**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!**
For sale
$799,000
38 Pintail Dr, Ocean Pines, MD 21811
2beds
1,904sqft
Single Family Residence
Built in 1982
10,500 Square Feet Lot
$759,600 Zestimate®
$420/sqft
$132/mo HOA
What's special
Designer cabinetryRecently remodeled kitchenNewer walk-in tiled showerOversized deckFreshly painted throughoutUnbelievable three-season roomSpacious primary suite
- 1 day
- 482
- 35
Zillow last checked:
Listing updated:
Listed by:
Debbie Bennington 410-603-8065,
Berkshire Hathaway HomeServices PenFed Realty - OP 4102083500
Source: Bright MLS,MLS#: MDWO2040964
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 2
- Full bathrooms: 2
Basement
- Area: 0
Heating
- Central
Cooling
- Other, Central Air, Ceiling Fan(s), Electric
Appliances
- Included: Microwave, Built-In Range, Dishwasher, Disposal, Dryer, Self Cleaning Oven, Oven/Range - Electric, Refrigerator, Washer, Water Heater
- Laundry: Main Level
Features
- Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-in Features, Ceiling Fan(s), Combination Dining/Living, Open Floorplan, Pantry, Primary Bath(s), Upgraded Countertops
- Flooring: Carpet, Ceramic Tile, Laminate
- Doors: Insulated
- Windows: Double Pane Windows, Window Treatments
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,904
- Total interior livable area: 1,904 sqft
- Finished area above ground: 1,904
- Finished area below ground: 0
Property
Parking
- Total spaces: 6
- Parking features: Garage Faces Front, Garage Door Opener, Inside Entrance, Oversized, Asphalt, Attached, Driveway
- Attached garage spaces: 2
- Uncovered spaces: 4
Accessibility
- Accessibility features: Stair Lift, Grip-Accessible Features
Features
- Levels: Two
- Stories: 2
- Patio & porch: Deck, Enclosed, Porch, Patio, Screened
- Exterior features: Outdoor Shower
- Pool features: Community
- Has view: Yes
- View description: Creek/Stream, Bay
- Has water view: Yes
- Water view: Creek/Stream,Bay
- Waterfront features: Bay
- Frontage length: Water Frontage Ft: 100
Lot
- Size: 10,500 Square Feet
- Features: Bulkheaded
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 2403089665
- Zoning: R-3
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Coastal
- Property subtype: Single Family Residence
Materials
- Stick Built
- Foundation: Crawl Space
- Roof: Asphalt
Condition
- Excellent
- New construction: No
- Year built: 1982
- Major remodel year: 2024
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected
Community & HOA
Community
- Security: Smoke Detector(s)
- Subdivision: Ocean Pines - Pintail Isle
HOA
- Has HOA: Yes
- Amenities included: Baseball Field, Basketball Court, Beach Club, Boat Dock/Slip, Community Center, Dog Park, Gift Shop, Golf Club, Golf Course Membership Available, Jogging Path, Lake, Library, Marina/Marina Club, Picnic Area, Indoor Pool, Pool, Pool Mem Avail, Racquetball, Tennis Court(s), Tot Lots/Playground
- Services included: Common Area Maintenance, Management, Pier/Dock Maintenance, Reserve Funds, Road Maintenance
- HOA fee: $1,580 annually
Location
- Region: Ocean Pines
Financial & listing details
- Price per square foot: $420/sqft
- Tax assessed value: $577,700
- Annual tax amount: $4,766
- Date on market: 8/31/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Conventional,Cash,VA Loan
- Ownership: Fee Simple
Estimated market value
$759,600
$722,000 - $798,000
$2,694/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/31/2026 | Listed for sale | $799,000+32.4%$420/sqft |
Source:  Bright MLS #MDWO2040964 Report a problem | ||
| 7/29/2026 | Sold | $603,250+265.6%$317/sqft |
Source: Public Record Report a problem | ||
| 10/2/1997 | Sold | $165,000$87/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $514,100 +14.1% |
| 2024 | $4,311 +2.7% | $450,500 +2.7% |
| 2023 | $4,200 +2.7% | $438,833 -2.6% |
| 2022 | $4,088 +2.8% | $450,500 +8.4% |
| 2021 | $3,976 +3.8% | $415,500 +3.8% |
| 2020 | $3,830 +4% | $400,167 -3.7% |
| 2019 | $3,683 +5.2% | $415,500 +12.4% |
| 2018 | $3,499 +3.6% | $369,500 +3.6% |
| 2017 | $3,376 +35.8% | $356,533 +3.8% |
| 2016 | $2,485 | $343,567 +3.9% |
| 2015 | $2,485 | $330,600 |
| 2014 | $2,485 | $330,600 |
| 2013 | -- | $330,600 -19.7% |
| 2012 | -- | $411,600 |
| 2011 | -- | $411,600 |
| 2010 | -- | $411,600 -16.8% |
| 2009 | -- | $494,600 +6% |
| 2008 | -- | $466,562 +6.4% |
| 2007 | -- | $438,526 +6.8% |
| 2006 | -- | $410,490 +15.1% |
| 2005 | -- | $356,782 +17.7% |
| 2004 | -- | $303,076 +21.5% |
| 2003 | -- | $249,370 +12.4% |
| 2002 | -- | $221,822 +14.2% |
| 2001 | -- | $194,276 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 21811
Nearby schools
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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