Winter Park Homes for Sale

MLS Number O6212012

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 7,916
• Year Built 1996

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!

Listing Courtesy of IRON VALLEY REAL ESTATE CENTRAL FLORIDA

MLS Number O6183317

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 6,774
• Year Built 2024

Under Construction. Welcome to your custom-designed oasis of contemporary living in the esteemed Vias neighborhood of Winter Park, crafted by Z Properties. Scheduled for completion in late 2024, this rare opportunity is offered at a price reflective of its finished state. The buyer will seamlessly step into the process, with the price fully encompassing the cost of completion. This architectural gem is situated on a nearly half-acre lot spanning 6,774 square feet and perfectly balances a private retreat and an entertainer's paradise. Boasting five expansive bedrooms and six and a half baths, including a full pool bath, a first-level primary suite, a home office, and a wine cellar. The opulent pool/guest house provides ideal accommodation for guests or in-laws. As you enter the foyer, you will be captivated by the sprawling open floor plan and meticulously designed living space. You will be provided ample room for relaxation and entertainment, with the elevated pool and heated spa taking center stage. The expansive floor-to-ceiling windows flood the interior with natural light, creating an airy and inviting atmosphere. This modern residence is designed with clean lines and sleek finishes, showcasing impeccable attention to detail. High ceilings and porcelain tile flooring will define the interior on the main level, exuding an atmosphere of contemporary elegance. Laundry rooms are located on both levels for your convenience. The chef-inspired kitchen is a culinary masterpiece, featuring Gaggenau kitchen appliances, custom cabinetry, and quartz countertops. Whether hosting intimate gatherings or preparing gourmet meals, this kitchen will impress even the most discerning cooks. Complementing the gathering room adjacent to the kitchen, the vast 600-square-foot outdoor area seamlessly integrates with the contemporary luxury of the home. Enjoy your summer kitchen featuring a Kalamazoo gas grill and artisan pizza oven, perfect for alfresco dining, entertaining guests, or simply unwinding in the tranquility of nature. Step outside to your own private sanctuary, which includes an outdoor shower, where the landscaped areas are to be completed by Signature Landscape Contractors. The primary suite features a spa-like ensuite bath with a soaking tub and two spacious walk-in closets. The floating staircase leads to the upstairs lounge and family room with additional en-suite bedrooms that offer comfort and privacy, each thoughtfully designed with modern amenities and stylish finishes. Drive into your private and spacious three-car garage. Whether you're a car enthusiast or need ample storage space, this garage provides the flexibility and convenience you desire. Additional features include a complete Lutron system with KETRA lighting, Bang and Olufsen sound system and home theatre, IMG all aluminum window and door package, BOFFI kitchen and all baths, Dornbracht rain shower and fixtures, ITALdoor pivot front door, and Rimadesio interior doors. This one-of-a-kind new construction opportunity offers easy access to top-rated schools, upscale shopping, fine dining, and recreational amenities. Only minutes away from Park Avenue, Winter Park Racquet Club, and Interlachen Country Club. Enjoy a vibrant urban lifestyle while relishing the serenity of your private retreat. Why not have it all? Construction is progressing; secure this modern masterpiece before it's finished! Please inquire with the list agent for further details.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6240628

