Winter Park FL Waterfront Real Estate, Homes, Condos for Sale

3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code

Enjoy Lake front living with all the fabulous Baldwin Park amenities! This charming 3 bedroom 2 bath home features an Open Plan with a Large Living & Dining Room along with with stunning views of Lake Spier. This move-in ready remodeled home boasts new flooring, fixtures and paint throughout. A 500sqft screened-in, tiled patio also makes this home for entertaining guests while enjoying water skiing, great bass fishing and other freshwater sports on this scenic, private, spring fed lake in the highly desired Winter Park School Zone. Roof will be replaced prior to closing, with buyer choosing color of shingles!

1875 Lake Spier Drive, Winter Park

$554,900

2 Beds ⋅ 1 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Welcome to The Cloisters Condominiums, a sanctuary nestled between the serene Winter Park Chain of Lakes and the vibrant Park Avenue. This sophisticated condominium embodies the essence of Winter Park living, offering a perfect blend of elegance and convenience. As a resident, you'll enjoy a sought-after address that places you in the heart of this charming locale. This refined fourth-floor residence spans over 900 square feet and features two spacious bedrooms and one full bath. The moment you enter, you are greeted by a charming foyer that seamlessly connects to a well-appointed kitchen. Here, you will find stainless steel appliances, ample counter space, and abundant cabinetry, making it a dream for any culinary enthusiast. The inviting living area extends an open invitation to relax on the oversized balcony, covered in lush astroturf, where you can unwind while taking in the tranquil, scenic views. The Cloisters offers an array of amenities designed for the connoisseur of life. Enjoy leisurely days by the heated pool, surrounded by meticulously maintained grounds, or entertain in the social room. For boating enthusiasts, a boat dock with eight slips provides direct access to the picturesque Lake Osceola. Golfers can refine their skills on the private putting green. This exceptional home is just a short stroll from Park Avenue, where you can explore an array of dining and shopping options. Whether you prefer to meander through Hannibal Square or embark on a serene boat ride along the Winter Park Chain of Lakes, this location offers a lifestyle of sophistication and convenience. Notable features include European white oak wide-plank flooring, Carrera marble porcelain tile in the bath, new Kohler bath fixtures, designer light fixtures throughout, plantation shutters, and a Lutron system for select lights, all combining to create a harmonious living space. For the discerning buyer, The Cloisters offers a unique opportunity to experience the art of living in a serene yet connected environment. This is more than just a home – it's a statement of refined living. The condominium fee covers cable TV, common area taxes, an escrow reserves fund, building insurance, internet, maintenance (grounds, exterior, repairs, pool), a condominium association manager, sewer, trash collection, and water, ensuring a maintenance-free lifestyle.

100 S Interlachen Avenue Unit 410, Winter Park

$1,575,000

7 Beds ⋅ 5 Baths ⋅ Lakeside Estates SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. PRICE REDUCED! This stunning lakefront estate features 7 bedrooms and 5 full baths, all within a spacious 5,000+ square foot "Del Rio" open floor plan. As a certified 100% Energy Star home, it boasts top-of-the-line appliances in the kitchen, wet bar, and butler's pantry, complemented by granite countertops. The home offers two master suites—one on each level—each featuring plush carpeting, porcelain tile, soaking tubs, glass showers, and ample his-and-hers vanity space. The main living areas are adorned with wall-to-wall tile flooring, and the bedrooms feature new carpet through most. Additional highlights include plantation shutters, freshly painted, fully insulated attic for energy efficiency, a gorgeous wooden staircase, 7-inch baseboards, Brand new dual HVAC units, internal pest control ports, a home theater room with raised flooring, and updated lighting throughout. Accordion doors lead to a vast brick paver patio with a covered lanai, where you can enjoy fruit trees in abundance and breathtaking sunsets over Garden Lake. Only you, as a lucky homeowner will be able to enjoy a little rest and relaxation on your boat! The 1 ACRE water front oversized lot offers plenty of room to add a basketball court and pool. The property includes a three-car garage (with one tandem space) extra storage racks included and a large extended driveway, providing ample parking for family and guests. This home exudes luxury, style, and comfort, all conveniently located near Winter Park, Oviedo, UCF, and top-rated schools like Trinity Prep, with shopping and dining just a short distance away.

1460 Via Sangro Place, Winter Park

$1,795,000

4 Beds ⋅ 3 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

Discover serene lakefront living at its finest in this exquisite 4-bedroom 3 bath home at 279 Rippling Lane. Set against a picturesque backdrop, this property offers breathtaking views and direct lake access, complete with a covered boat dock for your aquatic adventures. The residence seamlessly blends modern luxury with timeless elegance, featuring spacious living areas, high-end finishes, and large windows that invite natural light and lake views indoors. Custom kitchen with quartz and wood counter tops, six burner pro style range. New roof in 2023 and upgraded electric panel 2018 and Air conditioner in 2020. A split floor plan with 3 bedrooms and 2 baths up front and a spacious primary bedroom and bath have vaulted ceilings and a large walk-in closet and overlooking the lake. Enjoy the tranquil ambiance of your private retreat while being just moments away from Winter Park’s vibrant dining, shopping, and cultural attractions. Don’t miss this rare opportunity to own a slice of paradise in one of Winter Park’s most sought-after locations.

