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.
Sold for $659,000
Zillow last checked:
Listing updated:
Bought with:
Jenny Sheppard, 502797
Sheppard Realty Inc
Source: Bright MLS,MLS#: MDWO2038004
Price history
| Date | Event | Price |
|---|---|---|
| 7/31/2026 | Sold | $659,000-3.1%$429/sqft |
Source:  Bright MLS #MDWO2038004 Report a problem | ||
| 6/16/2026 | Contingent | $679,900$443/sqft |
Source: Bright MLS #MDWO2038004 Report a problem | ||
| 5/29/2026 | Listed for sale | $679,900+172%$443/sqft |
Source: Bright MLS #MDWO2038004 Report a problem | ||
| 1/16/2019 | Sold | $250,000-7.4%$163/sqft |
Source: Public Record Report a problem | ||
| 9/8/2018 | Listing removed | $269,900$176/sqft |
Source: Shamrock Realty Group, Inc. #1002079008 Report a problem | ||
| 9/2/2018 | Pending sale | $269,900$176/sqft |
Source: Shamrock Realty Group, Inc. #1002079008 Report a problem | ||
| 8/28/2018 | Price change | $269,900-3.6%$176/sqft |
Source: Shamrock Realty Group, Inc. #1002079008 Report a problem | ||
| 7/21/2018 | Listed for sale | $279,900-20%$182/sqft |
Source: Shamrock Realty Group, Inc. #1002079008 Report a problem | ||
| 5/18/2008 | Listing removed | $349,900$228/sqft |
Source: Visual Tour #441459 Report a problem | ||
| 3/7/2008 | Listed for sale | $349,900$228/sqft |
Source: Visual Tour #441459 Report a problem | ||
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Estimated market value
$659,100
