Refine Search
Sort by
$800,000
3 Beds 2 Baths Kenilworth Shores SubDv. 32789 Zip Code
**AGGRESSIVE PRICE ADJUSTMENTS ARE DUE TO JOB RELOCATION** 3 bedroom PLUS a dedicated office (add a closet and you’ve got your 4th bedroom!). Beautifully updated traditional Florida ranch home in one of the most prized neighborhoods in the City of Winter Park. Public records states 2267 sq ft. Total heated sq.ft. is 2,308, including the laundry area, which is under air. The original home was built in 1955. In 2001, two approximate 400 square foot additions, creating a square "U", with a deck in between each side, was added, providing more room without compromising the beautiful large fenced back. On one side of the home is a 400 sq. ft. family room, with windows on three walls, looking out onto the tree-framed back yard...the perfect place to unwind and binge your favorite show. French doors lead to a cozy deck, just the spot for barbecuing and quiet evenings. On the other side is the private primary with en-suite, which opens up to the deck. The primary bedroom offers a large walk in closet. The en-suite and front bathroom have both had recent remodels, with glass enclosures, stand alone quality vanities, etc. The en-suite also has a large jacuzzi tub, separate updated shower and large linen closet. The parquet flooring in the original home was recently replaced with engineered hardwood to match the flooring already in place. The kitchen has also had upgrades including updated counter tops, new or newer stainless steel appliances and new flooring. The dedicated office, off of the dining room, has panoramic views of the backyard...the perfect place to hide so you can focus on work and with plenty of room for a large desk and bookshelves. The spacious backyard and side-yard offers plenty of space to add a pool, large lanai, swingset, etc. And no power lines as they are now undergound. A fun FX Luminar Landscape lighting system provides all variations of lighting colors, perfect for the holidays, and controlled through a phone app. If walks are your thing, you will never be bored with the neighborhood. Windsong is a block away. Stroll down to Lake Berry or Lake Mizel and visit with the peacocks or over to Lake Baldwin for a great workout along the Lake. Downtown Winter Park is an easy 15 minute walk, where you'll enjoy shops, restaurants, concerts in the park, the Winter Park Arts Festival, Saturday farmers market, and so much more. AND, you are a short drive to downtown Orlando, The Milk District, Thornton Park, Lake Eola and Dr. Phillips Center. Updates include: New Roof: 9/2022 ( wind mitigation report available), AC: 2012, with new blower motor installed April 2023 and regular maintenance contract. New well pump for irrigation: 2023. Full Exterior Paint: 2023. <iframe width='853' height='480' src='https://my.matterport.com/show/?m=p2kpnTj13Sn&mls=1' frameborder='0' allowfullscreen allow='xr-spatial-tracking'></iframe>

1825 Loch Berry Road, 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

$2,050,000
5 Beds 5 Baths Windsong Lakeside Sec 02 43/71 SubDv. 32789 Zip Code
Residing in one of Winter Park’s most sought-after communities, this gorgeous Windsong Estate awaits. From the expansive layout and beautiful outdoor living space to the stunning Brazilian Walnut floors and detailed, high ceilings throughout the downstairs living areas, no aspect was overlooked in its construction or care since. The custom double entry doors and 19’ entry foyer welcome you into the formal living and dining, and flow into the remainder of the home. There are 5-bedrooms and 5-bathrooms (one being used as an office), a family room, formal living and dining rooms, bonus room, and a chef’s dream of a kitchen. Here you will find high-end Thermador, Monogram, and Bosch appliances, as well as custom cabinetry, granite counters, two large islands, breakfast bar, and walk-in pantry. The primary bedroom sits on the main level and is extremely spacious, offering a spa bath with dual vanities, large shower, soaking tub, and double walk-in closets with custom organizers. Upstairs is the bonus room along with 3 En-suite bedrooms, all quite spacious with large closets. Accessible from either the family room, formal living room, or primary bedroom to the outdoor living space is sure to be a favorite for everyone. The covered lanai boasts remote controlled screens, tongue and groove ceilings, tile floors, and a custom outdoor kitchen. All overlooking the custom pool by Southern Designs and lovely pond views. Community residents are zoned for A-rated schools and have access to 2 community pools, a splash park, playgrounds, and chain of lake access. With the recent price reduction, it is now the lowest priced home in Windsong Lakeside while enjoying a premium oversized, waterfront lot.