279 Rippling Lane, Winter Park

$5,950,000

7 Beds ⋅ 6.5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Welcome to the epitome of refined luxury in the heart of Winter Park. This exceptional canal front estate home was completely redesigned and transformed by E2 Homes and finished in 2023 including a brand new boathouse just completed in 2024 with access to the Winter Park Chain of Lakes. Elegant features and impeccable craftsmanship throughout, boasting 6 bedrooms and 5.5 baths in the main home within its expansive almost 5000 square feet of thoughtfully laid out living space. Upon stepping inside, one immediately notices the meticulous attention to detail from the stunning white oak hardwood floors throughout to the impressive winding staircase. The open and spacious living room with its gorgeous wine wall that holds over 175 bottles of wine plus a separate wine refrigerator makes this the perfect place to host and entertain. The downstairs front office has tons of windows that allow natural light to flood in. The chef-inspired kitchen is a focal point, equipped with an abundance of custom solid-wood cabinets with plenty of storage, beautiful quartz countertops, a large island, and top-of-the-line Thermador SS appliances including a 6-burner natural gas stove, double ovens and even a warming drawer plus a Sub Zero refrigerator — ensuring that entertaining and meal prep are effortless. Overlooking this exceptional kitchen is the cozy family room as well as easy access to the dining area, all with a view of the impressive private backyard and pool area. This outdoor oasis includes a spacious covered lanai overlooking the Salt-water pool- the perfect place to relax and unwind with Family and Friends. Tucked away on the first floor is the elegant primary suite, featuring a spa-inspired bath with double sinks, custom cabinetry and exquisite tile work, along with a large walk-in shower with 2 shower heads, a luxurious soaking tub, and a water closet. This elegant owner’s retreat also features an expansive custom walk-in closet. Two guest suites are also on the first floor just off of the family room with a full bathroom with shower that they share as well as the impressive laundry room with storage cabinets and a utility sink. Upstairs, you'll find 3 more well-appointed ensuite bedrooms that are all generous in size with custom walk-in closets and meticulously appointed bathrooms. Detached guesthouse truly offers unparalleled comfort and privacy with 2 full bedrooms, a full bathroom with dual sinks and an accessible shower and a separate living room with full kitchen featuring a 5 burner gas range. Additional amenities include solid-core doors, wide base moldings, transferable Termite Bond, and 3 tankless water heaters. This remarkable home is flooded with natural light and ambiance, exuding a warm and cozy atmosphere. Plenty of parking for you and your guests with the front circular driveway and the gated porte cochere area with side entry into the home. Zoned for some of the best public schools in the area, including Winter Park High School, and conveniently located near Park Ave with its fine restaurants and shopping. Don't miss your chance to own this exquisite WINTER PARK PROPERTY with LAKE ACCESS and experience Florida living at its finest! Truly nothing like this on the market today! Welcome Home! **please note the guest house was originally a 3 car gargae that could easily be converted back. Owners have a sketch plan.**

1246 Alabama Drive, Winter Park

$375,000

2 Beds ⋅ 1.5 Baths ⋅ Albert Lee Ridge First Add SubDv. ⋅ 32789 Zip Code

Opportunity awaits with this 1956 block construction home, nestled on a spacious .34-acre lot in the desirable Winter Park neighborhood of 32789. Offering private lake access and stunning lake views from the backyard, this property presents an ideal canvas for a complete remodel, allowing the next owner to create their dream home in a picturesque setting. The home features a garage and is situated in a great community, providing the perfect foundation for a transformative renovation project. Don't miss the chance to bring new life to this charming property and make it your own. Roof is 2003. HVAC is 2023. Plumbing Repiped in 2016 to CPVC. Septic Replaced in 2012.

2345 Albert Lee Parkway, Winter Park

$399,999

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability). Assigned parking space, community storage & mail just outside the back door. Walk to Trader Joe's, Hillstone's, Winter Park Village, Publix, movies, restaurants, shopping, etc. Bike or walk to Downtown Winter Park and Sunrail. Fully renovated unit with extra care to space planning. o Highest ceilings in the community. Solid bamboo wood flooring. Recessed lights. Surround sound & TV mount . Textured walls & ceiling . Custom trim . 4 panel sliding glass and transom windows looking over lakeview & lawn . Large renovated kitchen with glass tower cabinets . Drink bar and large island . Granite counters . Stainless steel appliances. Downlighting, under & over cabinet lighting o stainless steel appliances. End your day enjoy the lake views while making dinner. Shower cubbies & candle cubbie for baths . Italian space enhancing vanity . Upgraded fixtures . Frame mirrored medicine cabinet for hidden extra storage o Custom expanded master closet system. Community amenities include o Lakefront dock with boat slips o Private boat ramp o Lakeside pool & large lawn with Adirondacks o Grills & picnic tables o Paddle board / canoe / kayak racks o Bass fishing . Bike racks, shuffleboard . Assigned Parking space just outside the door . Storage Space o Gym, laundry rooms, community storage, and recycling. **Furniture is not inlcuded in the listing price**

