Winter Park Homes for Sale

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Winter Park Homes for Sale

5 Beds 6.5 Baths Ellno Willo SubDv.
Experience luxury living at its finest with this custom-built masterpiece on the shores of Lake Virginia, proudly crafted by the renowned Phil Kean Design Group. Boasting five or six bedrooms, six full baths, and two half baths (plus library/office, second office, loft and lounge area, exercise room, theatre, bonus/flex room and lots of storage) sprawled across 8,188 heated square feet over three levels (includes high-quality residential elevator), every detail of this home exudes sophistication and elegance. Step through the grand entrance adorned with a custom steel front door from Cantera, where natural marble stone flooring leads you into a space illuminated by art lighting from Troy Lighting and picturesque views directly toward Rollins College Chapel. The wood-paneled walls and ceiling design perfectly complement the custom three-story Alan Mizrahi chandelier, setting the tone for opulent living. Entertain guests in the formal sitting room, complete with a custom Nero marble fireplace and a breathtaking 60" Alora chandelier. Eurowall 14-foot full collapsing doors seamlessly merge indoor and outdoor living spaces, while the kitchen beckons with Plato cabinetry, an Italian 60-inch range, and 4 slabs of Calacatta Italian marble. The double island, featuring countertops by Grothouse, is a chef's dream, accompanied by amenities like the Amuneal wine cabinet and Dacor full-height wine refrigerator. Relax in the family room under vaulted ceilings, where a 16-foot Eurowall opens to reveal views of the serene outdoors. A custom Nero Marquina marble fireplace adds warmth and charm, while automated draperies offer convenience at your fingertips. Retreat to the primary suite, complete with a beverage center and separate laundry room, before indulging in the luxurious primary bath featuring a bateau cast iron tub imported from London and heated floors. Additional bedrooms, all ensuite with walk-in closets, provide comfort and privacy for family and guests alike. Stay active in the fitness room equipped with wall-to-wall rubber gym flooring and a fully equipped "Mr. Steam" steam room. For entertainment, head to the third-floor theater boasting a 120-inch screen with a Sony projector and Triad surround sound speakers. Outside, professional hardscape and landscape design by Corey Mills and Signature Landscape create a picturesque backdrop for outdoor living. Enjoy 148 feet of lake frontage with seawall spanning property, a renovated boathouse, and a newly installed dock with Trex decking and boat lift. Experience resort-style living with a pool designed and installed by Paradise Pools, featuring knife edge and Infinity edge designs, Pentair equipment with mobile app control, and an outdoor kitchen equipped with DCS appliances, Sunbrite television, and more. Resting on an elevated (approximately 3/4 acre lot) on Lake Virginia of the Winter Park Chain of Lakes, this exceptional property offers unparalleled luxury and waterfront living. Don't miss the opportunity to make this your own private paradise.

181 Virginia Drive, Winter Park

6 Beds 6.5 Baths Cloister Grove Sub SubDv.
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.

1210 Via Capri, Winter Park

4 Beds 4.5 Baths Winter Park SubDv.
**500 N. INTERLACHEN AVENUE, WINTER PARK, FL 32789** INCREDIBLE OPPORTUNITY – HISTORIC LAKEFRONT ESTATE ON THE SHORES OF LAKE OSCEOLA – ONE BLOCK FROM 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

