Winter Park Real Estate

Winter Park Real Estate

Located in Orange County, Florida, Winter Park is a charming city that offers a unique blend of natural beauty, cultural attractions, and a vibrant community. Known for its picturesque lakes, tree-lined streets, and historic architecture, Winter Park is a highly sought-after destination for both residents and visitors alike.

One of the main draws of Winter Park is its stunning chain of lakes, which provide endless opportunities for outdoor activities such as boating, fishing, and paddleboarding. Lake Virginia, Lake Osceola, and Lake Maitland are just a few of the many lakes that dot the city's landscape, offering breathtaking views and a tranquil atmosphere.

In addition to its natural beauty, Winter Park is home to a thriving arts and culture scene. The city is renowned for its prestigious Rollins College, which boasts a top-ranked liberal arts education and hosts various cultural events throughout the year. The Charles Hosmer Morse Museum of American Art is another notable attraction, housing the largest collection of Louis Comfort Tiffany's works, including his famous stained glass.

With its close proximity to downtown Orlando, Winter Park offers the perfect balance between a peaceful suburban lifestyle and easy access to urban amenities. The city's Park Avenue district is a popular shopping and dining destination, featuring a wide array of boutiques, restaurants, and cafes.

Whether you're looking for a serene place to call home or a delightful vacation spot, Winter Park's natural beauty, cultural attractions, and vibrant community make it an ideal choice.

Newest Listings in Winter Park

4 Beds 4.5 Baths O6215116 MLS
Newer Constructed four bedroom four bath Winter Park pool home is walkable to the East End Market. This Modern styled home has a coastal feel with its straight lines and West Indies touches of wood. Located in the Northwood Terrace neighborhood you experience the best locations of Baldwin Park, Winter Park, and the close market area. A lush Zoysia lawn with tropical landscaping and blooming annuals wow you as you walk up the expansive double drive and entry. An 8 foot French glass door with side lights, adorns the front elevation. Modern sconce lighting as well as additional cedar wood above completes this custom feel. Entering the home, a twelve foot high foyer with inlayed wood and LED lighting completes the entrance. To the right there is a thoughtfully designed first floor guest suite. This suite lends a multi-generational space for guests. Within, another French door offer natural light to the suite. A walk-in shower with beautiful tile/fixtures are just to the right. The grand feel down the hallway continues as double doors roll open to a reveal a large office space. Entering the Great Room there is an incredible 2-story expansive ceiling. This generous room features a 4-panel sliding door, with views to the rear garden/pool and custom landscaping. Adjacent, is the dining area with a modern/bright lighting fixture. A dual panel slider leads out to a covered patio perfect for coffee and breakfast. Back inside, the kitchen is quite the showstopper. Double slab quartz counter tops give a rich feel as does the Thermador Appliance Package. The 48" Freestanding range features six-star burners, as well as a griddle, perfect for quick appetizers or searing your favorite steak or tuna. The 36" Thermador refrigerator offers much space and thoughtful design. An undercounter micro-wave is quiet and out of site. A walk-in pantry has high shelf racks for storage. There is a large glass window behind the sink allowing an abundant amount of sunlight light. As your walk on the opposing side there is a pool 1/2 bath perfect for active kiddos. The primary bedroom is situated behind and features high ceilings with five windows. Hunter Douglas motorized shades are at your beckoning call for complete light out or just filtered light. Another rolling door reveals a luxury treat as you enter the primary bath. Eight-foot glass surround with wall/rain shower heads is just the prescription as is the grand soaking tub. Separate vanities offer private space for each owner to have plenty of room. A custom walk-in closet is in the shape of the letter L and has floor to ceiling shelving for all of your special accoutrements. At the end of the closet is the convenient washer/dryer/laundry room with an ample utility sink. Upstairs there is an open loft/flex space. This area can serve as a play place or exercise area. Two additional bedrooms, each en-suite keeps everyone happy...The backyard private tropical oasis features a 14x32 heated/saltwater pool. A covered lanai as well as the outdoor kitchen makes grilling a snap. Motorized screens on the lanai extend the fun into the evening as there is also a cable hook up for television and entertaining. A whole house generator is included for any power outages. A sought after 3 - Car garage is perfect for the car enthusiast. The home is school zoned for the newly constructed Audubon Park K-8, and the Winter Park School district. This coastal inspired home is available for a private showing. Schedule a visit soon.

