Winter Park Real Estate

Winter Park Real Estate

Welcome to Winter Park, Florida – a picturesque city that beautifully blends charm, culture, and community. Nestled just north of Orlando, Winter Park is renowned for its stunning lakes, lush greenery, and vibrant arts scene, making it a desirable destination for both residents and visitors alike.

One of Winter Park's most captivating features is its scenic lakes, including the serene Lake Osceola, where you can enjoy leisurely strolls along the picturesque waterfront or embark on a relaxing boat tour. The city is also home to the enchanting Central Park, a perfect spot for family picnics, outdoor concerts, and seasonal festivals that foster a sense of community.

Culture enthusiasts will find their haven in Winter Park, as the city boasts an impressive array of museums and galleries. The Charles Hosmer Morse Museum of American Art is a must-visit, showcasing an extensive collection of Tiffany glass and other exquisite artworks. Additionally, the city hosts the renowned Winter Park Sidewalk Art Festival, attracting artists and art lovers from all over.

Shopping and dining options abound in the charming downtown area, where you can explore boutique shops and savor culinary delights at a variety of restaurants and cafes. Whether you're in the mood for casual bites or fine dining, Winter Park’s culinary scene will surely tantalize your taste buds.

With its rich history, beautiful landscapes, and a strong sense of community, Winter Park is more than just a city; it's a lifestyle. Come discover the magic of Winter Park, where every day feels like a vacation in paradise!

Newest Listings in Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS VACANT LAND WITH THE MLS #O6431538.

540 N Pennsylvania Avenue, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code

Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor. 2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park

Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code

Welcome to this beautiful lot located in one of Winter Park’s most desirable neighborhoods. This exceptional location presents the perfect opportunity to build your dream home in one of the most sought after school zones Winter Park has to offer. Set along picturesque brick streets shaded by mature trees, the location is hard to beat. It is within walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. Enjoy the chance to create a home tailored to your lifestyle with a perfect blend of classic Winter Park character, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park

4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code

Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

3 Beds ⋅ 3 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code

Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out balconies). This light-filled residence offers an open floor plan and raised ceiling heights. From the moment you enter, you are drawn to the breathtaking lake views and understated elegance of this spacious home. The lakefront great room includes a large living area with adjacent bar and dining areas. The living area opens to the kitchen allowing the lake view to be enjoyed in all main living areas. The kitchen has been updated with white wood cabinetry, a built-in stainless Bosch oven, Bosch glass induction cooktop, Bosch microwave, Subzero refrigerator with two freezer drawers and two additional built-in refrigerator drawers. The custom mirrored backsplash adds a luxury feel, and the flexible center console provides additional work space. The primary suite offers a large walk-in closet and en-suite bathroom with a large walk-in shower, custom floating vanity and elegant fixtures. Bedroom #2 includes two closets and is directly across the hall from a large full bathroom with tub/shower. The 3rd bedroom is currently configured as a large Family Room and includes built-in cabinetry, a private door to the South hallway, two closets and an adjacent alcove ideal for office space. In the photos you'll see a floor plan virtually depicting bedroom #3 with a wall and doorway to the main hallway and living areas. Bathroom #3 is just across the hall and features a large walk-in shower. Wait, there's more! Residence 1-5 includes your own covered boat slip (#1). The entire residence features new seagrass floor covering in all the main living areas. This neutral, organic flooring makes for the perfect contemporary, elegant foundation for your furnishings and for showing off your own custom carpets and rugs. Additional features include plantation shutters throughout, additional storage closet in the garage, and a designated parking space in the gated under-building garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. Residence 1-5 is the jewel of Whispering Waters. This home provides the very finest of Lakefront "lock and Leave" living in the heart of Winter Park. All measurements are approximate and Buyer to verify all dimensions. Please see attached Disclosures and Governing Documents.

