Homes for Sale in Winter Park

The richness of an artist is the fusion of influences that have shaped his life and work, ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, derives it's over 4800 sq/ft of essence and uniqueness by fusing vibrant colors and eloquence with high-end home features and artistic details. Upon entry, visitors are greeted by a gorgeous rotunda accented with stained glass panels and vaulted, recessed ceilings. With 4 bedrooms, 3 full baths, and 2 half baths, this split plan is anchored on the first floor by the oversized owner's suite complete with walk-in closets, steam shower with dual stations and multi shower heads, jacuzzi tub, separate vanities and bidet. Make your way through the spacious living and dining areas while continuing on to the gourmet/chefs kitchen equipped with state-of-the-art appliances including Thermador refrigerator, Thermador gas range and double oven, hidden walk-in pantry, a large working island, multiple food prep zones, wine fridge, and bar height seating areas. Lounge with family and friends while entertaining via the great room generously apportioned with floor to ceiling views of the back patio, water front, and canal leading out to Lake Maitland. Meander upstairs via the winding staircase where you will find 3 additional bedrooms, 2 full baths, and 2 loft spaces ideally set for gaming and leisure complete with a wet bar, all centralized around the stunning scopes of the rotunda. Move adjacent and enter the large media room complete with home theater, and an additional flex space perfectly situated for a gym/workout room, playroom, office space, or additional large bedroom. Host formal or informal gatherings on the backyard porch and vast paver patio. Use the private boat dock to store the boat of your choice complete with remote operated boat lift and boat lift cover. Relax while cruising through the canal then head out to Lake Maitland for all of your boating and water recreational activities. Take a trip out to Dog Island and relish the views of the Isle of Sicily. Enjoy morning coffees and/or your favorite evening beverage at sundown utilizing either of two second floor balconies. Bike, walk, or run the local trails, public sidewalks, and paths. Venture to downtown Park Avenue for fine dining and upscale shopping. Or visit Maitland's local eateries and green spaces. Easy access to the Winter Park Racquet Club, and Kraft Azalea Gardens via Lake Maitland. Zoned for top-rated OCPS Schools; Dommerich Elementary, Maitland Middle School, and Winter Park High School. All of the latest styles, vibrant colors, and unparalleled designs will be part of your everyday life! Relaxation and a renewed sense of self await!

A unique opportunity to own a direct waterfront condominium in downtown Winter Park on Lake Virginia with the finest views, in exclusive Perle Du Lac. This one owner unit is wrapped on a spacious corner, flanked with windows and drenched in light, and exudes understated luxury. This three-bedroom three-bath split bedroom plan condominium boasts nearly 2,700 square feet of open spaces for modern function. A marble floor foyer and warm wood floors and volume ceilings invite you into a neutral palette and timeless finishes. A European SieMatic luxury kitchen with beautifully crafted solid wood cabinetry, stainless appliances and center island with solid Corian counters, which open to dining space with wine storage and dry bar, for ease of entertainment. Living spaces overlook the lake and seamlessly blend into balcony with second-floor unobstructed views of Lake Virginia overlooking the Windsong preserve and a long view to soak in the Chain of Lakes sunsets. Primary bedroom is lakefront with doors to patio and large custom European closet cabinetry, and primary suite is appointed in Italian Carrera marble add to the elegance of the finishes. Unit includes a deeded boat slip to enjoy lake life through the Venetian-style canals connecting five lakes. Other highlights of the community include secure entrance with double gates for convenience, secure buildings, community pool, underground parking with elevator to units, storage, greenspace and ample parking. Walk to Park Avenue where restaurants and shopping are abundant, art festivals, community events and more. Indoor laundry, enhanced lighting package, custom window treatments add to the list of features. Perle Du Lac neighbors Rollins College and president of Rollins home, there is not a more breathtaking setting than Perle Du Lac. Fully gated with underground parking and community pool making everyday life simple with everything within arm’s reach. A rare opportunity for the most discerning buyer.

Occupy or invest in this outstanding location. Excellent 2 bed 2 bath condo in Winter Park. Walking distance to Full Sail University and a short drive to University of Central Florida. University Blvd. is 2 minutes away. There's a community pool to enjoy and laundry on site. Several restaurants are close including many new ones. Shopping is close. Bus stop out front. Access to major highways. Plenty of parking. Freshly painted and cleaned. Straight shot to Orlando International Airport down SR 436. Minutes from downtown Winter Park and around the corner from Baldwin Park. Easy to show. Make an offer.

