Killarney Circle Homes for Sale

Welcome to Killarney Circle, a hidden gem nestled in the heart of Winter Park, Florida. This enchanting subdivision is known for its picturesque tree-lined streets, friendly community atmosphere, and proximity to some of the best amenities that Orlando has to offer. Killarney Circle is perfect for families, retirees, and anyone seeking a serene lifestyle without sacrificing access to vibrant city life.

Homes for sale in Killarney Circle boast a variety of architectural styles, from charming bungalows to modern masterpieces, ensuring that there’s something for everyone. Many of these residences feature spacious yards, inviting outdoor spaces, and updates that cater to today’s discerning buyers. Imagine sipping your morning coffee on a sun-drenched patio or hosting weekend barbecues in your lush backyard oasis. With homes typically ranging from three to five bedrooms, Killarney Circle provides ample space for growing families or those looking to downsize without compromising comfort.

The subdivision is conveniently located near top-rated schools, beautiful parks, and a plethora of shopping and dining options. Enjoy weekends exploring the vibrant downtown Winter Park, known for its boutique shops, art galleries, and delightful cafes. Additionally, the nearby scenic lakes and nature trails offer endless opportunities for outdoor recreation.

If you’re looking for a community that combines charm, convenience, and a strong sense of belonging, Killarney Circle is the perfect place to call home. Explore the homes for sale today and discover the lifestyle that awaits you in this delightful Winter Park neighborhood!

Newest Killarney Circle Homes for Sale

$495,900

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Back on market. Previous contract was canceled due to buyer circumstances. Seller is motivated and ready to move forward. Fully renovated and carefully reimagined, this 3 bedroom, 3 bath residence in the heart of Winter Park offers a compelling combination of quality, functionality, and long term value. Designed with intention and attention to detail, the property presents a refreshed, modern interior that is both visually appealing and highly practical for everyday living. The home features a completely updated kitchen with new cabinetry, brand new appliances, and a clean, contemporary design that integrates seamlessly with the main living areas. All bathrooms have been renovated, and new flooring has been installed throughout the home, creating a cohesive and polished environment. The layout has been optimized to provide comfort, flow, and usability, making the space feel open while still maintaining defined living areas. Additional improvements include updated front facing windows that enhance natural light, a new main entry door that strengthens curb appeal, and two A/C units offering efficient and flexible climate control. A detached storage structure adds valuable extra functionality, providing additional space for storage or utility use. Situated on a 0.21-acre lot, the property offers a balanced outdoor area with room for enjoyment, customization, or future enhancements. The lot configuration, which includes a portion of an adjacent lot, provides a sense of added space and flexibility not commonly found in similar properties within the area. Located in a well-established Winter Park neighborhood with consistent demand, the home benefits from convenient access to major roadways, shopping centers, dining, and key destinations. Its positioning makes it attractive for both owner occupants seeking a move-in ready home and investors looking for a well located asset with strong fundamentals. This is a property that delivers on both presentation and practicality an opportunity for buyers who recognize the value of thoughtful renovations, a strategic location and a home that is ready to be enjoyed from day one while maintaining long term upside

525 Ololu Drive, Winter Park

$899,000

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

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