Refine Search
Sort by
$6,000,000
7 Beds 8 Baths J Kronenberger Sub SubDv. 32789 Zip Code
Casa Bianca, the extraordinary Winter Park estate, has entered the market for the first time available in over 40 years. Perfectly positioned on the corner of Via Tuscany and Alabama Drive in the distinguished Vias of Olde Winter Park is one of the area's finest and most notable properties. Resting on an expanse of premier, elevated acreage and surrounded by lush landscaping with gorgeous palms and majestic oaks, this elegant lakefront estate showcases breathtaking sunset scenes over Lake Maitland, the largest lake on the Winter Park Chain of Lakes. House, guest apt, pool and boat house are being sold “AS IS” as the inherent value for this property is in the land… This remarkable lakefront estate property presents a rare, once-in-a-lifetime opportunity to own a landmark property in Winter Park.

1311 Via Tuscany, Winter Park

$2,750,000
5 Beds 7 Baths Golfview Terrace SubDv. 32789 Zip Code
This fairytale property is located in the gracious neighborhood surrounding Park Avenue known for homes of unique character & historic architecture. The main home was originally built in 1918 & has been thoughtfully renovated to modernize the home’s function while maintaining the architectural integrity. It is located in the heart of Winter Park on a rare half acre, corner lot w/ charming views of the Winter Park Country Club & golf course. The semi-circular driveway that connects to both Webster & Old England provides convenience & enhances the curb appeal. Upon arrival, your guests will immediately appreciate the lush landscape, the dynamic & steeply pitched roof, overlapping, front-facing gables & charming, arched front door popular w/ Tudor style homes. Inside the foyer & through the arched doorway to the left, this home opens to an expansive, formal living space featuring cathedral style, volume ceilings ornamented w/stained, hand hewn oak, wood floors, tall windows, french doors overlooking the brick courtyard & an elegant, floor to ceiling, wood burning fireplace. To the right of the foyer are the formal dining & sitting rooms w/ long, rectangular windows clustered together offering an abundance of natural light to these richly detailed yet comfortable interior spaces. Towards the back, right side of the home, the spacious kitchen opens to an eat-in area, family room & stairs leading down to the basement wine storage. The kitchen features real wood cabinets, black granite counter tops, a sizable island w/seating for five, a Subzero refrigerator, Viking gas range & oven w/stainless steel vent hood, double-bowl, under-mount sinks, commercial style faucet, ice maker, prep sink, under counter microwave, a pantry & a large closet-style storage space allowing for easy access to your favorite serving pieces. The eat-in area & family rooms feature multiple sets of french doors through which you are provided beautiful views of the fountain at the center of the courtyard, pool & backyard haven. The layout of the main house includes a 3-way split plan w/ all bedrooms & bathrooms on the 2nd floor. The primary is located on the left side of the home and is accessed through a rear stairwell. This spacious suite is equipped w/ a walk-in closet, Juliet balcony & charming bathroom featuring a wood vanity, marble countertop & a shower/tub combination w/ floor to ceiling white subway tile. The two alternate bedrooms & bathrooms are accessed from the entry stairwell. The front, right alternate bedroom suite features a spiral staircase w/ loft. The rear, alternate bedroom suite is adjacent to the roof top deck. Both are rich w/ character showcasing wood floors, extensive millwork, renovated baths w/shower-tub combination, white subway tile, bead-board & pedestal sinks. The guest house was built in 1925 & is located on the far side of the courtyard. It includes a full kitchen, general living space, laundry room & half bathroom on the 1st floor as well as 2 bedrooms & 1 ½ bathrooms on the 2nd floor. This flexible space could be used in myriad ways. A rear, gated driveway w/ access from Old England is located at the NE corner of the property & is discretely hidden behind a jasmine covered wall. This is the first time this century that this Old Florida property w/ its storybook exterior architecture, majestic oaks & private courtyards that leaves you w/ a rare feeling of deep connection & an undeniable sense of place is being offered for sale.