1428 Holts Grove Circle, Winter Park

$2,350,000
4 Beds 5 Baths Green Terrace SubDv. 32789 Zip Code
Brand new construction!! Ready to move in! A stunning modern transitional home located in the heart of Winter park minutes from Park Ave. As you enter this home through the large double door entryway you are greeted with a expansive open floor plan and a stunning floating staircase. The open space encompasses, a modern kitchen, great room, dining room, and living/flex room lending itself to large and small conversational areas. The space further opens up through the 30 ft stackable glass doors that opens up to a large lanai with tongue and grove ceiling, lap pool, and summer kitchen. Offering you the best of indoor and outdoor living. The primary suite located on the main floor has a incredible walk-in closet outfitted for the most discerning homeowner leading to a luxurious bathroom. The laundry room and powder bath are tucked near the air conditioned 2 car garage offering a great drop zone area and privacy. As you ascend up the floating staircase you are welcomed into a cosy loft space with 3 en-suite bedrooms with one being a large junior suite. No need to wait for your new custom home offering the best schools, shopping, and lifestyle. This house is move in ready for you to call home.

170 S Phelps 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 4 Baths Sharon Place SubDv. 32789 Zip Code
This Elegant & Charming Cape Cod Revival home is fully renovated with 5 bdrms/3 full baths/2 half baths & is situated on a large lot. It's ideally located on a secluded cul de sac with towering trees in the heart of Winter Park. It features spacious Living & Dining rooms for formal entertaining with wood floors, crown molding & plantation shutters. The Kitchen hosts new GE Stainless appliances, wine refrigerator with built in wine rack plus eat in breakfast area. The Family room offers a built in media center, travertine mosaic tile & stone fireplace, surround sound & French doors out to spacious Lanai. Lanai comes with new brick paver flooring, bead board composite ceiling & designer fans. Enormous Master has a separate sitting/exercise area & a gorgeousnew bath. One of the best features of the home is the new detached home office/media room or playroom with wonderful wood floors, crown molding & inset lighting. All the additional baths have also been redone with travertine, granite & custom wood cabinetry. The expansive backyard offers plenty of space for play & room to add a pool & pool cabana, if desired. Its walking distance to Winter Park Racquet Club & minutes from downtown WP restaurants & shops. Don't miss the opportunity to live in this architecturally unique & appealing home in the very desirable WP School District! Also available for lease at $4750/month.

1217 Sharon Place, Winter Park

$?
4 Beds 4 Baths Fontainebleau SubDv. 32789 Zip Code
Great Winter Park home ~ meticulously maintained & move-in ready! Brand new A/C & brand new carpet installed January 2014. Three bedroom + office and three full baths in main house with gorgeous hardwood floors, family room with fireplace, French doors with views of the picturesque backyard, a covered patio, a spacious master suite with dual vanity master bath & large walk-in closet. All bedrooms are freshly painted. The detached two-car garage offers a second floor guest/in-law suite complete with full bath ~ perfect for overnight guests, a fitness room, art studio or home office. Central location, closet to Grade A schools, Maitland & downtown Winter Park. Walk to the Winter Park Racquet Club or bike to Kraft-Azalea Park.

2350 Temple Drive, 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

$?
5 Beds 5 Baths Justamere Camp Rep SubDv. 32789 Zip Code
An amazing opportunity to own a Winter Park lakefront estate. Located on the shores of Lake Killarney with 100 feet of lake frontage, renovations include open pool with waterfall, covered boat dock, and numerous patios and balconies with gorgeous lake views! Almost every room offers breath-taking views! The new kitchen has stainless steel appliances and custom cabinets. The living room has a river rock floor-to-ceiling fireplace, built-ins and beautiful wood floors. The master suite is brand new with sitting room, luxurious bath and a spectacular closet. A family room with loft and grand windows connects to a second master suite with fireplace. Extras include a second family room, a Florida room, plantation shutters, vaulted ceilings, wood floors, and much more! Lake Killarney is a beautiful private ski lake with wonderful wildlife and scenery!

2411 Euston Road, Winter Park