Courtesy: MAROON REALTY GROUP LLC
407-774-7083
ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart of Winter Park, offering the perfect blend of luxury and convenience. Whether you're looking for a full-time residence or a lock-and-leave property, this home delivers on every level. Designed with entertaining in mind, the open-concept layout creates a seamless flow from the kitchen into the main living areas. The kitchen features high-end appliances, including a Wolf refrigerator and GE Monogram suite, along with dedicated wine and beverage refrigeration—perfect for hosting or everyday use. A new A/C unit has also been installed, providing added peace of mind. That same attention to entertaining continues outdoors, where a screened-in kitchen, hot tub, and professionally installed turf create a private, low-maintenance space ideal for hosting or relaxing. Inside, the home offers a very spacious primary suite complete with a walk-in closet. A full bathroom is conveniently located downstairs adjacent to the study, which can also function as a third bedroom, adding flexibility to the layout. The two car garage has been upgraded with a durable epoxy-coated floor for a clean, finished look. Located just minutes from Winter Park Village and only a short drive to major roadways including Interstate 4 and State Road 436, this home offers unmatched access to shopping, dining, and downtown. Enjoy the charm of tree-lined streets and historic surroundings, all just steps from the shops and restaurants of Park Avenue. This is a rare opportunity to own a turnkey property in one of Winter Park’s most desirable locations.
Courtesy: EXP REALTY LLC
888-883-8509
This is the kind of place that feels easy the moment you arrive, tucked into one of the most loved pockets of Winter Park, Florida. A place where mornings are quiet, afternoons stretch a little longer, and the backyard becomes your favorite place to unwind. This well-maintained single-story home offers 1,396 square feet of comfortable living across three bedrooms and two bathrooms, with a layout that lives larger than expected. Natural light fills the main living areas, creating a warm and inviting space that feels like home from the start. A separate bonus room adds flexibility for the way you live today, whether you need a second living area, home office, playroom, or a space to unwind at the end of the day. The kitchen flows easily into the main living space, making everyday living and casual gatherings feel effortless. Step outside to a backyard designed for enjoying Florida living. A covered patio overlooks a charming firepit area, creating the perfect setting for relaxed evenings, weekend get-togethers, or simply enjoying the outdoors year-round. Ideally positioned to enjoy the Winter Park lifestyle, Cady Way Park is just moments away with its pool, tennis and pickleball courts, playground, and beach volleyball. Park Avenue offers boutique shopping and exceptional dining, while UCF, Rollins College, and Full Sail University are all within easy reach, along with AdventHealth Winter Park and Orlando International Airport. Zoned for top rated Winter Park schools, this home brings together location, lifestyle, and everyday comfort in a way that truly stands out.
Courtesy: THE AGENCY FL
407-335-4119
Pre-Construction. To be built. A Generational Opportunity in the Heart of Winter Park Presenting an exceptionally rare opportunity to build a fully custom luxury estate on one of Winter Park’s most extraordinary homesites. Situated on an expansive 1/2-acre corner lot, an offering virtually unheard of in this coveted location, this property represents the pinnacle of luxury new construction potential. Scheduled for Summer 2027 completion, this bespoke residence offers the flexibility to bring the current architectural concept to life, collaborate with the builder to tailor the design, or create an entirely custom vision with your own architect and design team. The proposed architectural concept showcases an impressive modern estate designed for elevated living and grand-scale entertaining, featuring a dramatic double-height foyer, soaring two-story great room, expansive walls of glass that flood the interiors with natural light, a highly desirable 4-car garage, oversized bedroom suites, and thoughtfully curated indoor-outdoor living spaces throughout. Designed to deliver a true resort-style experience, the outdoor living concept includes a saltwater pool and spa, covered lanai, summer kitchen, and expansive entertaining areas ideal for year-round Florida living. Further elevating this offering is deeded access to Lake Sue, providing an exclusive lifestyle opportunity rarely available in this location. Enjoy the best of both privacy and recreation while being moments from everything Winter Park is known for. Perfectly positioned just minutes from renowned Park Avenue, residents enjoy immediate access to premier fine dining, luxury boutiques, private clubs, and cultural attractions, all while being zoned for top-rated schools. Oversized parcels of this caliber with deeded lake access are exceptionally scarce, making this a true legacy acquisition, an opportunity to create a one-of-one estate in one of Central Florida’s most sought-after neighborhoods. Luxury, land, lake access, and limitless potential—this is Winter Park living at its absolute finest.