5 Beds 6.5 Baths Chapman & Chase Plan/Town/Wint SubDv.
Exquisite Winter Park estate designed by award winning architect Larry Boerder. Located just steps from Park Avenue’s upscale boutique shopping and restaurants, this architectural masterpiece is the epitome of luxury Winter Park Living. From the Restoration Hardware lighting, to the Thassos marble floors, nero marquina marble fireplace, laser cut stainless steel art panels, and designer finishes throughout, no expense was spared during the construction of this stunning residence. As you step through the custom glass front doors, you’re immediately greeted by the soaring 18-foot ceilings of the great room. The expansive kitchen is a chef’s dream, featuring imported custom cabinetry, marble countertops, Wolf & Subzero appliances, and the crown jewel, a French La Cornue gas range. Owners can choose from two primary bedroom suites, both with top-of-the-line custom closets, rich wood floors, and spacious spa baths. On the second floor there are three additional ensuite bedrooms, two of which have access to a 25 ft long balcony overlooking the pool and impeccably maintained grounds. At the end of the 90 ft grand hallway, you will find a magnificent, curved staircase with a striking chandelier, and the entrance to the lower level which is an entertainers dream, featuring a bar, theater, fitness room, and a full bathroom. Additional features include a home office, lounge, wine cellar, and multiple laundry rooms. Exterior amenities include a travertine driveway, dual 2 car garages with room for car lifts if you’re a car enthusiast, a resort style back yard with a summer kitchen, 50 ft covered lanai for entertaining, a massive pool and spa, and a private putting green to practice your short game. Don’t miss your opportunity to own one of Winter Parks most remarkable residences.

1001 Anchorage Court, Winter Park

5 Beds 5.5 Baths Sicilian Shores SubDv.
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

6 Beds 6.5 Baths Cloister Grove Sub SubDv.
Welcome to the epitome of refined luxury. Nestled in the heart of "The Vias" in Winter Park, this exceptional estate is the ultimate blend of timeless sophistication with contemporary comfort. Boasting 7,535 square feet of living space on a sprawling half-acre lot, this residence was built with impeccable craftsmanship and an array of upscale amenities, including a charming guest house and a distinctive natural slate roof complemented by timeless copper gutters. Designed with meticulous attention to detail, this distinguished home boasts 6 bedrooms and 8 bathrooms. The main level hosts an inviting primary suite with dual oversized walk-in closets, along with a chef's kitchen meticulously appointed to accommodate a dinner party of any size. Featuring dual Wolf ovens, dual Miele dishwashers, a Sub-Zero refrigerator and wine fridge, custom Busby cabinets, and rare Italian Calacatta Gold marble countertops, this kitchen is a culinary haven. Adjacent, the living room showcases exquisite Pecky Cypress beams and one of three wood-burning fireplaces placed throughout the residence. Floor-to-ceiling accordion glass doors in the great room seamlessly blend indoor and outdoor spaces, leading to the picturesque Hampton's style pool and a fully equipped summer kitchen, ideal for both entertaining and enjoying the meticulously landscaped grounds. The spacious second floor reveals four generously proportioned bedrooms and three bathrooms, each complete with spacious custom walk-in closets. Additionally, the upper level features a convenient second laundry room, private home gym, and a sizable flex space adaptable to various lifestyle needs. Above one of the two-car garages, a detached mother-in-law suite awaits, comprising a full bedroom, a bathroom, and a separate living room, offering unparalleled comfort and privacy. Come experience the laid-back elegance and vibrant energy 1460 Via Tuscany has to offer.

1460 Via Tuscany, Winter Park

5 Beds 6.5 Baths Tuscania SubDv.
Nestled in the esteemed The Vias area and near the WPRC, resides a home signifying the essence of sophistication and luxury. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to a double-height foyer and great room separated by a glass-railing catwalk. The property boasts exclusive features like a formal dining room endowed with a glass-encased wine display as well as an intimate den/office safeguarded by private entrance doors. The airy master bedroom is adorned with sliding doors that open up to reveal a private lanai overlooking the pool area; one cannot overlook its distinctively vast his-and-hers walk-in closets complemented by a spa-like luxurious bathroom suite. A state-of-the-art kitchen featuring gold Calacatta Quartz countertops/backsplash matched alongside an oversized walk-in pantry, creating everyday usability flanked with indulgence! Two separate upper and lower level laundry rooms serve this expansive open floor plan a win-win situation for convenience! Adding exceptional charm to this stunning home is a family room equipped with zero corner sliding doors opening up towards the summer kitchen leading onto a large covered patio encased in travertine pavers-- making it your personal haven for enhancing entertainment moods. Venturing upstairs via an elegant Quartz staircase leads you to an additional four en-suite bedrooms (each with walk-in closets). Complementing your leisure needs flawlessly are a comfy lounge space and fun-filled game room with a wet bar setup; creating a direct pathway onto a sprawling balcony exhibiting glass railings overlooking backyards - commanding mesmerizing views of your saltwater gas-heated pool and cozy gas firepit with a seating area for social gatherings! A dedicated full-bath pool with a steam shower. Home gets fully enveloped using high-quality materials fashioned from Large Porcelain format tiles, European tiles, Travertine pavers, and Swiss-origin WPL catering to its strength quotient. Tor uniquely detailed outlook, the property also offers a detached additional building that has been thoughtfully renovated to deliver an extra 600 sq ft of living space - not part of the main house size calculation (6475 sq ft). With 1 bedroom, 1 full bath, a fully functional kitchen circumvented by a living area, and a covered/tiled porch; it makes for a rare addition delivering discernible usefulness. Think creativity! Convert it into a guest house, in-law suite, gym space, professional office setup, or even a hobby room - multiple endless usage options make its possession a valued choice! The home is available now and move-in ready! Get one step closer to owning the realization of your dream dwelling experience!

