Winter Park real estate

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

$825,000

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

$2,475,000

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

$4,325,000

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

$599,999

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

$1,925,000

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

$2,725,000

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

$1,319,950

4 Beds ⋅ 5 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code

Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 4-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find luxurious plank flooring flowing through the entryway, family room, and guest bedrooms, complemented by polished marble in the formal living room and opulent primary suite. The interior showcases meticulous craftsmanship with recessed lighting, custom cabinetry, and coffered ceilings that add architectural charm. The heart of the home is a gourmet chef’s kitchen, a culinary dream featuring sleek custom cabinetry, a stylish farmhouse sink, a practical pot filler, and top-of-the-line appliances, perfect for both everyday meals and grand entertaining. Outside, a covered lanai invites relaxation. The sparkling pool, featuring a tranquil waterfall, soothing hot tub, and private pool bath creates a private oasis perfect for unwinding or hosting gatherings. The meticulously landscaped backyard, framed by lush greenery, offers a serene retreat for outdoor enjoyment. Soaring vaulted ceilings enhance the airy, open feel throughout the home. Located near the esteemed Rollins College and vibrant Park Avenue, this property is nestled in a charming neighborhood, offering both prestige and access to Winter Park’s finest dining, shopping, and cultural attractions. With a paved parking area, a two-car garage, and dual-zone AC for year-round comfort, this exquisite home is as practical as it is beautiful. Don’t miss the opportunity to own this Winter Park masterpiece, where timeless elegance meets modern luxury. Schedule a showing today and step into a lifestyle of comfort, sophistication, and unparalleled charm at 952 Moss Ln; this true gem is ready to become your forever home.

952 Moss Lane, Winter Park

$629,000

2 Beds ⋅ 2 Baths ⋅ Orangewood Park SubDv. ⋅ 32789 Zip Code

Virtually Staged. Enjoy the best of Winter Park living from this charming 2-bedroom, 2-bath home just minutes from Park Avenue, Baldwin Park, Mills 50, Downtown Orlando, local parks, shopping, and dining. The home offers a versatile layout with a bonus room that can be used as an office, den, playroom, or additional living space, plus a second bedroom with a built-in Murphy bed for added flexibility. Outside, the circular driveway provides convenient parking, while the fenced yard and separate hobby/storage shed add both privacy and functionality. The home has also seen several important improvements, including a newer roof from 2021, A/C replaced in 2025, updated electrical systems, new security system and a new fence. A great opportunity to own a well-located Winter Park home with flexible living space and many of the major updates already completed.

2825 Mulford Avenue, Winter Park

$586,567

5 Beds ⋅ 3 Baths ⋅ Attilio G Panacciones Sub SubDv. ⋅ 32789 Zip Code

SOVERA Realty is gifting the buyer a one-year home warranty! Discover a versatile investment opportunity in desirable Winter Park. This duplex offers a combined five bedrooms and three bathrooms across two well-appointed residences. Unit A features two bedrooms and one bathroom, luxury vinyl flooring, tile flooring in the kitchen, and ceiling fans throughout. Unit B provides ample living space with three bedrooms and two bathrooms, luxury vinyl plank and tile flooring, and ceiling fans throughout. Unit B is currently tenant occupied through October, offering immediate rental-income potential. Seller currently occupies Unit A and may consider a post-closing leaseback arrangement with the buyer. Terms are subject to mutual written agreement. All existing appliances, including the washer and dryer, convey with the sale. Conveniently located near Winter Park shopping, dining, entertainment, and major roadways, this property offers an appealing opportunity for investors or future owner-occupants.

1421 Michigan Avenue, Winter Park

Hot Winter Park Properties