645 S Orleans Road, Orleans, MA, 02653 | $2,700,000

For the first time in generations, this extraordinary Pleasant Bay compound--featuring the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, legacy waterfront estate. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation potential. Both homes enjoy sweeping 270-degree views across the water to Eastward Ho, the Chatham Yacht Club, and the Atlantic beyond. ''Topside'' offers 5 bedrooms and 4. 5 baths with timeless coastal character and spaces designed for gathering, while the ''Boathouse'' sits just above the shoreline, featuring 2 bedrooms, 1 bathroom, and its own deck for quiet moments by the sea. A secluded garden patio and broad waterfront lawn offer a blend of intimacy and scale. With a strong rental history and immense potential for expansion or personalization, this is a lifestyle property that invites multigenerational living, savvy investment, or a private retreat. A once-in-a-lifetime opportunity to own one of Cape Cod's most storied waterfront settings.

Features

  • Rooms: 12
  • Bedrooms: 7
  • Baths: 6 full / 1 half
  • Style: Antique
  • Year Built: 1945
  • Heating: Hot Water
  • Cooling: None
  • Basement: Bulkhead Access, Partial, Crawl Space
  • Approx Sq. Feet: 3,548
  • Acreage: 0.25
  • Est. Taxes: $10,740
  • Water Front: Yes
  • School District: Nauset
  • Appliances: Electric Water Heater
  • MLS#: 22502226
  • Website: https://www.raveis.com
    /eprop/22502226/645sorleansroad_orleans_ma?source=qrflyer
Courtesy of
All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than William Raveis Real Estate include the name of the listing company. Neither the listing company nor William Raveis Real Estate shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. 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.

Room Information

Type DescriptionDimensions
Kitchen Fireplace(s): Wood Burning13.4 x 14.7
Living Room Fireplace(s): Wood Burning13.4 x 14.7

William Raveis Family of Services

Our family of companies partner in delivering quality services in a one-stop-shopping environment. Together, we integrate the most comprehensive real estate, mortgage and insurance services available to fulfill your specific real estate needs.

Sabrina DiPaterioLicensed Real Estate Salesperson

914.500.7035

Sabrina.DiPaterio@Raveis.com

Our family of companies offer our clients a new level of full-service real estate. We shall:

  • Market your home to realize a quick sale at the best possible price
  • Place up to 20+ photos of your home on our website, raveis.com
  • Provide frequent communication and tracking reports showing the Internet views your home received on raveis.com
  • Showcase your home on raveis.com with a larger and more prominent format
  • Give you the full resources and strength of William Raveis Real Estate, Mortgage & Insurance and our cutting-edge technology

To learn more about our credentials, visit raveis.com today.

Vincent DiMellaVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 24240

914.494.1459

Vincent.DiMella@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
  • Is in constant contact with a full processing, underwriting, and closing staff to ensure an efficient transaction

Jennifer HartRegional Sales Manager, William Raveis Insurance

978.457.6220

Jennifer.Hart@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
  • Partners with major insurance companies including Chubb, Kemper Unitrin, The Hartford, Progressive,
    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

645 S Orleans Road, Orleans, MA, 02653

$2,700,000

Sabrina DiPaterio

Licensed Real Estate Salesperson

William Raveis Real Estate

Phone: 914.500.7035

Sabrina.DiPaterio@Raveis.com

Vincent DiMella

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 914.494.1459

Vincent.DiMella@raveis.com

NMLS Mortgage Loan Originator ID 24240

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,160,000 $2,160,000 $2,160,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.375% 6.125% 5.875%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.117% 6.235% 6.058%
Monthly Tax Payment $895 $895 $895
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $12,095 $13,124 $18,082
Total Monthly Payment $13,115 $14,144 $19,102

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.