2161 Sharon Road, Winter Park

5 Beds 5.5 Baths Maitland Shores First Add SubDv.
Gorgeous Winter Park home beautifully curated with designer details and recently featured in June’s “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded section in the Via’s of Winter Park. This designer home has been significantly enhanced inside and out by the current owner and is in “brand new condition.” The home features 5,100 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms, 1 half bathroom, 3 car garage, pool, patio, outdoor shower and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler’s pantry. Past the foyer you are led to a spacious and grand formal living room with lacquered walls and 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef’s kitchen includes newly painted white custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women’s dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include new slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine new iron French doors, new ebony-stained white oak hardwood floors, lacquered walls, newly renovated master bath and two ensuite baths. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It’s also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for A-rated Dommerich Elementary, Maitland Middle School, and Winter Park High School.

2228 Azalea Place, Winter Park

5 Beds 4.5 Baths Virginia Heights SubDv.
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

5 Beds 7.5 Baths Osceola Shores Sec 03 SubDv.
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

5 Beds 5.5 Baths Robert Dhu Macdonald Park SubDv.
One or more photo(s) has been virtually staged. Pre-Construction. To be built. Customize the finishes-to-suit on your new home located on one of the most sought-after streets in Winter Park. Lincoln Circle is a quiet street next to Park Avenue restaurants and shopping. Easily walk to your favorite shops, restaurants, and the Winter Park Golf Course. Presented by an established, award winning luxury home builder, this bespoke home includes premium features, appliances, fixtures and finishes as follows: ELEVATOR, WOLF/SUB ZERO appliances, wine cooler tower, built-in coffee maker, trash compactor, AUTOMATED LIGHTING and window treatments, full house SOUND SYSTEM, first floor primary bedroom with ensuite washer/dryer and two-person shower, additional GUEST SUITE FIRST FLOOR, 11’4” FIRST FLOOR CEILINGS with 10’ DOORS, wet bar, large vaulted loft, bonus room, three full suites upstairs, trey ceilings, master-carpentry detail throughout, “store-front” window and door system in front, two 10’x10’ full-view garage doors, circular driveway, heated pool with spa and wet sun deck, plenty of pool deck space, and exquisite landscaping. A 6’ masonry-stucco wall encompasses the rear perimeter. The rear cabana houses the summer kitchen, a pool bar, pool-bath and outdoor shower. Enjoy two fireplaces: a linear electric fireplace in living room and natural gas fireplace on rear lanai. Life-like virtual renderings show sample finishes only. You may select your own finishes and colors upon pre-construction purchase. Call now to schedule your meeting with the Builder and get started on your new home!

