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44 Boston Dr, 
Ocean Pines, MD 21811

$679,900


2

Beds


3

Baths


1,536

Sq Ft


Single Family

Active

Listed by

Bethany A. Drew

Hileman Real Estate-Berlin, (410) 208-9200, debbie@hilemanrealestate.com

Last updated:

June 4, 2026, 10:23 AM

MLS#

MDWO2038004

Source:

BRIGHTMLS

About This Home

44 Boston Dr

Nestled along the water in Ocean Pines, 44 Boston Drive is a beautifully renovated waterfront retreat offering the perfect blend of luxury, comfort, and outdoor living. Extensively remodeled in 2019, this stunning home was thoughtfully redesigned with raised ceilings, an open-concept floor plan, new siding and windows, and upscale finishes throughout. Step inside and immediately appreciate the light-filled great room featuring luxury vinyl plank flooring, a striking stone electric fireplace with space for a large-screen TV, and a wall of sliders that frame peaceful water views. The gourmet kitchen is truly the centerpiece of the home, boasting upgraded appliances, a large center island with granite countertops and dramatic waterfall edges, plus a convenient pantry for extra storage. This home offers 2 spacious bedrooms and 2.5 beautifully updated baths, each showcasing custom tile work, vessel sink, designer paint selections, and elegant finishes. The primary suite provides a relaxing retreat with a gorgeous private bath and generous closet space. Outdoor living is where this property truly shines. Step through the expansive sliders onto the huge wraparound deck with sleek glass panels designed to maximize the breathtaking water views and surrounding nature. A newer pier and dock make waterfront living effortless, whether you enjoy boating, kayaking, or simply soaking in the scenery. One of the most unique features of this property is the oversized backyard — a rare find in this section of Ocean Pines — offering endless possibilities for entertaining, family gatherings, cookouts, and lively cornhole tournaments. Beneath the deck, you’ll find an additional covered outdoor living area perfect for creating your own private patio retreat, complete with your own hot tub to enjoy year-round. Additional highlights include mature landscaping and a spacious 2-car garage ideal for storage of all your beach and boating essentials. This exceptional waterfront home has been meticulously updated and designed for easy coastal living. A must-see property that truly delivers the Ocean Pines lifestyle — you won’t be disappointed.

Home Facts

Single Family

3 Baths

2 Bedrooms

Built in 1983

Price Summary

679,900

$442 per Sq. Ft.

MLS #:

MDWO2038004

Last Updated:

June 4, 2026, 10:23 AM

Added:

7 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

1,536 Sq. Ft.


Structure

Structure

Architectural Style:

Raised Ranch/Rambler

Building Area:

1,536 Sq. Ft.

Year Built:

1983


Lot

Lot Size (Sq. Ft):

7,840


Finances & Disclosures

Finances

Price:

$679,900

Price per Sq. Ft:

$442 per Sq. Ft.

Source:BRIGHTMLS
The information being provided by Bright Mls is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2026 Bright Mls All rights reserved.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.