Winter Park Single Family Homes For Sale - 315 homes

Remarks: Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and kitchen are arranged in a way that supports an open and functional feel, making the home especially appealing for hosting and daily routines alike. The family room adds valuable extra living space and creates a natural hub for movie nights, casual gatherings, or a second lounge area. The floorplan also shows a sun room extending off the family room, giving the home even more flexibility for relaxing, hobbies, or enjoying a bright bonus space with views of the backyard. The bedroom layout is thoughtfully separated from the main entertaining areas, offering privacy and comfort. The primary suite is positioned apart from the secondary bedrooms and includes its own bath and closet space, creating a peaceful retreat within the home. Three additional bedrooms provide flexibility for guests, a home office, or changing household needs. Outside, the open patio and private yard add to the home’s lifestyle appeal, creating space to enjoy outdoor dining, weekend get-togethers, gardening, or quiet mornings in the Florida sunshine. Together with the interior layout, these outdoor features help make the home feel both versatile and welcoming. Located in Winter Park, the property is set in a highly desirable area known for its established residential feel, attractive surroundings, and convenient access to shopping, dining, parks, and everyday amenities. The neighborhood adds to the home’s appeal by offering both comfort and accessibility in one of Central Florida’s most sought-after locations. **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.**

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

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

Remarks: Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and space with a layout designed for everyday living and entertaining. The home features a inviting living area along with a unique sunken sunroom just off the two-car garage; perfect for a relaxing sitting room, home office, or play space. The well-appointed kitchen and dining areas flow easily into the main living spaces, creating a warm and functional environment for family and guests. Step outside to your private backyard retreat where you’ll find a sparkling pool and hot tub surrounded by a huge yard, offering plenty of room for outdoor gatherings, gardening, or simply enjoying Florida living. With its generous lot size, thoughtful layout, and prime Winter Park location close to shopping, dining, and top-rated schools, this home is a wonderful opportunity for anyone looking to enjoy the best of Central Florida living.

Listing is courtesy of: EXIT REAL ESTATE PROPERTY SOL (386-763-3008)

Listing Agent: Jami Giles (386-478-8284)

Remarks: One or more photo(s) has been virtually staged. BACK ON MARKET; BUYERS GOT COLD FEET! Perfect for a growing family, this home is located in the highly sought-after Kenilworth Shores community, where tree-lined streets, friendly neighbors, top-rated schools, and an unbeatable Winter Park location create a lifestyle people rarely want to leave. Surrounded by excellent schools and just minutes from parks, dining, and shopping, this is the kind of neighborhood where families can truly settle in and grow for years to come. From the moment you step inside, the home offers a warm and inviting feel with spaces designed for both gathering and unwinding. The front living room creates the perfect setting for quiet mornings with coffee, catching up with friends, or relaxing with a good book, while the dedicated dining room is ready for holiday dinners, celebrations, and memorable nights around the table. At the center of the home, the kitchen naturally becomes the heart of daily life — a place where conversations happen while meals are prepared, homework gets finished, and guests always seem to gather. Just beyond, the spacious family room with a cozy fireplace invites movie nights, game days, and relaxed evenings spent together. Upstairs, the thoughtful layout provides the perfect balance of comfort and privacy. Guest bedrooms provide flexibility for family, visitors, or working from home, while the oversized primary suite feels like a true retreat with space to recharge at the end of the day. Step outside and embrace the Florida lifestyle with a covered patio and large fenced backyard ideal for weekend barbecues, kids and pets playing freely, or simply enjoying beautiful evenings outdoors. The home also offers peace of mind with major updates already completed, including a 2020 A/C system and 2021 water heater. Living in Kenilworth Shores means having some of Central Florida’s best lifestyle amenities just minutes away. Spend weekends biking the trails at Cady Way Park, enjoying community events in Baldwin Park and Winter Park, grabbing dinner along Park Avenue, or exploring nearby shops, coffee spots, and local restaurants. With easy access to 417, 408, and I-4, commuting downtown, heading to the airport, or taking a quick beach trip becomes incredibly convenient. More than just a home, this is the kind of neighborhood and lifestyle people move to Winter Park for — connected, comfortable, and centered around enjoying everyday life. Schedule your showing today as this home will not last long.