341 E Webster Avenue, Winter Park

$1,587,381
5 Beds 5 Baths Lake Knowles Terrace Add 02 SubDv. 32789 Zip Code
**SELLER IS OFFERING OWNER-FINANCING - 25% DOWN, 5.2% INTEREST RATE, 3-YEAR BALLOON** This stunning custom-built 5 bedroom, 3 full & 2 half bathroom home boasts a wonderful floor plan, detached 2-car garage with covered space and a salt system pool with gas fire pit, perfect for those who love to entertain or simply relax in style. The formal living and dining rooms are filled with natural light, making it the ideal place to host gatherings with family and friends. The newly renovated kitchen features exceptional stainless appliances; brand new wood cabinetry; beautiful quartzite countertops and spacious eat-in dining area. The kitchen opens to the family room with a gas fireplace and double french door that open onto the back porch. The master suite includes a walk-in closet and luxurious ensuite bathroom with a large, lighted Roman tub and separate shower. The master connects to a spacious office for those who work from home or need a quiet space to focus. The remaining 4 bedrooms are upstairs and are generously sized with ample closet space. The second floor also features a large bonus room situated between the bedrooms and 2 full bathrooms, one being an ensuite. The home's interior is further enhanced by archways, custom millwork and iron stair rail with patina brass banister plus designer touches throughout. Step outside and enjoy the Florida lifestyle with nicely sized pool for hot summer days, along with a gas fire pit for cool winter nights. The covered lanai provides the ideal spot to relax with family and friends. Additional amenities include plantation shutters, large laundry, travertine and wood floors, powder bath downstairs and copper rain gutters. The Massey termite bond on the home is transferable - $95 fee to transfer. Shingle roofs replaced in 2018.

1331 Hibiscus Avenue, Winter Park

$2,200,000
6 Beds 6 Baths Lake Knowles Terrace SubDv. 32789 Zip Code
Welcome to this stunning contemporary home on a brick-lined, tree street in the heart of Winter Park. Boasting a seamless blend of timeless charm and modern luxury, this 1963 home was fully remodeled in 2018. This residence showcases impeccable craftsmanship and thoughtful design, ensuring a comfortable and stylish living experience. Upon entering, you'll be greeted by an inviting foyer that leads you into the heart of the home. The main level features an open-concept layout, allowing for effortless flow and an abundance of natural light. The spacious living area is perfect for entertaining guests or relaxing with loved ones. The kitchen exudes modern sophistication with its sleek cabinetry, high-end appliances and exquisite countertops, and offers plenty of dining space for hosting friends and family. The first floor has three bedrooms and 3.5 baths, and extra space that could be an additional bedroom or office space. A highlight of this property is the addition of a second floor completed during the 2018 remodel. Here, you'll find a luxurious primary suite that serves as a private oasis. The main bedroom offers a tranquil retreat, featuring generous proportions and ample closet space. The accompanying main bath is a spa-like sanctuary, complete with a walk-in shower and contemporary fixtures, providing the ultimate in relaxation and comfort. The second floor also offers an additional bedroom with its own private bath and a flexible space that could be another bedroom, media room or additional office. Throughout the home, attention to detail is evident in the choice of finishes and fixtures, which perfectly complement the contemporary style. From the sleek flooring to the designer lighting, every aspect has been carefully selected to create a cohesive and visually striking environment. The outdoor spaces are equally impressive, with a professionally landscaped yard and a spacious patio area. Whether you prefer to unwind in the privacy of your own backyard or host gatherings for friends and family, this property offers the ideal setting. Located in a wonderful neighborhood, this home is conveniently situated near top-rated schools, Park Avenue shopping and dining, and the Winter Park Racquet Club and Interlachen Country Club. With its ideal blend of classic charm and modern updates, this fully remodeled residence is a rare find, offering an exceptional opportunity for those seeking a contemporary lifestyle in a sought-after location.

1340 Chestnut Avenue, Winter Park

$9,250,000
5 Beds 6 Baths Cloister Grove Sub SubDv. 32789 Zip Code
Proudly presenting a unique opportunity to acquire one of the most significant lakefront estates in Winter Park, on beloved Via Tuscany, moments from downtown Park Avenue's shopping and restaurants. This iconic and historic property boasts the rarity of 1.57+ acres elevated above Lake Maitland, with 138 feet of waterfrontage and breathtaking views from sunrise to sunset. Built in 1919 in the Georgian Revival style, the home captures the essence and elegance of a bygone era but is resplendent in every aspect to withstand the test of time. Spectacular curb appeal with stunning mature landscaping, a park-like backyard with a gazebo and sweeping lawn to the lake, a boat dock, an outdoor fireplace, and an impressive screened indoor pool provide endless enjoyment and entertaining possibilities. The grand entry foyer welcomes with a balance of informal and formal rooms on the first floor, ideal for large-scale entertaining, both inside and out. The first floor features an oversized living room, a formal dining room, a den, a study, a kitchen, a breakfast room, a Butler's pantry, and two sunporches. Two sets of staircases lead to 5 bedrooms and 4 full baths, plus numerous flex spaces. The upstairs owners' suite is luxurious with a fireplace, a sitting area, oversized walk-in closets, a small bar area, a closet with a second washer/dryer, elevator access, a private porch, and a rooftop terrace. There is also a guest cottage with a bedroom, a bathroom, a living room, and a kitchen. The enormous attic and basement offer large amounts of storage. Features include soaring ceilings (12-14'), heart pine floors, plantation shutters, an elevator, intricate millwork and crown molding, and a 4-car garage. The total of 8,353 heated square feet includes 7,367 sq ft in the main house and 986 sq ft in the guest cottage. The property has been meticulously maintained and enormously loved. Prime location and unrivaled lot quality.