Courtesy: COLDWELL BANKER REALTY
407-647-1211
Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready. But what truly sets this property apart is the location and land. With new construction and beautifully updated homes all around, this is the perfect spot for anyone looking to build something special. Enjoy the home as it is, rent it out for steady income, or start planning your future build in a prime Winter Park setting. A property with this kind of potential doesn’t come around often.
Courtesy: LPT REALTY, LLC
877-366-2213
BELOW APPRAISAL GEM IN WINTER PARK. Welcome to this beautifully and luxuriously updated 4-bedroom, 4-bath pool home located in the highly desirable Kings Cove community of Winter Park. Offering over 3,000 square feet of living space on a spacious 0.31-acre lot, this home blends comfort, functionality, and major system upgrades. The kitchen is designed for both everyday living and entertaining, featuring a gas stove, double oven, warming drawer, extra-large refrigerator, and custom pull-out cabinetry. The oversized island includes an additional sink, built-in microwave, and new (2025) under-counter ice maker. Recent upgrades and improvements include: New roof (2021) New first-floor A/C system (2021) New septic tank (2023) New hot water heater (2025) The primary suite has been thoughtfully updated in 2026, featuring a fully renovated bathroom with dual sinks and in-drawer electrical outlets, along with a custom-designed closet system completed in March 2026. New carpet was installed in April 2026. Additional highlights include a dedicated laundry room with sink and wine storage, a custom pantry with oversized pull-out drawers, built-in entertainment center, and a ceiling-mounted audio system controlled by phone. Step outside to enjoy your private in-ground pool and a quiet, established neighborhood close to top-rated schools, shopping, dining, and major highways. This is a move-in-ready home with major systems already updated and high-end functional upgrades throughout—don’t miss this opportunity.
Courtesy: RE/MAX TOWN & COUNTRY REALTY
407-695-2066
Located on a quiet cul-de-sac with NO HOA, this adorable Winter Park home sits on an oversized lot with an incredible backyard and endless room for entertaining, relaxing, or play. With a mid-century modern feel and charming curb appeal, this 3-bedroom, 2-bath home is full of character and functionality. As you enter through the foyer, you’re welcomed by an oversized living room to the left, complete with a cute flex space perfect for a home office, reading nook, or play area. The updated kitchen sits at the center of the home and features quartz countertops, bar seating, and views overlooking the dining room, creating a seamless flow for everyday living and entertaining. Laminate flooring runs throughout all main living areas and bedrooms for a clean and modern look. Down the hallway, you’ll find all three bedrooms and two bathrooms, including the spacious primary suite with a large closet and an updated ensuite bathroom featuring a brand-new vanity and stylish paneling details. The dining room and flex area both lead out to the screened-in patio, giving you the perfect indoor-outdoor setup. Step outside to the true showstopper — a massive backyard with endless possibilities, a fire pit area, and plenty of room for activities, gatherings, pets, or even future additions. (zoned R-1A) Additional highlights include an extra-long driveway with space for up to 6 cars plus a 2-car garage. A rare find in Winter Park!
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Enjoy the Winter Park lifestyle in this beautifully renovated 2-bedroom, 2-bath lakefront condo offering 2,304 square feet in the heart of downtown Winter Park. Located on the second floor of Building 1, this light-filled residence was extensively remodeled in 2023 with an open floor plan and raised ceiling heights that give the home an airy, comfortable feel throughout. The spacious living room and kitchen take full advantage of the breathtaking views of Lake Osceola, while two fireplaces—one in the living room and another in the primary bedroom—add warmth and character to the space. The kitchen has been updated with white cabinetry, stainless steel appliances, double ovens, induction cooktop, tile backsplash, center island, and wine/beverage refrigerator. Formal living and dining spaces offer plenty of room for entertaining, and the oversized entertainment room off the primary bedroom features a closet and separate entry, making it a great option for a third bedroom, media room, or home office. The primary suite offers a walk-in closet and en-suite bathroom with a shower and dual sinks. The secondary bedroom includes two closets along with a separate alcove ideal for a reading nook or office space. A Florida room, currently used as a storage room, features brick flooring. Other highlights include plantation shutters throughout, beautiful exposed beams, additional storage closet in the garage, and two designated parking spaces in the covered 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. A rare opportunity to enjoy spacious lakefront living in one of Winter Park’s most desirable communities.