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: David Miller (407-323-4210)

Remarks: Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living spaces that all blend into a covered porch to backyard retreat. The kitchen is the center of the home with custom double-stacked cabinetry to ceiling, upgraded appliances, large pantry with barn door, center island with bar seating, and full granite slab backsplash and counters add to the artistry of the kitchen. Ceilings are upgraded throughout with floating box details with ambient lighting that gently wash the ceilings and colors can be changed as you wish. Dining and living spaces are generous, and lined with transom windows for privacy and natural light that creates a beautiful backdrop to gather and entertain in. Invisible back doors fully open to the lanai and slide into the wall, staying hidden, an elegant upgrade. Covered porch with tongue and groove ceiling overlooks saltwater pool with hot tub and spillway. Professionally landscaped includes a turfed putting green for the golf enthusiast. Additional main floor flex space can be additional living or home office. Secondary bedrooms are upstairs with generous bonus space and laundry. First-floor primary suite is light and bright, with coffered ceilings and a large walk-in closet. Primary bath is neutrally appointed with dual floating vanities with vessel sinks, a soaking tub, and walk-in shower with seamless glass. A transom window provides privacy and a glow of sunshine and warmth. Lots of seller upgrades. This property is turnkey. Orwin Manor is a special neighborhood blending historic homes with new builds and great neighborhood park to go to. It is also a strategic location, minutes to Park Avenue in Winter Park, known for its upscale dining, elevated cafés and luxury local shopping, also a short distance to Orange Avenue corridor in WP featuring Foxtail Coffee & Buttermilk Bakery and more, and minutes to the Mills district, Advent Health on Rollins as well as major roadways. Great schools, zoned for Edgewater High, known for its magnet program and close to Lake Highland and many other private school options.

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

Listing Agent: Alison Mosley (407-304-6458)

Remarks: Under contract-accepting backup offers. A house in Winter Park under $500K?! No way! Let's not forget, everything was fully gutted and remodeled in 2023. New roof, water heater, AC, electrical wiring and panel, plumbing, double pane windows, water softener, flooring, exterior paint, bathrooms, kitchen, outdoor french drains, garage door, screened-in lanai — ALL ONLY THREE YEARS OLD. This home is the absolute definition of MOVE-IN READY. Situated on a 1/4 acre oversized lot, there's plenty of room for you to add a pool, park your boat, or create that true backyard oasis you've been dreaming of. Fully fenced-in and NO HOA. The kitchen features high-end quartzite countertops with a built-in pantry and newer stainless steel appliances. Open floor plan with high ceilings and tons of natural light. Almost 2,000 sqft of living area with an inside utility room that houses your washer/dryer (which are included with the purchase!). Master bedroom is equipped with a massive 8'x11' walk-in closet and a show-stopping en-suite bathroom! Conveniently located 10 minutes from Park Avenue, 15 minutes from Valencia and/or UCF, and right around the corner from highway ramps making commuting a breeze. Homes like this don't come often. Don't miss your chance to live in Winter Park!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Angie Kollcaku (407-454-4078)

Remarks: 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.

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

Listing Agent: Kirstie Hines (321-440-7716)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Back on the market and better than ever! New water heater and minor repairs addressed and ready for the new owner! Come see this newly renovated home in the Eastbrook neighborhood of Winter Park. Offering 3 bedrooms and 2 full baths it’s the perfect sanctuary for families and entertainers alike. You will enjoy the bright, airy feel of the open floor plan accentuated by the vaulted ceilings that flood the space with natural light. The stylish interior includes luxury vinyl plank flooring throughout, complemented by elegant tile in the bathrooms and laundry room. Relax in not one, but two generous living areas, perfect for family gatherings, entertaining or cozy nights in. Cook like a pro in your eat-in kitchen featuring brand new ENERGY STAR stainless steel appliances, ample cabinetry, and convenient carport access for effortless unloading. The generous backyard provides a private oasis for outdoor activities, barbecues, and gardening enthusiasts. Plus, the expansive driveway and two-car carport ensure plenty of parking for your guests. Recent upgrades include ceiling fans, blinds, fresh paint, stainless steel appliances, a newer roof (2017) and a well-maintained air conditioner (only 4 years old) ensuring peace of mind for years to come. Located in Seminole County, known for great schools and in a community with NO HOA fees, giving you the freedom to enjoy your space. Plus, you're just moments away from shopping, dining, and parks!

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

Listing Agent: Brenda Feliciani (407-405-0931)

Remarks: Tucked into one of Winter Park's most convenient pockets, this thoughtfully updated residence offers a seamless blend of comfort, style, and convenience. With three bedrooms and two bathrooms, the layout provides flexibility for a variety of living arrangements while maintaining a warm, welcoming feel throughout. The updated kitchen is both functional and inviting, featuring a gas stove and a dedicated coffee bar that adds a touch of everyday luxury. Living spaces flow effortlessly to the outdoors, where a large screened-in porch invites year-round enjoyment, complemented by a paved patio with a firepit that's ideal for relaxed evenings. The yard is perfectly sized for easy maintenance and enjoyment, complete with built-in swings that add a unique and playful detail. Positioned in a highly desirable location, this home is just moments from Interlachen Country Club, Full Sail University, and AdventHealth Winter Park, with everyday essentials like Costco nearby. Enjoy quick access to the shopping and dining of Park Avenue, just 15 minutes away. A rare opportunity to enjoy a move-in-ready home in one of Winter Park’s most convenient and connected areas. Recent updates include a 2021 roof, offering peace of mind and move-in ready convenience.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Hannah True (407-923-9330)

