$949,000

Under Contract

1499 Westcliff Dr, Pasadena, MD, 21122

5

Beds

5

Baths

4,763

Square feet

1.59

Acres

Close your laptop for a moment and picture this instead. It's Saturday morning. Sunlight pours through the windows as fresh coffee brews in the kitchen. The doors are open to a gentle breeze, the dogs are already racing across the backyard, and your biggest decision today is whether to spend the afternoon gardening, hosting friends on the deck, throwing a football across the lawn, or doing absolutely nothing at all. This is what life feels like at 1499 Westcliff Drive. Perfectly positioned on 1.59 beautifully wooded acres in one of Pasadena's most sought-after neighborhoods, this extraordinary residence offers nearly 5,000 finished square feet designed around something far more valuable than square footage—it was designed around the way people truly want to live. Beautifully maintained and extensively updated, the home offers the confidence and convenience of major improvements already completed, including a beautifully renovated kitchen (2020), roof replacement (2021), HVAC replacement (2018), well replacement (2009), driveway replacement (2015), and fresh interior paint and carpeting. From the moment you step inside, soaring cathedral ceilings, dramatic skylights, and walls of windows flood the home with natural light. Every space feels bright, open, and effortlessly welcoming, creating an atmosphere that's impressive enough for entertaining yet comfortable enough for everyday living. At the heart of the home is the stunning renovated gourmet kitchen. Completed in 2020, it features premium appliances, abundant cabinetry, generous prep space, and timeless finishes. Holiday dinners become traditions here. Birthday cakes are decorated at the island, friends linger long after dinner is finished, and Sunday mornings begin with pancakes, coffee, and conversations that somehow last for hours. The adjoining family room, anchored by a warm fireplace, naturally becomes the place where everyone ends up. Nearby, elegant formal living and dining rooms stand ready for everything from intimate dinner parties to Thanksgiving with the entire family. Then, almost effortlessly, life moves outdoors. The expansive deck becomes the backdrop for summer cookouts, milestone celebrations, and evenings beneath a sky full of stars. The screened porch offers a quiet escape for morning coffee, afternoon rainstorms, or a favorite book at sunset. Beyond it lies one of the property's greatest luxuries—a sprawling, level backyard surrounded by mature trees. There's room to envision a pool, spectacular gardens, an outdoor kitchen, a fire pit, or simply an incredible stretch of lawn where children play and dogs run. As life evolves, this home evolves with you. A spacious main-level bedroom and full bath provide exceptional flexibility for long-term guests, multi-generational living, or the convenience of main-level living. The fully finished walk-out lower level adds another remarkable dimension to the home. Complete with its own kitchen, it provides tremendous flexibility for extended family, private guest accommodations, recreation and entertaining space, a home gym, media room, or an exceptional secondary living area. And while the home itself is remarkable, its location makes it even more compelling. Set within a peaceful, established community, you'll enjoy the privacy and breathing room of a 1.59-acre homesite while remaining convenient to marinas, waterfront parks, dining, shopping, schools, and commuter routes to Annapolis, Baltimore, Fort Meade, and Washington, D.C. Some homes simply provide shelter. Others become the backdrop for life's most meaningful moments. 1499 Westcliff Drive offers nearly 5,000 finished square feet, 1.59 acres, substantial recent improvements, exceptional indoor and outdoor living, and the flexibility to accommodate the way you live today—and the way you may want to live tomorrow. This is more than an exceptional home. It's the place where your next chapter begins.

Listing Details

OfficeColdwell Banker Realty
Contact Info4102638686

Facts & Features

MLS® # MDAA2150744
Price $949,000
Bedrooms 5
Bathrooms 5.00
Full Baths 5
Square Footage 4,763
Acres 1.59
Year Built 1993
Type Residential
Sub-Type Detached
Style Colonial, Craftsman
Status Active Under Contract

Community Information

Address 1499 Westcliff Dr
Subdivision WINDERMERE ESTATES
City Pasadena
County ANNE ARUNDEL-MD
State MD
Zip Code 21122
Senior Community No

Amenities

Amenities Attic, Bar, Bathroom - Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Built-Ins, Carpet, Ceiling Fan(s), Formal/Separate Dining Room, 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
Utilities Under Ground
Parking Circular Driveway
# of Garages 2
Garages Garage - Side Entry, Garage Door Opener, Inside Access, Oversized
View Garden/Lawn, Trees/Woods
Is Waterfront No
HOA Amenities Common Grounds

Interior

Interior Features Floor Plan - Open,Floor Plan - Traditional
Appliances Built-In Microwave, Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned
Heating Heat Pump(s), Zoned, Programmable Thermostat, Forced Air
Cooling Central A/C, Ceiling Fan(s), Programmable Thermostat, Zoned
Fireplace Yes
# of Fireplaces 2
Fireplaces Wood, Gas/Propane
Stories 3

Exterior

Exterior Vinyl Siding
Exterior Features Boat Storage,Bump-outs,Exterior Lighting,Play Area,Deck(s),Porch(es),Screened,Enclosed,Rear
Lot Description Backs to Trees, Landscaping, Cleared, Front Yard, Premium, Private, Rear Yard, Secluded, SideYard(s)
Windows Skylights, Casement, Double Pane, Palladian, Screens
Roof Asphalt, Shingle, Architectural Shingle
Construction Stick Built, Advanced Framing, Vinyl Siding
Foundation Concrete Perimeter
Other Structures 10000001172,10000001174

School Information

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

Additional Information

Date Listed July 10th, 2026
Days on Market 39
Zoning R1
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Map

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