151 N Orlando Avenue Unit 131, Winter Park

$1,249,000

3 Beds ⋅ 2 Baths ⋅ Georgeann Homes SubDv. ⋅ 32792 Zip Code

WINTER PARK LAKEFRONT HOME! Schedule your showing today for this Beautiful 3/2/2 Pool home with an office! NO HOA! It is situated on Lake Waunatta and part of a chain of lakes. As you enter the home, your eyes are automatically drawn to the Gorgeous views of Lake Waunatta! Wide Open Floorplan with large dining, living and family rooms and a cozy den. 2 tiled bedrooms located downstairs and the entire upstairs is the Primary Suite and large office space. There are 2 spacious closets with lots of storage space! The Primary bath is huge! Soaker tub and a newly remodeled shower! Enjoy your morning coffee or glass of wine on the private balcony outside the Primary bedroom overlooking the lake. and soaking in the sunrise or sunset. The spacious brick paved pool deck and surface was completely redone in 2021. Enjoy the evening sunsets from your covered 30' x 10' mahogany patio with teak ceilings, hard wired stereo system and outdoor lighting- just Gorgeous! Perfect home for entertaining! Private covered area over the 2021 hot tub and take a boat ride from your mahogany dock. There is plenty of room to park your boat or RV in the long driveway. The lake fed irrigation system helps to lower your water bill. 2019 ROOF, HVAC is well-maintained with service every 6 months. This home is zoned for all the top Winter Park schools! A little piece of paradise that is conveniently located to shopping, restaurants and SR 417!

7801 Georgeann Street, Winter Park

$1,499,000

32792 Zip Code

Expansive Elegance on the Water | 3.9 Acres Build Your Dream Estate at 2726 Lake Howell Lane, Winter Park, FL 32792 Step into a world of grandeur with this exceptional 3.9-acre waterfront lot at 2726 Lake Howell Lane, Winter Park, FL 32792. Priced at $1.499M, this expansive property features a remarkable 180ft dock, perfect for indulging in the ultimate lakefront lifestyle. This prime lot is ready for you to create a magnificent estate tailored to your vision of luxury. With owner financing options available, now is the perfect time to invest in your future. Positioned in a market where properties of this caliber are snapped up quickly, this superbly priced lot offers unparalleled value. Encompassed by a spring-fed lake, the lot provides pure tranquility and serenity, making it a heartwarming haven for equestrian enthusiasts. Key Features: 3.9 acres of premier waterfront property 180ft private dock with breathtaking views Ample space for a custom luxury estate Owner financing options to suit your needs Unbeatable pricing in an elite neighborhood Encompassed by a spring-fed lake in an equestrian-friendly area Secure Your Future in Luxury This is your chance to own a piece of Winter Park's most coveted real estate. Contact us today to arrange a viewing and begin the journey to your dream home. With a motivated seller eager to hand over the keys, this extraordinary opportunity won't last long. Make your move now!

2726 Lake Howell Lane, Winter Park

$1,099,000

32792 Zip Code

A Secluded Waterfront Gem in Winter Park, FL | 2.3 Acres Your Private Retreat Awaits at 2726 Lake Howell Lane, Winter Park, FL 32792 Discover an exclusive opportunity to own a pristine 2.3-acre waterfront lot at 2726 Lake Howell Lane, Winter Park, FL 32792. Encompassed by a spring-fed lake, this enchanting parcel, priced at $1.099M, features a 70ft private dock, offering direct access to serene lake views and tranquil sunsets. With owner financing available, this superbly priced lot is ready for you to build your dream estate. Imagine waking up to the gentle sounds of the water and enjoying unparalleled privacy in one of Florida's most prestigious neighborhoods. The location is a true equestrian's dream, providing a harmonious blend of pure tranquility and serenity. Key Features: 2.3 acres of prime waterfront land 70ft private dock with direct lake access Ideal for custom estate development Owner financing options available Superb pricing in a highly desirable location Encompassed by a spring-fed lake in an equestrian-friendly area Why Wait? Opportunities like this are rare. Contact us today to explore the potential of this exquisite property and start planning your luxurious waterfront escape. Your private retreat on Millionaire's Row is just a call away!

2726 Lake Howell Lane, Winter Park

$4,200,000

7 Beds ⋅ 5 Baths ⋅ Lords Sub SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Welcome to Winter Park lakefront living at its finest. In the heart of Winter Park, this new construction residence promises to be a masterpiece of luxury and modern living. Spanning over 5,500 square feet, this magnificent lakefront residence offers an unparalleled lifestyle with breathtaking panoramic sunset views. Tolaris Homes, an esteemed custom builder in Central Florida with over 45 years of expertise, will guide you from conceptualization to realization of your dream home. Designed to capture the essence of serene lakeside living, the home is ideally positioned to provide scenic vistas of the water and the vibrant hues of the setting sun. As you step onto the expansive balcony, the splendor of this property unfolds. The balcony, designed for relaxation and entertainment, offers a front-row seat to nature's nightly show, where the sky transforms into a canvas of oranges, pinks and purples. Imagine enjoying a glass of wine or hosting a gathering with friends and family, all while soaking in the tranquil beauty of the lake and its surroundings. Inside the home, elegance blends harmoniously with modernity, featuring spacious open-plan living areas that seamlessly transition from one room to the next. High ceilings and large windows ensure natural light illuminates the interior, enhancing the feeling of openness and connection to the outdoors. The thoughtful design includes luxurious finishes and state-of-the-art amenities, catering to every need and desire of its future owners. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Beyond the walls of this exquisite home, Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity.

