Kenilworth Estates 1st Add Homes for Sale

Welcome to Kenilworth Estates 1st Addition, a hidden gem nestled in the heart of Winter Park, Florida. This charming subdivision is known for its picturesque tree-lined streets and a vibrant community atmosphere, making it an ideal place for families and individuals alike. With its prime location in Orange County, residents enjoy easy access to the best of Winter Park, including its renowned dining, shopping, and cultural attractions.

Homes for sale in Kenilworth Estates 1st Add. showcase a delightful mix of architectural styles, from classic Florida ranches to modern designs, all exuding warmth and character. Each property is thoughtfully designed to provide ample living space, with beautifully landscaped yards that offer a perfect backdrop for outdoor gatherings or quiet evenings under the stars. Whether you're seeking a cozy family home or a stylish retreat, you’ll find a variety of options that cater to different tastes and budgets.

One of the standout features of Kenilworth Estates is its close-knit community. Residents enjoy the benefits of nearby parks, top-rated schools, and recreational facilities, promoting an active and engaged lifestyle. The area is also known for its excellent public transportation options, making commuting a breeze.

If you’re ready to find your dream home in a community that feels like family, look no further than Kenilworth Estates 1st Addition. Explore the homes for sale today, and discover the charm and warmth that await you in this idyllic Winter Park neighborhood. Your dream home is just a visit away!

Newest Kenilworth Estates 1st Add Homes for Sale

$675,000

4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code

Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, Winter Park

$675,000

4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code

Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern pool residence beautifully harmonizes timeless architectural soul with stylized contemporary updates. Bathed in glorious natural sunlight, the open-concept interior unfolds beneath soaring vaulted ceilings, where durable wood-look flooring flows seamlessly across expansive living and dining spaces. At the center of it all lies a true chef’s haven—an exquisitely updated kitchen equipped with solid wood cabinetry, rich granite countertops, a sprawling prep island, sleek stainless steel appliances, and a bold over-range hood. Thoughtfully arranged along a private bedroom wing, the four spacious bedrooms blend exceptional comfort with versatile living spaces. The fourth bedroom is framed by views of the sun-drenched pool deck—an inspiring backdrop for a home office, creative sanctuary, or private gym. The primary retreat serves as a peaceful haven, complete with an elegant ensuite bath showcasing custom tile work and a glowing vanity mirror. Step through the doors into your own fully fenced tropical oasis, where quintessential Florida living takes center stage. Spend your afternoons lounging beside the sparkling swimming pool, entertaining guests from the custom Tiki bar, or relaxing with a cool drink under the shade of the gazebo surrounded by fresh, plush, mature landscaping and fresh sod. Modern convenience and major infrastructure upgrades ensure total peace of mind, featuring updated plumbing, electrical, and windows, along with a brand-new 2026 HVAC heat pump system (complete with a 10-year warranty) and a 2026 water heater. Complete with a two-car carport, dual storage rooms, indoor laundry, and a well-water irrigation system, every practical detail has been addressed. All of this is situated within top-tier school zones (Brookshire, Glenridge, and Winter Park High), just moments from the boutique shopping and dining on Park Avenue, Rollins College, Baldwin Park, Cady Way Trail, medical hubs, and the energy of downtown Orlando.

2215 Woodcrest Drive, Winter Park

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