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Set on an approximately one-quarter acre homesite in a desirable Winter Park location, this property presents an exceptional opportunity to build a custom residence in one of Central Florida’s most sought-after communities. The existing property features a one-story pool home offering approximately 2,723 heated square feet with four bedrooms and three baths; however, the value is primarily in the land. A brick-paver circular driveway enhances the property’s curb appeal, while the generous lot size provides ample space to create a beautifully tailored new construction home. Ideally located just minutes from the vibrant shopping, dining, and community events of downtown Winter Park and Park Avenue, the property also offers convenient access to downtown Orlando, major area hospitals, Orlando Executive Airport, and Orlando International Airport. Zoned for highly regarded Audubon K-8 and Winter Park High School.
Courtesy: EXP REALTY LLC
888-883-8509
This is the kind of place you dream of, set on one of the most beautiful streets in Winter Park, Florida, the kind you can’t wait to come home to. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your door for morning runs, bike rides, and everything in between. This custom-built two-story residence offers 3,971 square feet of thoughtfully designed living across four bedrooms and four en suite bathrooms, where luxury finishes meet the warmth of a true Winter Park neighborhood. A grand mahogany front door welcomes you into a home where soaring ceilings and oversized interior and exterior doors set the tone from the moment you arrive. Every detail of the kitchen was chosen with intention, from the gas cooktop and double oven to the built-in coffee machine and steamer, all seamlessly integrated into premium cabinetry that elevates everyday living. This home offers the rare luxury of two primary suites, one on each floor. The upstairs primary suite features a beautifully appointed en suite bathroom and custom closets. The expansive downstairs suite offers the perfect setup for a private guest retreat or multigenerational living. Two additional bedrooms each feature their own private en suite bath. A generous flex space upstairs offers endless possibilities, whether a movie room, playroom, upstairs den, or even a fifth bedroom. Outside, the pool is in a class of its own. A stunning dark pebble finish defines the look, while a sun shelf with built-in bubblers and color lighting creates a resort experience right at home. A natural gas heater, fully automated controls, a 3 horsepower variable speed pump, a Levolor electronic water fill system, and a robot pool cleaner make this pool as effortless as it is spectacular. A dedicated pool bath keeps wet feet outside where they belong, and mahogany rear patio doors connect the interior to the outdoor living space beautifully. Exterior uplighting makes the entire property glow after dark. The mechanical systems here are exceptional and worth every word. Two independent 19 SEER HVAC units serve the first and second floors separately with individual WiFi controls for precision comfort and outstanding efficiency. Natural gas is piped in from TECO Gas, powering the cooktop, the pool heater, and a whole house instant hot water system that delivers on demand. Insulated flooring between the first and second floors keeps the home quieter and more energy efficient throughout. An insulated hurricane rated garage door with WiFi opener and double insulated low-e windows complete a home built to an exceptional standard from the ground up. Perfectly positioned for the Winter Park lifestyle, Cady Way Park is nearby with its pool, tennis and pickleball courts, playground, and beach volleyball. Park Avenue beckons with boutique shopping and exceptional dining, while UCF, Rollins College, and Full Sail University are all within easy reach, as are AdventHealth Winter Park and Orlando International Airport. Zoned for top rated Winter Park schools, this is a home that delivers on every level, location, lifestyle, and lasting quality.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!