571 Lake Front Boulevard, Winter Park

$520,000

1 Beds ⋅ 1 Baths ⋅ Whispering Waters SubDv. ⋅ 32789 Zip Code

Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box located just steps from Park Avenue. This fully renovated, one-bedroom, one-bathroom condo offers 900 ft² of single-story, ground-floor, corner-unit living. The 2018 full renovation was extensive and included new electrical re-wiring and plumbing. The scope of the renovation extended to creating new conditioned space, currently being used as the dining room from old patio space. The kitchen and bathroom updates were numerous. A few highlights are new cabinets, stainless steel appliances, quartz countertops, a farmhouse-style sink, lighting, hardware, knobs/pulls, a bathroom vanity with a marble top, and more! The corner-unit calls for expansive windows which were replaced and certainly add to the light and airy feeling inside. A LG washer-dryer combination unit that is vented to the outside was installed to make laundry easier and more enjoyable. The sparkling community pool is adjacent to Building 7, but wet feet are no concern on the neutral-colored, large-format tile that was installed in all of the main living areas. There is one deeded parking space in the gated/secured, basement-level parking garage with a small storage space and elevator service. Amenities include an on-site manager, pool, club room, and wonderful outdoor spaces throughout the community and boat slips on the shore of Lake Osceola. The charming water features and meandering walking paths complete the charming character of the community. The condominium fee includes electricity, water, trash, gas, exterior/building maintenance, budget reserves, exterior/building insurance, and maintenance of the beautiful common areas. Don't miss the rare opportunity to make this fully renovated, ground-floor, corner unit in the heart of Winter Park your new home!

311 E Morse Boulevard Unit 7-2, Winter Park

$2,190,000

4 Beds ⋅ 5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

New price on this 1/2 acre property with boat house on Lake Sue! Ready for a new owner to update or build their dream home with around the corner access to deeded private boathouse. Winter Park's desirable Forest Hills neighborhood on brick lined street with 30' on Lake Sue. Sprawling Mediterranean Ranch style home on large corner lot with secluded patio and oversized swimming pool with waterfall feature. Interior features include 4 bedrooms and 5 bathrooms. Spacious gourmet kitchen opens to family room with open wood beams and wood burning fireplace. Watch the sunset across Lake Sue from the boathouse which fronts on Fawsett Road with lift, screened enclosure, water and power. Downtown Park Avenue shopping and dining district only 1.4 miles away. Don't miss this opportunity to live the Winter Park Lake life in style!

1941 Englewood Road, Winter Park

$824,900

4 Beds ⋅ 3 Baths ⋅ Lost Crk Tr F SubDv. ⋅ 32792 Zip Code

Welcome to your very own private personal retreat! This truly one of a kind oasis of a property features 1.9 acres of lushly landscaped garden in Winter Park. A four-bedroom, three-bathroom main house with a two-car attached garage and a luxurious pool. With paid-for solar panels and a 37 seer Geo-Thermal HVAC means you will enjoy significant savings on your power bills. The additional detached garage (24x36) includes a roughed-in 20x22 space, perfect for an in-law suite, workshop, more garage space (the possibilities are endless) and an additional one car garage. This property boasts a picturesque pond and a private creek with a charming dock and seating areas for serene relaxation. As you approach the home the circular driveway leads to a large tranquil fountain welcoming you, setting the tone for the beautifully landscaped property. Step inside to find a spacious living room with a wood-burning fireplace, seamlessly flowing into the dining room and a dream kitchen. The kitchen is a chef's paradise, featuring a gas range, built-in oven, large island with seating, granite counters, a stylish tile backsplash and so much more. A bonus room off the kitchen and living room leads to the screened-in pool deck, perfect for entertaining. The saltwater pool with a spa and gas heater offers year-round enjoyment. Back inside, the split bedroom plan ensures privacy for all. The large primary suite includes an ensuite bathroom with a soaking tub, separate walk-in shower, and ample closet space with both a walk-in closet and an additional closet. The second bedroom is adjacent to a full bathroom, while the two additional bedrooms at the rear of the home share the third full bathroom. The outdoor space is equally enchanting, with your own pond and creek. Zoned agricultural, the property also includes a chicken coop, making it ideal for those looking to embrace a more self-sufficient lifestyle. This property is very unique in that the part to the west of the pond is not in the HOA, while the part East of the pond is. The wall along Dike Rd in front of this parcel is owned by the parcel The great location has you able to enjoy the best of Winter Park! Great shopping and dining awaits you! Don't miss the opportunity to see this beautiful property in person. Schedule your showing today and experience the tranquility and luxury of this unique home!

