Winter Park Homes For Sale & Real Estate - 443 homes

Remarks: Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while enjoying sunset views over the water. This stunning Michelson floorplan offers the perfect blend of elegance, comfort, and functionality with spacious living areas designed for both everyday living and entertaining. Upon entry, you’re welcomed by a private office, formal dining room with custom accent features, recessed lighting throughout, beautiful wood-look tile flooring, and designer details at every turn. The open-concept family room features built-in speakers that continue throughout the main living spaces, upstairs, and outdoor lanai area, creating a seamless entertainment experience throughout the home. The gourmet kitchen is beautifully appointed with quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, modern backsplash, butler’s pantry with wine fridge, and an incredible walk-in pantry with custom built-in shelving. Massive 12-foot triple sliding glass doors open to the resort-style backyard featuring a beautiful open pool, custom fire pit, pergola seating area, pre-wire for a gas grill, and a backyard perfect for relaxing or entertaining. The first floor also includes a guest suite with a full bath and direct pool access, a mudroom, a coat closet, a convenient half bath, and an oversized three-car tandem garage with overhead storage. Upstairs, a beautiful wood tread staircase leads to an expansive loft and bonus room area along with spacious secondary bedrooms, all featuring walk-in closets. A Jack-and-Jill bathroom with dual sinks, additional full bath, oversized linen closets, and a large laundry room with sink and extensive cabinetry provide exceptional functionality and storage. The luxurious owner’s retreat is a true sanctuary featuring tray ceilings, built-in speakers, a stunning accent wall, coffee bar area, spa-inspired bath with an oversized walk-in shower, abundant storage, and an enormous walk-in closet with multiple sections. Additional highlights include a brand-new A/C unit and countless high-end finishes throughout. Ideally located near top-rated schools, shopping, dining, and major roadways, this meticulously maintained home offers elevated Florida living in one of the area’s most desirable gated communities.

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

Listing Agent: Abby Nelson (407-571-1445)

Remarks: Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated square feet of expertly crafted living space, this four-bedroom plus office, four-and-one-half-bath home blends timeless architecture, elevated finishes and effortless lakefront living. Designed with an open-concept floor plan ideal for everyday living and entertaining, the home showcases stunning European white oak hardwood flooring throughout all main living areas and bedrooms. The heart of the home is the spectacular chef’s kitchen, featuring two oversized islands, custom-designed wood cabinetry, an expansive walk-in pantry, and a premium Sub-Zero and Wolf appliance package highlighted by a 48-inch, eight-burner range. The private first-floor primary suite serves as a luxurious retreat, complete with an expansive walk-in closet and a spa-inspired bath adorned with marble tile shower walls and flooring. Also on the main level is a versatile office/den with a built-in closet. Upstairs, an expansive media/family room provides additional gathering space, accompanied by a dedicated office and three generously sized secondary bedrooms, each featuring en-suite baths and walk-in closets. The fourth bedroom offers exceptional flexibility and may easily serve as a secondary primary suite, ideal for guests or multigenerational living. Designed to embrace seamless indoor-outdoor living, expansive glass sliders extend from the gathering and dining rooms to a covered lanai overlooking the resort-style custom pool. Retractable screens create a setting for year-round enjoyment, while the fully equipped summer kitchen and generous lounge and dining areas make entertaining effortless. Expertly designed by Signature Landscape, the pool features a sun shelf, LED lighting and elegant travertine limestone decking, all surrounded by lush professional landscaping, Zoysia grass and privacy hedging for a serene outdoor setting. Additional notable features include a Brava slate tile roof and a striking custom glass front entry door, further elevating the home’s exceptional curb appeal. Ideally just minutes from the vibrant shops and dining of Park Avenue, this remarkable residence also offers convenient access to major roadways, leading area hospitals and top private schools, all within an A-rated school district. An exceptional opportunity to enjoy luxury lakefront living in one of Central Florida’s desirable settings.

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

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

Remarks: Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in 2023, Range 2019, Refrigerator in 2020, A/C in 2020, Double-Pane Windows and Sliding Door in 2016, Updated Electric Panel, Replaced Ductwork and added Attic Insulation. Master Bath has Double-Sink Vanity. Guest Bath has newer Vanity and Retiled Shower with replaced Shower Pan. Unit recently Replumbed. Plantation Shutters, recently Repainted and Carpeted. Short Walk to Shopping, Restaurants, Theaters, and minutes to Park Avenue with it's Village Style Shopping, Central Park with Bandstand, Spring and Fall Art Festivals, Farmer's Market and Downtown Train Station. Drive into the Community, catch a view of the Lake, watch a Sunset on the Deck and you will know "you're Home"! OWNER WILL CONSIDER REPLACING CARPET IN LIVING AREA WITH LUXURY VINYL FLOORING WITH ACCEPTABLE OFFER!

Listing is courtesy of: REALCOM REAL ESTATE SERVICES INC (407-621-6856)

Listing Agent: Janice Erickson (407-621-6856)

Remarks: Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless estate, this is your canvas to bring that vision to life. What makes this opportunity even more compelling is the location. Just minutes from the charm and sophistication of Park Avenue, you’ll find yourself surrounded by brick-lined streets, boutique shopping, fine dining, and vibrant cultural experiences. Spend your mornings enjoying coffee at local cafés, your afternoons exploring art galleries, and your evenings dining under the lights of one of Central Florida’s most beloved destinations. Living in Winter Park is more than owning a home—it’s embracing a lifestyle. From the scenic beauty of the Winter Park Chain of Lakes, to the historic elegance of Rollins College, this area blends natural beauty, culture, and community in a way few places can. Residents enjoy: Boat tours and waterfront living along the chain of lakes Weekly farmers markets and local events A thriving arts scene including museums, galleries, and theaters Top-rated dining and boutique retail experiences A true sense of community with timeless charm This is more than just land. This is where vision meets opportunity. This is where your next chapter begins. Build the life you’ve been dreaming of—in the heart of Winter Park