985 Lincoln Circle, Winter Park

6 Beds 6.5 Baths Comstock Park SubDv.
Introducing 861 Bonita Drive, located within Winter Park's charming brick-lined streets. This exquisite custom estate spans nearly 7,000 square feet, boasting Mediterranean architecture complemented by lush landscaping, creating a serene oasis in the heart of the city. As you step through the grand double glass-paneled door you're led to an elegant parlor room divided by ornate cast stone columns. Every detail of the home has been custom-selected with luxurious designer finishes. The walls of the home are adorned with modern Venetian plaster, while Forbes and Lomax light switches, Waterworks faucets and custom vent covers add a touch of sophistication throughout the home. The gourmet kitchen is at the heart of the home featuring custom cabinetry, marble counter tops, and design elements from Portugal. A Lacanche range offers the convenience of gas and electric ovens. The kitchen is equipped with a spacious pantry room, two Sub-zero refrigerator drawers, a Sub-zero Pro 48 glass door refrigerator, a pebble ice machine, and paired with dual sinks and dishwashers. A butler's pantry, situated between the kitchen and dining area, offers a perfect space for entertaining, complete with a long marble counter for serving, a Sub-zero wine refrigerator, two additional Sub-zero refrigerator drawers, two warming drawers, and plaster shelving for storage. A generously sized primary bedroom is conveniently located off the main living area with privacy in mind, filled with natural light and complete with a sitting area and views of the pool. The primary bathroom suite, renovated in 2019, features designer touches from top to bottom. Connected to the bathroom is a thoughtfully designed closet equipped with custom shelving with plenty of room for storage and dressing. Upstairs is a state-of-the-art home theater, three additional bedrooms, and a dedicated laundry room with the largest capacity washer and dryer. A desk/office area caters to the needs of a home manager. Outside is a covered patio area overlooking the tranquil saltwater pool and spa. An in-law suite with a separate entry and guest quarters over the garage provides privacy and comfort for visitors. The rear garage, boasting three spaces and air conditioning, coupled with the front garage's single space, offers ample parking and storage options. The home has a four-zone air conditioning system ensuring year-round comfort. Additionally, the property is equipped with two tankless water heaters, one on each side of the house, a whole-house generator, and a water softener system. With its timeless elegance and modern amenities, this home offers a unique lifestyle of comfort and sophistication in the heart of Winter Park.

861 Bonita Drive, Winter Park

4 Beds 5.5 Baths Virginia Heights SubDv.
Welcome to 1391 Richmond Road. A true work of art and surreal living experience now on the market for the very first time. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of Winter Park, a short stroll to Park Avenue along the stunning shores of Lake Virginia. This handcrafted Georgian style home, designed to emulate New York City townhouse living was masterfully crafted on a magical lot abundant with pristine natural vegetation. Enjoy the Florida lifestyle with frontage on Howell Creek…kayak or paddleboard amongst incredible wildlife to the Winter Park Chain of Lakes. As you arrive, you are greeted by an enticing mix of traditional and old Florida plantings, highlighted by Bevolo exterior lighting and gas lanterns leading the way to your custom mahogany/iron work front entry door. The grand foyer with soaring ceilings, stunning black and white marble flooring, and grand staircase which was built in place, with hand molded railing providing a welcoming signature. Flanked by separate formal living and dining areas on either side, the formal dining room features custom hand painted Gracie brand wallpaper and leads to the butler’s pantry with wine refrigerator. The gourmet kitchen boasts Busby cabinetry, new six burner Decor gas range, new Bosch dishwasher, Subzero refrigerator, large island with prep sink, built-in oven, and naturally lit breakfast area overlooking the backyard oasis. The kitchen opens to the spacious family room with extensive venetian painted millwork, gas/wood burning fireplace with custom Italian made marble surround, 11’4” ceilings, and French doors leading to the terrace and backyard retreat. The formal living room complete with venetian plaster, gas fireplace with custom marble is connected to the family room with a stunning barreled ceiling hallway conveniently located to a chic powder bath. The main floor also includes a full pool bath with access to one of the two garages with air conditioned work room, and a 2nd back staircase. The upstairs primary suite is a sanctuary, graced with an antiqued mirror entry, gas fireplace, double French doors leading to the serene balcony overlooking the statement backyard, and two custom closets with vast cabinetry and lighting. The spa-like bath features Walker Zanger flooring, generous walk-in shower, soaking tub and dual vanities with make-up area. Two additional ensuite bedrooms are also upstairs along with an office/flex room, full bath and laundry room. The second detached garage features a bonus room/convenient home gym. No expense was spared when building which displays antique and unique lighting fixtures, custom millwork, surround sound, central vacuum, reverse osmosis water filtration, and extensive storage throughout. Notable window treatments from the finest textile manufacturers worldwide (Clarence House, Elitis, Nancy Corzine, Carragio), wallcoverings (Fornasetti, Gracie, Schalamandre), lighting (Aerin, Niermann Weeks). This bespoke home is an entertainer’s dream with multiple outdoor areas to relax amongst the secret garden of terraced landscaping and four thoughtfully placed fountains. Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High!

