck with multiple sitting areas, and a dingy dock on West Bay. All info. should be verified.

Single-familyProperty Type

1991Year Built

1.03 acresLot Size

$1,565Est. Price/Sq.Ft.

3 car garageParking

Listed by John Hopkins • Frank A Sullivan Real Estate

Bought with Chuck Tuttle • Kinlin Grover Real Estate

Redfin checked: 2 minutes ago

•Source:CCIMLS #21602217

Redfin Estimate

$8,943,951

$3.5M since sold in October 2018$957K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 151.4% higher than the average sale price ($3.56M) of 6 comparable homes.

SOLD OCT 3, 2025
$3,400,000
A
4 beds4 baths5,762 sq ft
780 Sea Vw, Osterville, MA 02655
SOLD JUN 1, 2026
$3,995,000
B
5 beds4.5 baths6,239 sq ft
268 Parker Rd, Osterville, MA 02655
SOLD NOV 6, 2025
$3,000,000
C
4 beds3.5 baths3,720 sq ft
355 Bridge St, Osterville, MA 02655
SOLD DEC 3, 2025
$5,275,000
D
5 beds5.5 baths4,637 sq ft
245 North Bay Rd, Osterville, MA 02655
SOLD AUG 17, 2026
$3,475,000
E
4 beds4 baths4,364 sq ft
82 Crystal Lake Rd, Osterville, MA 02655
SOLD APR 27, 2026
$2,200,000
F
4 beds5 baths6,294 sq ft
804 Main St, Cotuit, MA 02635

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Sell

$4,843,689

Est. take-home

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Est. cash available

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Rent

$4,666/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

EARLY ACCESS
$1,485,000
3 beds3 baths1,844 sq ft
23-27 Swift Ave, Osterville, MA 02655
EARLY ACCESS
$999,000
2 beds3 baths1,564 sq ft
16 2nd Ave #4, 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
OPEN SAT, 11AM TO 1PM
$629,000
3 beds1 bath1,156 sq ft
112 Osterville West Barnstable Rd, Osterville, MA 02655
See all

Provided by Redfin

Sale history for 58 South Bay Rd

Year

Property tax

Land + Additions

Assessment*

2023

$70,615 (+37.9%)

$7,214,200 + $1,252,800

$8,467,000

2022

$51,195 (−0.6%)

$4,156,400 + $1,154,300

$5,310,700

2021

$51,496 (−9.0%)

$3,918,900 + $990,200

$4,909,100

2020

$56,593 (+11.2%)

$4,276,400 + $887,200

$5,163,600

2019

$50,899 (−4.5%)

$3,801,400 + $710,900

$4,512,300

2018

$53,276 (+4.9%)

$4,001,400 + $746,900

$4,748,300

2017

$50,811 (+0.4%)

$4,001,400 + $720,800

$4,722,200

2015

$50,589

$3,968,900 + $693,700

$4,662,600

Tax history for 58 South Bay Rd

Year

Property tax

Land + Additions

Assessment*

2023

$70,615 (+37.9%)

$7,214,200 + $1,252,800

$8,467,000

2022

$51,195 (−0.6%)

$4,156,400 + $1,154,300

$5,310,700

2021

$51,496 (−9.0%)

$3,918,900 + $990,200

$4,909,100

2020

$56,593 (+11.2%)

$4,276,400 + $887,200

$5,163,600

2019

$50,899 (−4.5%)

$3,801,400 + $710,900

$4,512,300

2018

$53,276 (+4.9%)

$4,001,400 + $746,900

$4,748,300

2017

$50,811 (+0.4%)

$4,001,400 + $720,800

$4,722,200

2015

$50,589

$3,968,900 + $693,700

$4,662,600

*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

Stories

Lot width

—

Lot depth

—

Lot size

1.03 Acres

Year renovated

—

Sq. Ft.

