Killarney Circle Homes for Sale

Killarney Circle Homes for Sale

Welcome to Killarney Circle, a hidden gem nestled in the heart of Winter Park, Florida, within the vibrant Orange County. This charming subdivision offers a unique blend of suburban tranquility and urban convenience, making it an ideal place for families, retirees, and everyone in between. With its picturesque tree-lined streets and beautifully manicured lawns, Killarney Circle exudes a warm and inviting atmosphere that feels like home the moment you arrive.

Homebuyers will be delighted to discover a variety of homes for sale in this sought-after neighborhood. From cozy single-family residences to spacious modern designs, Killarney Circle features a diverse range of properties that cater to different lifestyles and preferences. Many homes boast stunning architectural details, expansive backyards, and inviting outdoor spaces perfect for entertaining or enjoying the Florida sunshine.

The community is known for its friendly neighbors and a strong sense of camaraderie, making it easy to feel connected and welcomed. Residents enjoy access to nearby parks, recreational facilities, and top-rated schools, all contributing to the area's family-friendly reputation. The vibrant downtown Winter Park, with its delightful boutiques, gourmet restaurants, and cultural attractions, is just a short drive away, offering endless opportunities for entertainment and leisure.

Whether you’re looking for a peaceful retreat or a lively community, Killarney Circle has something to offer everyone. Explore the homes for sale in this enchanting subdivision and discover the perfect place to create lasting memories in Winter Park, Florida. Your dream home awaits!

Newest Killarney Circle Homes for Sale

2640 Beverly Avenue, Winter Park
$305,000
3 Beds ⋅ 1 Baths ⋅ Killarney Circle SubDv.
Solid 1949 bungalow on a usable 50 x 150 lot (approx. 7,553 sq ft) in unincorporated Orange County with a Winter Park mailing address, just blocks from Lake Killarney. A clean shell for a fix-and-flip or a hold-and-rent strategy, with detached ADU potential under Orange County rules. 3 bed, 1 bath, approx. 1,216 sq ft of living area on approx. 0.17 acre, FEMA Zone X (minimal flood hazard). Straightforward single-story footprint with room to improve, not expanded. Out back, a canopy of mature trees creates a shaded, private backyard sanctuary. Already handled: brand-new roof (October 2026) and a replaced water heater. Kitchen cabinets are in very good shape; if you choose to update the countertops, keep the cabinets and simply resurface and repaint. The deck is in good condition today (plan on rebuilding down the road). Still to do: central HVAC is not operational (home is cooled by window units), the shower needs a light spruce-up, and a cosmetic refresh throughout. Strong bones and a good shell for a focused remodel. Location: Lake Killarney, a 234-acre spring-fed lake, is just blocks away, where seaplanes drop in for lunch at Hillstone. Centrally located to I-4 at Fairbanks Avenue, with downtown Orlando about 15 minutes away. Less than 2 miles to the newly renovated Winter Park Village with its Regal cinema, restaurants, boutiques and patio dining, and minutes to Park Avenue, Rollins College, the Morse Museum, the Saturday Farmers Market, Trader Joe's, Whole Foods, AdventHealth Winter Park and the Winter Park SunRail station. ADU snapshot: under Orange County R-1A (Sec. 38-1426), a detached one-story ADU is typically limited to 50 percent of the primary living area or 1,000 sq ft, whichever is less, about 608 sq ft here. The lot appears to meet the 7,500 sq ft minimum. Homestead and owner-occupancy rules apply. Buyer to verify all zoning, setback, ADU eligibility, homestead and permitting items directly with Orange County Zoning. Figures are informational only and not a guarantee of approval. Renovate the primary and add a rental ADU for a two-income setup, or flip it. New roof and water heater done, interior ready for a focused remodel.

2640 Beverly Avenue, Winter Park

560 Ololu Drive, Winter Park
$849,000
2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv.
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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