1391 Richmond Road, Winter Park

5 Beds 5.5 Baths Ripples Sub 18 SubDv.
Pre-Construction. To be built. by Element Home Builders and designed by leading architect Dan Delong Origins Residential Design. This two-story, 4,483-SF home sits on almost a half acre of land in sought-after Winter Park next to Lake Sue and Beeman Park. Absolutely breathtaking in location and design, this 5-bedroom, 5 full/2 half-bathroom, custom home is meticulously designed with the perfect blend of elegance, comfort, and only the finest finishes and stylish accents in mind. The stunning foyer calls in natural light and welcomes residents and guests alike into the home's flowing open floor plan. Stepping into the massive great room, the space is open yet comfortable and offers views of the sparkling pool area. The expansive dining room is an entertainer's dream with plenty of space for hosting parties or events. The open flow design continues into the gourmet kitchen, which is a chef's dream and ideally located with open views through to the dining and great rooms. Carefully chosen, top of the line appliances and tons of space make the kitchen ideal for creating culinary masterpieces for family or friends, while the cafe eating area is wonderful place for sharing morning meals or late-night snacks. Just off the magnificent great room rests the private master suite complete with a jaw-dropping wardrobe suited for any fashionista. The luxurious spa-like master bathroom is a true retreat after a long day and features double sinks, an oversized shower, and soaking tub. A sizable guest room is also downstairs just off the foyer, offering guests privacy, comfort, and easy accessibility to the home's downstairs features. Upstairs are three spacious bedroom suites, each with its own full, private bath, closet space, and large windows for welcoming natural light into the space. The three suites surround a roomy loft area, which is ideal for gathering together for movie or game nights. Stepping outside, you'll fall in love with the gorgeous pool area and unrivaled cabana space, perfect for enjoying the Florida lifestyle, lounging, and entertaining. A pool bathroom and storage area make for added convenience when spending time outdoors. The three-car garage offers tons of vehicle space, as well as ample storage. The back side of the lot is lined by natural, towering trees, offering plenty of privacy, and the entire yard is the perfect canvas for creating the oasis of your dreams.

2379 Forrest Road, Winter Park

5 Beds 5.5 Baths Windsong-Lookout Lndg Add 01 SubDv.
Virtual Tour. Welcome to this stunning custom-built pool home located in the highly sought after Windsong community. The home offers 5,066 sq. ft. of living space with 5 bedrooms, 5 and a half bathrooms, oversized 3 car garage and private in-law suite. Built in 2013 by Dave Cahill Company Homes, this thoughtfully designed home has left no detail overlooked and is an entertainers’ dream. Enjoy an open floor plan, high ceilings, gas fireplace and a spacious covered lanai that seamlessly blends indoor and outdoor living. The first floor features an eat-in kitchen, living room, dining room as well as the primary suite, additional bedroom ensuite, office, laundry room, wine room and powder/pool bath. The generously sized primary suite overlooks the backyard and boasts his and her vanities, soaking tub with separate shower and a large walk-in closet. The gourmet kitchen is enhanced with solid wood custom cabinetry, exotic blue granite, top of the line appliances, multiple dish washers, beverage drawers, and a large hidden pantry. The living space opens to a beautiful covered lanai with summer kitchen and bar overlooking the resort style pool complete with waterslide, fire bowls and spa. The second floor includes two bedroom ensuites with a large bonus/media/game room and wet bar for entertaining. The private in-law suite has its own entrance with stairway and offers a kitchenette, living and dining room with a separate bedroom ensuite. Play or swim in the lush backyard or enjoy the amenities of the Windsong community including clubhouse, community pools, splash pad, playgrounds and access to the beautiful Winter Park Chain of lakes. Conveniently located to Winter Park, Baldwin Park, Park Avenue, downtown Orlando. Top rated Winter Park Schools as well as Lake Highland Preparatory School are only minutes away. Call for your private showing today.

