Ad #7690523
MLS #MDAA2150744
Some homes are simply built well. Others become the backdrop for
1499 WESTCLIFF Dr, Pasadena, Maryland, 21122
$975,000
5Beds
5Baths
4,763Sqft
1.590Acres
About this property
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.
Property Features
5 Beds
5 Baths
4,763 Sqft
Built in 1993
1.590 Acres
3 Stories
Garage - Attached, Driveway
Siding: Stick Built
Has Fireplace
Zoned, Heat Pump (Heating)
$7,545 / yr property tax
Anne Arundel County
WINDERMERE ESTATES Community
Additional Photos
Contact Information
Wendy T Oliver
Coldwell Banker Residential Brokerage
443-336-5091
Location
Listing Agent: Wendy T Oliver (License #: 17673) 443-336-5091
Broker: Coldwell Banker Residential Brokerage 410-224-2200 Listing Site
Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Coldwell Banker Residential Brokerage 410-224-2200 Listing Site
Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BeachHouse.com
Printed Jul 21, 2026
Photo Gallery
$975,000
5
Beds
5
Baths
4,763
Sqft
1499 WESTCLIFF Dr, Pasadena, Maryland, 21122
By contacting this agent you agree to these Terms and Conditions.
MLS# MDAA2150744
Some homes are simply built well. Others become the backdrop for
$975,000
1499 WESTCLIFF Dr, Pasadena, Maryland, 21122
5
Beds
5
Baths
4,763
Sqft
1.590
Acres
$975,000
1499 WESTCLIFF Dr, Pasadena, Maryland, 21122
5 Beds
5 Baths
4,763 Sqft
1.590 Acres
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.
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Property Details
HOME DETAILS
5 Beds
5 Baths
4,763 Sqft
Built in 1993
1.590 Acres
3 Stories
EXTERIOR
Garage - Attached, Driveway
Siding: Stick Built
INTERIOR
Has Fireplace
Zoned, Heat Pump (Heating)
FINANCIAL & COMMUNITY
$7,545 / yr property tax
Anne Arundel County
WINDERMERE ESTATES Community
See More Details
Location
Mortgage Calculator
Ad Statistics
Ad Number
7690523
Viewed
17 times
Listing Status
Active
Added
Jul 10, 2026
Last Refresh
Jul 21, 2026 12:05:46 PM
Listing Information
Data Source
Bright MLS
Source Property ID
MDAA2150744
Listing Agent: Wendy T Oliver (License #: 17673) 443-336-5091
Broker: Coldwell Banker Residential Brokerage 410-224-2200 Listing Site
Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
Broker: Coldwell Banker Residential Brokerage 410-224-2200 Listing Site
Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
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