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Photo 1 of 48: Legacy Waterfront Estate
Legacy Waterfront Estate
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63 Main Street, Osterville, MA 02655

Barnstable County

Key Facts

7Beds
8Baths
9,011Sq Ft
1920Year Built
1.38Lot (acres)
2Garage

Description

Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Set aside any reservations of the year built...the entire foundation and structure were comprehensively reinforced and renovated by E.J. Jaxtimer. Any changes or modifications a buyer might want would be aesthetic alone. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage with vaulted ceilings and additional charm. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.

Property Information

Property Type

Residential

Sub-Type

Single Family Residence

Style

Other

Year Built

1920

Living Area

9,011 sq ft

Lot Size

1.38 acres

Garage Spaces

2

Zoning

RF

Days on Market

2

MLS® Listing#

22603124

Property Features

Interior:
Wet Bar, Recessed Lighting, Pantry, In-Law Floorplan
Exterior:
Garden
Appliances:
Dryer, Trash Compactor, Washer, Range Hood, Washer/Dryer Stacked, Refrigerator, Gas Range, Other, Microwave, Dishwasher, Gas Water Heater
Cooling:
Central Air
Heating:
Hot Water
Flooring:
Hardwood, Carpet, Tile
Basement:
Finished, Interior Entry, Full
Patio:
Deck, Porch, Patio
Lot Features:
On Golf Course, Near Golf Course, Waterfront
Construction:
Stucco
Foundation:
Other
Roof:
Asphalt
Sewer:
Septic Tank
Water Source:
Private, Well

HOA & Tax

HOA:
None
Annual Tax:
$46,774 (2026)
Assessed Value:
$5,972,400
Parcel #:
OSTE M:185 L:021

Directions

Going over Centerville/Osterville bridge from Centerville, second property on the left.

Affordability Calculator

$1,725,000

Estimated monthly payment

$45,906/mo

Principal $6,900,000 · Est. interest $9,626,114 over 30 yrs

Neighborhood Market Statistics

How this home compares to active listings in Osterville, MA

$1,000,000
Median Listing Price
59
Median Days on Market
3,133
Median Sq Ft
$725
Median Price / Sq Ft
36
Active Listings
  • This home’s price is 763% above the area median.
  • Its price per sq ft is 32% above the area median.

Market statistics compiled from active EXIT Realty® and MLS listings in Osterville, MA.

Location

  • 63 Main Street, Osterville, MA 02655

Nearby Schools

  • Centerville Elementary

    Elementary · 0.9 mi away

  • Bright Promises Pre School

    School · 1.5 mi away

  • Cape Cod Academy

    School · 1.6 mi away

  • Bayberry Christian School

    School · 1.9 mi away

  • Barnstable United Elementary School

    Elementary · 2.3 mi away

  • Vanguard Tabletop Gaming

    School · 2.3 mi away

  • West Villages Elementary School

    Elementary · 2.4 mi away

  • Barnstable High School

    Secondary · 2.5 mi away

  • Hyannis West Elementary School

    Elementary · 2.5 mi away

  • Barnstable Intermediate School

    Secondary · 2.6 mi away

  • Marstons Mills Elementary School

    Elementary · 2.9 mi away

  • Fair Acres Country Day School

    Elementary · 3.0 mi away

  • Sturgis West

    School · 3.2 mi away

  • Sturgis Charter Public School

    School · 3.2 mi away

  • Barnstable Community Innovation School

    Elementary · 3.8 mi away

  • Crystal Garden Children's Learning Center

    School · 3.8 mi away

  • St. John Paul II School

    Secondary · 4.0 mi away

  • Sturgis Charter Public School

    Secondary · 4.1 mi away

  • Waldorf School of Cape Cod

    School · 4.3 mi away

  • West Barnstable Elementary

    Elementary · 4.8 mi away

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Cape Cod and Islands MLS logo

Listing Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties - 5089455553

Presented by: Christa Zevitas

The data relating to real estate for sale on this site comes from the Broker Reciprocity of the Cape Cod & Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than the brokerage firm owning this website are marked with the IDX Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor the brokerage firm owning this website shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. All properties are subject to prior sale, changes, or withdrawal. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright ©2026 Cape Cod & Islands Multiple Listing Service, Inc. All Rights Reserved.

Last Updated: 2026-06-26

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of one or more Multiple Listing Services (MLS). Listing information is deemed reliable but is not guaranteed accurate. Copyright © EXIT Realty® and respective MLS providers.

Data provided by CapeCod. MLS® Listing#22603124. © 2026EXIT Realty®. All rights reserved.