For sale

$1,950,000

Est. $11,516/mo —

•

2,972

sq ft

56 Rip Van Winkle Way, Bourne, MA 02532

About this home

Set on its own peninsula overlooking Buttermilk Bay, this landmark waterfront residence offers an extraordinary 485 feet of direct water frontage and vibrant views in every direction. With water visible from nearly every window, the home captures the beauty, light, and that define life on the Cape. The front garden welcomes you with mature plantings and picturesque arches that create a peaceful and inviting approach. Inside, the home blends Mediterranean architectural character with thoughtful modern updates, offering generous space for entertaining while maintaining the warmth and charm of a classic villa. Bay views greet you immediately and continue to unfold as you move through the living spaces and into the sunroom with panoramic views over the large yard. The main living areas are designed to bring the outdoors in, filling the home with natural light. Upstairs the bedrooms enjoy western exposure, offering serene sunset views over the water at the end of each day.

Single-familyProperty Type

1939Year Built

0.51 acresLot Size

$656Price/Sq.Ft.

1 garage spacesParking

Listed by James Abdu • Upper Cape Realty Corp.

Listed by • Upper Cape Realty Corp.

Listing updated: May 26, 2026 at 11:46am

Redfin checked: 2 minutes ago

•Source:MLS PIN #73369737

Payment calculator

$11,516 per month

Principal and interest$10,248

Property taxes

$846

HOA dues

Home insurance

$423

Utilities

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Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN TODAY, 1AM TO 3PM
$815,000
2 beds2.5 baths2,196 sq ft
68 Gold Leaf Ln, Mashpee, MA 02649
OPEN TODAY, 10AM TO 12PM
$825,000
2 beds2.5 baths2,769 sq ft
24 Stratford Rdg #24, Mashpee, MA 02649
OPEN TODAY, 10:30AM TO 12:30PM
$875,000
3 beds2 baths1,637 sq ft
775 Shore Rd, Pocasset, MA 02559
OPEN TODAY, 11AM TO 1PM3D WALKTHROUGH
$799,000
4 beds3.5 baths2,450 sq ft
78 Gold Leaf Ln E, Mashpee, MA 02649
OPEN TODAY, 11AM TO 1PM3D & VIDEO TOUR
$675,000
2 beds2.5 baths1,612 sq ft
10 Red Cedar Rd #10, Mashpee, MA 02649
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65 Blue Spruce Way #65, Mashpee, MA 02649
OPEN TODAY, 12PM TO 2PM
$620,000
4 beds2 baths1,752 sq ft
133 Alewife Rd, Plymouth, MA 02360
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68 Gold Leaf Ln #68, Mashpee, MA 02649

Around this home

Schools

K - 12
Preschool & daycare

Bourne Intermediate School

Public 3-5 • Assigned • 1.8mi

5/10

Bourne Middle School

Public 6-8 • Assigned • 1.9mi

6/10

Bourne High School

Public 9-12 • Assigned • 1.8mi

4/10

Provided by GreatSchools

About Upper

Cape

Upper Cape, located between Buzzards Bay and Cape Cod Bay, is a coastal and village-centered Falmouth neighborhood with saltwater inlets and piney conservation land. The neighborhood’s character concentrates around Main Street in Woods Hole, where ferry docks, marine labs, and compact storefronts set a working-harbor rhythm. The Woods Hole Oceanographic Institution and the Woods Hole Science Aquarium act as cultural anchors, with The Knob adding a quiet shoreline counterpoint. Architecture leans toward shingled Cape cottages and weathered harbor-side buildings, with bikeable lanes linking beaches and ponds. Days track tides, ferry schedules, and the Shining Sea Bikeway’s steady flow. Small marinas and pocket parks keep the landscape open and maritime.

Provided by Walk Score and Local Logic

Market insights

56 Rip Van Winkle Way · $1,950,000

DAYS ON MARKET

The average home goes pending in 24 days.

SALE-TO-LIST

Most homes are selling 1% below list price.

LIST PRICE

Median list price in this area is $875,000. (55% lower than this home)

PRICE DROP

23% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Ceiling fans throughout
Sun room
Custom built cabinets
Upgraded countertops

Bedrooms
Main-level/first-floor bedrooms (3) with cathedral and beamed ceilings in the primary, ceiling fans, closets; some bedrooms have hardwood flooring and exterior access
Second-floor bedrooms with ceiling fans, closets and hardwood flooring

Bathrooms
Two full bathrooms
One half bathroom
First-floor full bath with ceiling fan and hardwood flooring
Second-floor full bath

Kitchen
Custom built cabinets
Hardwood and wood flooring
Upgraded countertops

Laundry & utility
First-floor laundry with vinyl flooring, upgraded cabinets and countertops, linen closet and utility sink
Washer and dryer included