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 8,752
• Year Built 2022

Distinctive. Inspirational. Timeless. Casa K is the ultimate in luxury and location. Designed by internationally respected architect, Kamal Rizk and constructed in 2022, it is a sanctuary in the heart of our city. The unique fusion of innovative design, superior craftsmanship & luxury finishes shaped this almost 9,000 SF, 5 bedroom, 7.5 bathroom residence w/ guest suite into the contemporary estate that it is today. Upon entry, the retreat-like elegance of the great room is remarkable. This commodious space incorporates the foyer, formal living, dining, bar & family rooms. It seamlessly opens to the outside via a Pella made “wall of sliding glass.” Italian wood flooring & elaborate millwork are appreciated features, as well as modern lighting, custom window treatments & sound operated w/ ease via Lutron. Beyond the family room is the kitchen & hidden scullery where livable luxury resides. Poliform cabinetry, Cambria countertops & top of the line appliances complete these exceptionally versatile spaces. The showcase glass enclosed floor to ceiling wine refrigeration anchors the kitchen & artfully displays up to 975 bottles. The outdoor living is a natural extension of the interior spaces & features a courtyard style pool complete w/ a hand carved, granite rear wall & 16' linear in-pool fire feature. The kitchen terrace offers a DCS grill, motorized screens, cooling misters & more. A private office, lounge & 1.5 bathrooms complete the downstairs. Bathrooms on both levels showcase elevated selections from Boffi, Zucchetti, Poliform, Inbani, Paffoni & other iconic brands that enforce the refined, contemporary style & quality throughout. Notable lighting in the office, lounge & throughout include artistic fixtures by FLOS, Moooi, Serge Mouille & more. Access to the 2nd floor is provided via the elevator or stairwell. The upper floor is composed of the primary suite, 2 alternate bedroom suites, a 2nd office/flex room w/ en-suite bath, laundry room, gym & flex use guest apartment. The dreamy primary bedroom was designed with a soft entry, private terrace & hidden closets. The closets are part luxury boutique, part meticulously organized space w/ Poliform customization, motion activated light & windows w/ motorized shades made w/ UV protection to shield the interior spaces. The elegant approach to the primary bathroom includes floating vanities secured to stone covered walls, glass enclosed shower, standalone tub, custom-made dressing table & private water closets. Set apart from the primary, the alternate suites & living areas are finished w/ consistent quality & design. With flawless connection, the guest apartment may be used as an extension of the main home or it can be securely separated at a point just beyond the gym. The current owners use one of the bedroom suites as a craft room, which opens to the guest apartment's main living spaces; the family room, a full kitchen w/ island seating, laundry & a final bedroom suite. Above is a magical roof top terrace with fireplace & bar. The owner's entry is at the rear of the property, via a concealed driveway that leads to the 4-car garage, from which a hidden door opens directly into the kitchen. Guest parking is available. In this haven of opulent serenity, you may live the life you want, where you want.

Listing Courtesy of KELLY PRICE & COMPANY LLC

MLS Number O6206309

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 4,581
• Year Built 1934

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.

Listing Courtesy of KELLY PRICE & COMPANY LLC

MLS Number O6231618

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,763
• Year Built 1994

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.**

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

MLS Number O6211406

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,096
• Year Built 2025

Pre-Construction. To be built. Permit is in hand and we can start construction as soon as you are ready! Rare, new construction opportunity in the heart of Winter Park, just 1 block from Park Avenue being built FG Schaub Custom Homes, known for grand open spaces and superior craftsmanship. No expense was spared in designing this Contemporary, two-story residence with 4 bedrooms, 4.5 bathrooms, office, gym, and sauna. As you enter into the grand two story foyer, you will be awed by the floating steel stair case with glass railings, large format porcelain tile flooring, modern light fixtures, and custom elevator. Walk into the great room that features a custom fireplace, wet bar, and folding doors to the transitional room. The kitchen is a chef's dream with state-of-the-art Wolf / Sub-Zero appliances, custom cabinetry, extensive quartz counters, and an oversized island with ample seating. The dining area is located right off of the kitchen making it a perfect place for hosting dinner parties. The first-floor master suite features a private exit to the pool / spa area, a large custom walk-in closet with lighted LED rods, and a spa-like bathroom complete with a sauna. Upstairs you'll find your personal gym, allowing for private workouts any time of day or night along with three additional bedrooms with large walk in closets and en suite bathrooms. Plus, you'll love the convenience of having a laundry room both upstairs and downstairs. Open the folding doors in the great room and head out to your "Transitional Room," a staple in FG Schaub homes. This room boasts over 600 additional square feet featuring a full summer kitchen and electric roll away screens that open to your private oasis. Lounge and enjoy the best of the Florida lifestyle with a heated salt water pool, spa, fire pit, fire bowls, outdoor shower and travertine pool deck. This home is complete with an oversized 2 car garage, equipped with custom LED lighting on 12 foot high ceilings which could accommodate space for a car lift for your exotic vehicles. Interior design book is available upon request. Price is subject to change through construction.