Courtesy: DON HARKINS REALTY LLC
321-377-0341
Welcome to 819 Densmore Drive, a beautifully refreshed concrete block ranch home in the heart of Winter Park Estates, one of Winter Park's most established neighborhoods with no HOA. This move-in ready home checks every box for buyers who want turn-key condition with an accessible price and a coveted Winter Park address. From the moment you pull up, the curb appeal speaks for itself. A crisp white exterior with fresh paint, an extra large driveway with RV, Boat, or trailer parking, and a lush green lawn, sit against the quiet, tree-lined street that makes this neighborhood so beloved. Step inside and you'll notice the brand-new Palmer Oak Rigid Core Luxury Vinyl Plank flooring running throughout the entire home, installed in 2026! It delivers the warmth of hardwood with the durability Florida living demands, and ties every room together beautifully. The interior was freshly painted top to bottom in 2026, giving every room a bright, clean feel that makes the home feel completely renewed. The layout is open and functional, with generous living areas, a dining room anchored by a chandelier that stays with the home, and bedrooms filled with natural light and ceiling fans throughout. The kitchen comes equipped with the refrigerator included, a functional breakfast bar, recessed lighting, and plenty of storage. Blinds, decorative framed bath mirrors, ceiling fans, and keypad entry all stay. Both bathrooms received new vanities and toilets in 2026, delivering a completely fresh, modern look. The big-ticket systems are solid. The roof was replaced in February 2022. The HVAC system is less than two years old. The plumbing was repiped to PEX in 2016, and the home connects to city sewer, public water, and public irrigation. No well, no septic, no solar obligations. Clean, uncomplicated ownership. The backyard is shaded by a mature tree with room to spread out, BBQ, add playgrounds, pools, or bounce houses, and the property sits high and dry away from flood zones. Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School, this home places you in one of Orange County's most sought-after school districts. Minutes to Park Avenue dining and boutique shopping, Advent Health Winter Park, Winter Park Pines Golf Course, the Cady Way Trail, and easy access to SR-436, Aloma Avenue, and the 408. Winter Park Estates is the kind of neighborhood where properties like this, genuinely updated and truly move-in ready in a community this well-established and well-located, don't sit long. Schedule your showing today.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
One or more photo(s) has been virtually staged. Completely renovated pool home on a large corner lot, tucked away on a quiet dead-end street in Winter Park. Solid block construction adds peace of mind, and this one has been updated top to bottom—new laminate flooring throughout, recessed lighting, popcorn ceilings removed, and a fresh, clean feel the moment you walk in. The main living area is bright and open, with natural light pouring into the living room that flows right into the dining space. The kitchen sits just off the dining area and was fully redone with soft-close cabinetry, stainless steel appliances, quartz counters, and a matching quartz backsplash. Off the dining area you’ll find a bonus family room that works perfectly as a media room, playroom, second living space—whatever fits your needs. Sliding doors open straight out to the pool, making indoor-outdoor living easy. This space also connects to a separate wing of the home featuring its own bedroom, full bathroom, and sitting area. It can be closed off from the main house and even has private access through the two-car garage, giving you flexibility for guests, extended family, or potential rental use. On the opposite side of the home are three additional generously sized bedrooms and two full bathrooms, including a bedroom with its own en-suite that can easily function as a primary depending on how you want to use the layout. Out back, you’ve got a large yard with plenty of room to make it your own, a big sparkling pool, and a covered porch area. There’s also a side gate with space to bring in a boat, trailer, or work truck straight to the backyard. A dedicated laundry setup is located off the back porch area, adding convenience for pool days and the separate suite. No HOA, roof from 2019, and a location that’s hard to beat—just minutes to 436, Downtown Winter Park, Full Sail, and UCF. Two-car garage, top rated schools, flexible floor plan, and a ton of usable space inside and out. Call today to set up a private showing!
Courtesy: KELLER WILLIAMS REALTY FT MYER
239-236-4350
Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower fixtures in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is everything and this one delivers. Just minutes from downtown Winter Park, grocery stores, shopping and dining with access to I-4, 408,417, Semoran Blvd and State Road 50. Only 10 minutes to Full Sail, 20 minutes to UCF and close to Rollins College.