311 E Morse Boulevard Unit 1-5, Winter Park

5 Beds ⋅ 5 Baths ⋅ Forrest Hills SubDv. ⋅ 32789 Zip Code

Virtually Staged. Under Construction. Introducing THE READING RESIDENCE, an extraordinary NEW-CONSTRUCTION ESTATE by renowned luxury builder VIMARO HOMES, ideally situated at 250 WEST READING WAY IN WINTER PARK. Encompassing approximately 4,853 SQUARE FEET, WITH 5,922 TOTAL SQUARE FEET OF CONSTRUCTION, this FIVE-BEDROOM, FOUR-AND-ONE-HALF-BATH residence is a masterful expression of elevated design, uncompromising craftsmanship, and effortless Florida luxury. Vimaro Homes approaches every project with a singular philosophy: “The goal isn’t to spend less. The goal is to build something worth more.” That commitment to quality and value will be evident throughout this exceptional home, where thoughtful details, generous proportions, and refined finishes come together to create something truly remarkable. The main level delivers refined living and exceptional entertaining spaces, with SOARING CEILINGS enhancing the expansive living room and open kitchen and dining area. A substantial center island, generous pantry, dedicated laundry room, mudroom, and PRIVATE HOME OFFICE bring beauty, convenience, and functionality to the thoughtfully planned interior. The magnificent FIRST-FLOOR PRIMARY SUITE offers a private sanctuary with an impressive walk-in closet and spa-inspired bathroom featuring DUAL VANITIES, A FREESTANDING SOAKING TUB, AN OVERSIZED SHOWER, and a private water closet. Upstairs, a spacious SECOND GATHERING ROOM provides another inviting destination for relaxation and entertainment. A generous JUNIOR PRIMARY SUITE includes its own walk-in closet and private bathroom, while three additional bedrooms and two beautifully planned bathrooms—including a convenient JACK-AND-JILL BATH—provide exceptional comfort and privacy. Created to celebrate Florida’s coveted indoor-outdoor lifestyle, the residence opens to an expansive COVERED GRAND LANAI and fully equipped SUMMER KITCHEN overlooking the planned RESORT-STYLE POOL. This private outdoor retreat will provide an exquisite setting for alfresco dining, elegant entertaining, and sun-filled afternoons. A DETACHED GARAGE completes the beautifully composed property. The exceptional location places the best of WINTER PARK within easy reach, including celebrated dining, upscale shopping, picturesque parks, renowned museums, cultural destinations, and the timeless charm of PARK AVENUE. Currently under construction, THE READING RESIDENCE represents a rare opportunity to own a signature luxury home created with purpose, precision, and an unwavering dedication to quality. More than simply a home, this is a distinctive expression of the Vimaro Homes philosophy—GREAT HOMES ARE BUILT BY CREATING LASTING VALUE.

250 W Reading Way, Winter Park

2 Beds ⋅ 3 Baths ⋅ Hidden Oaks Condo Ph 02 SubDv. ⋅ 32792 Zip Code

Terrific townhome in the Hidden Oaks community featuring an updated interior and its own private, fenced patio! Step inside to a bright and spacious living/dining area with beautiful wood laminate flooring and a convenient wet bar. The galley-style kitchen includes a breakfast area, along with a laundry closet equipped with a full-size washer and dryer. Upstairs, you'll find two spacious bedrooms, including one with an oversized walk-in closet. Additional storage is available under the stairs and in the A/C closet. The monthly condo fee includes water, sewer, trash, exterior maintenance, grounds maintenance, and community amenities! Enjoy community amenities, including a refreshing pool! Conveniently located just off Goldenrod Rd, with easy access to E Colonial, 408, and 417 for a quick commute and nearby everyday conveniences. Full Sail University is just 1.8 miles away, Valencia College is 4.5 miles away, and UCF is only 6.2 miles away!

7476 Woodburn Court Unit 38, Winter Park

4 Beds ⋅ 2 Baths ⋅ Tanglewood Sec 3 Rep SubDv. ⋅ 32792 Zip Code

**RARE WINTER PARK OPPORTUNITY!** Bring your vision to this 1959 block home situated on a spacious 0.25-acre lot in the City of Winter Park, with the prestigious Interlachen Country Club golf course directly behind the property. Whether you choose to renovate the existing 4-bedroom, 2-bath home or pursue a complete redevelopment, this property offers an exceptional opportunity to create something special in a highly desirable location. The existing home features solid block construction, 4 bedrooms, 2 bathrooms, a concrete swimming pool, and a 2019 roof, providing a great starting point for renovation or redevelopment. The generous lot and established location offer plenty of potential for a new custom residence designed to take advantage of the surrounding Winter Park lifestyle and golf-course setting. Enjoy convenient access to some of Central Florida's most sought-after amenities, including Interlachen Country Club, Park Avenue, Downtown Winter Park, Winter Park Village, Rollins College, Central Park, shopping, dining, parks, and cultural attractions. Interlachen's 18-hole championship golf course provides a beautiful backdrop just beyond the property, while Winter Park's renowned Park Avenue district offers upscale shopping, restaurants, galleries and entertainment nearby. An excellent opportunity for builders, investors, renovators or buyers looking to create their own Winter Park residence in an established setting surrounded by golf, dining, shopping and recreation.