2125 Sycamore Drive, Winter Park

4 Beds 4 Baths O6214969 MLS
Beautifully updated Winter Park custom pool home located in the sought after “Tree Streets” neighborhood. Boasting almost 3,000 SF, this 4-bedroom, 4-bathroom home includes 2 main level suites & 2 2nd level suites. The current owners worked to enhance many features of the home, including the exterior landscape. As you arrive you will immediately notice the professionally landscaped yard where mature plants were installed to enhance all lines of sight & extend even more privacy to the interior & exterior spaces. A paver-covered drive & walkway lead you to the custom front door. Immediately inside & to the right is the well-appointed dining room with 2 chandeliers, soaring ceiling, multiple windows affording an abundance of natural light, extensive millwork & wide plank, hand-carved engineered wood flooring. The current owners recently painted the interior & exterior of home. Ample cabinets & a wet bar were conveniently installed btwn the dining room & kitchen. The kitchen opens to the family room w/ beautiful views of the backyard oasis. The kitchen features a large island w/ seating for 4, an undermount farm sink, quartz countertops, & stainless steel appliances including a new refrigerator (2022) & new gas-fueled cooktop (2023) w/ vent hood. The built-in oven operates as a convection oven as does the built-in microwave above it. The shaker-style upper cabinets are extended & include glass fronts at the top for display & visual interest. A large wine closet w/ glass door & custom organization was installed along the far wall. The family room scale is perfect with extensive millwork, ceiling detail, led lighting, an electric fireplace, a new chandelier & sliding doors that provide a seamless transition to the exterior. Off the family room & located at the rear of the property is the primary suite. The light filled and spacious bedroom is connected to the bathroom by walk-in closets on both sides. The bathroom includes a private water closet, walk-in shower w/ bench, built-in storage, nicely layered neutral tile selections, multiple shower heads, a glass enclosure, extended vanity w/ quartz countertops over more shaker style cabinets & drawers, dual sinks, designer selected mirrors, lighting, hardware & more. Another bedroom & full bathroom w/ similar finishes complete the 1st floor. 2 bedrooms, 2 bathrooms & a large bonus room are located upstairs. The current owners love to entertain outside & it shows! They renovated the Summer Kitchen w/ new refrigerator & grill. They extended the paver deck at the covered area to meet the deck surrounding the pool, added a knee wall, enhanced the landscaping, installed a new fan & a privacy wall for shade. The pool was designed with a wide water fountain & sun shelf which the owners can enjoy year-round thanks to the installed pool heater (2022/2023). Other features of the home include an attached 2-car garage w/ built-in storage & an indoor laundry room w/ cabinets & countertops similar to those used throughout the home. Energy-saving features include low E, double pane, insulated windows, zoned HVAC system, a tankless hot water heater, block walls injected w/ foam, R-38 batt insulation w/ radiant barrier foil, LP gas fireplace & 2x6 upstairs construction. Located a short distance from local favorites such as Interlachen Country Club, Winter Park Racquet Club, Phelps Park, Park Avenue, The Winter Park 9, the YMCA & more. Make this move-in ready, well-appointed & conveniently located home yours!

1521 Magnolia Avenue, Winter Park

2 Beds 2 Baths O6214420 MLS 694 BLDG.
LAKEFRONT COMPLEX IN THE HEART OF WINTER PARK! This wonderful community is perfectly located on Lake Virgina less than a mile from Park Avenue in Winter Park. Situated on the Fern Canal and seen from the 246 square foot screened in porch with new sliding glass doors. Two bedrooms and updated baths, December 2023-New hardwood floors in the dining room and kitchen, New carpet in the living room and both bedrooms, Interior repainted, linen and a coat closets and an interior laundry with a stackable washer and dryer. The kitchen has Granite Counters, Nice stone backsplash, New Refrigerator, Double oven, Microwave and a large double stainless steele sink. For the dog lovers there is a gated pet area on the canal side of the building. Big bonus is a one bedroom guest suite that can be reserved and rented by the night. Amenities include Lake Access to Lake Virgina, Community Pool, Dock, (Boat Slips available via waiting list HOA Approval) Fitness Center, Ground floor covered parking 1 assigned space, recently updated Recreation room with kitchen, outdoor gas grill, a fire pit, steam and sauna rooms and a storage rack for kayak, canoes or surf board PLUS included is the Water, Trash and City Sewer. Just down the street is Dinky Dock which is a public boat ramp on lake Virginia and access to the entire Chain of Lakes.Walking distance to outstanding restaurants, shoppes, Museums, Central Park, the Sunrail Station and Rollins College.

