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$949,000

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 5,066 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 1499 Westcliff Dr

General

  • Sold For: $949,000
  • HOA FEE: $10/month
  • Taxes: $7,545 (2026)
  • Status: Closed
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2150744
  • Added to Site: 95 day(s) ago

Interior

  • Rooms/Areas: 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
  • 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
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Wood, Gas/Propane
  • Appliances: Built-In Microwave, Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven - Wall, Oven/Range - Gas, Refrigerator, Stainless Steel Appliances, Washer, Water Conditioner - Owned
  • Flooring: Hardwood, Ceramic Tile, Carpet, Laminate Plank

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5
  • Upper Floor Baths: 3
  • Upper - Full Baths: 3
  • Main Floor Baths: 1
  • Main - Full Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 5
  • Bedrooms Upper: 3
  • Bedrooms Lower: 1
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Upper Floor, Washer In Unit, Dryer In Unit

Additional Information

  • Shared Amenities: Common Grounds
  • Security/Safety: Carbon Monoxide Detector(s), Smoke Detector

Exterior

  • Exterior Features: Boat Storage, Bump-outs, Exterior Lighting, Play Area
  • Porch/Patio/Deck: Deck(s), Porch(es), Screened, Enclosed

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking Features: Circular Driveway
  • Parking Type: Attached Garage, Driveway, Off Street
  • Garage Description: Garage - Side Entry, Garage Door Opener, Inside Access, Oversized

Location

  • County: ANNE ARUNDEL
  • Subdivision: WINDERMERE ESTATES
  • Driving Directions: Mountain Road to Forest Glen to Westcliff

School Information

  • School District: Anne Arundel County Public Schools
  • Elementary School: Bodkin
  • Middle School: Chesapeake Bay
  • High School: Chesapeake

Community

  • Association: Yes
  • Assoc. Fees Include: Common Area Maintenance
  • Pets Allowed: Yes
  • Pets: No Pet Restrictions

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central A/C, Ceiling Fan(s), Programmable Thermostat, Zoned
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Zoned, Programmable Thermostat, Forced Air
  • Heating Fuel: Electric
  • Water Heater: Electric

Utilities

  • Sewer: Private Septic Tank
  • Water: Well
  • Utility Description: Under Ground

Structural Information

  • Architectural Style: Colonial, Craftsman
  • Structure Type: Detached
  • Construction: Stick Built, Advanced Framing, Vinyl Siding
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Connecting Stairway, Full, Fully Finished, Heated, Improved, Interior Access, Outside Entrance, Sump Pump, Walkout Stairs, Windows
  • Foundation: Concrete Perimeter
  • Roof: Asphalt, Shingle, Architectural Shingle
  • Walls/Ceilings: 2 Story Ceilings, 9'+ Ceilings, Cathedral Ceilings, H
  • Windows: Skylights, Casement, Double Pane, Palladian, Screens
  • Doors: Atrium, French, Insulated
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 5,066
  • Sq. Ft. Source: Estimated
  • Living Area: 4,763 Sq. Ft.
  • Finished Above Grnd: 3,430 Sq. Ft.
  • Finished Below Grnd: 1,333 Sq. Ft.
  • Year Built: 1993
  • Year Built Source: Assessor
  • Property Condition: Excellent

Unit Information

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 1

Lot Features

  • Property View: Garden/Lawn, Trees/Woods
  • Lot Size (Acres): 1.59
  • Lot Size (Sq. Ft.): 69,260
  • Lot Size Source: Estimated
  • Street/Road Desc.: Black Top
  • Zoning: R1
  • Lot Description: Backs to Trees, Landscaping, Cleared, Front Yard, Premium, Private, Rear Yard, Secluded, SideYard(s)
  • Fencing (Description): Rear

Financial Considerations

  • Price Per Sq. Ft.: $276.68
  • Association Fee: $10
  • Assoc Fee Freq.: Monthly
  • Assessment Year: 2026
  • Tax w/Assessment: $693,167
  • Tax Amount: $7,545
  • Tax Year: 2026
  • Terms: Standard Sale
  • Tax Total Finished Sq. Ft.: 3128

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 1
  • Lot Number: 1

Meet the listing agents

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— 1499 Westcliff Dr —

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NMLS#: 1598647

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Schools serving 1499 Westcliff Dr

School District:Anne Arundel County Public Schools
NameGradesDistance
Bodkin Elementary School
8320 Ventnor Road, Pasadena, MD 21122
K-50.5 mi
Chesapeake Bay Middle School
4804 Mountain Road, Pasadena, MD 21122
6-81 mi
Chesapeake High School, Pasadena, MD
4798 Mountain Road, Pasadena, MD 21122
9-120.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1499 Westcliff Dr

Date
Details
Price
Change
Source
9/17/2026
Sold
$949,000
—
MLS
8/17/2026
Price Increased
$949,000
1.06%
MLS
8/05/2026
Price Reduced
$939,000
-3.69%
MLS
7/10/2026
Listed
$975,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1499 Westcliff Drive, Pasadena, MD 21122 (MLS# MDAA2150744) is a Single Family property that was sold at $949,000 on September 17, 2026. This property was listed by Wendy T. Oliver from our Annapolis Church Circle Office.Want to learn more about 1499 Westcliff Drive? Do you have questions about finding other Single Family real estate for sale in Pasadena? You can browse all Pasadena real estate or contact a Coldwell Banker agent to request more information.