5218 Lake Howell Road, Winter Park

2 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code

Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms and approximately 1,544 square feet of living space, plus an enclosed 260-square-foot sunroom, providing nearly 1,800 square feet of usable living area. Originally designed as a 3-bedroom home, the third bedroom has been converted into a versatile flex room—ideal for a home office, den, hobby room or additional living space. The primary suite features a spacious walk-in closet with custom built-ins. Recent updates include a new roof in 2023, new flooring, fresh interior paint and more. As an end unit, the home provides additional privacy and a more open feel than interior units. The enclosed sunroom offers additional space for relaxing, entertaining or enjoying your morning coffee. Windward Square residents enjoy community amenities including a swimming pool and tennis courts. The convenient location provides easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this move-in-ready home offers space, flexibility and an excellent Winter Park location.

2302 Barbados Drive, Winter Park

Capens Add SubDv. ⋅ 32789 Zip Code

Build in the heart of Winter Park. This cleared quarter-acre lot (approx. 10,807 sq ft, 50' x 216') sits on Symonds Avenue on the city's west side. It's just blocks from Hannibal Square, Winter Park Village and Martin Luther King Jr. Park, and minutes from the shops and restaurants of Park Avenue. The lot is ready for your plans. It's cleared, with mature shade trees, a paved street with sidewalk, and public water and sewer available. It's zoned R-2, in Flood Zone X, with no HOA. Builders and buyers have room to create a custom home or an investment project in one of Central Florida's most desirable cities. Land this close to Park Avenue rarely comes available. Buyer to verify zoning, setbacks and permitted uses with the City of Winter Park.

822 Symonds Avenue, Winter Park

5 Beds ⋅ 4 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

Pre-Construction. To be built. Pre-Construction. To be built. Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! Build-to-Suit! Buyers who act now can still pick finishes and style! Build your custom dream home with renowned Konkol Homes in one of Central Florida’s most desirable areas! This nearly 1/4-acre lot is perfectly situated near Baldwin Park, East End Market, Audubon Park K-8, Rollins College, and Advent Health. The stunning Transitional Modern design features 3,246 sq. ft. of living space, offering 5 bedrooms, 4 baths, and a loft. The first-floor primary and guest suites provide convenience and privacy, while the Chef’s Kitchen flows seamlessly into the oversized Gathering Room in this open-concept design. The second floor includes three additional bedrooms, two with walk-in closets, and a spacious loft. Enjoy the benefits of a No HOA community in a well-established neighborhood, all while staying close to Baldwin Park and Minutes to Downtown Orlando! Enjoy Winter Park’s vibrant events and amenities! Zoned for top-rated schools of Audubon K-8 and Winter Park High School! This is your opportunity to build your dream Oasis and enjoy the Florida lifestyle! Buyer can participate in build out if placed under contract prior to construction start.

2260 Mulbry Drive, Winter Park

5 Beds ⋅ 5 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined interiors, and effortless indoor-outdoor living. A striking façade creates an unforgettable first impression, while a marble mosaic entry introduces the artistry and attention to detail found throughout the home. The main living space is designed to feel both impressive and inviting, centered around a dramatic electric fireplace wrapped in fluted stone. Expansive sliding glass doors fill the room with natural light and create a seamless connection to the outdoor entertaining areas. Open to the living room, the chef’s kitchen is a true statement, pairing richly veined Calacatta Gioia countertops with custom cabinetry, a built-in refrigerator, and a full suite of Thermador appliances. A generous walk-in pantry provides abundant storage and preparation space while maintaining the kitchen’s clean, elevated aesthetic.The first-floor primary suite offers a private retreat with vaulted ceilings and direct access to the backyard. Its spa-inspired bathroom is a sanctuary of beautifully selected marble tile and a serene, sophisticated color palette. A freestanding soaking tub, oversized walk-in shower, dual vanities, and thoughtfully curated finishes create an atmosphere reminiscent of a luxury resort. Also located on the main level is a versatile secondary bedroom that could serve beautifully as a private home office or guest suite, along with a well-appointed powder bath and a combined laundry and mudroom designed for everyday convenience. Upstairs, three additional guest suites provide comfort and privacy, while a spacious loft offers flexibility as a second living room, media space, or playroom. A second laundry room adds another layer of functionality to the thoughtfully planned layout. Outside, the home continues to impress with a covered lanai and full summer kitchen, creating the perfect setting for year-round entertaining. A marble pool deck surrounds the sparkling pool and spa, while the spacious backyard offers room to relax, gather, and enjoy the Central Florida lifestyle in complete comfort. The location is what really sets this home apart. New construction opportunities are becoming increasingly rare within the up-and-coming Tree Streets, making this residence an especially compelling offering. Just a short walk from the Winter Park YMCA, Phelps Park, and Interlachen Country Club, the home places recreation and everyday conveniences close at hand. Hop on your golf cart and arrive to Park Avenue's boutiques, cafes, and restaurants within minutes. A home of this caliber in such a coveted location is a rare find and it won’t remain available for long.

1773 Walnut Avenue, Winter Park

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