Homes for Sale Near Winter Park High in Winter Park - 206 homes

Remarks: Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer. Located in a highly sought-after school district featuring Dommerich Elementary School, Maitland Middle School, and Winter Park High School, this property is ideal for homeowners and investors alike. Inside, you’ll find a Great Room floor plan with a separate dining room, split-bedroom layout, neutral interior paint and luxury vinyl plank flooring installed just four years ago throughout the home. The galley kitchen offers functional space and flows easily into the main living areas, while updated vanities and ceiling fans throughout add comfort and style. A large inside laundry room provides additional convenience. Sliding glass doors lead to a screened back porch overlooking the expansive backyard on this .23 acre lot — offering plenty of room to entertain, garden, expand, or create your dream outdoor retreat. Additional features include a 1-car carport and strong long-term investment appeal, as this property has been income-producing for decades. Whether you’re looking to personalize your forever home, secure a valuable investment, or break into Winter Park’s premier 32789 zip code at an exceptional price point, this property is packed with opportunity!

Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)

Listing Agent: Andrew Musashe (407-645-5700)

Remarks: Tucked away on a quiet cul-de-sac in highly sought-after Winter Park, this beautifully updated three bedroom, two bathroom duplex offers the perfect blend of comfort, style, and location—just steps from Winter Park Pines Golf Club. Once inside you discover open living spaces featuring warm wood flooring throughout the living areas and bedrooms, complemented by vaulted ceilings in the main areas and ceiling fans that enhance the home’s airy feel. The brand-new kitchen has tile flooring and is not only functional, but beautiful showcasing classic shaker cabinets, sleek quartz countertops, and stainless steel appliances—perfect for both everyday living and entertaining. There are three nice sized bedrooms, all with large closets. The primary bedroom features sliding glass doors that lead directly to the large backyard and open patio. Both bathrooms have been renovated with modern finishes, including new vanities, countertops, tub/showers, plus durable and stylish luxury vinyl plank flooring. Situated on a generously sized corner lot, the property offers plenty of outdoor space to enjoy, along with a charming paver front patio and the convenience of a one-car garage with opener. You will love the privacy of this end unit on the quiet cul-de-sac. Enjoy the ease of walking to nearby schools and being just moments from golf, shopping, dining, and all that Winter Park has to offer. With low HOA dues and located in a top-rated school district, this is an incredible opportunity in one of Central Florida’s most desirable neighborhoods.

Listing is courtesy of: SUN PROPERTIES, INC. (407-645-5700)

Listing Agent: Andrew Musashe (407-645-5700)

Remarks: Under contract-accepting backup offers. 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.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: Under contract-accepting backup offers. Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels intentional and refined, showcasing elegant finishes, designer touches, and a fresh, elevated aesthetic throughout. Recently fully repainted and enhanced with gorgeous new quartz countertops and a crisp white pearl subway tile backsplash, the home now feels both current and timeless while maintaining the charm and character buyers love about Winter Park living. At the heart of the home is a spectacular chef’s kitchen featuring top-of-the-line Viking and Bosch stainless steel appliances, including a Viking gas range with griddle, a large center island with counter seating, stunning cabinetry, and a dramatic 10-foot coffered ceiling. The kitchen flows seamlessly into the inviting family room with gas fireplace and custom window seating, creating the perfect setting for both everyday living and upscale entertaining. Triple French doors open to a generous covered lanai complete with a summer kitchen, built-in grilling station, and beautifully designed outdoor spaces beaming with old-world charm rarely found in newer construction homes. The turf backyard offers easy maintenance while creating a warm and private atmosphere for gatherings year-round. The formal dining room is equally impressive with crown molding, wainscoting, abundant natural light from the oversized bay window, and direct access to a convenient butler’s pantry and dry bar, making hosting effortless. Upstairs, the magnificent owner’s retreat offers oversized walk-in closets and a luxurious spa-inspired bathroom adorned with glorious marble tile work and elegant designer finishes. Two additional generously sized bedrooms share a marble bath and the 4th bedroom is currently shown as an office, with adjacent hall full bath. A downstairs powder room outfitted in new england blue theme is great for guests. Additional luxury features include hardwood flooring, plantation shutters, surround sound, tankless gas water heaters, an electric vehicle charger, oversized two-car garage with high ceilings and level 5 drywall finish, and countless thoughtful upgrades throughout. Located within the highly desirable Windsong community, residents enjoy access to incredible amenities including two resort-style pools, lakefront clubhouse, water park, playground, fishing pier, kayaks, paddleboards, and even a residents-only pontoon boat to explore the Winter Park Chain of Lakes. Just minutes from Park Avenue, Baldwin Park, and top-rated Winter Park schools, this is your opportunity to step directly into the Winter Park home of your dreams—fully upgraded, impeccably styled, and ready now.

