1499 WESTCLIFF DR, Pasadena, MD 21122
1499 WESTCLIFF DR, Pasadena, MD 21122
1499 WESTCLIFF DR, Pasadena, MD 21122
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My CU Home Connection

My CU Home Connection

+1(267) 525-7900
Listed by Wendy Oliver • Coldwell Banker Realty
$975,000
Est. payment /mo
5 Beds
5 Baths
4,763 SqFt
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Key Details

Property Type Single Family Home

Sub Type Detached

Listing Status Active

Purchase Type For Sale

Square Footage 4,763 sqft

Price per Sqft $204

Subdivision Windermere Estates

MLS Listing ID MDAA2150744

Style Colonial,Craftsman

Bedrooms 5

Full Baths 5

HOA Fees $10/mo

HOA Y/N Y

Abv Grd Liv Area 3,430

Year Built 1993

Available Date 2026-07-13

Annual Tax Amount $7,545

Tax Year 2026

Lot Size 1.590 Acres

Acres 1.59

Property Sub-Type Detached

Source BRIGHT

Property Description

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.

Location

State MD

County Anne Arundel

Zoning R1

Rooms

Other 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

Main Level Bedrooms 1

Interior

Interior Features 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

Hot Water Electric

Heating Heat Pump(s), Zoned, Programmable Thermostat

Cooling Central A/C, Ceiling Fan(s), Programmable Thermostat, Zoned

Flooring Hardwood, Ceramic Tile, Carpet

Fireplaces Number 2

Fireplaces Type Wood, Gas/Propane

Equipment Built-In Microwave, Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned

Furnishings No

Fireplace Y

Window Features Skylights,Casement,Double Pane,Palladian,Screens

Appliance Built-In Microwave, Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned

Heat Source Electric

Laundry Upper Floor

Exterior

Exterior Feature Deck(s), Porch(es), Screened

Parking Features Garage - Side Entry, Garage Door Opener, Inside Access, Oversized

Garage Spaces 8.0

Fence Rear

Utilities Available Under Ground

Water Access N

View Garden/Lawn, Trees/Woods

Roof Type Asphalt,Shingle

Accessibility None

Porch Deck(s), Porch(es), Screened

Attached Garage 2

Total Parking Spaces 8

Garage Y

Building

Lot Description Backs to Trees, Landscaping

Story 3

Foundation Concrete Perimeter

Above Ground Finished SqFt 3430

Sewer Private Septic Tank

Water Well

Architectural Style Colonial, Craftsman

Level or Stories 3

Additional Building Above Grade, Below Grade

Structure Type 2 Story Ceilings,9'+ Ceilings,Cathedral Ceilings,High

New Construction N

Schools

Elementary Schools Bodkin

Middle Schools Chesapeake Bay

High Schools Chesapeake

School District Anne Arundel County Public Schools

Others

Pets Allowed Y

Senior Community No

Tax ID 020391790028973

Ownership Fee Simple

SqFt Source 4763

Acceptable Financing Cash, Conventional, VA

Listing Terms Cash, Conventional, VA

Financing Cash,Conventional,VA

Special Listing Condition Standard

Pets Allowed No Pet Restrictions

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1499 WESTCLIFF DR