1461 Via Tuscany, Winter Park

$9,700,000
5 Beds 8 Baths Isle Of Sicily SubDv. 32789 Zip Code
Elegant French Mediterranean gated lakefront estate on premier exclusive and private setting in Olde Winter Park… Extremely RARE opportunity to purchase a spectacular residence located on the Isle of Sicily (only 11 homes on this exclusive island) with dramatic water views on both sides of the property to enjoy sunrises and sunsets across Lake Maitland (largest lake on the 6-lake chain of lakes). This property is a one owner custom built home resting on approximately 3/4 acre upland (1.41 total acres per tax records) of property secluded on a private island off the Via’s neighborhood inclusive of the Winter Park Racquet Club walking/boating distance away… This custom-built residence was completed only 9 years ago with wonderful bright-open floor plan and flooded with light from extensive walls of glass… The interiors are not only light, but sleek, modern, and tastefully decorated with gorgeous lighting, extensive moldings and top-quality craftsmanship that will captivate you from the moment you enter the grand foyer looking straight through the 2-story living room to breathtaking views of the pool, grounds & lake... Additionally, downstairs you will enjoy a private library, formal (but open) dining room, fabulous chef’s island kitchen with Sub-Zero, Thermador Italian ILVE appliances including a casual dining area open to the lakeside gathering room with masonry fireplace, plus wine room along with the lavish primary owner’s quarters including a “Four Seasons” spa-like bath & his/her dressing areas, bar with refrigerator, fireplace & steam room… Upstairs commences with a stunning winding stairwell of glass panels taking you up to an expansive, open lounge area with curved corner bar and separate billiards are all open to the lakefront terrace… Plus, 3 flexible rooms: currently utilized as a media room, massage room, and exercise room… As well as a junior oversized guest suite and three more bedrooms all with private en-suite baths… The outdoor lakefront living includes majestic Cypress trees, expansive covered lanai, summer kitchen, tropical heated salt pool and spa with beach entry, fiberoptic lighting, fire bowls & fountain, a dedicated fire pit seating area, complete boathouse & more… Other notable features include an elevator, 5 masonry fireplaces, 2 separate laundry rooms up/down, 2 dishwashers, butler’s pantry, wine room, Control4 home automation, 4 zoned AC systems, termite bond, lake irrigation, dedicated outdoor pool bath, “oversized 4-car garage”, automatic gated circular drive entry, & more…

4 Isle Of Sicily, Winter Park

$965,000
3 Beds 4 Baths Osceola Shores Sec 01 SubDv. 32789 Zip Code
PRICE IMPROVEMENT! PRIME LOCATION! .45 ACRE HOME SITE with Charming pool home in the Heart and Soul of Winter Park's Osceola Shores neighborhood. Walk to Polasek Museum, Rollins College, Dinky Dock Park and Park Avenue shops and restaurants. Just a great location! BUILD YOUR DREAM HOME or Enjoy This Classic property, originally built for the Miller Hardware family, is truly a one of a kind property. Expansive front lawn, Split floor plan and exceptional renovation offers a range of spaces inside and out. Wood floors, custom tiles and a wood burning fireplace adds warmth and charm to this relaxed and informal gem. Professionally equipped Kitchen featuring granite countertops, Sub Zero built in refrigerator and gas stove. The spacious Owners suite has a Jacuzzi tub, large glass shower and oversized vanity with marble floors. Split plan with All 3 bedrooms having access to their own baths. This home has a nice size Den/ office space as well as a Sunny Florida Room with bright windows and French door overlooking lush landscaping and tree canopy. Custom shutters throughout add a touch of class and sophistication. Have a delicious meal in your formal dining room or step outside to your private rear deck and pool area and enjoy a casual dining experience under your custom pergola. Seperate pool bath as well. Plenty of parking for guests on the long paver driveway. Just under a half acre and set back with an amazing landscaped lawn and garden. Welcome Home!