Listing is courtesy of: ORLANDO PROPERTY ADVISORS (407-808-3695)

Listing Agent: Justin Pekarek (407-808-3695)

Remarks: Under contract-accepting backup offers. Offering 25k BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C, and water heater. Step inside to a Sun-filled sanctuary featuring new luxury vinyl plank flooring and gorgeous tile. The heart of the home is the brand-new chef’s kitchen, featuring custom white oak wood cabinetry, rare Taj Mahal quartzite countertops, and elegant champagne bronze finishes throughout. The kitchen flows seamlessly into the living areas, where new tile work elevates the wet areas for a cohesive, upscale feel. Work from home in style in the dedicated bonus room, an ideal footprint for a private office or creative studio. This home features true functionally for a family to live in everyday. This one of a kind home features a custom in home laundry room, custom vanities, a fireplace made to enhance the homes aesthetic & custom doors through the entire home. Beyond the interior, your private Florida lifestyle awaits. Retreat to the expansive screened-in pool, patio and large backyard. Located just steps from the Winter Park Pines Golf Course and the scenic Cady Way Trail, this home offers more than just a renovation—it offers a lifestyle. Enjoy easy access to the clubhouse for dining, top-rated schools, and the vibrant culture of downtown Winter Park. With every detail thoughtfully curated and major systems already updated, this is the turnkey masterpiece you’ve been waiting for.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Rene Droz, Iii (407-484-8786)

Remarks: Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of grandeur like no other. Inside, the home unfolds across more than 3,600 square feet of impeccably designed living space, with every room telling a story of quality, craftsmanship, and comfort. Rich herringbone hardwood floors stretch throughout the residence, complemented by bespoke millwork, and soaring ceilings. At the core of the home, the designer chef’s kitchen is a true showpiece, crafted for culinary excellence and effortless entertaining. Outfitted with top-of-the-line stainless steel appliances, custom cabinetry with designer hardware, and striking quartz countertops, the space is as functional as it is beautiful. A large island provides a natural gathering place, while an adjacent walk-in pantry offers seamless storage and prep. The primary suite is a retreat unto itself; a serene oasis tucked away for ultimate privacy. The spa-inspired en-suite bathroom rivals the finest resorts, featuring a soaking tub, walk-in shower with rainfall fixtures, designer lighting, dual vanities with custom cabinetry, and luxurious stone finishes throughout. A large, custom walk-in closet completes this elegant retreat. Beyond the main living areas, this home offers unique and thoughtfully designed spaces that elevate everyday living including a dedicated home office, a spacious loft, and a grand 3rd floor bonus room. Outdoors, a resort-style pool, covered lanai, and fully equipped summer kitchen create a private haven for year-round entertaining under the Florida sun. For the car enthusiast, this home offers a perfect fusion of elegance and functionality with a stately porte-cochere, a detached garage connected to the home by a breezeway, and an expansive motor court ideal for guest parking or showcasing a prized collection. Every element of this home speaks to impeccable taste and thoughtful design, from the curated finishes and luxury fixtures to the breathtaking architecture and designer lighting. Located just moments from Park Avenue, Rollins College, and Winter Park’s finest shopping and dining, you are truly in the heart of it all. More than a residence, this is a rare architectural masterpiece by Vimaro offering an unmatched lifestyle in the heart of one of Central Florida’s most coveted neighborhoods.

Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)

Listing Agent: Julie Christensen (407-592-2055)

Remarks: Under contract-accepting backup offers. 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!