One or more photo(s) has been virtually staged. Welcome to this charming, upgraded 2-bedroom, 2-bathroom condo in Winter Park—an exceptional find at an affordable price! As you enter, you'll be greeted by beautiful ceramic tile flooring throughout, complemented by stylish light fixtures that add a modern touch. The open and spacious living/dining area provides the perfect space for both relaxing and entertaining. Step outside onto your private screened-in porch, complete with a storage closet, ideal for enjoying the Florida weather in peace and privacy overlooking lush green area. Inside, you'll find a sleek kitchen with designer tile backsplash, maple cabinetry, and luxurious granite countertops. High-end stainless steel appliances—including a French-style refrigerator with freezer drawer, flat-top stove, and above-range microwave—make this kitchen a true standout. For added convenience, a high-efficiency washer and dryer are neatly tucked away in a nearby closet. The downstairs features a full bathroom with a stylish stand-up shower, complete with a glass enclosure and beautiful tile work, along with a granite vanity. Upstairs, the second floor is fully tiled and includes additional storage. The spacious master bedroom offers a large walk-in closet and a ceiling fan, while the adjacent upgraded bathroom features a stand-up shower with a glass frame and a granite vanity. The versatile second bedroom is perfect for use as a guest room, home office, or anything in between. It includes built-in shelving and an organized closet for maximum functionality. This small, well-maintained community boasts a sparkling pool, a clubhouse, and ample parking with 2 designated spaces. 2022 Roof. Located just minutes from UCF, Full Sail University, Rollins College, and a wide variety of dining, shopping, and medical options, this condo offers both convenience and comfort. Short distance to downtown Winter Park and Orlando. The modest condo association fee covers a vast majority of services like, exterior maintenance, water/sewer utilities, clubhouse and access to the community pool. Don’t miss your chance to make this beautiful condo your new home!

Experience the best of lakeside living in this stunning 2-bedroom, 2-bathroom condo on beautiful Lake Virginia, part of the Winter Park Chain of Lakes. Just a short walk from Park Avenue, Rollins College, top-notch dining, and vibrant cultural spots, this sparkling 6th-floor condo offers serene treetop views overlooking the Fern Canal. The light-filled space was renovated in 2020 with a thoughtfully designed kitchen featuring white cabinetry, quartz countertops, and Bosch appliances. Additional upgrades include updated bathrooms, new piping and flooring, crown molding, and a premium hurricane-rated patio door. A new Trane air conditioner was added in July 2023. The Lake Virginia Condominium amenities include a dock, sauna, pool and spa with lake views, fire pit, gas grill, rentable guest suite, party room, dog walk, and storage for small watercraft. The HOA fee covers water, cable, and internet.

Discover the ideal space to grow and elevate your business with this prime C1-zoned property, perfectly situated on a bustling main street with high foot traffic and endless possibilities! This versatile LIVE/WORK property is perfect for an owner/operator seeking a seamless integration of business and personal life. Located in the vibrant Winter Park area of Orlando, your business will benefit from exceptional visibility, ample parking, and easy access to major transportation routes. Whether you envision a fitness studio, bridal gallery, photography studio, custom tailoring shop, legal or consulting practice, aesthetic services, or a pet grooming or daycare facility, medical office, dispensary, highest retail, real estate office, pawnshop, this space is ready to bring your vision to life with endless possibilities. In addition to the commercial potential, enjoy the luxury of a spacious 3-bedroom + den, 4.5-bath residence with a private grand entrance, a gourmet kitchen, and a private salt water pool. The flexibility of the property allows you to live on-site while keeping your business separate, just like the current owners operate from their office with a separate entrance, or to convert the entire building to suit your business needs. The expansive layout also offers easy opportunities for expansion, making this an excellent investment for future growth. A standout feature is the prominent plaza sign included with the sale, saving you thousands in signage costs. Plus, the property is not located in a flood zone, offering peace of mind for your investment. Your next business success story starts here, just minutes from downtown Orlando, with the privacy of your own backyard oasis. The possibilities are endless—don’t miss out on this incredible opportunity!