5,697

Year built

1991

Style

Single Family Residential

County

Barnstable County

APN

2231617

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Property details

Parking

Garage Infromation
Has Garage
Has Attached Garage
Garage Spaces: 3

Interior

Master Bedroom Information
Master Bedroom Features: Walk-In Closet(s),View
Master Bedroom Level: First

Bedroom #2 Information
Bedroom 2 Description: Flooring: Wood
Bedroom 2 Features: Bedroom 2,View,Closet
Bedroom 2 Level: Second

Bedroom #3 Information
Bedroom 3 Description: Flooring: Wood
Bedroom 3 Features: Bedroom 3,Closet,View
Bedroom 3 Level: Second

Bedroom #4 Information
Bedroom 4 Description: Flooring: Wood
Bedroom 4 Features: Bedroom 4,View,Closet
Bedroom 4 Level: Second

Dining Room Information
Dining Room Description: Flooring: Wood
Dining Room Features: Dining Room
Dining Room Level: First

Living Room Information
Living Room Description: Flooring: Wood,Door(s): French
Living Room Features: Built-in Features,Living Room,Ceiling Fan(s),Cathedral Ceiling(s)
Living Room Level: First

Bathroom Information
# of Bathrooms (Full): 3
# of Bathrooms (1/2): 2
Master Bathroom Features: Private Full Bath

Kitchen Information
Kitchen Description: Countertop(s): Granite,Flooring: Tile
Kitchen Features: Kitchen,Upgraded Cabinets,View,Kitchen Island
Kitchen Level: First

Basement Information
Basement: Full, Partial

Laundry Information
Laundry Features: Laundry Room, First Floor

Fireplace Information
FireplacesTotal: 2
Has Fireplace

Other Room Information
Total Rooms : 12

Interior Features
Flooring: Wood, Tile
Appliances: Electric Water Heater
Door Features: French
Patio And Porch Features: Deck

Exterior

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

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

Lot Information
Lot Features: In Town Location, Near Golf Course, Marina, Level, South of Route 28
Lot Size Source: Assessor
Has Waterfront
Waterfront Features: Bay
Zoning: Residential

Building Information
Year Built: 1991

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: West Bay Road to Bridge Street, cross over the drawbridge and follow to 1st street on your left.

Public facts

Beds: 6
Baths: 4.0
Sq. Ft.: 5,697
Stories: 2.0
Lot Size: 1.03 acres
Style: Single Family Residential
Year Built: 1991
Year Renovated: —
County: Barnstable County
APN: 2231617

Home facts updated by county records on Jul 19, 2023

Around this home

Schools

Barnstable United Elementary School

Public 4-5 • Assigned • 2.7mi

3/10

Barnstable High School

Public 8-12 • Assigned • 4.6mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

3/10 Flood Factor

Estimated 13-19% 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, 18 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

$8.50M – $10.29M

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Nearby similar homes

$839,900

3 beds2.5 baths2,100 sq ft

177 Bayview Cir, Osterville, MA 02655

$589,000

2 beds1 bath1,056 sq ft

30 Patience Ln, Cotuit, MA 02635

3D WALKTHROUGH

$4,950,000

5 beds7.5 baths5,970 sq ft

313 Bridge St, Osterville, MA 02655

VIDEO TOUR

$8,800,000

5 beds5 baths7,157 sq ft

25 Oyster Way, Osterville, MA 02655

NEW CONSTRUCTIONVIDEO TOUR

$4,795,000

5 beds6 baths4,100 sq ft

22 Scudder Rd, Osterville, MA 02655

$1,750,000

3 beds2.5 baths3,084 sq ft

81 Osterville-west Barnstable Rd, Osterville, MA 02655

New listings for sale in 02655

EARLY ACCESS

$1,485,000

3 beds3 baths1,844 sq ft

23-27 Swift Ave, Osterville, MA 02655

EARLY ACCESS

$999,000

2 beds3 baths1,564 sq ft

16 2nd Ave #4, 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

OPEN SAT, 11AM TO 1PM

$629,000

3 beds1 bath1,156 sq ft

112 Osterville West Barnstable Rd, Osterville, MA 02655

Home values near 58 South Bay Rd

Data from public records.

Address	Redfin Estimate
121 S Bay Road, Osterville, MA 4 Beds \| 3 Baths \| 2871 Sq. Ft.	$2,518,404
107 S Bay Road, Osterville, MA 6 Beds \| 3.5 Baths \| 3201 Sq. Ft.	$2,644,671

Address	Redfin Estimate
132 S Bay Road, Osterville, MA 7 Beds \| 7 Baths \| 6496 Sq. Ft.	$13,713,451
93 S Bay Road, Osterville, MA 5 Beds \| 4 Baths \| 6250 Sq. Ft.	$4,605,506

Address	Redfin Estimate
40 S Bay Road, Osterville, MA 4 Beds \| 4.5 Baths \| 3674 Sq. Ft.	$1,993,336
92 S Bay Road, Osterville, MA 7 Beds \| 7 Baths \| 8929 Sq. Ft.	$10,350,563

Property information provided by CCIMLS when last listed in 2016. This data may not match . Learn more.

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