Kenilworth Estates Homes 

Kenilworth Estates in Winter Park, FL, is a sought-after real estate community offering an array of stunning homes in a picturesque setting. Nestled in the heart of Winter Park, this neighborhood boasts a tranquil atmosphere while being conveniently located near various attractions and amenities. The homes in Kenilworth Estates showcase exquisite architecture and modern design, providing residents with a luxurious living experience. The area is renowned for its tree-lined streets, creating an idyllic ambiance that complements the charm of Winter Park.

Residents of Kenilworth Estates have easy access to a plethora of nearby attractions, including the renowned Morse Museum, which features an impressive collection of Tiffany glass art. The Charles Hosmer Morse Museum of American Art is a cultural gem just a stone's throw away, offering a unique opportunity to explore exquisite artistry. Moreover, the neighborhood's proximity to Park Avenue adds another layer of allure, as it presents an array of boutiques, art galleries, and dining options, catering to various preferences.

The appeal of Kenilworth Estates is further enhanced by its close proximity to a range of essential amenities. Residents can enjoy easy access to shopping centers, grocery stores, and recreational parks, ensuring a convenient and enjoyable daily life. With its blend of elegant homes, nearby cultural attractions, and essential conveniences, Kenilworth Estates stands as a prime example of upscale living in Winter Park, FL, appealing to those who value both sophistication and practicality.

Available Kenilworth Estates Homes For Sale

2237 Woodcrest Drive, Winter Park
$1,425,000
4 Beds ⋅ 5 Baths ⋅ TB8563139 MLS
Under Construction. Nestled on a quiet street on an oversized homesite in Winter Park, this stunning new construction home by David Weekley Homes blends timeless design with modern comfort. Featuring 4 spacious bedrooms and 4.5 beautifully appointed baths, the home offers an ideal layout for both everyday living and entertaining. A private study provides a perfect work-from-home retreat, while the dedicated media room invites movie nights and game-day gatherings. Upstairs, a versatile loft adds flexible living space for a playroom, lounge, or fitness area. Thoughtfully designed with high-quality finishes and abundant natural light, this home delivers exceptional craftsmanship in one of Central Florida’s most desirable neighborhoods—just minutes from top schools, parks, dining, and shopping.

2237 Woodcrest Drive, Winter Park

Courtesy of WEEKLEY HOMES REALTY COMPANY

2322 Woodcrest Drive, Winter Park
$650,000
4 Beds ⋅ 2 Baths ⋅ O6445796 MLS
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

Courtesy of KELLER WILLIAMS WINTER PARK

2215 Woodcrest Drive, Winter Park
$637,500
4 Beds ⋅ 2 Baths ⋅ O6442348 MLS
PRICE JUST REDUCED!! 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. Don't miss out on one of the lowest priced homes in Winter Park School district!!

2215 Woodcrest Drive, Winter Park

Courtesy of KELLER WILLIAMS WINTER PARK

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