This custom lakefront home on Winter Park's Chain of Lakes offers stunning views of Lake Virginia and is in the historic Virginia Heights neighborhood, just a short walk from Rollins College and downtown Park Avenue. Facing north, it provides picturesque sunrise views over the lake, highlighting Rollins College and its chapel. Lovingly maintained and improved over time, the 4279 square feet does not include an additional 310 square foot finished bonus room with separate HVAC, perfect for game room or office. Upon entering, you are greeted by lake views and a foyer that leads to separate formal living and dining spaces, featuring wood floors, crown molding, plantation shutters, and 10’ ceilings throughout the first floor. The main living space showcases an open-concept kitchen and family room, and flows to the outdoor patio. The spacious kitchen has a gas cooktop, a built-in desk, island seating, an eat-in breakfast space, a walk-in pantry, and a built-in bar with beverage refrigerator. The family room has custom built-ins and a gas fireplace, and overlooks the manicured backyard, pool, and lake. The large downstairs owners’ retreat with picture windows overlooks the lake and a private screened porch with unobstructed views, and the updated bathroom has double vanities and sinks, glass shower, spa tub, and custom walk-in closet. Upstairs there are three bedrooms with attached bathrooms, two bonus spaces, and a media room, offering abundant flex space and storage. Comfort, luxury, and tranquility abound in the backyard with a pool surrounded by paver patio, grassy yard, and boathouse with a lift. The property also includes an oversized two-car garage. Improvements include new roof/2023, whole-house generator/2021, boathouse deck replaced with Trex decking and new roof/2021.

Introducing an exquisite Modern English Cottage by Floridian Custom Homes. This pool home will offer just over 2,700 s/f with 4 bedrooms and 3 1/2 bathrooms of luxury living. Step inside and discover the European influence in both classic design and luxury selections. Level 4 drywall, soft arches, vaulted ceilings, custom scissor beams, 1-3/4 solid core doors with Emtek hardware—just to name a few. The Andersen window and door package is oversized, filling the space with natural warmth and light. Downstairs offers a strategic office/bedroom option at the front of the house with an adjacent half bath featuring a European wall-mounted toilet. The first-floor owner's suite boasts warm, natural Calacatta marble on both the floor and the shower and a custom furniture piece with a Lacava sink, a full soaking tub with satin-etched glass provides privacy, plus a private bonus outdoor space for evening enjoyment—all crafted with breeze blocks for added privacy and design. The gathering and kitchen space are expansive and boast a Thermador appliance package, custom executive cabinetry, quartz tops, a hammered nickel-plated sink with designer hardware and faucet. Just off the kitchen is a private dining room with a vaulted ceiling, walls of windows, and natural light. Upstairs are two additional en-suite bedrooms with 13’5” volume ceilings in each bedroom. Oversized closets could also be converted to additional living space. As a complement, this home offers several outdoor living spaces, all covered with Gabriella marble limestone imported from Turkey. Completing this house is a seamless transition from the indoor living space to the outdoor pool and entertainment space.

This stunning custom home, completed in 2021, is located among the highly desirable “tree streets” in the heart of Winter Park, and was custom-built by M. Lahr Homes, showcasing exquisite craftsmanship and thoughtful design. With high-end finishes and custom details hand-selected by the owners, this home is sure to check every box. Designed with both luxury and functionality in mind, the home is equipped with natural gas for the cooktop, water heater, pool heater, grill, and fireplaces, while smart technology enhances modern living with app-controlled kitchen appliances, thermostats, irrigation, pool equipment, and garage doors. Neutral wood flooring, Restoration Hardware lighting, and custom electronic window treatments by The Shade Store add to the home’s understated sophistication. Additional highlights include copper gutters, level 5 finished walls, designer wall coverings, and custom storage throughout. Offering nearly 4,000 sq. ft. of organic, modern design, the open floorplan blends functionality with timeless elegance. The expansive living and dining areas flow seamlessly into the kitchen, which features Thermador smart appliances, quartz countertops, and a massive island with a stylish open-shelving detail. A hidden walk-in pantry behind the kitchen adds a bar fridge, microwave, and abundant prep space. The downstairs Primary Suite is a serene retreat with pool views through a picture window, a spa-like bathroom with a soaking tub and glass-enclosed shower, and an oversized, custom walk-in closet. A second main-level suite with a full bath and walk-in closet is currently used as an office overlooking the front lawn. Upstairs, a spacious bonus room/living area is surrounded by (3) additional bedrooms, each with walk-in closets, and (2) full bathrooms. The outdoor living space is an entertainer’s dream. The 8 ft sliding glass doors, with 2 ft. transom windows above, open to a covered lanai with motorized screens, a gas grill, and a fireplace for year-round enjoyment. Beyond the lanai is a meticulously landscaped backyard, fully fenced for privacy, with a heated saltwater pool wrapped in artfully laid out artificial turf and travertine pavers. Storage is abundant, with a custom-outfitted mudroom and laundry room, an oversized 2-car garage featuring storage shelves, and custom designed closets throughout. Ideally located, this home offers easy access to downtown Winter Park, Park Avenue, the YMCA, Aloma shopping center, and Whole Foods.