Listing Courtesy of CORCORAN PREMIER REALTY

MLS Number O6209613

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,636
• Year Built 2024

Welcome to this new 2024 elegant Hampton's style residence, the epitome of luxury and sophistication. As you enter through the remote-operated gated entrances, a grand circular driveway welcomes you to a private motor court. The stunning two-story foyer features a glass panel staircase wrapping a temperature-controlled wine room and a transparent glass elevator seamlessly connecting all floors, including the expansive third-floor unique attic/multi-purpose room. ** Note: Elegant new RH furnishings package showcased in main living, dining areas as well as entry foyer to accelerate your move-in process enjoying this home seamlessly.* This well thought-out floor plan is ideal for modern living with a spacious open living areas including an oversize gathering room with multiple French doors opening to the lanai, a large dining area with a glass wall viewing a tranquil backyard with sparkling pool and spa. This exquisite property has four-bedroom suites in the main residence, plus a detached pool cabana or a fifth bedroom-guest suite, private hidden office and den, an expansive wonderful upstairs lounge area designed to accommodate media room, flex area with bar or even a billiards table. The gourmet kitchen, ideal for entertaining, boasts two 10-foot-long stone islands, a 60-inch Wolf range, two 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, a beverage center and a 120-bottle Sub-Zero dual zone wine cooler. There is also a separate pantry-kitchen equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample storage cabinetry ideal for catering. The luxurious first level primary suite offers a serene seating area, an all-marble primary bath featuring a glass-enclosed shower with multiple body sprays and shower heads, a soaking tub, and French doors leading to a hidden Zen Garden including a shower and fountain. The second level enjoys three additional bedrooms with en suites, an expansive family lounge, a bar, a full bath and a generous laundry room with a full complement of cabinetry. The third level is accessible via a standard staircase and the elevator, offering almost 800 additional square feet of versatile space, not counted in the square footage quoted in MLS. The outdoor living features and expansive lanai with motorized screens, a gas fireplace, a dining space and a summer kitchen with 54-inch Coyote grill, wood or gas, and separate burner covered by a remote-controlled louvered roof. The detached cabana serves multiple purposes, including a guest suite, fitness room, additional office, game room or nanny quarters, complete with a full bath, mini kitchen and washer/dryer. Luxurious finishes, Andersen windows, 10-foot solid doors, high-end plumbing and electrical fixtures, and Trane HVAC units speak to the quality of construction. The property is surrounded by mature grounds featuring magnolia trees, bamboo and cypress, creating a lush, private meticulously landscaped oasis. Close to ICC, WPRC, Phelps Park/YMCA and Park Avenue.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6203847

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,681
• Year Built 1985

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!

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6234338

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,633
• Year Built 2005

Experience the pinnacle of luxury living in this stunning five-bedroom estate situated on an oversized 120-foot wide lot on a tranquil and premier Vias brick street. This elegant Tuscan Mediterranean enjoys over 5,600 square foot of living space offering an exceptional blend of elegance and comfort, ideal for both intimate gatherings as well as grand entertaining. As you step through the foyer, you are welcomed to the open formal living and dining areas, with a wall of glass straight ahead capturing grand views of the sparkling pool and beautifully landscaped backyard. The heart of the home is the spacious, chef-inspired island kitchen, featuring top-of-the-line appliances, a hidden walk-in pantry, and a 12-by-12 breakfast nook. This space seamlessly connects to the main casual gathering room and additional flex/media room beyond, making it perfect for hosting large gatherings. The gathering area is anchored by gorgeous built-ins and a modern linear fireplace, with large sliding glass doors that open to the expansive covered lanai, blending indoor and outdoor living. The flex/media room is bathed in natural light, thanks to oversized picture windows that frame lush backyard/pool views as well. It also features a glass-enclosed, temperature-controlled wine room and a powder/pool bath that leads to an outdoor shower. On the opposite side of the main level, there is a stately office/library, with its wall of built-ins, providing a peaceful workspace with full views of the front courtyard. The grand primary suite is a true retreat, the gracious space includes a sitting area, a spa-like primary bath, two ample walk-in closets, and access to a private, trellis-covered courtyard with a fountain. The first floor also includes a hidden full guest suite with an ensuite bath. Upstairs, you'll find a large loft/bonus room with built-ins, along with three additional bedroom suites, each boasting ensuite baths and walk-in closets. The private backyard is an oasis, featuring a beautiful, tropical pool with a waterfall feature, a relaxing spa and lush mature grounds. The covered lanai extends your living space outdoors, complete with a seating/lounging area with a gas fireplace and TV, a summer kitchen, and room for alfresco dining. A split three-car garage and a picturesque brick paver driveway enhance the home's curb appeal. Situated in the highly sought-after The Vias neighborhood of Winter Park, 1231 Via Salerno offers the perfect blend of privacy and convenience, just minutes from upscale dining and shopping on Park Avenue, the Winter Park Racquet Club, Interlachen Country Club, and top-rated schools. This is a rare opportunity to own a truly exceptional home in one of Winter Park's most desirable locations.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6153641

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,847
• Year Built 1957

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…

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY