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$129,900
2 Beds ⋅ 1 Baths ⋅ S5146352 MLS ⋅ Waterfall Cove / Bldg E BLDG.
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
$435,000
3 Beds ⋅ 2 Baths ⋅ O6393594 MLS
One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Winter Park home at 405 Lake Fair Ln has been completely transformed from top to bottom, with all major systems updated and no detail overlooked, enhanced by custom architectural wood paneling that gives the exterior a modern, high-end presence and standout curb appeal. Positioned on a quiet dead-end street with no side or rear neighbors, this 3 bedroom, 2 bathroom home offers a level of privacy that is rarely found in the area. Inside, a clean, modern layout is complemented by new LVP flooring throughout, large-format designer tile in the bathrooms, fresh knockdown texture, and integrated recessed lighting that creates a bright, cohesive feel from room to room. The kitchen is anchored by an oversized quartz island designed as a central gathering point, paired with modern shaker cabinetry and a full suite of brand new, never-used appliances. The space is built for both everyday functionality and entertaining. Both bathrooms have been fully reimagined with large-format designer tile, a matte fixture package, and frameless glass shower enclosures, delivering a clean, elevated finish throughout. Beyond the finishes, the true value is in the infrastructure. The home features a new roof, new HVAC system, updated plumbing, and electrical brought to current standards, along with two new water heaters. Additional upgrades include all new interior and exterior doors with coordinated hardware, updated lighting, fresh interior and exterior paint, new blinds, and refined finishes throughout. This is a renovation executed with long-term quality in mind. The location ties everything together. Just minutes from Park Avenue and Winter Park Village, the home offers immediate access to some of the area’s most sought-after dining, shopping, and lifestyle amenities, along with convenient access to I-4 for commuting throughout Orlando. Continued growth in the area adds long-term appeal, including a new Life Time Fitness being developed just minutes away. Education options further strengthen the location. The home is near St. Margaret Mary School, a highly regarded PK–8 private institution, as well as Bishop Moore High School, consistently ranked among the top private schools in Florida and known for strong college preparation and athletics. Edgewater High School is also nearby, offering a well-established public school option within close proximity. Nearby Full Sail University, Rollins College, and AdventHealth Winter Park further support long-term demand and stability in the area. This is a move-in ready home positioned in one of the most stable and steadily growing pockets of Winter Park, offering both lifestyle, privacy, and long-term upside. A full home warranty is included. Seller is highly MOTIVATED. BRING YOUR OFFERS

405 Lake Fair Lane, Winter Park
$994,000
4 Beds ⋅ 3 Baths ⋅ NS1087637 MLS
Virtually Staged. JULY 2026 NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS! PRICE IMPROVEMENT! NO HOA! SEPTIC INSPECTED AND CERTIFIED. Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools: Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

1800 Magnolia Avenue, Winter Park
$574,900
3 Beds ⋅ 2 Baths ⋅ O6387500 MLS
Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle. The beautifully renovated interior features a modern kitchen, quartz countertops, soft-close shaker cabinets overlooking the dining room & family room. The updated bathrooms and fresh finishes throughout create a move-in ready home that feels brand new! The spacious layout flows seamlessly into the outdoor living area where you’ll find a large fenced-in backyard with a pavered patio and a cozy fireplace perfect for entertaining, relaxing or enjoying Florida evenings. Located just minutes from shopping, dining, parks, and top Winter Park amenities this property is an excellent opportunity for first-time homebuyers or investors looking for a turnkey home in a prime location. A rare opportunity to own a fully updated home with modern style and a spacious backyard in the heart of Winter Park!

1354 Indiana Avenue, Winter Park
$258,000
2 Beds ⋅ 2 Baths ⋅ O6385626 MLS ⋅ Building 20 BLDG.
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
$820,000
5 Beds ⋅ 3 Baths ⋅ O6381009 MLS
*Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental income potential. The main home offers three bedrooms and two bathrooms with real wood floors, Spanish Colonial architectural details, abundant natural light, and a functional open living layout. The primary bedroom and bathroom offer the opportunity to be expanded, allowing a future owner to customize and enhance the suite to their needs. Interior features include a wood beamed dining room, fireplace, and a built in bar with mini fridge, making this home ideal for entertaining and everyday living. Major updates include a 2015 roof, 2018 windows, and a 2022 HVAC system, providing added peace of mind for buyers seeking an updated home in Winter Park Florida. The detached in law suite cottage includes two bedrooms and one bathroom, along with a modern eat in kitchen featuring white cabinetry, butcher block countertops, and contemporary finishes. The guest house also offers its own laundry area and skylights that enhance the bright, open feel. A private brick paver patio creates a separate outdoor living space exclusively for the ADU. This ADU has the ability to be separately metered from the main house and can have its own independent address if desired. The main home’s outdoor living area includes an outdoor kitchen, brick paver patio, and a private backyard designed for relaxing and gatherings. Conveniently located near Lee Road, State Road 17-92, and Interstate 4, this property provides easy access to Winter Park, Maitland, College Park, and downtown Orlando. Buyers searching for a Winter Park home near Park Avenue, Rollins College, Winter Park Village, Trader Joe’s, SunRail, and the Winter Park Farmers Market will appreciate the central location and walkable lifestyle. This is a rare opportunity to own a versatile single family home with an in law suite ADU in one of the most desirable neighborhoods in Winter Park FL.

1927 Eland Avenue, Winter Park
$1,595,000
3 Beds ⋅ 2 Baths ⋅ O6379697 MLS
Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park
$184,900
1 Beds ⋅ 1 Baths ⋅ O6368580 MLS ⋅ 1 BLDG.
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
$630,000
5 Beds ⋅ 3 Baths ⋅ S5139410 MLS
SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort and its own ATTACHED 2bed/1 Bath IN-LAW SUITE!!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park
$108,000
2 Beds ⋅ 1 Baths ⋅ O6366205 MLS ⋅ E BLDG.
Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. Brand new a/c unit. This condo is perfectly located in a desirable area with lots of nearby shopping, restaurants, and amenities

1695 Lee Road Unit E204, Winter Park
$899,000
2 Beds ⋅ 2 Baths ⋅ O6344540 MLS
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
$290,000
2 Beds ⋅ 1 Baths ⋅ O6362403 MLS ⋅ # 151 BLDG.
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
$630,000
5 Beds ⋅ 3 Baths ⋅ S5137596 MLS
SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!! Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper — boasting shaker cabinets, quartz countertops, subway tile backsplash, and stainless steel appliances with stylish hardware accents. Located just a 10 minute walk to Lake Killarney and a 3 minute walk to Killarney Elementary School! What is even more fantastic is the distance to I-4 is literally just 2 minutes away for fast and convenient travel to and from downtown Orlando and just 10 minutes from Park Avenue Winter Park!! So many restaurants, parks, local shops and family activities, Especially during the holidays!! Come see this home with potential income and your own private 3/2 as well. This home includes a versatile 2-bedroom, 1-bath in-law suite with its own private entrance, perfect for extended family, guests, or rental potential. Enjoy extra living space in the spacious Florida room, ideal for entertaining, relaxing, or creating the perfect indoor-outdoor flow. With its thoughtful upgrades and multi-generational layout, this home blends functionality with timeless design — truly move-in ready and waiting for you to make it your own!

2612 Roxbury Road, Winter Park
$279,000
1 Beds ⋅ 1 Baths ⋅ O6337061 MLS ⋅ Whisering Waters BLDG.
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