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Marystuart Day (407-620-8683)

Remarks: This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate the interior space, but they are also impact-resistant, energy-efficient, noise-reducing, and offer UV protection. The interior renovation was designed with minimal barriers between living areas, creating open, fluid spaces that enhance day-to-day living. The bedroom and bathroom layout is ideal, offering maximum privacy: two large bedrooms share one full bathroom on one side of the house, another bedroom with an en-suite bathroom is at the center, and the primary bedroom and bathroom are on the other side. Wood or natural stone flooring, extensive millwork, vaulted ceilings, new paint, updated lighting fixtures, and new fans enhance the spaces throughout. The kitchen was renovated to include an oversized, under-mount farmhouse sink, commercial-grade faucet, new LED lighting, and quartz countertops with a waterfall edge. The primary suite was updated by a former owner but was renovated by the current owner to add a second walk-in closet with custom organization. All bathrooms received light renovations, ranging from hardware and paint to new fixtures or vanities and countertops. In addition to the visually appealing renovations, the roof was replaced in 2019 and the house was re-plumbed in 2020. The outdoor improvements may be the most valued, as they created endless opportunities for outdoor living and entertaining on the newly constructed deck and enhanced landscape. All of the outdoor living benefits Florida provides are available here. A natural gas line was brought to the house as part of the renovation, allowing for easy future modifications such as a tankless gas-fueled water heater or gas-fueled outdoor grill. Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Come home to this gorgeous 3 Bed/3 Bath Winter Park masterpiece on a premier corner lot at the intersection of the coveted Alabama Drive and Palmer Avenue. FULLY RENOVATED DOWN TO THE STUDS IN 2020. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic tree-lined brick streets of the Chain of Lakes district and surrounded by historic estate homes. The Lifestyle: Central Florida's Premier Luxury Destination Living at 1110 Alabama Drive means immersing yourself in the rich culture and timeless elegance of Winter Park. This historic city is celebrated for its deep canopy oak trees, world-class amenities, and a laid-back atmosphere. A Walker's & Boater's Paradise: You are just a short, scenic stroll from the exclusive boutiques, acclaimed sidewalk cafes, and Michelin-starred dining lining Park Avenue. Spend your weekends grabbing fresh produce at the famous local farmers' market or launching a boat onto the stunning interconnected freshwater Chain of Lakes. Surrounded by Beauty: This home places you moments from the breathtaking, massive cypress trees and vibrant blooms of Kraft Azalea Gardens, as well as the private, historic Winter Park Racquet Club. The Residence: Fully Renovated & Refined No detail has been spared in this total home transformation, seamlessly blending a classic, highly coveted location with cutting-edge modern amenities. Gourmet Kitchen: Discover a massive chef’s footprint appointed with premium granite countertops and high-end finishes, making it the focal point for both daily living and grand entertaining. Designer Upgrades: Rich hardwood flooring flows effortlessly throughout the home, beautifully complemented by high-efficiency upgraded Pella windows that provide enhanced aesthetics and excellent energy savings. Modern Infrastructure: Enjoy total peace of mind with meticulously updated systems, including a 5-year-old tankless water heater, a custom-designed garage door, and a well-maintained 12-year-old roof. The Ultimate Outdoor Oasis Designed intentionally for the true Florida lifestyle, the exterior of this property serves as a completely private sanctuary. Signature Screened Porch: Step out into an expansive outdoor living space anchored by a cozy gas fireplace—serving as the ultimate venue for year-round entertaining. The Grounds: Relax by the private, open-air pool surrounded by lush, tropical landscaping and a fully irrigated lot, capturing resort-style living in your own backyard. Whether you are searching for a turnkey luxury residence or looking to secure a rare, premier canvas in Central Florida’s most coveted zip code, this estate has it all.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Omar Albaba (813-951-7475)

Remarks: Under contract-accepting backup offers. Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.

Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)

Listing Agent: Mick Night (407-629-4446)

Remarks: Under contract-accepting backup offers. 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!

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Christina Frucci (321-303-6881)