2804 Dike Road, Winter Park

$424,900

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

LAKEFRONT COMPLEX IN THE HEART OF WINTER PARK! This wonderful community is perfectly located on Lake Virgina less than a mile from Park Avenue in Winter Park. Situated on the Fern Canal and seen from the 246 square foot screened in porch with new sliding glass doors. Two bedrooms and updated baths, December 2023-New hardwood floors in the dining room and kitchen, New carpet in the living room and both bedrooms, Interior repainted, linen and a coat closets and an interior laundry with a stackable washer and dryer. The kitchen has Granite Counters, Nice stone backsplash, New Refrigerator, Double oven, Microwave and a large double stainless steele sink. For the dog lovers there is a gated pet area on the canal side of the building. Big bonus is a one bedroom guest suite that can be reserved and rented by the night. Amenities include Lake Access to Lake Virgina, Community Pool, Dock, (Boat Slips available via waiting list HOA Approval) Fitness Center, Ground floor covered parking 1 assigned space, recently updated Recreation room with kitchen, outdoor gas grill, a fire pit, steam and sauna rooms and a storage rack for kayak, canoes or surf board PLUS included is the Water, Trash,City Sewer, inside monthly Pest Control and Spectrum Internet. Just down the street is Dinky Dock which is a public boat ramp on Lake Virginia and access to the entire Chain of Lakes.Walking distance to outstanding restaurants, shoppes, Museums, Central Park, the Sunrail Station and Rollins College.

690 Osceola Avenue Unit 209, Winter Park

$649,000

3 Beds ⋅ 1 Baths ⋅ Grand SubDv. ⋅ 32792 Zip Code

Discover your own slice of paradise with this exceptional 3-acre property in Winter Park, Seminole County. Nestled within a serene, wooded setting, this lot offers a tranquil escape under a picturesque canopy of oak trees. Enjoy peaceful living with the convenience of nearby shops and grocery stores just moments away. The property features a small, charming pond perfect for stocking with fish or simply relishing the view. Though there are two small homes on-site, their value is not factored into the land's price, offering a fantastic opportunity to build your dream home from the ground up. Don't miss out on this unique chance to create your custom retreat in a peaceful yet conveniently located area of Winter Park. 2 Lots - 1297 and 1299 being sold as bundle.

1299 Grand Road, Winter Park

$649,000

32792 Zip Code

Discover your own slice of paradise with this exceptional 3.18-acre property in Winter Park, Seminole County. Nestled within a serene, wooded setting, this lot offers a tranquil escape under a picturesque canopy of oak trees. Enjoy peaceful living with the convenience of nearby shops and grocery stores just moments away. The property features a small, charming pond perfect for stocking with fish or simply relishing the view. Though there are two small homes on-site, their value is not factored into the land's price, offering a fantastic opportunity to build your dream home from the ground up. Don't miss out on this unique chance to create your custom retreat in a peaceful yet conveniently located area of Winter Park. 2 Lots - 1297 and 1299 being sold as bundle.

Grand Road, Winter Park

$7,500,000

5 Beds ⋅ 5.5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland - the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes luxury and sophistication. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100 sf with 4 bedrooms, 4 full bathrooms, and 3 half bathrooms. The detached Guest House/In-Law is approx. 500 sf, with 1 bedroom, 1 bathroom, two closets, and a wet bar. The detached Catering Room with half (pool) bath is approx. 350 sf with an additional refrigerator, wall-to-wall built-in storage, and is conveniently attached to one of the two-car garages. Enjoy expansive entertaining areas that seamlessly blend indoor and outdoor spaces, offering a grand setting for lavish gatherings. Outfitted with the finest custom finishes, gourmet chef’s kitchen, equipped with top-of-the-line appliances, an oversized island, and large dinette space. Awe-inspiring private courtyard with heated pool and spa, covered porch, outdoor grill, and several separate terraces. Impressive primary suite with office and sitting area has separate his and hers ensuite bathrooms and closets. Stunning two-story closet with office on the second floor and laundry room on first floor. Impressive entertainment/media room with state-of-the-art projector, media equipment and electronic blackout shades. Second story features a spacious loft, 3 bedrooms, 2 full bathrooms, a laundry room and two balconies. Storage is abundant throughout this property. You will find two 2 car garages behind the electronic gated side facing driveway, one garage with a kennel and a Tesla charging station. Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. More upgrades than can be mentioned. This home is a must see! <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=Q6kQoBGQuVY&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

