Date
Details
Price
Change
Source
5/22/2026
Listed
$679,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/7
$679,900 Coming Soon
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/7
Property Description
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.
Full Property Details
Full Property Details for 44 Boston Dr
General
- Price: $679,900
- HOA FEE: $76/month
- HOA FEE FREQ.: Annually
- Taxes: $2,366 (2025)
- Status: Coming Soon
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDWO2038004
- Updated: 5/22/2026
- Added to Site: 4 day(s) ago
- Expected Market Date: 5/29/2026
Interior
- Rooms/Areas: Primary Bedroom, Sitting Room, Kitchen, Bedroom 1, Great Room, Laundry, Primary Bathroom, Full Bath, Half Bath
- Interior Features: Ceiling Fan(s), Central Vacuum, Carpet, Window Treatments
- Fireplace: Yes
- Number of Fireplaces: 1
- Fireplace(s): Electric
- Appliances: Dryer, Washer, Dishwasher, Exhaust Fan, Disposal, Microwave, Refrigerator, Icemaker, Stove, Water Heater
- Flooring: Luxury Vinyl Tile, Partially Carpeted, Ceramic Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
- Main Floor Baths: 2
- Main - Full Baths: 1
- Main - 1/2 Baths: 1
- Lower Floor Baths: 1
- Lower - Full Baths: 1
Bedrooms
- Total Bedrooms: 2
- Bedrooms Lower: 1
- Bedrooms Main & Up: 1
Other Rooms
- Laundry: Lower Floor
Additional Information
- Shared Amenities: Baseball Field, Basketball Courts, Beach, Beach Club, Boat Dock/Slip, Club House, Common Grounds, Dog Park, Gated Community, Golf Club, Golf Course, Golf Course Membership Available, Jog/Walk Path, Marina/Marina Club, Picnic Area, Pier/Dock, Pool - Indoor, Pool - Outdoor, Pool Mem Avail, Racquet Ball, Recreational Center, Soccer Field, Swimming Pool, Tennis Courts, Tot Lots/Playground
- Shared Pool: Yes
- Pool: Yes
Exterior
- Exterior Features: Gutter System
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 6
- Parking Type: Attached Garage, Driveway
- Garage Description: Garage Door Opener
Location
- Area: Worcester Ocean Pines
- County: WORCESTER
- Subdivision: OCEAN PINES - NANTUCKET
- Driving Directions: Head northeast on Cathell Rd, Turn left onto Ocean Pines/Ocean Pkwy, Turn right onto Boston Dr, Destination will be on the right
- Location Details: Creek/Stream
School Information
- School District: Worcester County Public Schools
- Elementary School: Showell
- Middle School: Stephen Decatur
- High School: Stephen Decatur
Community
- Association: Yes
- Assoc. Name: OCEAN PINES ASSOCIATION
- Assoc. Fees Include: Common Area Maintenance, Reserve Funds, Road Maintenance, Snow Removal
Heating & Cooling
- Cooling Type: Heat Pump(s)
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric, Tankless
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electric Available, Cable TV Available, Sewer Available, Water Available
Structural Information
- Architectural Style: Raised Ranch/Rambler
- Structure Type: Detached
- Construction: Vinyl Siding
- Foundation: Slab
- Roof: Architectural Shingle, Metal
- Walls/Ceilings: Cathedral Ceilings, Dry Wall
- Windows: Screens
- Doors: Storm
- Stories Description: Lower 1, Main
- Square Feet: 1,536
- Sq. Ft. Source: Assessor
- Living Area: 1,536 Sq. Ft.
- Finished Above Grnd: 1,536 Sq. Ft.
- Year Built: 1983
- Year Built Source: Assessor
- Property Condition: Very Good
Unit Information
Unit 1
- Bathrooms-Lower: 1
- Bedrooms-Lower: 1
Lot Features
- Property View: Creek/Stream
- Lot Size (Acres): 0.18
- Lot Size (Sq. Ft.): 7,675
- Lot Size Source: Assessor
- Zoning: R-3
Water Features
- Water View: Yes
Financial Considerations
- Price Per Sq. Ft.: $442.64
- Association Fee: $915
- Assoc Fee Freq.: Annually
- Other Fee: $200
- Other Fee Freq.: One Time
- Assessment Year: 2026
- County Tax: $2,080
- County Tax Freq: Annually
- Tax w/Assessment: $272,733
- Tax Amount: $2,366
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 1536
Disclosures and Reports
- Ownership: Fee Simple
- Exclusions: Staging items
- Inclusions: Picnic table, hot tub, surround sound
- Section: 11
- Lot Number: 50
Listed by Hileman Real Estate-Berlin, Bethany A. Drew
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 44 Boston Dr —
Bethany A. Drew
Hileman Real Estate-Berlin
Listing Office Email: debbie@hilemanrealestate.com
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 44 Boston Dr
School District:Worcester County Public Schools
| Name | Grades | Distance |
|---|---|---|
Showell Elementary School 11318 Showell School Road, Berlin, MD 21811 | PK-3 | 2.2 mi |
Berlin Intermediate School 309 Franklin Avenue, Berlin, MD 21811 | 4-6 | 4.7 mi |
Stephen Decatur Middle School, Berlin, MD 9815 Seahawk Road, Berlin, MD 21811 | 7-8 | 3.6 mi |
Stephen Decatur High School 9913 Seahawk Road, Berlin, MD 21811 | 9-12 | 3.4 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 44 Boston Dr
Tax History
Tax History for 44 Boston Dr
Year
Property Taxes
Change
Tax Assessment
Change
2023
$2,152
—
$255,267
11%
2023
$2,152
6%
$229,000
4%
2021
$2,023
—
$220,200
4%
2021
$2,023
—
$211,400
—
2020
$2,023
-23%
$211,400
-23%
2019
$2,617
2%
$276,300
2%
2018
$2,574
2%
$271,800
2%
2017
$2,531
2%
$267,300
2%
2016
$2,489
7%
$262,800
—
2015
$2,318
—
$262,800
—
2014
$2,318
—
$262,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 44 Boston Dr
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,646Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 2Total Baths
- 2,068Sq. Ft.
- Townhouse
- Active
- Updated 4 days ago
- 3Beds
- 4Total Baths
- 1,695Sq. Ft.
Listed by Nancy Reither (410) 603-5050
- Condo
- Active
- Updated 4 days ago
- 2Beds
- 2Total Baths
- 960Sq. Ft.
- Condo
- Active
- Updated 4 days ago
- 3Beds
- 3Total Baths
- 1,581Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Condo
- Active
- Updated 19 hours ago
- 2Beds
- 2Total Baths
- 1,040Sq. Ft.
Listed by Nancy Reither (410) 603-5050
- Townhouse
- Active
- Updated 3 days ago
- 3Beds
- 4Total Baths
- 2,376Sq. Ft.
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
- Single Family
- Closed
- 4Beds
- 3Total Baths
- 2,528Sq. Ft.
Listed by Daniel Clayland
Sold by Long & Foster Real Estate, Inc., CANDY WILLIAMS
Sold by Long & Foster Real Estate, Inc., CANDY WILLIAMS
44 Boston Drive, Ocean Pines, MD 21811 (MLS# MDWO2038004) is a Single Family property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 44 Boston Drive is currently listed for $679,900 and was received on May 22, 2026. Want to learn more about 44 Boston Drive? Do you have questions about finding other Single Family real estate for sale in Ocean Pines? You can browse all Ocean Pines real estate or contact a Coldwell Banker agent to request more information.