911 Osceola Avenue, Winter Park

$4,200,000
4 Beds 6 Baths Morse And Pennsylvania SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. Under Construction. “UNDER CONSTRUCTION” Completion end of November. This custom-built Winter Park home is the epitome of luxury. Located at Morse and Pennsylvania is neighboring Park Avenue and Hannibal Square for fabulous dining and shopping. This Phil Kean-designed home features an open porch entry showcasing a courtyard heated pool/spa with a dramatic waterfall feature. The Summer Kitchen is perfect for indoor/outdoor entertaining. This 3-level home, with a walnut-finished elevator, offers multiple gathering and entertaining areas, a study or office, and a 3-car garage with an electric car charging station. The spacious gourmet kitchen features a Wolf professional range and 54” Dacor column refrigerator and freezer. The kitchen has a huge island, coffered lighted ceilings, beautiful custom wood cabinets that extend to the 10-foot ceilings, storage space, and a walk-in pantry. The adjacent wet bar features a built in Wolf coffee maker, Dacor wine tower, and ice maker. The lower level gathering space showcases a 20-foot ceiling with clerestory Anderson windows for a healthy lifestyle. The private owner’s suite, located on the second level, has separate his and hers closets with custom built-ins, a spa-like master bath with separate vanities, expansive mirrors, a free-standing soaking tub, and glass glass-enclosed shower. Outside the owner’s suite is a bright, airy loft that opens to a second-floor balcony. The Game room with a double coffered ceiling, located on the third level, includes golf simulator and wet bar. The massive entertaining balcony has expansive views of Winter Park. Additional exceptional features include; Anderson doors and windows, Smart house wiring, speakers, lighted staircase, elevator, upstairs balcony wired for projector, ensuite secondary bedrooms, water filtration system, tankless hot water, linear AC ventilation, prewires for window shades, ice maker, glass garage doors, and many more fabulous custom features.

664 W Morse Boulevard, Winter Park

$6,850,000
8 Beds 10 Baths 0000 SubDv. 32789 Zip Code
One or more photo(s) has been virtually staged. This magnificent estate was originally built in 1938 with a major addition in 1999. The estate is nestled on nearly 2 acres of prime property on Lake Maitland on the Winter Park Chain of Lakes and walking distance to all the shops and restaurants on Park Avenue. As you drive up to the estate, you will be impressed by the entry gate that leads to the huge circular paved driveway complete with a fountain. For the car enthusiast, there are 2 separate garages totaling 7 spaces. There is plenty of additional parking as this house was built for luxury living and entertaining! The home spans 19,304 square feet under air and 25,124 square feet under the roof. There are two separate grand foyers to welcome you, with high ceilings, gorgeous staircases, and magnificent lake views. This home was built to showcase the stunning lake views from almost every room. There are multiple patios and balconies to offer the perfect spots to take in the incredible views. With a total of 8 bedrooms, 3 of which are master suites with ensuite bathrooms and massive walk-in closets there is no shortage of space in this home. In total, there are 9 full baths and 5 half baths making sure everyone has plenty of space in this Park Avenue Estate. Plus, there is a caregiver’s suite with private entries for live-in help. This home is equipped with 3 kitchens making any large gathering a breeze to accommodate! As well as 3 elevators so everyone can move about the estate with ease. The expansive estate is perfect for a multi-generational family, with plenty of bedrooms and bathrooms for everyone to comfortably live together. The grounds are simply beautiful, with mature landscaping and expansive lake views there is truly nothing like it. The possibilities are endless with this home! If you are looking for a one-of-a-kind property, this is it! The grandeur of this estate and its prime location makes it a truly unique find. Don’t miss your chance to own a piece of Winter Park history!

1190 N Park Avenue, Winter Park

$?
5 Beds 7 Baths Sicilian Shores SubDv. 32789 Zip Code
Live in the Via's of Winter Park in this brand new Italian Inspired Tuscan Farm House Design. Walk to the Racquet Club! Dramatic floating Grand Staircase topped with silver flaked dome and magnificent chandelier as you enter the front door. These are someof the special features of this Five En Suite Bedroom home: Oversized kitchen and fully equipped service bar for entertaining, top of the line appliances, Bali imported Teak columns in family room, 23' ceilings throughout first floor, imported granite countertops, Olde World brick and wood beam ceilings in kitchen, oversized laundry room with pet care station and shower, three stone fireplaces, Italian Travertine floors, Hand Hewned Walnut floors, Knotty Alder doors throughout, all custom cabinetry, 4 zoned A/C, Clay Tiled Roof, Groin ceilings, faux finishes and niches throughout, game room, media room, seperate office, formal living and dining, wired for sound system, oversized corner lot with plenty of room for a pool, 3 car garages.

1800 Via Amalfi, Winter Park