Date
Details
Price
Change
Source
8/31/2026
Listed
$799,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/98
$799,000 Just Listed
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1/98
Property Description
**Live the Coastal Dream in Pintail Isle!** This unique coastal-style home in the desirable Pintail Isle section of Ocean Pines offers the waterfront lifestyle you've been waiting for, with gorgeous canal and bay views and boating access just seconds from your private dock. Imagine starting your mornings with peaceful water views, spending afternoons on the bay, and ending the day entertaining friends and family as the sun sets over the water. Inside, the recently remodeled kitchen is a true showstopper, featuring beautiful granite countertops, upgraded stainless appliances, and designer cabinetry. The unbelievable three-season room is the perfect place to relax and take in the ever-changing views of the bay, with expansive windows bringing the outdoors in. Step directly onto the oversized deck and enjoy the ultimate setting for outdoor dining, entertaining, or simply soaking up the coastal breeze. The spacious primary suite features a newer walk-in tiled shower, while the second bath offers a tub/shower combination with ceramic tile surround and tiled flooring. Freshly painted throughout, the home also features new carpeting in the bedrooms and new laminate flooring in the kitchen, great room, and first-level family room that could easily be converted into a third bedroom creating a fresh, inviting, move-in-ready atmosphere. The oversized garage is truly a dream, offering abundant storage, a dedicated workroom, and plenty of room for parking. An oversized driveway provides ample space for guests, boats, and all your coastal toys. Energy-efficient central oil-fired hot-water heat keeps the home warm and comfortable throughout the year. Roof is only 4 years old! Whether you're looking for a year-round residence, coastal getaway, or waterfront retreat, this Pintail Isle gem delivers the best of **boating, beautiful views, outdoor living, and relaxed Eastern Shore style.** Bring your boat, unpack your bags, and start enjoying the coastal lifestyle-**this home is truly move-in ready!**
Full Property Details
Full Property Details for 38 Pintail Dr
General
- Price: $799,000
- HOA FEE: $132/month
- HOA FEE FREQ.: Annually
- Taxes: $4,766 (2025)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDWO2040964
- Updated: 8/31/2026
- Added to Site: 2 day(s) ago
Interior
- Interior Features: Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-Ins, Carpet, Ceiling Fan(s), Combination Dining/Living, Floor Plan - Open, Pantry, Primary Bath(s), Upgraded Countertops, Window Treatments
- Appliances: Built-In Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Oven - Self Cleaning, Oven/Range - Electric, Refrigerator, Washer, Water Heater
- Flooring: Carpet, Ceramic Tile, Laminate Plank
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
- Upper Floor Baths: 2
- Upper - Full Baths: 2
Bedrooms
- Total Bedrooms: 2
- Bedrooms Upper: 2
Other Rooms
- Laundry: Main Floor
Additional Information
- Shared Amenities: Baseball Field, Basketball Courts, Beach Club, Boat Dock/Slip, Community Center, Dog Park, Gift Shop, Golf Club, Golf Course Membership Available, Jog/Walk Path, Lake, Library, Marina/Marina Club, Pickleball Courts, Picnic Area, Pool - Indoor, Pool - Outdoor, Pool Mem Avail, Racquet Ball, Tennis Courts, Tot Lots/Playground
- Shared Pool: Yes
- Pool: Yes
- Security/Safety: Smoke Detector
Exterior
- Exterior Features: Outside Shower
- Porch/Patio/Deck: Deck(s), Enclosed, Porch(es), Patio(s), Screened
Parking
- Garage: Yes
- Garage Spaces: 2
- Total Spaces: 6
- Parking Features: Asphalt Driveway
- Parking Type: Attached Garage, Driveway
- Garage Description: Garage - Front Entry, Garage Door Opener, Inside Access, Oversized
Location
- Area: Worcester Ocean Pines
- County: WORCESTER
- Subdivision: OCEAN PINES - PINTAIL ISLE
- Driving Directions: Route 589 to the South gate of Ocean Pines, Left on Ocean Parkway, , Right on Pintail Drive home is on the right
School Information
- School District: Worcester County Public Schools
- Elementary School: Showell
- Middle School: Stephen Decatur
- High School: Stephen Decatur
Community
- Association: Yes
- Assoc. Fees Include: Common Area Maintenance, Management, Pier/Dock Maintenance, Reserve Funds, Road Maintenance
- Pets Allowed: Yes
- Pets: Cats OK, Dogs OK
Heating & Cooling
- Central air: Yes
- Cooling Type: Other, Central A/C, Ceiling Fan(s)
- Cooling Fuel: Electric
- Heating Type: Central
- Heating Fuel: Central
- Water Heater: Oil
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV
Structural Information
- Architectural Style: Coastal
- Structure Type: Detached
- Construction: Stick Built
- Foundation: Crawl Space
- Roof: Asphalt
- Windows: Double Pane
- Doors: Insulated
- Stories Description: Upper 1
- Square Feet: 1,904
- Sq. Ft. Source: Assessor
- Living Area: 1,904 Sq. Ft.
