Windermere Estates Homes with Colonial Style

Windermere Estates Homes with Colonial Style

Welcome to Windermere Estates, a charming subdivision nestled in the heart of Pasadena, Maryland, within the picturesque Anne Arundel County. This delightful community is a hidden gem, offering a perfect blend of suburban tranquility and modern conveniences, making it an ideal place for families and individuals alike.

Windermere Estates boasts an array of stunning homes, each reflecting the timeless elegance of Colonial architecture. Characterized by their symmetrical facades, classic brick exteriors, and inviting front porches, these homes exude a sense of history and charm. Inside, you'll find spacious layouts designed for comfortable living, with ample natural light and modern amenities that cater to today’s lifestyle.

Living in Windermere Estates means embracing a community that values both connection and privacy. Residents enjoy beautifully landscaped grounds and tree-lined streets, perfect for leisurely strolls or bike rides. The neighborhood is conveniently located near local parks, schools, and shopping centers, ensuring that everything you need is just a stone’s throw away.

For those who appreciate outdoor activities, Windermere Estates is ideally situated near the scenic Chesapeake Bay, offering a plethora of recreational opportunities such as boating, fishing, and hiking. The nearby parks provide ample space for picnics and family gatherings, fostering a close-knit community atmosphere.

If you’re searching for a home that combines classic Colonial charm with modern living in a vibrant community, look no further than Windermere Estates. Come and discover the perfect place to call home in Pasadena, MD!

Newest Windermere Estates Homes with Colonial Style

$939,000
5 Beds 5 Baths
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. 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 both impressive enough for entertaining and comfortable enough for everyday living. At the heart of the home is a stunning gourmet kitchen that invites people to gather. Holiday dinners become traditions here. Birthday cakes are decorated at the island. Friends linger over charcuterie and wine long after dinner is finished. Sunday mornings begin with pancakes, newspapers, and conversations that somehow last for hours. Beautifully renovated with premium appliances, abundant cabinetry, generous prep space, and timeless finishes, it's a kitchen that feels every bit as exceptional as it looks. 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, while still feeling comfortable enough for an ordinary Tuesday evening together. 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 that's increasingly difficult to find. There's room for the pool you've always imagined, a garden worthy of magazine pages, an outdoor kitchen, a fire pit surrounded by Adirondack chairs, or simply an endless stretch of lawn where children laugh, dogs run, and memories unfold naturally year after year. 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 ease of one-level living. The finished walk-out lower level—with its own kitchen—creates endless possibilities for an in-law suite, private guest quarters, recreation room, home gym, media lounge, or the ultimate gathering space when family comes to visit. And while the home itself is remarkable, its location makes it even more compelling. Tucked within a peaceful, established community, you'll enjoy the privacy of a generous homesite while remaining just minutes from marinas, waterfront parks, local dining, shopping, highly regarded schools, and convenient commuter routes to Annapolis, Baltimore, Fort Meade, and Washington, D.C. It offers the rare luxury of feeling worlds away while keeping everything you need close at hand. Some homes simply provide shelter. Others become the backdrop for life's most meaningful moments. 1499 Westcliff Drive is where birthdays are celebrated, holidays become traditions, grandchildren race through the yard, neighbors become lifelong friends, and ordinary evenings somehow become the memories you'll treasure forever. This is more than an exceptional home. It's the place where your next chapter begins.

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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