690 Osceola Avenue Unit 209, Winter Park

3 Beds 2.5 Baths O6213521 MLS
Welcome to an incredible opportunity nestled in the heart of Winter Park! One of Winter Park 32789 most desirable neighborhoods - Osceola Shores. Directly across from Lake Osceola and .35 acres. This property presents a prime lot with endless possibilities for renovation or redevelopment. Situated on a spacious 100 x 154 lot, this home offers a coveted split floor plan and an open layout With a bit of creativity and investment, this property could be transformed into your dream home or an exceptional investment opportunity. Detailed remodel building plans may convey with the purchase. The generously sized living room and dining area offer sweeping views of the expansive front and backyard, providing inspiration for indoor-outdoor living and entertaining. The kitchen, updated with newer cabinets and granite countertops in 2015, serves as a focal point with its view of the back porch and pool area. Additional highlights include gas fire place, original parquet wood floors, utility room and plenty of closet space. The huge primary suite, with its private access to the pool and ensuite bathroom, offers a large space ripe for customization. Two additional bedrooms share a full bath with vintage tile and bathtub/shower, providing ample space for guests or family members. Beyond the home's potential, the location is unbeatable, with proximity to Park Avenue, Rollins College, The Alfond Inn, Winter Park SunRail station, shopping boutiques, grocery stores and restaurants. Whether you're looking to remodel and create your ideal home or explore the possibilities of redevelopment, this property offers a rare chance to own a piece of Winter Park's sought-after real estate. Don't miss out on this opportunity – schedule your showing today and bring your vision to life!

444 Lakewood Drive, Winter Park

3 Beds 3 Baths O6213510 MLS
Prepare to be impressed by this meticulously upgraded Winter Park home, where every detail has been carefully considered to offer the ultimate in comfort and convenience. Beautiful oversized and totally remodeled spit bedroom plan - 3 bed / 3 bath, single-story, brick construction with massive pool, wood-burning fireplace and entertaining screened porch and patio. All on a private .32 acre lot. Step through the newly installed exterior door handles and locks into a home transformed by a comprehensive renovation. From the garage to the outside pool area, all new electrical wiring ensures safety and reliability. Transformation in 2021 includes - all new ELECTRICAL WIRING, PANELS, tankless gas water heater, chimney flume. Roof replaced in 2017. Added propane gas hookup opens up a world of possibilities, whether it's cooking on the gas oven or envisioning outdoor gatherings around a pizza oven or grill. In 2021- new flooring, interior doors, handles, and custom trim throughout. The laundry room has been thoughtfully expanded - new dryer venting. Brand new AC system, updated ducting, and added insulation for optimal climate control and energy efficiency. Recessed lighting illuminates the main areas. The open kitchen has undergone a stunning remodel, featuring NEW APPLIANCES and custom shelving. Eat-in island, quartz countertops, coffee bar and designer tile backsplash. Two family rooms plus dining room that can also be used as an office! Bathrooms have been tastefully updated with new toilets and plumbing fixtures. Spacious primary suite overlooks pool area and has lots of closet space. Integrated wifi system including wifi boosters and hard wired throughout the house for remote workability. Outside, the enhancements continue with new sod and mulch, an electronic wifi-controlled irrigation system, and a dedicated irrigation well for sustainable landscaping. The pool area has been expanded for entertaining. Pool light replaced and Spanish tile on screened in porch. Perfect for large groups staying out of the sun and tons of dining and conversation area. Outdoor kitchen is ready to go once hooked up to gas. Porch is wonderful for pets too! Additionally, this home boasts a water softener, ensuring the highest quality water for your family. The outdoor patio off the master bedroom is prepped with 3 ft. slab to support future expansion, adding even more value and potential to this already remarkable property. Nestled within a friendly neighborhood on cul-de-sac and positioned atop a hill with excellent schools and a voluntary HOA offering community events, this home offers not just a place to live, but a lifestyle to embrace. Most coveted schools - Dommerich Elementary, Maitland Middle and Winter Park High School Don't miss the opportunity to make this your forever home – schedule a viewing today!

