Winter Park Homes For Sale & Real Estate - 449 homes

Remarks: Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation

Listing is courtesy of: OPENDOOR BROKERAGE LLC (480-462-5392)

Listing Agent: Karen Albright (480-462-5392)

Remarks: Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

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

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

Remarks: A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desirable locations. From the moment you step inside, a dramatic two-story foyer and soaring ceilings set the tone for a home that seamlessly blends sophisticated design with everyday comfort. The open-concept living areas are filled with natural light and anchored by a stunning feature wall with a sleek fireplace, creating an inviting space for both intimate gatherings and large-scale entertaining. At the heart of the home, the kitchen showcases a statement island, European-style cabinetry, premium finishes, and quality appliances, while a custom wine display tucked beneath the staircase adds a distinctive architectural touch. Designed with flexibility in mind, the first floor features a private guest suite with en-suite bath, a dedicated home office, and convenient laundry room. Expansive sliding doors open to a fully equipped outdoor kitchen, creating a seamless indoor-outdoor lifestyle perfectly suited to Florida living. Upstairs, the primary suite serves as a private retreat, complete with a custom walk-in closet and spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and elegant finishes throughout. Three additional bedrooms provide exceptional accommodations, including a Jack-and-Jill layout and an additional en-suite bedroom. Ideally positioned just minutes from Park Avenue, residents enjoy effortless access to Winter Park's renowned dining, boutique shopping, cultural attractions, parks, and top-rated schools. Combining exceptional craftsmanship, modern design, and an unbeatable location, this is a rare opportunity to own a brand-new luxury home in the heart of Winter Park.

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

Listing Agent: Nick Mckee (407-913-0171)

Remarks: Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the center of esteemed Winter Park. This beautifully updated upstairs unit sits within the serene Winter Park Gardens complex, where your views of the shimmering pond and pool anchor a lush sprawling landscape of live oaks draped in Spanish moss, mature manicured gardens, and lighted walkways- perfect for evening strolls. The unit itself has been thoughtfully renovated with brand-new luxury vinyl plank flooring, an open kitchen, updated granite countertops, and a fully renovated bathroom — all combining to deliver exceptional value in one of Central Florida's most coveted zip codes. This is a 55+ community with room for younger owners.

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

Listing Agent: Olivia Maxwell (407-222-4440)

Remarks: Virtually Staged. FABULOUS 3 bedroom 2 bath RENOVATED home with a 1 car garage located in a PRIME LOCATION!! Perfect for the first time homebuyer, investor or someone looking to downsize. The large family room benefits from natural lighting provided by the NEW WINDOWS installed(2024) throughout the ENTIRE house. The open kitchen overlooks the covered porch and large, FULLY FENCED backyard. The primary bedroom has LPV flooring with an UPDATED bathroom. NEWER carpets in the other two bedrooms. Second bath has a new toilet with a bidet, a tile bath/shower combo, and an updated vanity. NEW lighting, outlet and switch plate covers throughout. A NEW roof ridge vent was added for extra ventilation! NEW LANDSCAPING in the front. NEW DRAINFIELD (2026), water heater (2023), roof(2021). It is in Seminole County school district, 15 minutes to UCF, 5 minutes to shopping, and 10 minutes to the highway. HURRY, you don't want to miss this opportunity!!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)

Listing Agent: Heather Pryor (321-303-5393)

Remarks: Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One of the bedrooms has been converted into a large closet and dressing room, offering generous storage while still allowing the option to easily convert the space back into a traditional fourth bedroom if desired. The backyard extends the home outdoors with a patio and cobblestone brick area that is well suited for entertaining, outdoor dining, or quiet evenings at home. Set within the established Winter Park Pines community, the home offers sidewalks for excellent walkability, with Cady Way Trail just steps from your door for morning runs, bike rides, and everything in between. Nearby, Cady Way Park adds even more to the neighborhood lifestyle with its pool, tennis and pickleball courts, playground, and beach volleyball, while Park Avenue offers boutique shopping and exceptional dining just minutes away. 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 combines comfort, convenience, and the everyday appeal that continues to make Winter Park Pines one of Winter Park’s most established neighborhoods.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Melissa Johnson (407-681-4393)