1400 Alabama Drive, Winter Park

$3,500,000

4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Traditional Winter Park LAKEFRONT estate on the shores of Lake Virginia with stunning unobstructed views that overlook the Genius Drive nature preserve. This beautiful four bedroom, four bath, three level home is a rare find on the Winter Park Chain of Lakes. The main level, with hardwood floors throughout, offers speculator views of the lake from the moment you walk in the front door. Spacious separate dining and living rooms, family room, with french doors that open to the oversized balcony where you will have gorgeous panoramic views of Rollins College and the Winter Park skyline, two fireplaces, one wood-burning and one gas, a large office overlooking the lake, a guest bath, and a large kitchen with tray ceilings, a butcher block island, two pantries and a large dining area with french doors that open to the balcony. There is a green house with a watering system that is accessible from the kitchen and the balcony. The master suite on the second level offers spectacular views of the lake and two large custom walk-in closets. Three additional bedrooms and a guest bathroom complete the second level. There is a full stand up attic with a stairway in one of the bedrooms. The lower level offers a 33 x 18 game room with a wet bar and opens to the 20 x 40 newly refinished pool, a separate pool bath, laundry room, workshop and entry into the three car garage. The beautiful lushly landscaped backyard leads the way to a private boathouse and custom dock with over 100’ of lake frontage. This is an incredible opportunity to live in the existing home, remodel or build your own on the Winter Park Chain of Lakes.

681 Virginia Drive, Winter Park

$2,095,000

4 Beds ⋅ 3.5 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. This modern traditional one-story pool home is located in one of Winter Park’s finest neighborhoods, Sevilla. Situated on over ¾ of an acre on the creek of Mead Gardens with no rear neighbors. This special home features 4 bedrooms plus a den/office or nursery, boasting over 3600 square feet of living space. Lovely front porch, once inside one is greeted by a flood of natural light illuminating the large living and dining rooms. There are 2 primary bedrooms and spacious secondary bedrooms. The gourmet kitchen is a chef’s delight, appointed with custom wood cabinets providing an abundance of storage, ample counter and workspace, stainless steel appliances, granite countertops, an island, a workstation with a desk, and an eat-in area. Seamlessly connected to the kitchen is an oversized family room with vaulted beamed ceilings, fireplace and French doors to an outside oasis! The large covered lanai is perfect for entertaining, features an outdoor kitchen equipped with an Alfresco grill with side burner, refrigerator, sink, bar overlooking the large sparkling pool with a sun shelf, outdoor lighting, travertine and an expansive, private rear yard. The owner's retreat is a haven of tranquility with direct access to pool and a private terrace. Enjoy high ceilings and lots of natural light. It includes an attached den that could serve many uses. The spa-like bath is equipped with his-and-her baths, a soaking tub, a walk-in shower, and two walk-in closets. The exterior has been meticulously maintained with a newer roof, exterior paint (2018), pavered circular drive, a well and lush tropical landscape enhance the curb appeal. The home also features a three-car side entry garage, a super laundry room which offers plenty of additional storage, pool heater, designer light fixtures and colors throughout, engineered hardwood floors and crown molding. Situated within the sought-after Winter Park School District, with Audubon K-8 and Winter Park High School. Located just a short drive to Winter Park’s famed Park Avenue of shops, galleries and cafe's, Central Park, Rollins College, SunRail, the Farmer’s Market, and more. Call today for your private viewing of this pristine, well loved Sevilla home.

1711 Barcelona Way, Winter Park

$6,800,000

4 Beds ⋅ 4.5 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

HISTORIC LAKEFRONT ESTATE ON THE CHAIN OF LAKES – WALK TO PARK AVENUE! Absolutely stunning and timeless, this historically designated home sits on an oversized 0.74 acre lot and features a private boathouse with approximately 50’ of waterfrontage. Originally built in 1934 the 4 bedroom, 4.5 bath home embraces Spanish-revival style through its elegant use of sun-kissed terracotta floors, arched entries, ironwork details, dark wood accents, and imported chandeliers. Formal living spaces are complimented by hand-painted ceilings, custom moldings, marble fireplaces, and handcrafted built-ins. The gourmet kitchen features professional grade appliances, custom cabinetry, emerald green granite countertops, and a large island. Laid out extremely well, the interior floorplan offers a first-floor primary bedroom with walkouts to the terrace and an en suite bath with dressing room. Upstairs are three guest rooms, each with a private bath, and generously sized closets. Unlike many homes in the area, this residence offers a lower level, or finished basement, that showcases a several hundred bottle wine room and additional storage area. Inspired by its Spanish-Mediterranean roots the home relies on several outdoor courtyards, patios, terraces, and balconies to extend living space outdoors, creating the ideal setting for large gatherings with friends and family. With it’s resort-like setting, this home provides year-round opportunity to enjoy the Florida weather along with a private salt-water pool and expansive rolling green space down to the shores of Lake Osceola. Located in charming Winter Park, FL, this magnificent estate is just a short walk to award-winning dining and boutique shops as well as the Alfond Inn, Rollins College, and many other nearby historic sites and attractions.