Courtesy: KELLER WILLIAMS REALTY AT THE PARKS
407-629-4420
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully maintained and updated over time, this property combines functional living with key improvements that add long-term value and peace of mind. Inside, the open floorplan creates a bright, connected flow across the main living areas—ideal for both everyday living and entertaining. The separate family room adds valuable versatility, perfect as a media room, home office, playroom, or relaxed second living area. The bedroom layout is practical and comfortable, providing a solid foundation for personal touches and customization. Recent updates enhance both the appeal and functionality of the home, including a roof installed in 2020, HVAC system replaced in 2019, a new garage door with opener (2019), and fresh exterior paint completed in 2024. The bathroom has been refreshed with a new sink, toilet, and tub surround in 2025, offering a clean, updated feel. The outdoor spaces further elevate the property. An enclosed front porch provides a welcoming spot to enjoy a quiet morning or unwind in the evening, while the open rear patio is perfect for grilling, dining, or relaxing outdoors. The private backyard offers plenty of space to expand your vision, with strong potential to create a personalized outdoor retreat. With its solid layout, meaningful updates, and room to grow, this home presents an excellent opportunity for buyers looking to settle into a well-located property while continuing to enhance it over time. Situated in desirable Winter Park, the home benefits from a location known for its established charm, tree-lined streets, and convenient access to shopping, dining, parks, and everyday essentials, making it one of Central Florida’s most sought-after communities.
Courtesy: KELLER WILLIAMS REALTY AT THE PARKS
407-629-4420
Welcome to 721 Dunbar St in Winter Park, a 2-bedroom, 2-bath home with a simple layout and plenty of potential. This property offers a comfortable starting point for everyday living and a great opportunity for buyers who want a home they can make their own over time. Inside, the home offers practical living spaces and a layout that works well for daily routines. The two-bedroom, two-bath setup adds flexibility for guests, a home office, or changing needs. The home has a solid foundation for updates, giving the next owner the chance to improve and personalize the space to match their style and preferences. Outside, the property gives you room to enjoy the yard and think about future possibilities. Whether you want to refresh the outdoor space, add your own touches, or simply enjoy the home as it is, there is a lot of opportunity here. Located in Winter Park, the home is close to shopping, dining, parks, and major roads, while still being in an established residential area. The neighborhood adds to the appeal with its convenient location and access to everything that makes Winter Park a popular place to live.
Courtesy: FANNIE HILLMAN & ASSOCIATES
407-644-1234
Graceful and timeless, this classic Southern-inspired residence by esteemed builder Charles Clayton sits on a generous lot in Park Grove—one of Winter Park’s most coveted neighborhoods—and makes a striking first impression with beautifully composed architecture, charming dormer windows, a sweeping columned front porch with reclaimed-style brick flooring, and curated landscaping. Inside, the foyer unfolds with rich wood floors, classic raised-panel wainscoting, layered crown molding and detailed millwork which sets the tone for depth and quiet sophistication throughout the home. Just off the entry, a beautifully appointed office with finely crafted built-in shelving, thoughtfully designed for both display and function. The same refined trim details carry through, while generous windows introduce soft natural light—an ideal setting for work or a quiet retreat. Across, the dining room is both elegant and inviting—bathed in natural light from multiple windows and enhanced by more detailed millwork that adds character and creates a polished backdrop for everything from intimate dinners to larger gatherings. Continue through to an expansive great room anchored by a classic fireplace with custom built-ins, while a wall of French doors across the back of home invites natural light to pour in and extends the living space seamlessly to the covered verandah and pool beyond, creating perfect living space to gather, lounge or entertain. Open to the Great room, the beautifully designed kitchen stands out with a coffered ceiling, marble countertops, and crisp white cabinetry, featuring illuminated upper cabinets and open shelving for thoughtful displays. A central island is complimented by an integrated breakfast table—perfect for casual dining or morning coffee. Professional-grade appliances like a Wolf gas range and Sub Zero refrigerator offers refined function and the substantial walk-in pantry around the corner, has ample storage for effortless organization. Positioned between the kitchen and living area, additional flexible space creates a natural extension for casual dining, conversation, or a cozy sitting area tailored to your lifestyle. The 1st floor primary suite offers a true retreat, with private verandah access and two walk-in closets. The marble bath includes a generous glass-enclosed shower with multiple shower heads, pedestal soaking tub, a pair of vanities, and a private water closet. Completing the 1st floor is a large mud room with custom built-in bench seating and integrated storage, an oversized laundry room that blends utility with style and provides generous storage and work surfaces, and a stylish, well-appointed guest bath. Upstairs, a versatile loft area and bonus room are laid out to easily accommodate multiple uses—an ideal lounge area, work-from-home space, or media retreat. The 2nd floor split-bedroom floor plan features a spacious guest suite, with a private living area or study and en-suite bath, a 3rd bedroom suite with an en-suite bath and walk-in closet, and two additional bedrooms connected by a Jack-and-Jill bath, plus an enormous, air-conditioned storage room. Outdoor living is elevated, with a covered veranda and built-in gas grill, overlooking a sleek, resort-style pool, stone decking, and a beautifully landscaped backyard. Every element of this home reflects livable elegance in an exquisite setting, all just a stone’s throw from the WP-9 Golf Course and downtown Park Avenue.
