1499 Westcliff Drive • Pasadena, MD 21122

$975,000 Beds: 5 • Baths: 5 full • Sq. Feet: 4763 • MLS ID: MDAA2150744 • Subdivision: WINDERMERE ESTATES • School Dist: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Some homes are simply built well. Others become the backdrop for the best years of your life. Welcome to 1499 Westcliff Drive, a spectacular custom residence privately tucked away on 1.59 wooded acres in the coveted community of Windermere Estates, where over 5,000 finished square feet of thoughtfully designed living space create a home that is as unforgettable as the moments you'll share here. From the instant you step inside, soaring cathedral ceilings, dramatic skylights, and walls of windows flood every room with natural light, creating a breathtaking sense of openness that immediately feels warm, welcoming, and alive. This is the home where holidays become traditions, dinner parties effortlessly turn into late-night conversations, and every gathering feels just a little more special. The beautifully remodeled gourmet kitchen is the heart of it all, opening seamlessly to gracious living spaces designed for entertaining on every scale—from intimate family dinners to celebrations filled with laughter and lifelong friends. Imagine Thanksgiving with everyone gathered around one table, birthdays celebrated on the expansive deck, summer cookouts overlooking your private wooded sanctuary, music playing as guests linger beneath the stars, or quiet mornings with nothing but coffee, birdsong, and the peaceful beauty of nature surrounding you. Outside, the lifestyle is every bit as extraordinary. Beautifully landscaped grounds invite gardening, backyard games, evening fires, and endless adventures, while the fenced yard provides plenty of room for children and four-legged family members to run, explore, and simply be kids. It's the kind of setting that's becoming increasingly rare—private, peaceful, and surrounded by nature, yet only minutes from everything. Designed with flexibility in mind, the spacious main-level bedroom and adjoining full bath—currently serving as a private executive office—offer an exceptional option for one-level living, luxurious guest accommodations, extended family, or a quiet workspace. The fully finished walk-out lower level, complete with its own kitchen, private entrance, and expansive living areas, creates incredible opportunities for multigenerational living, an au pair or in-law suite, long-term guests, a home business, or the ultimate recreation and entertaining retreat. Every detail reflects pride of ownership, including a beautifully remodeled kitchen (2020), new roof (2021), HVAC system (2018), repaved driveway (2015), new well (2009), and an oversized two-car garage that completes this remarkable property. Perfectly positioned just minutes from Downs Park, marinas, waterfront dining, shopping, Annapolis, Baltimore, BWI Airport, Fort Meade, Johns Hopkins, and major commuter routes, and located within the highly regarded Chesapeake school district, this is a rare opportunity to own a home that offers exceptional privacy without sacrificing convenience. Homes like this are seldom available because they offer something that cannot be built overnight or easily replicated—a feeling. A place where children grow up, grandchildren return, friends never want to leave, and every season brings a new memory worth keeping. More than a luxury home, 1499 Westcliff Drive is the place you'll find yourself comparing every other home to. View this listing at: http://gundackergroup.com/mls=MDAA2150744

Property Features

  • Garage: 2
  • Taxes: $7,545
  • Basement: Yes
  • Roof Type: Asphalt,Shingle
  • Exterior: Stick Built
  • Parking Notes: 8 Total Parking Spaces
  • Special View Info: Garden/Lawn,Trees/Woods
  • Lot Size: 1.59 Acres
  • Lot Dimensions: 1.59 Acre(S)
  • Heating: Heat Pump(s),Zoned,Programmable Thermostat
  • Fuel Type: Electric
  • Cooling: Central A/C,Ceiling Fan(s),Programmable Thermostat
  • Year Built: 1993
  • Fireplaces: 2
  • Water: Well
  • Sewer: Private Septic Tank
  • Stories: 3.0
  • HOA Fee: $10.00/Monthly
  • Additional Structures: Above Grade,Below Grade
  • Fencing Description: Rear
  • Lot Description: Backs to Trees, Landscaping
  • Structure Type: Detached
  • Total Garage/Parking Spaces: 8
  • Pet Restrictions: No Pet Restrictions
  • Appliances: Built-In Microwave,Cooktop,Dishwasher,Dryer,Exhaust Fan,Oven - Wall,Oven/Range - Gas,Refrigerator,Stainless Steel Appliances,Washer,Water Conditioner - Owned
  • Rooms: Living Room,Dining Room,Primary Bedroom,Bedroom 2,Bedroom 3,Bedroom 4,Bedroom 5,Kitchen,Family Room,Den,Foyer,Breakfast Room,Exercise Room,Laundry,Other,Recreation Room,Storage Room,Utility Room,Primary Bathroom,Full Bath,Screened Porch
  • Basement: Connecting Stairway,Full,Fully Finished,Heated,Improved,Interior Access,Outside Entrance,Sump Pump,Walkout Stairs,Windows
  • SQFT Total Finished: 4763
  • SQFT Above Finished: 3430
  • SQFT Below Finished: 1333
  • Exterior: Boat Storage,Bump-outs,Exterior Lighting,Play Area
  • Interior: 2nd Kitchen,Attic,Bar,Bathroom - Soaking Tub,Bathroom - Stall Shower,Bathroom - Tub Shower,Bathroom - Walk-In Shower,Breakfast Area,Built-Ins,Carpet,Ceiling Fan(s),Family Room Off Kitchen,Floor Plan - Open,Formal/Separate Dining Room,Kitchen - Country,Kitchen - Eat-In,Kitchen - Gourmet,Kitchen - Island,Kitchen - Table Space,Pantry,Primary Bath(s),Recessed Lighting,Skylight(s),Upgraded Countertops,Walk-in Closet(s),Water Treat System,Wet/Dry Bar,Wood Floors,Crown Moldings,Entry Level Bedroom,Floor Plan - Traditional
  • Fireplace: Wood,Gas/Propane
  • Flooring: Hardwood,Ceramic Tile,Carpet
  • Windows: Skylights,Casement,Double Pane,Palladian,Screens
  • Utilities: Under Ground

School Information

  • High School: CHESAPEAKE
  • Middle School: CHESAPEAKE BAY
  • Elementary School: BODKIN
  • School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS
Printed July 20, 2026


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