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.
For sale
$975,000
1499 Westcliff Dr, Pasadena, MD 21122
5beds
4,763sqft
Single Family Residence
Built in 1993
1.59 Acres Lot
$947,600 Zestimate®
$205/sqft
$10/mo HOA
What's special
Private wooded sanctuaryExpansive deckSoaring cathedral ceilingsDramatic skylightsBeautifully remodeled gourmet kitchenBeautifully landscaped groundsOversized two-car garage
- 10 days |
- 817 |
- 38 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Wendy Oliver 443-336-5091,
Coldwell Banker Realty 4102638686,
Co-Listing Agent: Catherine Marucci 443-883-1609,
Coldwell Banker Realty
Source: Bright MLS,MLS#: MDAA2150744
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 5
- Main level bathrooms: 1
- Main level bedrooms: 1
Rooms
- Room types: 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
Primary bedroom
- Features: Flooring - HardWood, Primary Bedroom - Sitting Area, Primary Bedroom - Dressing Area, Skylight(s), Ceiling Fan(s), Walk-In Closet(s), Attached Bathroom
- Level: Upper
Bedroom 2
- Features: Ceiling Fan(s), Flooring - Carpet, Attached Bathroom
- Level: Upper
Bedroom 3
- Features: Flooring - Carpet, Ceiling Fan(s), Attached Bathroom
- Level: Upper
Bedroom 4
- Features: Crown Molding, Flooring - HardWood
- Level: Main
Bedroom 5
- Features: Flooring - Carpet, Crown Molding, Ceiling Fan(s)
- Level: Lower
Primary bathroom
- Features: Flooring - Ceramic Tile, Double Sink, Countertop(s) - Quartz, Soaking Tub, Bathroom - Walk-In Shower, Skylight(s)
- Level: Upper
Breakfast room
- Features: Flooring - Ceramic Tile
- Level: Main
Den
- Features: Flooring - Carpet, Crown Molding, Recessed Lighting
- Level: Lower
Dining room
- Features: Flooring - HardWood, Crown Molding
- Level: Main
Exercise room
- Features: Flooring - Carpet
- Level: Lower
Family room
- Features: Fireplace - Wood Burning, Flooring - HardWood, Cathedral/Vaulted Ceiling, Ceiling Fan(s), Skylight(s)
- Level: Main
Foyer
- Features: Flooring - Ceramic Tile
- Level: Main
Other
- Features: Bathroom - Walk-In Shower
- Level: Lower
Other
- Features: Walk-In Closet(s), Flooring - Ceramic Tile, Countertop(s) - Quartz
- Level: Main
Other
- Features: Flooring - Ceramic Tile, Bathroom - Tub Shower, Attached Bathroom
- Level: Upper
Other
- Features: Flooring - Ceramic Tile, Bathroom - Tub Shower
- Level: Upper
Kitchen
- Features: Flooring - Ceramic Tile, Countertop(s) - Quartz, Breakfast Bar, Double Sink, Kitchen Island, Recessed Lighting, Breakfast Nook, Breakfast Room, Kitchen - Country, Eat-in Kitchen, Kitchen - Gas Cooking, Lighting - Pendants
- Level: Main
Laundry
- Level: Upper
Living room
- Features: Flooring - HardWood, Fireplace - Gas, Crown Molding
- Level: Main
Other
- Features: Breakfast Bar, Wet Bar, Built-in Features, Flooring - Ceramic Tile, Recessed Lighting
- Level: Lower
Recreation room
- Features: Built-in Features, Recessed Lighting, Flooring - Carpet
- Level: Lower
Screened porch
- Level: Main
Storage room
- Level: Lower
Utility room
- Level: Lower
Heating
- Heat Pump, Zoned, Programmable Thermostat, Electric
Cooling
- Central Air, Ceiling Fan(s), Programmable Thermostat, Zoned, Electric
Appliances
- Included: Microwave, Cooktop, Dishwasher, Dryer, Exhaust Fan, Oven, Oven/Range - Gas, Refrigerator, Stainless Steel Appliance(s), Washer, Water Conditioner - Owned, Water Treat System, Electric Water Heater
- Laundry: Upper Level, Laundry Room
Features
- 2nd Kitchen, Attic, Bar, Soaking Tub, Bathroom - Stall Shower, Bathroom - Tub Shower, Bathroom - Walk-In Shower, Breakfast Area, Built-in Features, Ceiling Fan(s), Family Room Off Kitchen, Open Floorplan, Formal/Separate Dining Room, Kitchen - Country, Eat-in Kitchen, Kitchen - Gourmet, Kitchen Island, Kitchen - Table Space, Pantry, Primary Bath(s), Recessed Lighting, Upgraded Countertops, Walk-In Closet(s), Crown Molding, Entry Level Bedroom, Floor Plan - Traditional, 2 Story Ceilings, 9'+ Ceilings, Cathedral Ceiling(s), High Ceilings