Courtesy: COLDWELL BANKER REALTY
407-647-1211
LAKEFRONT living just steps from the shore of 239-acre, spring-fed Lake Killarney! Welcome to Lakeside Manor and this charming second-floor end-unit condo offering partial lake views, private lake access, and an ideal blend of comfort and convenience. This 1-bedroom, 1-bath unit features a bright and inviting layout with luxury vinyl plank flooring throughout the main living areas, complemented by granite countertops and a stylish backsplash in the kitchen. Pella energy-efficient windows fill the space with natural light while helping maintain efficiency. Additional highlights include a new HVAC system (11/2025) and an A/C closet providing extra storage. Residents enjoy a variety of amenities designed to enhance the lakefront lifestyle, including a pool and clubhouse overlooking the water, private boat ramp, boat slips (first-come, currently $35/month), guest parking, community laundry facility, and an outdoor grill and picnic area. A beautifully maintained central courtyard offers a peaceful, park-like setting right outside your door, with a laundry room conveniently located nearby. Low HOA fees add to the value, making this property even more attractive. Ideally located with quick access to I-4 and 17-92, and just minutes from Winter Park Village, Park Avenue dining and shopping, Rollins College, UCF, Valencia College Downtown Campus, and Downtown Orlando, this condo offers both tranquility and accessibility. Enjoy lakefront living in one of Winter Park’s most convenient locations—an excellent opportunity for a primary residence, second home, or investment.
Courtesy: SERHANT
786-296-8626
Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet, and its own French doors to the huge covered, insulated patio. The light and bright kitchen includes a large breakfast bar, built-in pantry, and white cabinetry and appliances, and opens to the family room with a wood-burning fireplace and built-in desk. A separate bedroom wing provides four generous guest bedrooms and two full baths, including a Jack-and-Jill setup with walk-in closet, plus a true pool bath with access to the backyard and an inside utility/laundry room. Outdoor living is a highlight, with a fenced backyard, kidney-shaped pool, plenty of deck space, and ample yard beyond the pool so you’re not sacrificing green space. The large covered, insulated patio is ideal for year-round use. Major updates include a new roof (2022), new electric panel and updated outlets (2022), water lines re-piped to CPVC by a previous owner, new fence (2023), new dishwasher (2024), new water heater (2025), newer stove, washer, and dryer, new light fixtures throughout, and bathrooms updated with modern colors and fixtures. The exterior, garage, patio, and pool deck have all been freshly painted, giving the home a clean, move-in ready feel. This is a rare opportunity to own a well-maintained pool home in a prime Winter Park location—just steps from Cady Way Park and Trail and moments from Winter Park Pines Golf Course, with Winter Park High School and the nearby hospital campus within short distance and quick access to downtown Orlando, major highways, both airports, Disney, and Universal.
Courtesy: DOUGLAS EDMUND REAL ESTATE LLC
407-853-4402
Welcome to this well-maintained 2-bedroom, 2-bathroom duplex with a 1-car garage, located in the desirable Seminole County side of Winter Park. This home offers a functional layout with comfortable living spaces, natural light, and a private residential setting perfect for everyday living or investment opportunities. Enjoy a convenient location with easy access to major roads, shopping, dining, and top-rated schools. Just minutes from Full Sail University and Downtown Orlando, this property provides both accessibility and a peaceful neighborhood environment. Whether you are looking for a primary residence or an income-producing property, this duplex offers great potential in a highly sought-after area. HOA restrictions may apply, including leasing, rental, pet, and amenity access limitations. Access to community amenities is subject to HOA rules. Buyers and buyer’s agents are responsible for verifying all HOA rules, regulations, fees, approvals, and amenity access directly with the Association.