1737 Lookout Landing Circle, Winter Park

5 Beds 5.5 Baths Charmont SubDv.
Under Construction. Step into the realm of unparalleled luxury with this contemporary masterpiece, a fusion of architectural brilliance and refined elegance constructed by Davila Homes scheduled for completion in late 2024. This exceptional residence boasts five spacious bedrooms, five and a half bathrooms and an impressive 4,188 square feet of meticulously designed living space. Nestled within the exclusive enclave of Winter Park, this new construction opportunity redefines opulent living with its meticulous design. This architectural marvel boasts a unique contemporary design, expertly crafted to seamlessly integrate form and function. From the moment you arrive, the striking facade will captivate you with its sleek lines, expansive windows, and thoughtfully curated landscaping, setting the stage for the unparalleled elegance that lies within. Step inside, where an abundance of natural light cascades through the open-concept living spaces, creating an inviting atmosphere that is both luxurious and welcoming. Entertain with ease in the gourmet kitchen, featuring top-of-the-line appliances, custom cabinetry, spacious island, and wine bar while the adjacent living and dining areas provide the perfect backdrop for hosting gatherings large and small. Retreat to the lavish primary suite located on the first level, where serenity awaits amidst a private sanctuary of comfort and style. Indulge in the spa-like en-suite bath, complete with a soaking tub, oversized shower, and dual vanities, creating the ultimate oasis for relaxation and rejuvenation. An additional bedroom is located on the first level for convenience. Ascend to the upper level of this exquisite residence and discover a spacious gathering room, designed for relaxation and entertainment. With ample space for lounging and socializing, this upstairs haven offers endless possibilities for creating cherished memories with family and friends. Adjacent to the gathering room are three generously sized bedrooms, each offering its own unique blend of comfort and style. Whether for family members, guests, or a home office, these bedrooms provide versatile spaces that can adapt to your lifestyle needs. Outside, discover your own personal paradise in the meticulously landscaped backyard, where a sparkling pool/spa, expansive patio, and outdoor kitchen await, providing the perfect setting for alfresco dining and entertaining year-round. With additional features, including a two-car garage that conveniently leads to your mud room and laundry area, every aspect of this residence has been carefully considered to exceed the expectations of even the most discerning homeowner. Situated in a coveted locale, this residence enjoys an enviable address surrounded by top-rated schools and mere moments from renowned attractions such as East End Market, Baldwin Park, and the acclaimed Park Avenue. The East End Market is just around the corner stands as a culinary oasis, boasting an array of artisanal vendors that promise unique shopping experiences unparalleled elsewhere. Experience the pinnacle of luxury living with this exceptional new construction home. Inquire with the listing agents for further details, and prepare to be captivated by a lifestyle beyond compare.