2421 Mandan Trail, Winter Park

3 Beds 3.5 Baths O6213697 MLS 1762 BLDG.
Introducing a stunning brand-new modern brownstone in the heart of Winter Park, offering access to Lake Killarney. Located in an exclusive community of 30 contemporary townhomes, each meticulously designed residence boasts exquisite finishes, expansive storefront-style windows, and 11' ceilings to flood the interiors with natural light. This 3-bedroom, 3 ½ bath home boasts luxury features that exceed expectations for its price point. A unique layout featuring the main living space on the second level allows you to revel in the seamless flow of the modern kitchen, dining room, and great room. Also located on the second level, a stylish primary bedroom and spa-inspired bath are located in the secluded rear of the home. This retreat includes two walk-in closets, a sitting area, a beautifully appointed bath with designer tile, a frameless glass shower, and a private water closet - thoughtfully designed for your comfort. Additionally, our highly advantageous split bedroom design offers two additional bedroom suites on the first level, providing ample space and flexibility for your lifestyle. With the added convenience of a full-size laundry room, this townhome redefines elegance and functionality. A rooftop oasis complete with an outdoor kitchen, pergola, hot tub spa, and breathtaking views can be found on level three, this thoughtfully crafted space offers the ideal blend of comfort and sophistication. Located in the picturesque Winter Park just north of downtown Orlando, residents can indulge in lakeside living with access to a private boat slip, community kayaks, and a lakefront Pavilion. Whether you seek serene relaxation or vibrant entertainment, this prime location places you moments away from top-tier dining, shopping, and recreational amenities, ensuring a lifestyle of unparalleled convenience and luxury. Additional highlights include the elegant touch of level four drywall throughout, providing a seamless and flawless finish that exudes sophistication in every corner of your home. Illuminate your space with designer-selected lighting fixtures that are sure to make a statement and create the perfect ambiance in every room. Say goodbye to clutter and hello to organization with custom closet systems in every corner, from coat closets to pantries to bedrooms, ensuring maximum storage and style. Walk with grace on Mohawk engineered flooring that offers both durability and beauty, creating a warm and inviting atmosphere throughout your home. Experience the ultimate cooking experience with our Samsung appliance package, featuring a natural gas cooktop and tankless water heater for efficiency and convenience. Embrace luxury with quartz countertops and a stunning waterfall edge island in the kitchen, perfect for cooking, entertaining, and creating unforgettable memories. Step outside to relax and unwind on level three's composite cool decking, a perfect spot for outdoor gatherings and enjoying the fresh air. Park with ease in the oversized two-car garage with an epoxy-painted floor, equipped with a 220V EV outlet for electric vehicles, making it convenient and eco-friendly to power up your ride. Welcome to your dream home, where every detail has been carefully crafted to elevate your lifestyle and offer the perfect blend of comfort, style, and sustainability. Live the life you deserve in our exceptional townhome!

1762 Mondrian Circle, Winter Park

4 Beds 4 Baths O6213583 MLS
Exceptional Custom-Built Home in the Heart of Winter Park Located on a peaceful brick street with park views, this unique 4-bedroom, 4-bathroom pool home is perfectly situated between Corrine Drive and Park Avenue. As you arrive, the meticulously manicured landscape, inviting front porch, and charming weeping mortar greet you with warmth. Upon entering the grand foyer, your guests will be captivated by the impressive design. The open floor plan boasts soaring ceilings and hardwood floors, with all bedrooms conveniently located on the main floor. The dramatic kitchen, which opens to the family room, features a stunning tongue and groove ceiling. It includes custom-built cabinetry, an exquisite ceiling-high backsplash, marble countertops, a 5-burner gas cooktop, Thermador appliances, and a cozy breakfast nook with a built-in bench and large window overlooking the pool. The primary bedroom offers a private vestibule, a beautiful tray ceiling with a designer chandelier, fixed windows for added light, and French doors with views of the serene backyard and pool. The elegant primary bathroom includes dual sinks, a soaking tub, a spacious shower, and a custom-built closet. The spacious laundry room is equipped with custom cabinetry and a built-in desk. Upstairs, you will find an exercise room, a generous second family or bonus room with a tongue and groove ceiling, a music room or office, a playroom/storage room, and a full bath. The serene private backyard, surrounded by a concrete wall adorned with gorgeous roses and lush landscaping, is perfect for family gatherings. The generous saltwater pool and spa offer a refreshing retreat during hot summers. Enjoy morning coffee or evening wine on the covered back porch, equipped with remote screens to keep bugs at bay. Additional features of this stunning home include remote shades throughout, all LED and designer lighting, incredible millwork, surround sound, 3-way split plan and a central vacuum system. Excellent K-8 Audubon Park School and Winter Park High School.

350 E Reading Way, Winter Park

Start Your Search