Courtesy: PREMIER SOTHEBY'S INTL. REALTY
407-644-3295
Step into the Winter Park lifestyle with a fully turnkey home designed to make daily living feel effortless. Set on an oversized corner lot, this fully updated home blends clean design with thoughtful upgrades. Inside, the home is built to bring people together. The open-concept layout flows seamlessly from living to dining to kitchen, anchored by a striking 9-foot Carrera Thassos quartz island. A full KitchenAid black stainless steel appliance suite, generous storage, and refined finishes make this a space that works as well on a busy weekday as it does when hosting a full house. Out back, everything is ready to enjoy. A private, resort-style setting features a saltwater pool with fire bowls, custom lighting, and a dedicated outdoor dining area, all framed by professionally designed landscaping and low-maintenance artificial turf. Beyond the aesthetics, this home delivers real, everyday value. A reverse osmosis system, fully updated electrical and plumbing, a 5-ton air conditioning system, and a metal roof provide peace of mind. An 18.4-kilowatt solar system keeps utility costs remarkably low, with many months producing surplus energy credits. Located in sought-after school zones and just minutes from Cady Way Park, with easy access to Orlando, this is a home where everything has already been considered. No projects, no waiting, just move in and start living. Buyer to assume $75,000 solar panel loan, offset by minimal to near-zero electric costs and ongoing energy credits during high-production months. Utility bills available on request.
Courtesy: ALL REAL ESTATE & INVESTMENTS
407-917-8206
Located in the heart of Winter Park, this 3-bedroom, 2-bathroom condo offers an excellent opportunity for both investors and buyers looking to customize a space in a highly desirable location. Whether you’re looking to renovate and create a strong rental or take advantage of the value for a primary residence, the potential here is undeniable. Inside, the spacious living and dining areas are filled with natural light, creating an open and inviting layout. The split floor plan offers three generously sized bedrooms, each with ample space and storage. A dedicated laundry room with washer and dryer adds everyday convenience. Step outside to your private courtyard with peaceful pond views, offering a quiet place to enjoy your morning coffee or unwind in the evening. The community features a pool, clubhouse, and well-maintained common areas, creating a welcoming environment for residents. This pet-friendly community also includes cable and high-speed internet through the HOA. Ideally located just minutes from shopping, dining, and major roadways including I-4, with easy access to downtown Orlando, area beaches, and theme parks. A great opportunity to own in Winter Park with flexibility, location, and value.
Courtesy: ONE LUXURY INTERNATIONAL LLC
407-312-8003
2026 PARADE OF HOMES ENTRY! - Positioned on an expansive corner lot in the heart of Winter Park, this extraordinary new masterpiece is a true architectural statement, delivering a level of craftsmanship and detail that is simply unforgettable. Framed by a massive front yard and a canopy of mature trees, the bold modern façade creates an immediate sense of arrival and sets the tone for what lies within. A grand set of double doors opens to a breathtaking two-story entry, where a dramatic marble mosaic feature establishes the home’s elevated design from the moment you step inside. The main living space is nothing short of stunning, anchored by a sleek electric fireplace and custom built-ins with integrated LED underlighting. At the heart of the home, the chef’s kitchen is a true showpiece, outfitted with Dekton Cosentino countertops, a paneled refrigerator, a full suite of Thermador appliances, and a hidden walk-in pantry. The kitchen flows effortlessly into the dining room which is bathed in natural light from an oversized statement window, making it perfect for hosting at any scale. Designed with versatility and luxury in mind, the home features two primary suites, one on each level. The downstairs primary offers soaring 12-foot ceilings and a serene, spa-like bath wrapped in marble mosaic tile. Upstairs, the main primary suite is a true showstopper, defined by its scale and attention to detail. Dual custom closet systems include an expansive hers closet complete with a dedicated makeup vanity, while the bathroom delivers a resort-caliber experience with stunning marble floors, a freestanding soaking tub, and dual vanities. The upper level continues to impress with a spacious loft designed for both relaxation and entertaining, complete with a custom entertainment center, wet bar, wine fridge, and a full bath. Each additional bedroom is ensuite, offering privacy and comfort for family and guests alike. Outdoor living rivals that of a private resort. A massive covered lanai features a fully equipped summer kitchen with tile backsplash, overlooking an expansive lounging area framed by a wall of glass. The heated pool and spa create the ultimate setting for year-round enjoyment, while the oversized front yard (an incredibly rare find in Winter Park), adds an unmatched sense of space and setting rarely found in this market. Additional features further elevate the home, including a sleek metal roof, striking hex LED lighting in the garage, and curated designer lighting fixtures throughout. Perfectly positioned just moments from Lake Chelton and Virginia Heights Park, with easy access to the boutiques and dining of Park Avenue and the charm of Hannibal Square, this residence offers a lifestyle that is as elevated as the home itself.