Remarks: Culture, Convenience, Community! Discover refined living in the heart of Winter Park, where timeless luxury meets an unmatched lifestyle. This beautifully designed single-story residence offers three spacious bedrooms, a private office, two elegantly appointed baths and over 2,000 square feet of living space complete with a two-car garage and no HOA. Thoughtfully curated with sleek tile flooring throughout and no carpeting, the home exudes both style and comfort. The well-equipped kitchen features granite countertops, a pantry, and a charming breakfast area, flowing effortlessly into the expansive family and dining rooms. French doors open to a generous screened lanai and a private fenced backyard, creating the perfect setting for seamless indoor-outdoor entertaining. Designed with a desirable split floor plan, the luxurious primary suite offers private backyard access, dual walk-in closets plus an additional storage closet and a private bath with a spacious walk-in shower. Two additional guest bedrooms share a beautifully appointed bath with shower/tub, while one bedroom enjoys direct access to a dedicated office space, ideal for guests or working from home. Winter Park is celebrated for its distinctive blend of arts and culture, charming sidewalk cafés, acclaimed museums, upscale accessible neighborhoods, scenic lakes, outdoor recreation and year-round festivals. Surrounded by top-rated schools and picturesque tree-lined streets, this exceptional location offers premier conveniences. Near AdventHealth, Cady Way Trail and recreational parks, YMCA of Central Florida, public golf courses, Rollins College, Full Sail University and UCF. Whether you're seeking outdoor adventure, cultural enrichment, or everyday convenience, this location delivers it all. Schedule your private showing today and discover the best of Winter Park living. Roof - 2018, AC - 2015.

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

Listing Agent: Farah Novin (407-234-0501)

Remarks: Located in the heart of Winter Park, Winter Park Pines is a well-established neighborhood known for its convenience, school zoning, and access to outdoor living. 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 back door for morning runs, bike rides, and everything in between. One of the standout features is having the Cady Way pool, pickleball courts, and beach volleyball courts all just a short walk away. The home is zoned for Brookshire Elementary School, Glenridge Middle School, and Winter Park High School, making this location a consistent choice for buyers prioritizing long-term value. In addition to the location, the home benefits from key updates already completed, including a 2022 roof, 2021 HVAC system, updated windows installed in 2017, along with an updated kitchen and bathrooms, offering peace of mind and modern functionality for the next owner. Ideally positioned to enjoy the Winter Park lifestyle. Close proximity to Park Avenue’s boutique shopping and exceptional dining, while the University of Central Florida, Rollins College, and Full Sail University are all within easy reach. AdventHealth Winter Park and Orlando International Airport are also close by, making both daily routines and travel simple. This is a home that delivers on every level, location, lifestyle, and lasting quality.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Melissa Johnson (407-681-4393)