210 E Lake Sue, Winter Park

4 Beds 4.5 Baths Valencia Terrace SubDv.
Quintessential Downtown Winter Park home with all of the character and amenities that make this lifestyle so sought -after. Well designed floor plan combines expansive open kitchen/gathering room as well as a large formal dining room and separate living room. Three way split bedroom plan offers two bedrooms downstairs and two bedrooms plus an additional office or media room upstairs. Each of the bedrooms has a private bath. Well-appointed kitchen with Wolf gas range, unique onyx mosaic backsplash, loads of storage and island seating. Ideal for entertaining with French doors leading to large covered terrace overlooking we an incredible waterfall pool. The backyard feels like a private resort- in addition to the heated pool and spa, enjoy a gas firepit with built-in seating and an outdoor kitchen- all surrounded by lush tropical landscaping. Relaxing upstairs terrace with views of WP golf course. Other notable features include three year old HVAC systems, newly painted interior, charming front porch. Ten foot ceilings and walls of windows throughout afford abundant natural light. There is a charming second entry designed with built-ins for an ideal mudroom/drop zone. Architectural details include crown moldings, custom designed wrought iron, stone columns and a beautifully lit tray ceiling in primary bedroom. Real (not paver) brick driveway, porches and pool deck. Mature landscaping with tropical palms, magnolias and signature oaks. This home has been impeccably maintained and exudes quality throughout. Of course, the location is one of the most outstanding features of this home- Walk to Farmers market, Park Avenue shoppes and restaurants and of course the Winter park 9 just one house away.

1108 N New York Avenue, Winter Park

5 Beds 5.5 Baths Comstock Park SubDv.
Welcome to 1563 Lakehurst, a stunning five-bedroom, 5.5 bath pool home that epitomizes luxury living and has been meticulously remodeled. This residence won the prestigious Orlando Parade of Homes 2021 first place and grand award and is a masterpiece of design and craftsmanship. Initially conceived by the local architect Gary Hancock, this home was reimagined by the renowned Ted Maines and Hardwick General Contractors, resulting in a comfortably elegant living space deserving of accolades and awards. On an oversized lot on a charming brick-lined street in one of the most desirable neighborhoods of Central Florida, this home boasts an enviable address just moments from shops and restaurants of Winter Park and Park Avenue. Spanning over 4,300 square feet, the main house offers spacious and inviting living areas flooded with natural light. Every detail was considered throughout the renovation: top-of-the-line Anderson windows, custom inset cabinetry, luxury bi-fold Origin door, designer lighting, engineered oak floors, solid-core interior doors, custom mahogany front door, and many more finishes discerning buyers will recognize and appreciate. The kitchen is the heart of the home, featuring Wolf and Sub-Zero appliances, extensive custom inset cabinetry, Cambria luxury quartz, and a center island spanning almost 20 feet. The separate breakfast bar allows quick and easy coffee, tea and breakfast prep without disturbing the clean aesthetics of the kitchen. The open living space has an Origin luxury bifold door for indoor-outdoor living, and a vaulted cathedral ceiling finished with designer lighting. The lounge and bar offer a pre-dinner retreat before using the artfully designed formal dining room, with smoked glass, dramatic navy wood paneling, and custom herringbone wood floor. The light-filled primary bedroom is also on the ground floor. Updated in 2022, this bedroom has Phillip Jeffries wall covering and Flos pendants. The bath has two independent vanities and separate closets. A full pool bath with shower, additional powder room and large office or flexible space complete the first story. Three additional bedrooms provide ample space for family or guests. The largest bedroom has an en-suite bath, and two additional bedrooms are connected by a large bath with a double vanity. For those needing additional accommodations, the in-law suite over the garage offers an additional 400-plus square feet of living space, ideal for guests or multigenerational living. The extensive back patio has multiple areas for dining, entertaining and enjoying Florida living. The summer kitchen was installed in 2021, and there is additional wine and refrigeration space. The front parking pad and landscaping were completed in spring 2024. All the systems are from 2020 or newer. The roof was installed in 2020, two tankless water heaters were added in 2020, upstairs and downstairs Carrier air conditioners are from 2023, the guest house air conditioning is from 2021, and the guest house water heater is from 2024. All drywall, ceilings and tongue-and-groove were replaced, the home was taken down to the studs, and has an effective date for the build as 2020. With its unparalleled location, luxury, and craftsmanship, this home is a rare find. Don't miss your opportunity to own a piece of Winter Park's finest. Schedule your private showing today!

