Winter Park Homes with Pickleball Court(s) Amenities

Winter Park Homes with Pickleball Court(s) Amenities

Welcome to Winter Park, Florida, a picturesque city nestled in Seminole County that perfectly blends small-town charm with urban sophistication. Known for its stunning lakes, lush parks, and vibrant arts scene, Winter Park is a haven for those seeking a balanced lifestyle. With its historic architecture, delightful boutiques, and a variety of dining options, this city offers an inviting atmosphere that captivates residents and visitors alike.

One of the standout features of Winter Park is its commitment to recreational activities, particularly for those who love sports and wellness. Among the many amenities available, homes with pickleball courts are becoming increasingly popular. Pickleball, a fun and engaging sport that combines elements of tennis, badminton, and table tennis, is perfect for all ages and skill levels. Imagine stepping out of your back door to enjoy a friendly match with friends or neighbors, all while basking in the beautiful Florida sunshine.

Properties in Winter Park with pickleball court amenities provide not just a home, but a lifestyle. These residences often feature spacious layouts, beautifully landscaped yards, and easy access to the city’s extensive network of parks and recreational facilities. Whether you’re an avid player or just looking for a unique way to stay active, these homes offer the perfect blend of comfort and convenience.

Discover the joys of living in Winter Park, where community spirit thrives, and every day feels like a vacation. Explore the homes with pickleball courts today, and experience the vibrant lifestyle that awaits you in this enchanting city!

Newest Winter Park Homes with Pickleball Court(s) Amenities

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated three-bedroom, two-bathroom pool home offering nearly 1,800 square feet of thoughtfully designed living space on a spacious lot backing to a peaceful conservation easement. Featuring separate living and family rooms, a remodeled kitchen, and an exceptional outdoor retreat, this inviting home is perfectly designed for both everyday living and entertaining. From the moment you arrive, the classic brick entry creates a warm first impression. Inside, the flexible floor plan provides plenty of space to gather, relax, work from home, or host guests. Laminate wood flooring and updated baseboards (2022) complement plantation shutters, recessed lighting, and ceiling fans throughout. Multiple storage closets add everyday functionality, while updated windows and French doors fill the home with natural light and seamlessly connect the indoor and outdoor living spaces. The remodeled kitchen (2021) features crisp white shaker cabinetry, quartz countertops, a subway tile backsplash, stainless steel appliances, an oversized stainless-steel sink, and a breakfast bar with seating for four. A dedicated coffee bar and pantry add convenience, while the large bay window overlooks the pool and private backyard, creating the perfect backdrop for everyday living. The spacious primary suite offers a walk-in closet and ceiling fan. Its ensuite bathroom, renovated in 2022, features large marble-look tile, a double vanity with quartz countertops, and a beautifully updated walk-in shower with a frameless glass enclosure. Two additional guest bedrooms and an updated full bathroom complete the bedroom wing. Step outside to the true centerpiece of the home. Backing to a conservation easement, the backyard offers a peaceful setting with enhanced privacy. The screened, in-ground chlorine pool was completely refreshed in 2025 with new tile, repaired beam, resurfacing, and new pool light. The lanai deck was also resurfaced, creating an ideal space for swimming, outdoor dining, and entertaining family and friends. The outdoor improvements continue with fresh landscaping completed in 2025, including new sod, a stone pathway, French drains for improved drainage, and an updated irrigation timer. The fully fenced backyard (2023) provides additional privacy for pets, play, and gatherings. Ideally located near Cady Way Trail and Winter Park Pines Golf Course, you'll also enjoy convenient access to Cady Way Park amenities, including a community pool, playground, tennis and pickleball courts, beach volleyball, and walking trails. AdventHealth Winter Park and the Crosby Wellness Center are just minutes away, while Rollins College, Full Sail University, UCF, and Orlando International Airport are all within easy reach. Zoned for Brookshire Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines modern updates, flexible living spaces, and a private backyard retreat in one of Winter Park's most desirable locations. ROOF - 2024 ELECTRICAL PANELS - 2021

433 Gilbert Road, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code

Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park

3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.

2339 Inagua Way, Winter Park

1 Beds ⋅ 1 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code

Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower fixtures in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is everything and this one delivers. Just minutes from downtown Winter Park, grocery stores, shopping and dining with access to I-4, 408,417, Semoran Blvd and State Road 50. Only 10 minutes to Full Sail, 20 minutes to UCF and close to Rollins College.

262 Lewfield Circle Unit 262, Winter Park

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Corey Lott

As a Native Floridian, and with 23 years of experience in Real Estate sales, 13 Years as a Broker, I pride myself in consistently providing exemplary services that I provide my clients. I guide you through the process of selling or buying your NextHome, and make that experience a positive outcome that helps you reach your goals! When you hire me, I am your confidant, your trusted partner, leading you through the sale or purchase of your NextHome with diligence, care, and persistence, as your advocate throughout the transaction and for years to come! I am a Florida Native, a career educator, a Master’s Degree in Leadership, and a Seasoned Real Estate Broker for over 20 years. Coverage Area includes all of Central Florida, Palm Beach, Broward, St. Lucie, Martin, as well as Miami-Dade. My brokerage is a member of Orlando Regional Realtor Associations covering 19 counties, Lake-Sumter, and Beaches MLS.

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Eric Stalnaker - Realtor

Eric-Stalnaker

I’m here to make your real estate journey not just smooth, but truly rewarding. Whether you’re buying your first home, upgrading, or investing, you deserve an agent who leads with honesty, patience, and care—and that’s exactly what I bring to the table. As a retired elementary school teacher, I know the value of trust, courtesy, and commitment. Just as I once guided my students with dedication, I now guide my clients with that same steady hand—always taking the time to listen, explain, and go the extra mile. With me, you’ll never feel rushed or pressured. Instead, you’ll have a trustworthy partner who ensures you’re informed and confident every step of the way. From navigating the market to negotiating the best deals, I’ll always put your needs first—and our relationship will never end at the closing table. Let’s build more than a transaction. Let’s build a partnership rooted in trust and care. I’d be honored to help you find your place to call home—reach out today, and let’s begin this exciting journey together.

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Shannon Bass

Looking for an agent who is both committed to your needs and capable of delivering results? Your search ends here - I am a full-time agent who provides top-notch service. With a strong work ethic and a focus on my clients' best interests, I work alongside a team of skilled professionals who know how to get the job done. As a NextHome agent, I prioritize #humansoverhouses and am excited to demonstrate my abilities to you.I am passionate about real estate for a variety of reasons! The excitement of buying or selling a property, the challenge of negotiating deals, the opportunity to help people find their dream homes or investments, and the satisfaction of seeing a project through from start to finish in a constantly changing and dynamic industry are just a few!I serve the Central Florida area specializing in Lake, Sumter, Marion, and Citrus counties. I live in Grand Island, Florida and enjoy helping my friends and neighbors find their next home, first home, or sell their current home! Not ready to buy? I can also help you find a rental!

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