500 N Interlachen Avenue, Winter Park

$4,650,000

5 Beds ⋅ 4.5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Amazing opportunity to own a lakefront home on Lake Virginia footsteps from Rollins College, nestled in walking distance to downtown Park Avenue shops and restaurants, and located on the coveted Chain-of-Lakes! A magnificent five-bedroom, four-and-a-half-bath home offers breathtaking lake views, capturing the essence of Florida living at its finest. This sprawling 5,600-plus square foot residence sits on an expansive .84-acre lot with a huge backyard, gracing a charming brick street, and includes an additional parcel across the street, featuring a covered boat dock/lift, ensuring endless days of waterfront lifestyle enjoyment. Step inside to discover an impressive layout designed for both grand entertaining and comfortable living. Generously sized rooms include formal living and dining areas, a cozy den/library, and a sprawling 18-by-27-foot family room seamlessly connected to the centrally located kitchen. Enjoy the sun-filled 40-by-16-foot Florida room, featuring two sets of sliding glass doors that open to the pool and lush backyard. The second floor features the primary suite with beautiful lake views, a spacious ensuite bath and two large walk-in closets. Three additional bedrooms grace this level, one with a private bath and two sharing a Jack and Jill bath, providing ample space for family and guests. A convenient fifth-bedroom suite on the first floor offers versatility, ideal for guests, a nanny, or an in-law retreat. Step outside to your private paradise, complete with a putting green, gazebo, expansive lawn, and a tropical pool perfect for refreshing dips on warm summer days. With a spacious driveway and a three-car attached garage, there's plenty of room for parking and storage. Location is key, and this home delivers. Again, enjoy the convenience of being steps away from Rollins College and within walking distance to the charming boutiques and eateries of Park Avenue. Don't miss your chance to own this exceptional lakefront estate property, where every day feels like a vacation. Schedule your private tour today!

1135 Lakeview Drive, Winter Park

$495,000

2 Beds ⋅ 2.5 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

Welcome to lakefront living at its best! This lovely direct lakefront condominium is nestled on the shores of Lake Killarney with breathtaking views from almost every room. This unit was the original model featuring 2 bedrooms, 2.5 baths, Cathedral ceilings throughout, crown molding and a spacious screened in balcony overlooking the lake. The balcony is the perfect spot to enjoy your morning coffee or a cocktail in the evening while watching all that nature has to offer. The floor plan has a nice open feel with a generous great room for living/dining and showcases a lovely wood burning fireplace. The kitchen is so spacious featuring granite countertops, stainless steel appliances, wood cabinets, breakfast nook and two openings so you can enjoy the view while cooking. The generous primary bedroom has incredible lake views, two closets, a door to the balcony and a spacious bathroom with a large updated shower and dual sinks. There is also a full attic with easy access where you can store all your holiday décor. The secondary bedroom is an en suite featuring a spacious vanity and tub. Enjoy the convenience of an indoor laundry closet with room for a full-size washer and dryer, and a beautiful powder bath is located just off the living room. Many recent updates include; all new luxury vinyl flooring, all new hardware, designer lighting and mirrors, entire interior painted, ceiling fans and new dishwasher. HVAC (2018) and Water Heater (2019). Killarney Bay is tucked away off the beaten path; however, it is one of the most walkable locations in the area being only one block from the newly updated Winter Park Village with all its wonderful shops and restaurants, and many more restaurants and shopping along N. Orlando Ave, including Publix and Trader Joe’s. Do not miss this opportunity to live in this beautiful waterfront community featuring a community dock and pool along the lake. There are only a handful of lakefront units and they do not come up very often.

620 Killarney Bay Court Unit 2, Winter Park

$5,750,000

5 Beds ⋅ 5.5 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code

Under contract-accepting backup offers. Luxurious lakefront living with unparalleled view of Lake Maitland, part of the famed Winter Park chain of lakes with 180 feet of water frontage. Enjoy tranquil views from the lake from almost every room. This custom home is located in the Via's of Winter Park and is close distance to downtown Park Ave and the Winter Park Racquet Club. This home was built by Gallimore and features five bedroom, five & one half bath. As you enter the foyer, you are immediately greeted by high ceilings, open floor plan and panoramic views of the lake. The family room is a fantastic place for entertaining, featuring a gas fireplace, wet bar with refrigerator and opens to the screened pool and gorgeous lakefront. The gourmet kitchen is a chef’s dream featuring a large center island, custom cabinetry, quartz surfaces, top of the line Thermador appliances, and walk-in pantry. The spacious master bedroom is a retreat of its own with amazing views of the lake and a sitting area. The master bathroom has custom cabinets with dual sinks, makeup vanity, modern stand alone tub, walk-in shower and a large walk around closet. There is a guest suite on the first floor with en suite bathroom and walk in closet. Two additional bedrooms upstairs with en suite bathrooms and a huge bonus room or fifth bedroom. This home also features a 3 car garage, a home office, laundry room and walk-in storage room with a large wine refrigerator. Step outside to the backyard paradise, where the pool, heated spa and sun shelf beckons you to relax and unwind. The large covered boat dock is a perfect place to watch the colorful sunset at night and has a separate enclosed storage room. Bring your boat and all your toys and enjoy lakefront living at its best! Roof and boathouse roof updated 2022.