- Finished Above Grnd: 1,904 Sq. Ft.
- Year Built: 1982
- Year Built Source: Assessor
- Property Condition: Excellent
Lot Features
- Property View: Creek/Stream, Bay
- Lot Size (Acres): 0.24
- Lot Size (Sq. Ft.): 10,500
- Lot Size Source: Assessor
- Zoning: R-3
- Lot Description: Bulkheaded
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Front Type: Bay
Financial Considerations
- Price Per Sq. Ft.: $419.64
- Association Fee: $1,580
- Assoc Fee Freq.: Annually
- Other Fee: $200
- Other Fee Freq.: One Time
- Assessment Year: 2026
- County Tax: $4,190
- County Tax Freq: Annually
- Tax w/Assessment: $577,700
- Tax Amount: $4,766
- Tax Year: 2025
- Tax Total Finished Sq. Ft.: 1904
Disclosures and Reports
- Ownership: Fee Simple
- Section: 14A
- Lot Number: 70
Listed by Berkshire Hathaway HomeServices PenFed Realty - OP, Deborah K. Bennington
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 38 Pintail Dr —
Deborah K. Bennington
Berkshire Hathaway HomeServices PenFed Realty - OP
Listing Office Email: oceanpines@penfedrealty.com
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 38 Pintail Dr
School District:Worcester County Public Schools
| Name | Grades | Distance |
|---|---|---|
Showell Elementary School 11318 Showell School Road, Berlin, MD 21811 | PK-3 | 3.4 mi |
Berlin Intermediate School 309 Franklin Avenue, Berlin, MD 21811 | 4-6 | 5.6 mi |
Stephen Decatur Middle School, Berlin, MD 9815 Seahawk Road, Berlin, MD 21811 | 7-8 | 4.4 mi |
Stephen Decatur High School 9913 Seahawk Road, Berlin, MD 21811 | 9-12 | 4.3 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 38 Pintail Dr
Tax History
Tax History for 38 Pintail Dr
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,138
—
$577,700
12%
2025
$4,138
3%
$514,100
17%
2023
$4,011
6%
$438,833
3%
2021
$3,783
—
$427,167
3%
2021
$3,783
3%
$415,500
4%
2021
$3,669
69%
$400,167
4%
2020
$2,168
12%
$384,833
4%
2019
$1,937
1%
$369,500
4%
2018
$1,922
21%
$356,533
4%
2017
$1,593
-2%
$343,567
4%
2016
$1,621
-27%
$330,600
—
2015
$2,226
13%
$330,600
—
2014
$1,975
—
$330,600
—
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 38 Pintail Dr
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Sold by Kim Bounds
Sold by Kim Bounds
38 Pintail Drive, Ocean Pines, MD 21811 (MLS# MDWO2040964) is a Single Family property with 2 bedrooms and 2 full bathrooms. 38 Pintail Drive is currently listed for $799,000 and was received on August 31, 2026. Want to learn more about 38 Pintail 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.