Remarks: Nestled in one of Winter Park’s most sought-after neighborhoods, this charming and meticulously maintained home offers three bedrooms, two baths, an open floor plan, hardwood floors, and thoughtful updates throughout. Recent improvements include a new AC, new hot water heater, new driveway and walkway pavers, and refreshed front and backyard landscaping featuring a magnolia tree, camellias, gardenias, and more. Just minutes from Park Avenue’s beloved restaurants, cafés, and boutiques, as well as the scenic Winter Park Chain of Lakes, this home offers both character and convenience. With easy access to I-4, SR-417, Orlando International Airport, and top-rated schools, it is a wonderful opportunity to enjoy classic Winter Park charm in a beautifully cared-for home.

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

Listing Agent: Kyle Grafton (203-246-8512)

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: Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting front porch, the perfect place to relax, enjoy conversations with friends, and greet neighbors passing by. Inside, the home features recently painted interiors and new laminate flooring in the bedrooms, creating a fresh and move-in-ready feel. Pride of ownership shines throughout, as this home has been lovingly cared for over the years. Step outside and enjoy the spacious, landscaped backyard complete with a private irrigation well, screened-in porch ideal for morning coffee or evening unwinding, and a charming brick fire pit perfect for cooler Florida nights. There's even an outdoor shower, a unique and convenient touch after gardening or enjoying time outside on warm summer days.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Joseph Firmin (954-296-8861)

Remarks: Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning two-tone kitchen is a true centerpiece, featuring sleek quartz countertops, contemporary finishes, and new appliances to be installed at closing—perfect for both everyday living and entertaining. The upgrades continue in the fully renovated bathrooms, where carefully selected color palettes and high-quality finishes provide a fresh, sophisticated look designed to stand the test of time. Every detail of this home has been meticulously considered, leaving no space untouched. Outdoors, enjoy your private oasis with a newly resurfaced pool—ideal for relaxing weekends or hosting gatherings year-round in Florida’s sunshine. This move-in-ready gem offers the perfect opportunity to own a like-new home in a highly desirable location. Come experience the beauty, quality, and lifestyle that 2708 Lion Heart Rd has to offer—your dream home awaits.

Listing is courtesy of: EQUITYPRO LLC (407-203-6860)

Listing Agent: Navid Rokh (321-900-5977)

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 custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet, downstairs main and additional guest suite, and upstairs includes remaining beds and baths. An inviting foyer welcomes you with volume ceilings, wood floors and a large transom window that allows beautiful natural light in. The family room is spacious with a marble wrap electric fireplace with lighting detail and niche for a flat screen TV. Clear glass doors across the back of the house lead you to the outside covered porch for ease of entertainment. The kitchen is open, light and bright with 42-inch shaker double stack cabinetry, large pantry and great workspace, a peninsula with bar seating as well as an eat-in kitchen area for large gatherings. Stainless appliances, granite counters and creative backsplash round it all out. The oversized laundry room includes an extra refrigerator and a second pantry for added convenience. The dining with tray ceiling, designer fixture and textured wallpaper add to the style of the home as well as dedicated office or flex space. Luxury continues into a primary suite with built-ins, large spa-like bath with sleek finishes, soaking tub, large dual-head shower and spacious walk-in closet. The primary suite overlooks backyard and opens to an outdoor oasis with open-air lanai with generous covered porch to gather or enjoy a night of alfresco dining. State-of-the-art modern resort-style pool with heated spa, sun shelf with fountain feature, a fire feature runs along edge of pool and transforms the backyard into a luxurious tropical oasis particularly at night. Hardscaping elements include pathways trimmed with turf grass, professional landscape lighting that enhances and elevates the home. Don’t wait to tour this special home in the heart of Winter Park, close to the best schools with Lakemont Elementary, Glenridge Middle and Winter Park High. A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants.

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

Listing Agent: Alison Mosley (407-304-6458)

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: Beautifully updated 3 bedroom, 2 bath home with a sparkling in-ground pool, located in highly sought-after Winter Park. This move-in ready property features fully upgraded kitchen with features like quartz countertops and soft close cabinets, updated bathrooms, new stone composite plank flooring, and double pane windows that bring in abundant natural light. Major system updates include a new roof (2022) and full house re-pipe (2025). Freshly painted, this home offers both style and peace of mind. Escape to your own backyard Oasis with a beautiful pool surrounded by lush landscaping and a covered patio for entertaining friends and family. A true turnkey opportunity ready to impress the pickiest buyer.

Listing is courtesy of: HOUSE HUNTING IN FLORIDA LLC (407-676-4747)

Listing Agent: Byron Kirkpatrick (407-765-1583)