1761 Pinetree Road, Winter Park

$825,000

2 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code

Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet, this haven of light and serenity is designed to accentuate its breathtaking views. The primary suite is a harmonious retreat featuring an en-suite bath, a spacious dressing area with ample closet space, and potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen opens to a generous living and dining area, offering picturesque views of glistening Lake Osceola – perfect for intimate gatherings or quiet evenings at home. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Exclusive amenities such as covered parking with a dedicated space conveniently close to the elevator, enhance the living experience. Additionally, boat docks, a gym, and an elegant community room within the complex provide leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the rare opportunity to own a unit with one of the most desirable water views in The Cloisters. Schedule your private viewing today and discover how this exceptional residence can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$1,599,900

6 Beds ⋅ 4.5 Baths ⋅ Lake Florence Preserve SubDv. ⋅ 32792 Zip Code

Welcome to your luxurious retreat in the heart of Lake Florence Preserve, an exclusive gated community! This stunning 6 bedroom, 5+ bath, Winter Park pool home offers the perfect blend of elegance, comfort, and recreational indulgence. Nestled along the shores of skiable Lake Florence, this property defines contemporary living at its finest. Upon entering, you are greeted by a dramatic entrance with 20' ceilings leading into an open-concept design that seamlessly integrates the living, dining, and kitchen areas. The expansive living spaces feature high ceilings, large windows, and impeccable finishes, creating an inviting atmosphere bathed in natural light. The heart of the home is undoubtedly the chef's kitchen, a culinary masterpiece equipped with an 11' x 5' center island, top-of-the-line Samsung and GE appliances, a gas range and vent hood, plus an abundance of storage, including a 10' x 4' walk-in pantry! This hub of the home is perfect for casual family meals and intimate entertaining. This residence boasts 6 generously sized bedrooms including an in-law suite addding a touch of versatility, offering a private space for extended family or guests. Upstairs you will find 4 of the bedrooms, including the generously sized 18' x 16' primary bedroom with a lake view and spacious ensuite bath including 2 large closets! Conveniently located on the second floor, you will also find a large laundry room and 19' x 18' game room with a balcony overlooking the lake. One of the most unique features of this property is its direct access to Lake Florence, a private, skiable lake! Imagine starting your day with a peaceful morning paddle or enjoying thrilling water sports right from your backyard. Launch your boat or jet skis right from your private dock with an electric boat lift. This lake setting provides a picturesque backdrop for your daily activities and adds an extra layer of exclusivity to your lifestyle. When you are done on the lake, you can continue to relax in your private salt water pool or enjoy grilling in your outdoor tiki hut containing a grill, refrigerator and outdoor tv. There are so many extras with this home including a 3-car garage, tankless water heater, 12 custom closets, fully fenced back yard, ceiling fans and recessed lighting throughout. For a full list of upgrades, please see the feature sheet in attachments. Lake Florence Preserve is in a prime location, 2 miles to 436, 3 miles to the 417 and 15 minutes to Winter Park's Park Avenue. With its prime location in a gated community and the unparalleled amenities it offers, this home represents a unique opportunity to experience the best of both privacy and community living. Don't miss the chance to make this dream property your own! ROOF - 2018, HVAC (2) - 2018, PLUMBING - 2018, ELECTRIC - 2018.

2914 Reef Knot Place, Winter Park

$4,500,000

5 Beds ⋅ 7.5 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code

This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and meticulous, landscaped grounds, combined with elevated panoramic views from a spacious 3/4 acre lot, with approx. 140 feet on the street and approx.. 110 feet of prime lake frontage. This property offers a sense of privacy, tranquility and breathtaking views capturing both northern sunrises & sunsets… Inside, you'll find extensive renovations, over the years, that have elevated the space enhanced with Wolfe-Rizor Interior Design elements… There is plenty of natural light throughout, with extensive windows, numerous French doors and a thoughtful layout that seamlessly blends indoor and outdoor living spaces. The primary level includes a defined foyer entry, secluded library/home office, kitchen, gathering room, formal living and dining rooms. The chef’s kitchen is thoughtfully designed and enhanced by an expansive island, commercial grade range, lake side breakfast room, and catering area for creating culinary experiences in hosting family and friends. The lavish living room includes room for a grand piano and has its own fireplace open to an expansive 30’ long dining room with direct lake views… along with a screened lanai... The primary suite is conveniently located on the ground floor, offering a private expansive retreat with a sitting area and serene, picturesque lake views. The luxurious primary bathroom provides a spa-like experience including modern fixtures, his/her separate baths, and a generous walk-in closet/dressing room. The main level also includes a potential 6th bedroom used previously for a caretaker’s quarters tucked away by the garage entry... The upstairs living areas, include 4 additional bedroom suites (generous sizes) located on the second floor with a couple of bonus/flex rooms and sitting area... When you're not savoring the indoor elegance, step outside to enjoy the lakefront living with entertaining terrace, tropical pool, sprawling lawn with retaining walls, boathouse and majestic cypress, oak & palm trees to enhance the lakefront lifestyle... Located on private, quiet street with oversized 3-car garage… Note: roof replaced in 2021. All within walking distance to downtown Winter Park and famed Park Avenue…

421 Lakewood Drive, Winter Park

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