- Flooring: Hardwood, Ceramic Tile, Carpet, Wood
- Windows: Skylight(s), Casement, Double Pane Windows, Palladian, Screens
- Basement: Connecting Stairway,Full,Finished,Heated,Improved,Interior Entry,Exterior Entry,Sump Pump,Walk-Out Access,Windows
- Number of fireplaces: 2
- Fireplace features: Wood Burning, Gas/Propane
Interior area
- Total structure area: 5,066
- Total interior livable area: 4,763 sqft
- Finished area above ground: 3,430
- Finished area below ground: 1,333
Video & virtual tour
Property
Parking
- Total spaces: 8
- Parking features: Garage Faces Side, Garage Door Opener, Inside Entrance, Oversized, Attached, Driveway
- Attached garage spaces: 2
- Uncovered spaces: 6
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Porch, Screened, Screened Porch
- Exterior features: Boat Storage, Bump-outs, Lighting, Play Area
- Pool features: None
- Fencing: Back Yard
- Has view: Yes
- View description: Garden, Trees/Woods
Lot
- Size: 1.59 Acres
- Features: Backs to Trees, Landscaped
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 020391790028973
- Zoning: R1
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Craftsman
- Property subtype: Single Family Residence
Materials
- Stick Built
- Foundation: Concrete Perimeter
- Roof: Asphalt,Shingle
Condition
- Very Good
- New construction: No
- Year built: 1993
- Major remodel year: 2022
Utilities & green energy
- Sewer: Private Septic Tank
- Water: Well
- Utilities for property: Underground Utilities, Fiber Optic
Community & HOA
Community
- Subdivision: Windermere Estates
HOA
- Has HOA: Yes
- HOA fee: $10 monthly
Location
- Region: Pasadena
Financial & listing details
- Price per square foot: $205/sqft
- Tax assessed value: $693,167
- Annual tax amount: $7,545
- Date on market: 7/10/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
Estimated market value
$947,600
$900,000 - $995,000
$5,209/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/10/2026 | Listed for sale | $975,000$205/sqft |
Source:  Bright MLS #MDAA2150744 Report a problem | ||
| 6/2/2026 | Listing removed | $975,000$205/sqft |
Source:  Long & Foster Broker Feed #MDAA2144340 Report a problem | ||
| 5/21/2026 | Listed for sale | $975,000+54.8%$205/sqft |
Source: Bright MLS #MDAA2144340 Report a problem | ||
| 11/21/2008 | Sold | $630,000-3.1%$132/sqft |
Source: Public Record Report a problem | ||
| 9/27/2008 | Listed for sale | $649,900+10.2%$136/sqft |
Source: Listhub #AA6876220 Report a problem | ||
| 6/25/2004 | Sold | $590,000+82.1%$124/sqft |
Source: Public Record Report a problem | ||
| 10/5/1993 | Sold | $324,000$68/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,438 +10.6% | $653,733 +6.4% |
| 2024 | $6,727 +2% | $614,300 +1.7% |
| 2023 | $6,596 +6.3% | $604,067 +1.7% |
| 2022 | $6,206 +1.8% | $593,833 +1.8% |
| 2021 | $6,099 +1.7% | $583,600 +1.8% |
| 2020 | $5,996 +1.7% | $573,233 -1.8% |
| 2019 | $5,893 +5.2% | $583,600 +5.6% |
| 2018 | $5,602 +0.8% | $552,500 +1.3% |
| 2017 | $5,561 | $545,533 +1.3% |
| 2016 | -- | $538,567 +1.3% |
| 2015 | -- | $531,600 |
| 2014 | -- | $531,600 |
| 2013 | -- | $531,600 -0.8% |
| 2012 | -- | $535,800 |
| 2011 | -- | $535,800 |
| 2010 | -- | $535,800 -13.9% |
| 2009 | -- | $622,170 +12.7% |
| 2008 | -- | $551,916 +14.6% |
| 2007 | -- | $481,663 +17.1% |
| 2006 | -- | $411,410 +9.3% |
| 2005 | -- | $376,406 +10.3% |
| 2004 | -- | $341,403 +11.4% |
| 2003 | -- | $306,400 |
| 2002 | -- | $306,400 |
| 2001 | -- | $306,400 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: Lake Shore
Nearby schools
GreatSchools rating
- 7/10Bodkin Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 8/10Chesapeake Bay Middle SchoolGrades: 6-8Distance: 0.6 mi
- 7/10Chesapeake High SchoolGrades: 9-12Distance: 0.4 mi
Schools provided by the listing agent
- Elementary: Bodkin
- Middle: Chesapeake Bay
- High: Chesapeake
- District: Anne Arundel County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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