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.
Under contract
$679,900
44 Boston Dr, Ocean Pines, MD 21811
2beds
1,536sqft
Single Family Residence
Built in 1983
7,675 Square Feet Lot
$661,400 Zestimate®
$443/sqft
$76/mo HOA
What's special
Newer pier and dockElegant finishesMature landscapingCustom tile workDesigner paint selectionsRaised ceilingsUpscale finishes throughout
- 43 days |
- 513 |
- 12 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Bethany Drew 410-208-9200,
Hileman Real Estate-Berlin (410) 208-9200
Source: Bright MLS,MLS#: MDWO2038004
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
- Main level bathrooms: 2
- Main level bedrooms: 1
Rooms
- Room types: Primary Bedroom, Sitting Room, Kitchen, Bedroom 1, Great Room, Laundry, Primary Bathroom, Full Bath, Half Bath
Primary bedroom
- Level: Main
Bedroom 1
- Level: Lower
Primary bathroom
- Level: Main
Other
- Level: Lower
Great room
- Level: Main
Half bath
- Level: Main
Kitchen
- Level: Main
Laundry
- Level: Lower
Sitting room
- Level: Lower
Heating
- Heat Pump, Electric
Cooling
- Heat Pump, Electric
Appliances
- Included: Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Microwave, Refrigerator, Ice Maker, Water Heater, Oven/Range - Gas, Tankless Water Heater, Gas Water Heater
- Laundry: Lower Level, Laundry Room
Features
- Ceiling Fan(s), Central Vacuum, Cathedral Ceiling(s), Dry Wall
- Flooring: Luxury Vinyl, Carpet, Ceramic Tile
- Doors: Storm Door(s)
- Windows: Screens, Window Treatments
- Has basement: No
- Number of fireplaces: 1
- Fireplace features: Electric
Interior area
- Total structure area: 1,536
- Total interior livable area: 1,536 sqft
- Finished area above ground: 1,536
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Garage Door Opener, Attached, Driveway
- Attached garage spaces: 2
- Uncovered spaces: 4
Accessibility
- Accessibility features: 2+ Access Exits
Features
- Levels: Two
- Stories: 2
- Exterior features: Rain Gutters
- Pool features: Community
- Has view: Yes
- View description: Creek/Stream
- Has water view: Yes
- Water view: Creek/Stream
- Waterfront features: Creek/Stream
- Body of water: Manklin Creek
- Frontage length: Water Frontage Ft: 40
Lot
- Size: 7,675 Square Feet
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2403091600
- Zoning: R-3
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Raised Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Slab
- Roof: Architectural Shingle,Metal
Condition
- Very Good
- New construction: No
- Year built: 1983
- Major remodel year: 2019
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Available, Cable Available, Sewer Available, Water Available
Community & HOA
Community
- Subdivision: Ocean Pines - Nantucket
HOA
- Has HOA: Yes
- Amenities included: Baseball Field, Basketball Court, Beach Access, Beach Club, Boat Dock/Slip, Clubhouse, Common Grounds, Dog Park, Gated, Golf Club, Golf Course, Golf Course Membership Available, Jogging Path, Marina/Marina Club, Picnic Area, Pier/Dock, Indoor Pool, Pool, Pool Mem Avail, Racquetball, Recreation Facilities, Soccer Field, Tennis Court(s), Tot Lots/Playground
- Services included: Common Area Maintenance, Reserve Funds, Road Maintenance, Snow Removal
- HOA fee: $915 annually
- HOA name: OCEAN PINES ASSOCIATION
Location
- Region: Ocean Pines
Financial & listing details
- Price per square foot: $443/sqft
- Tax assessed value: $272,733
- Annual tax amount: $2,366
- Date on market: 5/29/2026
- Listing agreement: Exclusive Right To Sell
- Inclusions: Picnic Table, Hot Tub, Surround Sound
- Exclusions: Staging Items
- Ownership: Fee Simple
Estimated market value
$661,400
$628,000 - $694,000
$2,365/mo
Price history
| Date | Event | Price |
|---|---|---|
| 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 | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $2,225 -2.2% | $255,267 +7.3% |
| 2024 | $2,276 +3.8% | $237,800 +3.8% |
| 2023 | $2,192 +4% | $229,000 -3.7% |
| 2022 | $2,107 +4.2% | $237,800 +12.5% |
| 2021 | $2,023 | $211,400 |
| 2020 | $2,023 | $211,400 |
| 2019 | $2,023 -22.7% | $211,400 -23.5% |
| 2018 | $2,617 +1.7% | $276,300 +1.7% |
| 2017 | $2,574 +6.1% | $271,800 +1.7% |
| 2016 | $2,425 | $267,300 +1.7% |
| 2015 | $2,425 | $262,800 |
| 2014 | $2,425 | $262,800 |
| 2013 | -- | $262,800 -12.8% |
| 2012 | -- | $301,300 |
| 2011 | -- | $301,300 |
| 2010 | -- | $301,300 -24% |
| 2009 | -- | $396,190 +13.8% |
| 2008 | -- | $348,060 +16% |
| 2007 | -- | $299,930 +19.1% |
| 2006 | -- | $251,800 +13.6% |
| 2005 | -- | $221,612 +15.8% |
| 2004 | -- | $191,426 +18.7% |
| 2003 | -- | $161,240 +7.9% |
| 2002 | -- | $149,426 +8.6% |
| 2001 | -- | $137,613 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 21811
Nearby schools
GreatSchools rating
- 8/10Showell Elementary SchoolGrades: PK-4Distance: 2.2 mi
- 10/10Stephen Decatur Middle SchoolGrades: 7-8Distance: 3.7 mi
- 7/10Stephen Decatur High SchoolGrades: 9-12Distance: 3.4 mi
Schools provided by the listing agent
- Elementary: Showell
- Middle: Stephen Decatur
- High: Stephen Decatur
- District: Worcester County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
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- Maryland
- Worcester County
- Berlin
- 21811
- 44 Boston Dr
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