Remarks: Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement home located within one of Winter Park's most desirable pockets and zoned for Audubon Park K-8. From the moment of arrival, the home's striking blend of natural stone, warm white oak, rich textures, and beautifully composed architectural lines creates an unforgettable first impression. Step inside and you're immediately greeted by soaring ceilings, exposed oak beams, wide-plank white oak flooring, and expansive walls of glass that fill the home with natural light. The great room serves as the heart of the residence, anchored by a floor-to-ceiling natural stone fireplace with illuminated built-ins and expansive sliders that seamlessly connect indoor and outdoor living. At the center of the home, you'll find a beautifully executed kitchen designed for both entertaining and everyday living, featuring floor-to-ceiling custom white oak cabinetry, designer stone surfaces, a substantial center island, illuminated wine display, a 48-inch gas range, and abundant storage. Nearby, a walk-in pantry, fully built-out laundry room, and mudroom enhance functionality while maintaining the home's refined design language. Privately positioned on the main level, the dedicated office provides an inspiring setting for work, study, or creativity, while the primary suite serves as a true retreat. The spa-inspired bath is finished with floating oak vanities, rich stone surfaces, a freestanding soaking tub, and an expansive wet room that feels more like a luxurious resort. It's the kind of retreat you'll appreciate every morning and look forward to returning to at the end of each day. Upstairs, a versatile loft creates the perfect setting for a media room, playroom, study space, or secondary gathering area. One bedroom enjoys the privacy of its own ensuite bath and walk-in closet, while two additional bedrooms are connected by a beautifully appointed Jack-and-Jill bath. Step outside and you'll find yourself lingering a little longer than planned. A custom PebbleTec pool, covered tongue-and-groove lanai, fully integrated outdoor kitchen, and private backyard setting create an environment designed for effortless entertaining and low-maintenance enjoyment. Built by Structure Redevelopment, a boutique builder known for delivering thoughtfully crafted custom residences throughout Central Florida. Just minutes from Park Avenue, Rollins College, East End Market, Audubon Park, and Downtown Orlando, Casa Noir brings together exceptional architecture, thoughtful design, and everyday livability in one of Winter Park's most desirable locations - Schedule your tour today.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Ahmad Hassan, Pa (718-641-9358)

Remarks: Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights neighborhood, the location offers both prestige and convenience. From the moment you enter through the impressive double doors, you’re welcomed by a light-filled, open-concept design. Soaring 10-foot ceilings and elegant 8-foot doors create an airy, expansive feel, while abundant natural light highlights the home’s sleek, contemporary finishes. At the heart of the home, the chef-inspired kitchen truly shines. Outfitted with luxurious quartz countertops, stainless steel appliances, and a custom LED-lit wine display, it’s designed to impress. The seamless flow into the living and dining spaces—along with views of the backyard—makes it perfect for entertaining or everyday connection. The primary suite is a private sanctuary, offering a spa-like escape with dual vanities, a spacious dual-entry shower, and a freestanding soaking tub designed for relaxation. With three additional bedrooms, a dedicated office, and 3.5 beautifully appointed bathrooms, this thoughtfully designed single-story home provides nearly 2,500 square feet of flexible living space. Outdoors, your personal retreat awaits. Enjoy year-round Florida living on the covered lanai, complete with a built-in summer kitchen and a custom-designed pool—ideal for hosting or unwinding. The fully fenced yard features new vinyl fencing, fresh sod, and an automated sprinkler system for effortless maintenance. Perfectly positioned near Phelps Park, the Winter Park YMCA, Lakemont Elementary, and an array of top-tier shopping and dining destinations, this home delivers the ideal blend of privacy, craftsmanship, and everyday luxury.

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

Listing Agent: Nick Mckee (407-913-0171)

Remarks: New Construction – Carefully Curated by SGC Conctruction. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within walking or biking distance of premier restaurants, cafés, boutique shops, and entertainment venues. Designed for both daily comfort and elevated entertaining, the open-concept floor plan boasts thoughtful design and high-end finishes throughout. Luxury details abound, including engineered wood floors featuring an elegant herringbone pattern in the foyer, smooth finish Level 4 drywall, and a cozy electric fireplace that enhances the spacious great room, accentuated by LED mood lighting in the coffered ceiling. The expansive gourmet kitchen is a chef’s delight, equipped with ceiling-height cabinets for ample storage and premium Thermador appliances, including a 36” gas cooktop, wall oven, built-in microwave, French door refrigerator, and a wine fridge — all complemented by sleek cabinetry and contemporary details. A beautiful dry bar adjacent to the kitchen provides extra space for coffee, wine, or entertaining guests. Offering four generous bedroom suites, this home includes a luxurious primary suite on the main level, along with a versatile second suite on the first floor, ideal for use as an office or guest retreat. Upstairs, two additional suites are connected by a flexible bonus room — perfect for a home office, gym, second living area, or even a fifth bedroom. Step outside to your private outdoor oasis, featuring a covered lanai with automatic roll-down screens, a fully-equipped summer kitchen (complete with grill, sink, and refrigerator drawers), and a sparkling pool adorned with travertine decking — perfect for year-round Florida entertaining. The elegant exterior showcases outdoor lighting and lush landscaping, along with a gas generator to ensure your home is always prepared for storm season.Don’t miss your opportunity to own this exquisitely crafted home in one of Orlando’s most sought-after neighborhoods. Schedule your private showing today and experience the pinnacle of luxury living in Winter Park! There are special builder incentives available right now- Call for details!!

Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)

Listing Agent: Kim Griffin (407-314-5033)

Remarks: In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Now offered at a newly adjusted price, the home presents a compelling opportunity to experience design-forward new construction in the Vias neighborhood. Developed and designed by Steve & Jodie Warrick Konold of Scout & Co., the 3,850-sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway & garden courtyard—envisioned in collaboration w/ architect Cynde Norris—French antique gates open to a native-planted entry garden, creating a soft transition to the interior. A glass foyer introduces a tongue-and-groove ceiling & woven rattan chandelier, sourced & designed in London, leading to a sculptural stairwell positioned just off the main living spaces. The great room features soaring ceilings, a sleek fireplace & walls of glass windows & doors that blur the boundary between inside & out. Ten-inch baseboards meet level 5 drywall in a clean reveal, paired w/ micro-crete flooring on the main level & wide-plank European oak upstairs. In the kitchen, materials w/ function are elevated w/ a Thermadore dual-fuel range, custom plaster hood, full refrigerator & freezer columns & a large island topped in honed black quartzite. The surrounding cabinetry is crafted from hand-carved V-groove panels w/ soft-close hardware & integrated pullout storage. Caesarstone surfaces run along the perimeter while steel-and-glass open shelving w/ a sculptural black sconce balance the composition. A vintage chandelier from Prize Home & Garden sourced in Round Top completes the room. The primary suite occupies a private wing on the main floor accessed via antique gallery doors that lead to the rear courtyard. Vaulted ceilings, a custom walk-in closet w/ a spa-like bath provide a luxurious retreat. Features include a long double vanity, matte black Kohler fixtures, a freestanding tub, walk-in shower w/ built-in bench & separate water closet. On the mezzanine level, the powder bath makes a dramatic statement w/ a floating black quartzite trough sink w/ handwoven mirror. Across the hall, the laundry room blends beauty w/ utility w/ custom cabinetry, matching quartzite surfaces, matte black fixtures & a side-by-side front-load washer & dryer. A nearby guest suite is marked by an antique door entry. The en-suite bath features a hand-painted tile threshold & suede-framed mirror. Two upstairs bedroom suites feature en-suite baths, designer lighting, distinctive mirrors & continuous European oak flooring. Positioned at the front of the home, the rooftop terrace is accessible via the upper hallway. The detached casita opens to the pool courtyard through accordion glass doors & features micro-crete floors, a woven rattan chandelier & a full bath—ideal as a studio, gym or office. Outdoor spaces include two garden courtyards, a fully fenced backyard, a heated saltwater pool & a rooftop terrace, all enclosed by masonry walls & a board-on-board privacy fence. Additional features include a lower-level two-car garage, storage closet, 3 HVAC systems, Rinnai tankless water heater, Sierra Pacific windows, customized closets, solid core interior doors, 6” round gutters & a Barcelona barrel tile roof. Thoughtfully designed & beautifully executed, 1150 Via Salerno offers a refined lifestyle tucked within one of Winter Park’s most exclusive enclaves.