Remarks: Under contract-accepting backup offers. Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood cabinetry, granite countertops, black appliances, and a dishwasher replaced in 2023, perfect for everyday cooking and entertaining. Just off the kitchen, enjoy a dedicated dining area, ideal for hosting dinners or creating a flexible space for a home office or additional seating. The inviting living room provides plenty of space to relax and gather, with sliding glass doors that lead to your private, fully fenced, tree-shaded patio complete with a storage shed - an ideal spot to enjoy your morning coffee or unwind in the evenings. The patio also offers convenient access to your covered, deeded carport space, #49. Both bedrooms are generously sized, with the primary bedroom featuring dual closets and a ceiling fan for added comfort. The home includes a full bathroom and a convenient half bath, both thoughtfully updated with new toilets and upgraded vanities, including a quartz countertop and stylish shiplap accent in the guest bath. Additional interior highlights include custom closet features, a laundry closet with a new stackable washer and dryer(included), ceiling fans and blinds throughout, fresh interior paint (2024), and an HVAC system updated in 2023, providing peace of mind and modern convenience. Residents of Four Seasons enjoy access to a variety of amenities including 3 swimming pools, a clubhouse with fitness center, tennis and shuffleboard courts, all within a quaint, established neighborhood with tree-lined walkways. Ideally located just minutes from Ward Park, Winter Park Pines Golf Club, YMCA, AdventHealth Winter Park, and the Center for Health & Wellbeing. Enjoy easy access to shopping and dining along Aloma Avenue including Publix, Sprouts, and Aldi, as well as being less than 10 minutes from Park Avenue’s renowned restaurants and boutiques. Conveniently located near SR 436 with quick access to 417 and 408, and approximately 25 minutes to Orlando International Airport. Zoned for top-rated schools: Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss your opportunity to own in one of Winter Park’s most desirable communities—schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Amy Turner (407-803-3885)

Remarks: PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone fireplace and built in shelving for an elegant look in the Family Room. The kitchen has stainless steel appliances, wood cabinets with under cabinet lighting, and bar top seating. Primary Bedroom has a walk-in closet and a glass door shower with tile walls and built-in niches. The Primary bathroom has private access to the screened patio (Florida Room) and spacious backyard. The gated fence opens extra wide for boat, RV or your trailer entry. This entry is very convenient to back any trailer size. For outdoor activities, you just step out of the house and go on a Cady Way Trail for biking, skating, and walking activities. For tennis lovers there are very well kept tennis courts where sport enthusiasts practice their skills in pickleball. Right next to the tennis courts is a playground that offers cozy shaded areas with slopes, swings, and climbing walls. Publix, Costco, Walmart and the post office are all located nearby. For evening promenade the downtown Winter Park, located just a few miles away, offers unique restaurants, cozy coffee shops and bars. To see this amazing 3 bedroom home for sale in Winter Park, call today and schedule a showing! NOTE: Roof - July 2023. HVAC - 2015. No HOA, NO CDD.

Listing is courtesy of: IMPERIAL REALTY OF FLORIDA INC (407-346-4746)

Listing Agent: Tanya Vyushkina (407-346-4746)

Remarks: 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.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: John Harbuck (407-538-2841)

Remarks: Under contract-accepting backup offers. Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Mary Colton (407-222-7388)

Remarks: Under contract-accepting backup offers. 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.

Listing is courtesy of: MAROON REALTY GROUP LLC (407-774-7083)

Listing Agent: Larry Lanpher (407-383-8759)

Remarks: Just Reduced the Price! "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchen with Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI. And here is an inground pool in the back yard. You will enjoy entertaining in this home featuring a gourmet kitchen with granite countertops, and stainless steel appliances. This property may qualify for Seller Financing (Vendee). If property was built prior to 1978, Lead Based Paint Potentially Exists. Come tour this home today. We expect this one not to be on the market long at this REDUCED price.

Listing is courtesy of: WEATHERSPOON REALTY INC (407-878-4468)

Listing Agent: Eugene Weatherspoon (407-878-4468)

Remarks: Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home features floor-to-ceiling glass, a wraparound terrace, and a bold two-story façade. The quartz river rock and concrete drive leads to dual frosted glass garage doors, pre-wired for an EV charger. Inside, a dramatic floating staircase is framed by a 17’ window, anchoring the open-concept living space with views of the private backyard. The modern kitchen includes light gray touch-open cabinetry, soft-close drawers, black stainless appliances, and a Calacatta quartz waterfall island. The outdoor space is designed for entertaining, with a covered lanai, expansive marble terrace, and a mini-pebble pool with sun shelf and water features. Lush podocarpus hedging and a masonry wall provide privacy. The first floor offers a dedicated office and full pool bath. Upstairs features four bedrooms with Italian frameless doors and three European-inspired bathrooms. The primary suite includes a custom walk-in closet and private access to the wraparound terrace overlooking the pool. Surrounded by beautiful tree-lined streets ideal for strolling and golf-cart rides to nearby shops, restaurants, and friends’ homes, this property offers the best of the Winter Park lifestyle. The home is also zoned for top-rated Winter Park schools. A rare modern home in one of Winter Park’s most desirable locations. Call today for your private showing.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: Under contract-accepting backup offers. Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Liz Jones (407-619-6345)

Remarks: Under contract-accepting backup offers. 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.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)