Windermere Estates Real Estate

Windermere Estates Real Estate

Welcome to Windermere Estates, an enchanting subdivision nestled in the heart of Pasadena, Maryland, within the picturesque Anne Arundel County. This charming community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal choice for families, professionals, and retirees alike.

Windermere Estates boasts a variety of beautifully designed homes, each reflecting the unique character and warmth of the neighborhood. With spacious layouts, contemporary finishes, and lush green surroundings, residents enjoy a comfortable lifestyle that feels both inviting and luxurious. Whether you’re looking for a cozy single-family home or a modern townhome, Windermere Estates has something for everyone.

One of the standout features of this community is its proximity to nature and outdoor activities. Residents can take advantage of nearby parks, walking trails, and waterfront access, allowing for endless opportunities to explore the natural beauty of the area. The serene atmosphere makes it easy to unwind while still being just a short drive away from the vibrant amenities of Pasadena, including shopping centers, restaurants, and entertainment options.

Families will appreciate the highly-rated schools within the area, ensuring that children receive an excellent education. Additionally, Windermere Estates is conveniently located near major highways, providing easy access to Baltimore, Annapolis, and Washington D.C., making commuting a breeze.

In Windermere Estates, you’ll find not just a place to live, but a community to thrive in. Experience the charm, comfort, and convenience of this delightful subdivision today!

Newest Listings in Windermere Estates

$975,000
5 Beds 5 Baths
Close your laptop for a minute and imagine this instead. It's Saturday morning. The coffee is brewing, the windows are open, and the only thing on your agenda is deciding whether to spend the afternoon relaxing on the deck, planting flowers in the garden, playing football in the backyard, or inviting friends over for dinner. This is the kind of home that gives you choices—and the space to enjoy them. Welcome to 1499 Westcliff Drive. Set on a beautiful 1.59-acre homesite in one of Pasadena's most desirable neighborhoods, this is more than a house with nearly 5,000 finished square feet—it's a home designed for the way people really want to live. From the moment you step inside, soaring cathedral ceilings, dramatic skylights, and walls of windows fill the home with natural light, creating bright, welcoming spaces that feel open without ever feeling overwhelming. Every room invites you to slow down, settle in, and enjoy the people around you. The beautifully renovated gourmet kitchen is proof that the best memories are often made over great food. This is where holiday meals come to life, birthday cakes are decorated, Sunday breakfasts become family traditions, and friends gather with a glass of wine while dinner is on the stove. Outfitted with premium appliances, abundant cabinetry, generous workspace, and quality finishes, it's a kitchen that makes you want to cook—not because you have to, but because you'll love spending time here. The adjoining family room, with its inviting fireplace, naturally becomes the heart of the home, while the formal living and dining rooms are ready for everything from Thanksgiving dinner to milestone celebrations and quiet evenings spent catching up with the people who matter most. Then step outside. The expansive deck was made for summer barbecues, birthday parties, and evenings spent under the stars. The screened porch offers a peaceful place to begin your mornings or unwind at the end of the day. Beyond it all is one of the property's greatest assets—a lush, level backyard that offers room to truly live outdoors. Whether you've always wanted a custom pool, beautiful gardens, an outdoor kitchen, a fire pit, or simply a wide-open lawn where children and pets can play freely, you'll have the space to create exactly what you've always imagined. Life changes, and this home is ready for every chapter. The spacious main-level bedroom and full bath provide exceptional flexibility for guests, multi-generational living, or anyone seeking the convenience of one-level living. The finished walk-out lower level, complete with its own kitchen, offers endless possibilities as private guest accommodations, an in-law suite, recreation space, or the perfect retreat for family and friends visiting for the weekend. And while the home itself is exceptional, the location makes it even better. Here, you'll enjoy the peace and privacy that comes with a spacious homesite while remaining just minutes from marinas, waterfront parks, local restaurants, shopping, excellent schools, and easy commuter routes to Annapolis, Baltimore, Fort Meade, and Washington, D.C. It's a location that offers the best of both worlds—room to breathe without sacrificing convenience. Some homes simply give you a place to live. 1499 Westcliff Drive gives you room to grow, room to celebrate, room to entertain, and room to create the kind of memories that stay with your family for generations. If you've been searching for a home that offers exceptional space, thoughtful updates, remarkable flexibility, and a lifestyle that's increasingly difficult to find, you've just found it.

1499 Westcliff Dr, Pasadena

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$745,000
4 Beds 3 Baths
Set on a breathtaking .81-acre lot backing to peaceful woods, this quality-built Colonial offers exceptional space, privacy, and endless potential. Surrounded by mature landscaping in a picturesque community, the home features over 3,000 finished square feet above grade, plus an additional 1,909 square feet in the expansive unfinished lower level. Designed with generous room sizes and a timeless floor plan, the main level is ideal for both everyday living and entertaining. The spacious kitchen, complete with a center island and dining area, opens to the dramatic family room featuring a vaulted ceiling, wood-burning fireplace, skylights, and a triple atrium door leading to the sizable deck overlooking the beautifully landscaped backyard. The formal living and dining rooms showcase hardwood flooring and elegant crown molding. A versatile main-level bedroom or office, also accented with hardwood floors and crown molding, adjoins a full bath that is conveniently accessible from both the room and the foyer. Upstairs, three generously sized bedrooms provide comfortable accommodations. The primary suite features hardwood flooring, a walk-in closet, and a large private bath with a soaking tub, walk-in shower, dual vanities, and abundant room to create a luxurious retreat. A second full bath serves the additional bedrooms. Recent updates include a new roof (2022), skylights (2016), and HVAC system (2018). The attached side-entry two-car garage offers valuable workshop space for hobbies, projects, or extra storage. The unfinished lower level provides outstanding potential for future living space, whether envisioned as a recreation room, home gym, media center, guest suite, or all of the above. Outside, an irrigation system helps maintain the lush grounds, where mature trees, colorful plantings, and a serene wooded backdrop create a private oasis. The fantastic location enables residents to walk to the local AACPS school campus, ride bikes to Downs Park on the Chesapeake Bay and easily commute to Ft. Meade, Baltimore & Annapolis. Multiple marinas and favorite local restaurants are within just a couple of miles. While cosmetic updates will allow the next owner to add their own style and vision, the home's solid craftsmanship, desirable layout, and extraordinary setting provide an exceptional foundation for creating a truly remarkable residence. Schedule a tour today and experience everything peninsula life has to offer!

1482 Westcliff Dr, Pasadena

Listing courtesy of Keller Williams Flagship. Contact:

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