Updated Winter Park Home – No HOA! Welcome to 924 Beard Ave, a move-in-ready gem in the heart of highly desirable Winter Park. This charming property has been thoughtfully modernized with a host of recent improvements. Highlights include a refinished kitchen and bathrooms, new lighting fixtures, updated flooring throughout, complemented by rare original hardwood floors. The home’s classic design boasts plenty of windows, allowing natural light to flow through the interior. Fresh interior and exterior paint adds warmth, while newly updated ceilings and enhanced landscaping lend a polished, elegant appeal. A 2021 roof replacement ensures peace of mind, and the fully fenced backyard, with huge screened in porch, provides privacy, making this home a perfect retreat. Beyond the impressive updates, this property offers a prime location just minutes from Park Avenue. Enjoy Winter Park’s renowned dining, boutique shopping, cultural venues, and beautiful parks, with convenient access to Orlando and surrounding areas. The seller has made thoughtful updates, ensuring this home is move-in ready at an attractive price for the area. It’s the perfect opportunity to enjoy comfortable living now while personalizing it over time. This home is priced to sell without additional modifications, act fast—this home won’t last! The family room addition provides the flexibility to serve as a spacious primary 4th bedroom if needed.

Welcome to 1248 Park Green Place, Winter Park, Florida-a beautifully updated three-bedroom, two-bath home with a loft that perfectly blends style and practicality. All bedrooms feature vaulted ceilings, creating a bright and airy atmosphere. The primary bedroom showcases bamboo flooring and French doors leading to a private deck with a pergola, ideal for relaxing or entertaining. The living room, kitchen, and dining areas are finished with porcelain tile flooring, while the kitchen boasts elegant butcher block countertops. Outdoor spaces include a pavered patio, perfect for entertaining. Additional highlights include a double car garage, a hardwired security system with seven cameras for added safety, and a brand-new roof installed in 2024. This thoughtfully designed home is move-in ready and offers modern updates, timeless charm, and ultimate convenience in the heart of Winter Park just two minutes away from Whole Foods and minutes away from Park Avenue!

Professionally landscaped multi-generational 3-car garage Home loaded with upgrades including a custom Swimming Pool w/Beach entry located in the desirable 10 homes community of Seranza Park in Winter Park. Porcelain Tile & Crown Molding Throughout. Beautiful Stone Facade w/covered front Porch & custom Entry Door leads to the large Foyer providing a Drop Zone w/Cabinets, Under-Stairs walk in storage & access to the Formal Dining Rm offering Tray Ceilings, Upgraded Window Treatments & Wet Bar. Kitchen boasts Quartz counter tops, Island/Breakfast Bar, Upgraded Cabinets Lazy Susan, Spice Rack, Pull Out Bottom Shelving, SS appliances include a built-in Oven and plenty of Upgraded 42 Cabinet space plus large Walk-In Pantry & separate Dinette area. Oversized Family Rm overlooks Swimming Pool perfect for Entertaining. Multigenerational Suite includes separate rear outdoor access, large 16x15 room with complete bathroom including single Vanity, Upgrade Shower, stackable Washer/Dryer & oversized room which can server as a Closet, Office or Storage room. Guest 1/2 Pool Bath located on first floor also. The Engineered Wood Stairs w/Spindles showcases the custom Lighted Accent Wall and leads to the 2nd Floor. The 16x15 primary suite also offers Engineered Wood floors, Dual walk-in Closets & upgraded Window Treatments. The Primary Bathroom boasts Dual Quartz top Vanities, separate Make-Up area, plenty of Cabinets, Porcelain Floors, Private Water Closet, Towel Closet and a custom Shower with upgraded Designer Tile. The spacious bedrooms 3 & 4 are joined by a beautifully decorated Jack-and Jill full Bathroom including Tub/Shower Combo. The main 2nd Floor Laundry includes upgraded Cabinets, Utility Sink & separate Washer/Dryer. The 25 Ft long Enclosed/Screened with Sun Shades rear Lanai leads to the Pavered custom Salt Water Swimming Pool with Beach Entry, Self Cleaning equipment and Fire Pit for buyers to enjoy the peaceful setting of the upgraded yard Landscaping...enclosed by Vinyl Fencing. The 32x20 three car garage provides you with 2 Garage Openers and offers you plenty of space for cars and storage. The small and peaceful 10 homes community has no thru traffic and includes a Cul-de-Sac...Centrally located to major Hwys: 436, 417, Red Bug Lake Road, Aloma Ave which lead to innumerable restaurants/shopping stores & Hospitals close by. Orlando Intl Airport, Downtown Winter Park & Downtown Orlando just an easy drive away. This is your chance to take advantage of a turn-key Home on an Oversized Lot ready for a quick Closing. Bonus: 3 Separate Air Conditioning Unit with separate Controls for efficiency!!! New Exterior Paint 2021. Call to schedule an appointment to view this marvelous Home TODAY!!!