Flooring
Wood and hardwood flooring
Stone/ceramic tile
Vinyl in laundry

Heating & cooling
Electric baseboard heating
Heating present

Sale and tax history for 56 Rip Van Winkle Way

Sale History
Tax History

Date

Event

Price

CCIMLS #22502088

Apr 13, 2026

Price Changed

$1,950,000

$656/sq ft

Mar 9, 2026

Relisted

—

Feb 7, 2026

Listing Removed

—

Nov 5, 2025

Relisted

—

Oct 17, 2025

Listing Removed

—

Aug 28, 2025

Price Changed

$2,199,000

$740/sq ft

Jun 2, 2025

Relisted

—

May 12, 2025

Pending

—

May 6, 2025

Listed

$2,300,000

$774/sq ft

+51

Waterfront getaway on Cohasset Narrows and Buttermilk Bay. This Mediterranean inspired villa is positioned on a private point to take in views from every room. Even the garage! Each view is unique. The waters in front are full of clams and quahogs. Outdoor cooking area for preparing fresh caught seafood, and a private outdoor shower. With 485 feet of water frontage, and a lush green yard this property is perfect for both entertaining and relaxing. Walking through the front garden with mature plantings, patios, and arches is like entering another world. Fully refreshed in 2012 this home is move in ready. The front door opens up to views of the water greeting you. The kitchen countertops and backsplash tastefully bring the outside in with hints of the red tile roof. The primary bedroom has 18 foot vaulted ceilings and access to the side patio. Overlooking the point the heated solarium has180 degree views of the water. With three bedrooms on the first floor the original house is perfect for first floor living. The addition has a formal living room with sunset views and a gas fireplace. Upstairs are two large bedrooms are private & comfortable with the beds looking out at the water.

MLS PIN #73369737

Apr 13, 2026

Price Changed

$1,950,000

$656/sq ft

Mar 9, 2026

Relisted

—

Feb 7, 2026

Listing Removed

—

Aug 28, 2025

Price Changed

$2,199,000

$740/sq ft

Jun 2, 2025

Relisted

—

May 12, 2025

Contingent

—

May 5, 2025

Listed

$2,300,000

$774/sq ft

CCIMLS #21202965

Sep 17, 2019

Listing Removed

—

Mar 30, 2012

Listed

$695,000

$234/sq ft

CCIMLS #21105571

Sep 18, 2019

Listing Removed

—

Jun 17, 2011

Listed

$749,900

$252/sq ft

CCIMLS #20807001

Sep 20, 2019

Listing Removed

—

Jul 12, 2008

Listed

$998,500

$336/sq ft

MLS PIN #71415842

Nov 30, 2012

Sold

$582,000

$196/sq ft

Oct 14, 2012

Listing Removed

—

Jul 29, 2012

Listed

$660,000

$222/sq ft

CCIMLS #7027821

Dec 8, 1997

Sold

$280,000

$94/sq ft

Mar 18, 1997

Listed

$350,000

$118/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$8,943 (+5.3%)

$416,500 + $598,600

$1,015,100

2022

$8,490 (+2.9%)

$368,600 + $472,800

$841,400

2021

$8,248 (+2.7%)

$335,400 + $430,400

$765,800

2020

$8,035 (+5.5%)

$332,200 + $415,900

$748,100

2019

$7,616 (+13.8%)

$332,200 + $392,400

$724,600

2018

$6,695 (+1.0%)

$316,500 + $318,700

$635,200

2017

$6,630 (+16.1%)

$344,800 + $298,900

$643,700

2016

$5,713 (+0.9%)

$344,800 + $217,500

$562,300

2015

$5,662

$344,800 + $217,500

$562,300

Public record

Public record
Zoning

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

0.51 Acres

Year renovated

2000

Finished Sq. Ft.

2,772

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,772

Year built

1939

Style

Single Family Residential

County

Barnstable County

APN

2183474

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 19, 2023.

Climate risks

6/10 Flood Factor

Estimated 17-25% 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 93° expected this year, 16 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 3 days in 30 years

Provided by First Street

Historical weather

Bourne, MA • 02532

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.

10.1 hrs

6 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 56 Rip Van Winkle Way

$1,757,284

$193K under list price of $1.95M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $555K to $1.7M.

SOLD AUG 14, 2026
$555,000 Last sold price
5 beds2 baths1,836 sq ft
4 Van Bummel, Bourne, MA 02532
$354/sq ft
smaller lot
23 years newer
SOLD MAY 29, 2026
$680,000 Last sold price
4 beds2 baths2,112 sq ft
92 Choctaw, Buzzards Bay, MA 02532
$334/sq ft
smaller lot
18 years older
SOLD JUL 29, 2026
$1,685,000 Last sold price
6 beds5 baths4,205 sq ft
54 Arlington Dr, Bourne, MA 02532
$255/sq ft
larger lot
34 years older
SOLD JUN 12, 2026
$1,400,000 Last sold price
4 beds3 baths2,459 sq ft
8 Pine Tree Dr, Buzzards Bay, MA 02532
$87/sq ft
smaller lot
20 years newer
SOLD JUN 30, 2026
$795,000 Last sold price
3 beds2.5 baths2,155 sq ft
23 Starboard Dr #50, Buzzards Bay, MA 02532
$287/sq ft
84 years newer
basement
SOLD AUG 14, 2026
$790,000 Last sold price
3 beds2.5 baths1,462 sq ft
5 Bell Rd Ext, Bourne, MA 02532
$116/sq ft
50 years newer

Rental earnings

Est. $3,501 per month, based on comparable rentals

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

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About this home

Payment calculator

Mortgage resources

See this home in person

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 56 Rip Van Winkle Way

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 56 Rip Van Winkle Way

Early Access listings

Nearby similar homes

New listings for sale in 02532

More real estate resources