Listing is courtesy of: KELLY PRICE & COMPANY LLC (407-645-4321)

Listing Agent: Padgett Mccormick (407-645-4321)

Remarks: Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home. Have your morning coffee or afternoon cocktails sitting out back on the porch enjoying the birds. This large, fenced 120 x 80-foot yard provides plenty of room for little ones and pets to play, gardening, or simply unwinding. for comfortable Florida living! Perfectly situated in a desirable, close-in location and zoned for award-winning Seminole County schools, this remodeled, one-story home offers the ideal setting for all family households. Step inside and discover an inviting split floor plan featuring 3 spacious bedrooms and 2 modern bathrooms. The formal living and dining rooms create an elegant atmosphere for entertaining, while the stunning remodeled kitchen is light and bright, complete with contemporary finishes and new appliances. Relax in the cozy family room, where a charming brick wood-burning fireplace adds warmth and ambiance on cool evenings. You do have formal areas that have a multitude of options for space where YOU Need it. Once you get to the kitchen you will be amazed with the sleek white brand new cabinets with trendy quart counters and a gorgeous back splash. WOW! You can enjoy yourself while you are at the sink and watch whatever is going on in the backyard. No expense spared with banks of drawers too. Additional highlights include a 2-car garage, newer windows for energy efficiency, and NO HOA—giving you the freedom to truly make this home your own. Bring your camper, toys because you have loads of room in the backyard to work on multiple projects. Roof and A/C are 2021 adding to peace of mind with your insurance 4 point inspection. Garage is even 24x21. With ample parking, an amazing outdoor space, and proximity to top-rated schools, shopping, dining, and major highways, 3641 Oak Vista Lane delivers the ultimate Florida lifestyle for your family inside the home and outside. You deserve your own Backyard paradise. Don’t miss the opportunity to make this move-in ready Winter Park gem your forever home. Seminole County schools complete the package. Schedule your private tour today!

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

Listing Agent: Laurie Cain (407-484-9944)

Remarks: Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!

Listing is courtesy of: OPTIMA REAL ESTATE (407-366-4500)

Listing Agent: Deborah Morgan (407-314-8610)

Remarks: Tucked away along the tree-lined streets of the desirable Lost Creek community, this beautifully updated two-story residence is truly move-in ready. Major updates include a new roof in 2022 and a new water heater in 2026, offering peace of mind for years to come. Ideally situated in sought-after Winter Park, this exceptional home also includes exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—perfect for enjoying Florida’s outdoor lifestyle while remaining close to premier amenities and entertainment. Step inside to soaring ceilings and an abundance of natural light that fill the spacious great room, creating an open and airy atmosphere. The gourmet kitchen flows seamlessly into a sunny breakfast nook and overlooks the inviting family room, complete with a cozy wood-burning fireplace—ideal for both everyday living and entertaining. The primary suite serves as a peaceful retreat with relaxing views of the sparkling pool. The ensuite bathroom features an oversized vanity with framed mirror, a garden soaking tub, and a beautifully tiled walk-in shower. Upstairs, an expansive open loft offers versatile living space perfect for a media room, home gym, office, or guest lounge. Two additional generously sized bedrooms and a full bathroom complete the second floor. Step outside to your own private backyard oasis featuring a screened-in pool and ample green space beyond—perfect for holiday cookouts, family gatherings, or simply relaxing outdoors. Conveniently located near premier dining, shopping, medical centers, and recreation, this home is just minutes from Oviedo on the Park, Park Avenue, and Waterford Lakes Town Center. Major employers including Siemens, Lockheed Martin, and UCF are all within easy reach, along with quick access to SR-417 for effortless trips to Orlando’s attractions, beaches, and beyond. Zoned for highly rated Seminole County schools: Red Bug Elementary, Tuscawilla Middle, and Lake Howell High School. Lost Creek website: www.theLostCreekhoa.org

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Shirley Jones (407-719-9180)

