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$975,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 5 Full Baths
  • 5,066 Sq. Ft.
  • 2 Car Garage
  • Updated 10 hours ago
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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.

Full Property Details for 1499 Westcliff Dr

General

  • Price: $975,000
  • HOA FEE: $10/month
  • Taxes: $7,545 (2026)
  • Status: Active
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2150744
  • Updated: Today (7/10/2026)
  • Added to Site: Today

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

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

Exterior

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

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 8
  • Parking Type: Attached Garage, Driveway
  • 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
  • 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
  • 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
  • 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
  • Walls/Ceilings: 2 Story Ceilings, 9'+ Ceilings, Cathedral Ceilings, H
  • Windows: Skylights, Casement, Double Pane, Palladian, Screens
  • 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: Very Good

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
  • Zoning: R1
  • Lot Description: Backs to Trees, Landscaping
  • Fencing (Description): Rear

Financial Considerations

  • Price Per Sq. Ft.: $284.26
  • Association Fee: $10
  • Assoc Fee Freq.: Monthly
  • Assessment Year: 2026
  • Tax w/Assessment: $693,167
  • Tax Amount: $7,545
  • Tax Year: 2026
  • Tax Total Finished Sq. Ft.: 3128

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: 1
  • Lot Number: 1
Buyer's Brokerage Compensation: 2.5%
Not binding unless confirmed by separate agreement among applicable parties.

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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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/10/2026
Listed
$975,000
54.76%
MLS
11/21/2008
Sold
$630,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1499 Westcliff Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,438
13%
$653,733
6%
2023
$6,596
—
$614,300
2%
2023
$6,596
6%
$604,067
2%
2022
$6,206
11%
$593,833
2%
2018
$5,602
-13%
$583,600
2%
2021
$6,443
2%
$573,233
2%
2020
$6,340
5%
$562,867
2%
2019
$6,045
1%
$552,500
1%
2018
$6,002
—
$545,533
1%
2017
$5,974
—
$538,567
1%
2016
$5,945
-1%
$531,600
—
2015
$6,034
—
$531,600
—
2014
$6,055
—
$531,600
—
View All
Disclaimer: Historical tax 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 with 5 bedrooms and 5 full bathrooms. 1499 Westcliff Drive is currently listed for $975,000 and was received on July 10, 2026. This property is 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.

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