1563 Lakehurst Avenue, Winter Park

6 Beds 3.5 Baths Windsong-Knowles Place SubDv.
One or more photo(s) has been virtually staged. Exquisite Villa Style Masterpiece. With 6 bedrooms and 4 bathrooms, this residence redefines opulence, boasting a seamless fusion of timeless elegance and modern comfort. As you enter, prepare to be mesmerized by the sheer grandeur of soaring 11-foot ceilings and exquisite custom woodwork adorning every corner of this architectural gem. Crafted to perfection, this home is a testament to meticulous attention to detail and uncompromising quality.Nestled in one of Winter Park's most coveted neighborhoods, privacy and exclusivity are seamlessly woven into the fabric of everyday living. Yet, the convenience of proximity to top-rated schools, upscale dining, elite shopping destinations, and vibrant entertainment options ensures a lifestyle of unparalleled convenience and sophistication.Designed by the esteemed Morales-Keesee Design Associates, renowned for their visionary creations including the famed Casa Teresa, this residence stands as a true masterpiece. Every aspect of its design, from the majestic concrete Masonry walls to the intricately patterned travertine flooring, reflects unparalleled craftsmanship and artistry.Indulge in a sanctuary of tranquility and luxury, where double-pane hurricane and sound-proof windows envelop you in a haven of serenity. Marvel at the custom carved woodwork that graces every corner of this home, a testament to the dedication to creating an ambiance of timeless elegance and refinement.Immerse yourself in the allure of this Villa Style home, where every detail has been thoughtfully curated to evoke a sense of grandeur and sophistication. Your dream of owning a luxurious retreat in Winter Park awaits—schedule your private viewing today and elevate your lifestyle to new heights of splendor and distinction.

1824 Harland Park Drive, Winter Park

5 Beds 4.5 Baths Kenilworth Shores Sec 01 SubDv.
Pre-Construction. To be built. Located in the heart of Winter Park this exquisite modern residence is being built by Vimaro Homes and features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, porcelain countertops, a massive walk-in pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home.

1833 Loch Berry Road, Winter Park

5 Beds 6.5 Baths Winter Park Village SubDv.
Welcome to the sophistication and contemporary masterpiece by Parkland Homes. This exceptional residence features five spacious bedrooms, six and a half bathrooms, and 4,500 square feet of meticulously designed living space. Nestled within the exclusive enclave of Winter Park, this new construction opportunity redefines opulent living. The architectural marvel boasts a unique contemporary design, seamlessly integrating form and function. From the moment you arrive, the striking facade captivates with sleek lines and 10 foot ceilings on both levels of the home. Inside, natural light floods the open-concept living spaces, creating an inviting atmosphere that is both luxurious and welcoming. Entertain with ease in the gourmet kitchen, equipped with top-of-the-line appliances, Sub Zero, Wolf and Miele, custom cabinetry, a spacious island, and a wine cooler. The adjacent living and dining areas provide the perfect backdrop for gatherings, both large and small. The lavish primary suite, located on the first level, offers a private sanctuary of comfort and style. Indulge in the spa-like en-suite bath, featuring a soaking tub, oversized shower with dual shower rain shower heads , and dual vanities, creating the ultimate haven for relaxation. Escape to your outdoor oasis directly from the primary suite. An additional bedroom on the first level adds convenience, featuring a walk in closet and ensuite bathroom and currently staged as the home office. Retreat to the upper level to find a spacious loft that features a wrap around balcony, this space is ideal for relaxation and entertainment. Adjacent to the loft are three generously sized bedrooms, each offering a unique blend of comfort and style. Whether for family members, guests, or a home office, these bedrooms provide versatile spaces that adapt to your lifestyle needs. Outside, discover your personal paradise that sits on the largest lot on the street, featuring a sparkling pool, expansive patio, and outdoor kitchen, perfect for alfresco dining and year-round entertaining thanks to the retractable screens enclosing the lanai when needed. Additional features include a three-car garage with an EV car connection, leading to a mudroom and laundry area with ample storage, ensuring every aspect of this residence exceeds the expectations of the most discerning homeowner. Nestled in a highly sought-after location, this residence enjoys an enviable address surrounded by top-rated schools and is moments from renowned attractions such as Park Avenue, that promises unique shopping and upscale dining. Experience the pinnacle of luxury living with this exceptional new construction home.

2412 Chantilly Avenue, Winter Park

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