Remarks: Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus a private backyard oasis complete with a full summer kitchen, covered rear lanai, and saltwater pool with a heated spa. The large, covered front porch welcomes guests into a foyer that opens to a spacious and well-orchestrated floorplan. Just off the entry sits a versatile office/flex space, providing the perfect setting for a private workspace or playroom, while a conveniently located powder bath serves visitors with ease. The foyer unfolds with effortless flow into the heart of the home, where an expansive living room is designed for both everyday living and entertaining. The open-concept kitchen is both functional and refined, featuring a natural gas cooktop, built-in double ovens, and adjacent sunny dinette that overlooks the backyard and pool, creating a casual dining space filled with natural light. On the opposite end of the kitchen, a large walk-in pantry offers tons of storage, and a butler’s pantry/dry bar seamlessly adjoins the large dining room—ideal for hosting gatherings with a polished, intentional flow. At the rear of the living space, expansive stacking glass sliders open to the rear covered lanai, extending the living space outdoors. Enjoy space for dining, lounging, and entertaining with a full summer kitchen that includes a large gas grill, double gas burners, a sink, beverage fridge, and storage cabinets. The backyard beyond creates a true retreat that embodies the Florida lifestyle, where a heated spa overflows into a beautifully designed saltwater pool complete with a sun shelf, all wrapped in travertine decking, tropical landscaping, and a masonry wall for enhanced privacy. Situated at the rear of the home, the well-appointed primary suite offers a quiet escape with generous proportions, dual walk-in closets, and a sensible primary bath with split vanities, a soaking tub, separate shower, and private water closet. The main level continues with exceptional functionality, including a spacious laundry room lined with built-in cabinets for storage, and a 2-car garage with direct access to the side yard and overhead racks for additional storage capacity. Upstairs, a thoughtfully designed 2nd level provides incredible flexibility, featuring a central loft for a reading or study area, a large bonus room that's perfect for a game room or secondary living area, three additional bedrooms - each with walk-in closets, two full bathrooms, and a linen closet, plus an additional storage/media closet. This home is not just a residence—it’s a lifestyle. Windsong residents enjoy access to premier amenities, including multiple community pools, a splash pad, playgrounds, a clubhouse, and 2 community docks providing access to the Winter Park Chain of Lakes via Lake Berry & Lake Mizell. Ideally located just minutes from Park Avenue, Baldwin Park, and the vibrant Corrine Drive corridor, this property offers tranquility and convenience in one of Winter Park’s most desirable neighborhoods.

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

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

Remarks: Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low maintenance living in a thriving Winter Park location. The main level features a spacious living and dining room combo plus a separate family room and kitchen-perfect for entertaining. The kitchen includes a gas cooktop and range, granite counters, island, breakfast nook, and built-in cabinetry and desk. French doors open to a private side patio ideal for relaxing, pot gardening or grilling. The interior laundry off the kitchen leads out to the functional 2-car garage. Upstairs, the primary bedroom has a walk-in closet. The primary bath has a walk-in shower. Two secondary bedrooms offer flex space and share a bath with a tub shower. Wood floors downstairs and carpet upstairs. Recent updates include roof and gutters in 2022, exterior paint in 2023 and water heater in 2024.  Community improvements continue with road resealing in the Spring of 2026, enhancing a well-kept neighborhood. 1261 Indiana is a great fit for a buyer seeking comfort, urban convenience, and a simplified lifestyle. Close to 1-4, shops, restaurants, hospital, and museums.

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

Listing Agent: Megan Cross (407-353-9997)

Remarks: Virtually Staged. Beautifully RENOVATED and MOVE-IN READY/TURN-KEY home in the heart of Winter Park. From the moment you enter, you’re welcomed by an open, airy layout with VAULTED CEILINGS that make the home feel spacious and inviting. Beautiful TILE flooring throughout creates a seamless flow from room to room, while abundant natural light pours in through DOUBLE-PANED WINDOWS (2018) and German Velux SKYLIGHTS with remote control adjustable blinds (2021). The thoughtfully designed floor plan connects the living, dining, and kitchen areas in a natural, functional way, making the space ideal for both everyday living and entertaining. At the center of the home, the CUSTOM EUROPEAN-STYLE KITCHEN features high-end Cambria quartz countertops (2025) and upgraded appliances, including a NEW refrigerator (2025), BOSCH dishwasher (2024), and Maytag microwave (2022). Both bathrooms have been FULLY REMODELED with modern finishes, NEW VANITIES (2025), and all interior doors were replaced (2017), adding to the home’s updated feel throughout. Major system upgrades provide peace of mind, including a high-efficiency Amana AC with smart thermostat (2024) and a tankless water heater (2025). The home also features a complete PEX plumbing upgrade to the city connection (2025), modernized PVC drain in the bathrooms, laundry and kitchen (2025), new sinks and faucets (2025), and updated kitchen electrical wiring to current code (2025). Step outside to a private, fenced backyard (2018) with a screened patio (2022), perfect for relaxing or entertaining year-round. Additional exterior features include driveway pavers (2024), carport (2024), and a OVERSIZED Tuff Shed (2024) for extra storage. Modern conveniences such as electronic front door locks (2023), a smart ceiling fan (2023), and smart kitchen lighting (2025) complete this well-appointed home. Ideally located just minutes from Park Avenue and within walking distance to shopping, dining, parks, and everyday conveniences, this home offers the perfect combination of location, layout, and high-quality upgrades. SCHEDULE YOUR SHOWING TODAY!

