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Jackie Barbieri
REALTOR®
Cell: (410) 804-2947
Office: (410) 697-8100

1499 Westcliff Drive, Pasadena, MD 21122

$975,000
  • 1499 Westcliff Drive, Pasadena, MD 21122 Main Photo

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New to the Market
BEDS5 BATHS5 full SQUARE FEET4,763 MLS#MDAA2150744
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONWINDERMERE ESTATES SCHOOLANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Property Description

Welcome to 1499 Westcliff Drive, an extraordinary custom residence privately nestled on 1.59 beautifully wooded acres in the heart of sought-after Windermere Estates, where over 5000 finished square feet of exceptional living space creates the perfect balance of luxury, comfort, and everyday living. From the moment you enter, soaring cathedral ceilings, dramatic skylights, and walls of windows bathe the home in natural light, creating an open, airy atmosphere that is both impressive and inviting. Designed for the way families truly live, this remarkable home offers elegant formal living and dining rooms, a welcoming family room with fireplace, and a beautifully remodeled gourmet kitchen that naturally becomes the heart of every gathering, where conversations begin, meals are shared, and lifelong memories are made. Whether you're hosting Thanksgiving for the entire family, holiday celebrations, birthday parties, elegant dinner gatherings, or casual weekends with friends, this home was built for entertaining. Step outside onto the expansive deck where guests can dine al fresco, dance beneath the stars, enjoy summer evenings overlooking the private grounds, or simply relax with a morning cup of coffee surrounded by the peaceful sounds of nature. The beautifully landscaped grounds offer endless opportunities to garden, play, explore, or simply enjoy the privacy that only a setting like this can provide, while the fenced yard gives children and pets room to run and play freely. A tremendous asset is the spacious main-level bedroom and adjoining full bath, currently used as a private home office, offering the perfect solution for buyers seeking one-level living, a luxurious guest suite, accommodations for extended family, or a quiet executive workspace. The fully finished lower level expands the possibilities even further with its own private entrance, kitchen, generous living space, and exceptional flexibility for multi-generational living, an au pair suite, long-term guests, home business, or private retreat. Thoughtful improvements including a remodeled kitchen (2020), new roof (2021), HVAC (2018), repaved driveway (2015), and new well (2009) provide peace of mind and lasting value. Completing this exceptional property is an oversized two-car garage and an unbeatable location just minutes from Downs Park, marinas, shopping, waterfront dining, Annapolis, Baltimore, BWI Airport, Fort Meade, Johns Hopkins, and major commuter routes, all within the highly regarded Chesapeake school district. Homes of this caliber rarely become available, offering an unmatched combination of privacy, space, flexibility, and convenience. More than simply a beautiful residence, 1499 Westcliff Drive is a home where generations gather, lifelong friendships are built, holidays become traditions, and every day feels like a getaway. Professional photography is underway—stay tuned for the full reveal. This one is worth the wait.

1499 Westcliff Drive | MLS# MDAA2150744

This single family home located at 1499 Westcliff Drive, Pasadena, MD 21122 is currently listed for sale with an asking price of $975,000. This property was built in 1993 and has 5 bedrooms and 5 full baths with 4763 sq. ft. Westcliff Drive is located in the WINDERMERE ESTATES subdivision within the ANNE ARUNDEL COUNTY PUBLIC SCHOOLS school district. Search WINDERMERE ESTATES real estate on jackiebarbieri.homesale.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Connecting Stairway, Full, Fully Finished, Heated, Improved, Interior Access, Outside Entrance, Sump Pump, Walkout Stairs, Windows
Cooling: Central A/C, Ceiling Fan(s), Programmable Thermostat
Fireplaces: 2
Fuel Type: Electric
Garage: 2
Heating: Heat Pump(s), Zoned, Programmable Thermostat
Home Style: Colonial, Craftsman
Lot Size: 1.59 Acres
Roof Type: Asphalt, Shingle
Stories: 3.0
Taxes: $7,545
Year Built: 1993

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Appliances: Built-In Microwave, Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned
Exterior: Boat Storage, Bump-outs, Exterior Lighting, Play Area
Exterior: Stick Built
Fencing: Rear
Fireplace: Wood, Gas/Propane
Flooring: Hardwood, Ceramic Tile, Carpet
HOA Fee: $10.00/Monthly
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
Lot: Backs to Trees, Landscaping
Lot Dimensions: 1.59 Acre(S)
Parking Notes: 8 Total Parking Spaces
Pet Restrictions: No Pet Restrictions
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
Sewer: Private Septic Tank
Special View Info: Garden/Lawn, Trees/Woods
SQFT Above Finished: 3430
SQFT Below Finished: 1333
SQFT Total Finished: 4763
Structure Type: Detached
Total Garage/Parking Spaces: 8
Utilities: Under Ground
Water: Well
Windows: Skylights, Casement, Double Pane, Palladian, Screens

Local Schools

High School: CHESAPEAKE
Middle School: CHESAPEAKE BAY
Elementary School: BODKIN
School District: ANNE ARUNDEL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Coldwell Banker Realty
Agency Phone: 4102638686

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Estimated Payment

$ 3,083.05 per month $2,169.93 Principal & Interest $628.75 Property Tax $284.38 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/11/2026. The listing information on this page last changed on 07/11/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 07/11/2026 12:00:59 AM EST) or Bright MLS (last updated Fri 07/10/2026 11:49:42 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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