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$175,000
1 Beds ⋅ 1 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping! One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and Mirrored Closets and updated Bath, accessible for Guests and close to Master! Updated Windows! Private Balcony! Owner is providing a One-Year Home Warranty and a $3,000 Flooring Credit. Make this affordable Unit your own!

1500 Gay Road Unit 4D, Winter Park
$244,900
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
New Price/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park
$249,900
2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
At under $250,000, this renovated 2-bedroom, 2-bath condominium is truly move-in ready. The heart of the home is the custom kitchen (2025), which features soft-close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, white granite sink, and antique brass hardware. Additional updates include vinyl flooring throughout, renovated primary shower (2026) with Italian porcelain tile, tankless water heater (2025), renovated hallway bathroom (2024), fresh interior paint (2026), and a new A/C system (2024), which was most recently serviced in June 2026. Enjoy an exceptional HOA package including water, trash, high-speed internet, cable television (150+ channels), and popular streaming services. Set along scenic Lake Killarney, the community features a private dock, boating and kayaking access, abundant guest parking, and new landscaping, with community paving scheduled for August 2026. Schedule your tour today!

2500 Lee Road Unit 104, Winter Park
$750,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park
$239,500
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
ANOTHER PRICE ADJUSTMENT! BEST VALUE!!! Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in 2023, Range 2019, Refrigerator in 2020, A/C in 2020, Double-Pane Windows and Sliding Door in 2016, Updated Electric Panel, Replaced Ductwork and added Attic Insulation. Master Bath has Double-Sink Vanity. Guest Bath has newer Vanity and Retiled Shower with replaced Shower Pan. Unit recently Replumbed. Plantation Shutters, recently Repainted and Carpeted. Short Walk to Shopping, Restaurants, Theaters, and minutes to Park Avenue with it's Village Style Shopping, Central Park with Bandstand, Spring and Fall Art Festivals, Farmer's Market and Downtown Train Station. Drive into the Community, catch a view of the Lake, watch a Sunset on the Deck and you will know "you're Home"!

1500 Gay Road Unit 17D, Winter Park
$89,000
1 Beds ⋅ 1 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code
This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and dryer. Assigned parkingspace. Community features swimming pool, tennis court and playground. Rent price includes use of the amenities, free basic cable TV, free internet, and pest control.

1695 Lee Road Unit B210, Winter Park
$129,900
2 Beds ⋅ 1 Baths ⋅ Waterfall Cove Winter Park SubDv. ⋅ 32789 Zip Code
Virtually Staged. Virtually Staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a bright and spacious living area, perfect for relaxing or entertaining guests. The kitchen features modern new (2025) appliances and ample storage space, making cooking a breeze. The bedrooms are spacious and plenty of natural light, creating a peaceful ambiance. One of the highlights of living at Waterfall Cove is the stunning waterfall feature that gives the community its name. This serene setting is perfect for unwinding after a long day or enjoying a peaceful morning coffee. The community also features a pool and fitness center, providing residents with plenty of opportunities to stay active and healthy. Waterfall Cove is ideally located near Interstate 4, making it easy to commute to major job centers in Orlando. It's also just a short drive away from downtown Orlando and Winter Park, where you can explore a variety of dining, shopping, and entertainment options. Additionally, the condo is close to Rollins College, making it a great option for convenient housing. For those who enjoy the outdoors, Waterfall Cove is close to several parks and nature reserves, where you can hike, bike, or simply enjoy the beauty of the Florida landscape. And if you're a coffee lover, you'll appreciate the proximity to Starbucks, where you can grab your favorite drink on the go. In conclusion, Waterfall Cove offers the perfect blend of comfort, convenience, and natural beauty. With its modern amenities, convenient location, and affordable pricing, it's no wonder why living in this area is so desirable. Don't miss out on the opportunity to make Waterfall Cove your new home! THIS PROPERTY MAY QUALIFY FOR UP TO 40,000.00 IN DOWN PAYMENT ASSISTANCE.

1695 Lee Road Unit E103, Winter Park
$258,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA. CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE. BRIGHT SUN-FILLED 2 BEDROOM, 2 BATH USTAIRS UNIT WITH AN OPEN FLOOR PLAN AND PRIVATE BALCONY. THE PRIMARY BEDROOM IS A SUITE, AND THE SECOND BEDROOM FEATURES A SPACIOUS WALK-IN CLOSET. SOFT, WARM COLORS, TILE AND LUXURY VINYL FLOORS, RAISED KITCHEN CEILING AND GRANITE COUNTER ENHANCE THE SPACE. BRAND NEW WATER HEATER 6/2026! LARGE ROOMS MAKE IT EASY TO ARRANGE FURNITURE. ENJOY BOATING, SKIING AND WILDLIFE OF LAKE LIVING. COMMUNITY DECK, BOAT RAMP, HEATED POOL AND SAUNAS. MAKE AN APPOINTMENT TODAY TO SEE WINTER PARK'S BEST KEP SECRET!

1500 Gay Road Unit 20D, Winter Park
$184,900
1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

2500 Lee Rd. Unit 222, Winter Park
$290,000
2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit #115, Winter Park
$279,000
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park