Courtesy: THE WILKINS WAY LLC
407-874-0230
Great opportunity to own this RENOvated and Move-IN ready 2 bedroom 2 bathroom one-story condo. Whether you’re looking tor your establishments roots, downsize to something simpler or an investment property, this size/floor plan/location fits the bill. Enjoy the recently updated kitchen and both bathrooms along with matching tile flooring. AND all major mechanical updates already taken care of. With a New Roof, Updated Electrical, Newer A/C, Replaced Water Heater and so much more... plus the community amenities include a pool, sidewalks, pet stations, and a sought after Winter Park location within walking distance to restaurants, grocery stores, shopping and biking distance to Full Sail.
Courtesy: KELLER WILLIAMS ADVANTAGE 2 REALTY
407-393-5901
Beautifully updated, move-in ready home in Winter Park. A brand new A/C system is scheduled to be installed. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall that adds warmth and character. Just behind the wall, a renovated half bathroom is conveniently located on the first floor. The kitchen is one of the main features of the home, fully renovated with custom green cabinetry, quartz countertops, a farmhouse sink with a modern faucet, gold hardware, and a clean contemporary backsplash. The space includes abundant cabinetry plus a pantry for additional storage and comes equipped with new stainless steel appliances including refrigerator, range, and range hood. Pendant lighting and chandelier details add a designer touch. The living area includes a fireplace and sliding doors that open to a screened patio, creating a comfortable indoor-outdoor flow. The outdoor space provides a private setting with a low-maintenance yard and room to relax or personalize. Upstairs, you will find all bedrooms along with a conveniently located laundry area. The primary suite is oversized and designed as a true retreat, featuring dual pendant lighting and great natural light. The primary bathroom is fully renovated with a freestanding soaking tub, double vanity, glass-enclosed walk-in shower with rainfall shower head, and modern finishes. The suite also includes dual closets for added functionality. Secondary bedrooms are well-sized and provide flexibility for family, guests, office, or additional living space. Additional improvements include a new front door, updated lighting throughout, and thoughtful design details that make this home feel clean, cohesive, and move-in ready. Located in the Villas of Casselberry community, this property has a low HOA with access to a community pool and sidewalks. Conveniently situated near major roads, shopping, dining, Full Sail University, Rollins College, UCF, and just minutes from Downtown Orlando. Move-in ready with extensive updates and a functional layout, this is a strong opportunity in the Winter Park market.
Courtesy: COLDWELL BANKER REALTY
407-333-8088
Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute. From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right, a spacious step-down living room offers abundant natural light and lovely views of the front yard. To the left, the formal dining room flows effortlessly into the heart of the home—a stunning, fully renovated kitchen and inviting family room overlooking the private pool and patio. The kitchen is designed to impress, featuring solid wood cabinetry, stainless steel appliances, sleek modern lighting, ample counter space, and a center island perfect for gathering. The adjoining family room is anchored by a stylish electric fireplace, creating a cozy ambiance while offering serene views of the outdoor living area. This home features a desirable split-bedroom floor plan, providing privacy and flexibility. The primary suite is tucked away on one side, while two additional bedrooms and a full bathroom are located on the opposite wing—ideal for family or guests. Extensive upgrades provide peace of mind and modern appeal, including a newer roof (2021), a newer AC (2019) fully renovated kitchen and bathrooms, 5-inch baseboards, knockdown ceiling texture, textured walls, luxury vinyl plank flooring throughout, fresh interior and exterior paint, and updated electrical and plumbing fixtures. Step outside to your private oasis—a fully fenced backyard with a screened-in pool enclosure and lanai, perfect for relaxing or entertaining year-round in true Florida style. This move-in-ready gem truly has it all. Don’t miss your opportunity—schedule your private showing today!
Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.
The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.