Listing is courtesy of: ZEN LIVING HOMES LLC (407-800-2717)

Listing Agent: Nydia Marrero (407-620-6221)

Remarks: Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring throughout. Updates include (but definitely not limited to) BRAND new kitchen with Stainless Steel Appliances, new cabinets & quartz countertops. Formal living & dining rooms PLUS Family room with vaulted ceilings featuring a new electric fireplace for amazing ambiance and sliding doors inviting you to new brick pavered 31x 11 screened porch overlooking newly refinished sparkling pool & golf course (no rear or side neighbors!!) Bedroom wing of home offers a large inside laundry room, beautiful guest/pool bath with dual sinks & shower/tub and 2 fresh guest bedrooms. THE PRIMARY SUITE has been thoughtfully remodeled with sliding doors to pool, AMAZING primary bath with oversized work-of-art shower with dual shower heads, dual vanity, separate water closet & HUGE walk-in closet! Extras include: NEW double paned windows & 3 sliding doors to pool/patio, crown molding, NEW roof November 2024, oversized 2 car garage, NEW landscaping, all NEW ceiling fans & light fixtures, NO HOA!! Zoned for Brookshire Elementary, Glenridge Middle & Winter Park High. WELCOME HOME!

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

Listing Agent: Catherine D'Amico (407-252-3210)

Remarks: Virtually Staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately wood-burning fireplace which sets a welcoming feeling in the family room. The fully reimagined chef’s kitchen is a true showpiece, featuring solid maple cabinetry, quartz countertops, programmable Bosch stainless steel range and refrigerator and a striking brick backsplash—an elevated space designed for both culinary creativity and effortless entertaining. All three bathrooms have been luxuriously renovated, and new carpeting adds a soft, refined touch throughout all four bedrooms. French doors from the master suite, formal living room, and family room open to a breathtaking screened-in pool retreat. Surrounded by lush tropical landscaping, this private oasis has been thoughtfully upgraded with a new pool pump, a conversion to a sparkling saltwater system, and a beautifully refinished pool deck. An outdoor shower with both hot and cold water adds a resort-level convenience, perfect after a swim or a day in the sun. Every major system has been meticulously updated for peace of mind, including a new programmable HVAC system, a complete replumb of the entire home, all new ductwork, and an upgraded water heater. Additional enhancements—such as fresh interior and exterior paint, a new garage door opener in the over-sized garage, irrigation system and refreshed landscaping — ensure a truly turnkey experience. With its luxurious finishes and meticulous improvements, this residence is ready for the next family to make it their own. This property is located just 2 miles to AdventHealth Winter Park Hospital, less than 10 minutes to Park Ave, and zoned for top-rated schools such as Dommerich Elementary, Maitland Middle, and Winter Park High School. Just minutes from Winter Park’s boutiques, acclaimed restaurants, and the cultural charm of Park Avenue, this home offers a rare opportunity to enjoy elevated living in a setting that’s both secluded and connected. A truly private sanctuary designed for comfort, style, and the best of Florida living.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Kathy Summers (407-832-6986)