Listing is courtesy of: RE/MAX ASSURED (800-393-8600)

Listing Agent: William Grim, Iii (407-314-9784)

Remarks: Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an effortless sense of scale, defined by soaring vaulted ceilings and an abundance of natural light filtering through custom windows. Every detail has been meticulously curated—from the rich new flooring installed in 2025 to the soft glow of Currey & Co. lighting that adds warmth and sophistication to each space. Designed for both comfort and control, the residence is fully integrated with a wireless home automation system, allowing seamless management of lighting, climate, security, and more. Three A/C units ensure optimal comfort, while a new tankless water heater, water softener, and whole-home surround sound system elevate everyday living. A comprehensive security camera system and ADT Home Control provide peace of mind with modern convenience. Each of the four bedrooms is a private sanctuary, complete with its own en-suite bath, offering an elevated sense of privacy for residents and guests alike. The primary suite is a retreat unto itself, featuring custom built-in storage and electric storm shutters with blackout capability. The spa-inspired primary bath showcases a dual Grohe shower system, thermostatic auto tub filler and integrated TV - creating an environment of indulgence and serenity. At the heart of the home lies a newly renovated (2025) chef’s kitchen—an exquisite blend of form and function. Outfitted with premier appliances including a Wolf six-burner gas range, Sub-Zero refrigerator, Monogram built-in microwave, and dual dishwashers, the space is designed for both intimate meals and grand entertaining. Custom cabinetry with integrated lift features, dual sinks, filtered water dispenser, and elegant stone countertops complete this culinary haven. The living room invites relaxation with its newly renovated gas fireplace (2025), while a dedicated office offers bespoke built-in cabinetry with marble surfaces and glass shelving—ideal for sophisticated work-from-home living. Upstairs, the home transforms into an entertainment destination, complete with a projector theatre setup, wet bar, additional powder bath, and extensive storage. A dedicated A/V closet and the potential for an upstairs laundry add both function and flexibility. Outdoors, a private resort-style oasis awaits. The backyard has been completely reimagined, featuring lush turf, a sun deck platform, and even an in-ground trampoline—blending luxury with playfulness. The saltwater pool and spa, enhanced with upgraded LED lighting and a new heater (2025), were fully refinished and redesigned in 2021 to create a serene and visually stunning escape. A fully equipped summer kitchen—complete with a built-in gas grill, dual burners, refrigerator, and screened enclosure—sets the stage for unforgettable gatherings under the Florida sky. The three-car garage is equally impressive, featuring a Wallbox Level 2 electric vehicle charger (2023), seamlessly blending luxury with modern sustainability. This is more than a home—it is a statement of lifestyle, craftsmanship, and elevated living in one of Central Florida’s most sought-after lakefront communities.

Listing is courtesy of: KGV REALTY GROUP (407-474-0844)

Listing Agent: Kristin Vogt Pllc (407-417-7206)

Remarks: This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. The water heater was replaced in 2025, the AC was replaced in late 2021, and the roof in 2017. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.

Listing is courtesy of: MNT INTERNATIONAL (844-668-7589)

Listing Agent: Mostafa Boulhanna (407-536-1484)

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: 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 340 Killarney Bay, a beautifully maintained residence located within one of Winter Park’s most charming and sought-after communities. With access to Lake Killarney, residents enjoy a waterfront community pool, dock, and a peaceful setting that perfectly complements the relaxed Winter Park lifestyle. This home offers a spacious and inviting layout with both bedrooms located upstairs for added privacy, as well as a balcony off one of the upstairs bedrooms. Recent updates include newer appliances, newer water heater (2022), and fresh interior paint downstairs and in bathrooms. Ideally located just minutes from Winter Park Village, Park Avenue, Trader Joe’s, top dining, shopping, and major roadways, this home delivers the perfect blend of convenience, lifestyle, and serene community living. Schedule your showing today!

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

Listing Agent: Blaike Gill (407-545-6430)

Remarks: Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining room flow into the kitchen, where you’ll find lots cabinet storage, eat in space, and a view out to the backyard. The primary suite is conveniently located on the main floor, featuring generous windows that bring in natural light, a walk-in closet, and an updated en suite bath. A half bath downstairs adds convenience for guests. Upstairs, two spacious bedrooms share a full bath, offering comfortable separation from the main living areas. The Villas of Casselberry community has a pool for you to enjoy. The location places you just minutes from Park Ave’s shops, dining, events and great parks. With easy access to major roads and a central location close to Rollins, UCF, Full Sail and downtown Orlando, this home offers both comfort and connectivity. If you’ve been looking for space, privacy, and a well located Winter Park address, this one is worth seeing in person. Schedule your showing today!

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

Listing Agent: Barrett Spray (407-927-3650)

Remarks: **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.** Talk about location, location, location! Welcome to this beautifully updated and well-maintained 2-bedroom, 2-bathroom, 1-car garage home in Winter Park, perfectly situated in the charming Aloma Park community. Just about 1 mile from the 417 Greenway, this home offers easy access throughout Orlando, while also being walking distance to the Cross Seminole Trail and Cady Way Trailhead—perfect for biking, running, rollerblading, or simply enjoying an active lifestyle. Inside, this move-in-ready home feels bright, warm, and inviting with sandy-toned wood-look tile and laminate flooring that lighten the entire space. The kitchen has been beautifully updated with granite countertops, soft-close cabinets, stainless steel appliances, a new microwave, and ample storage. The popcorn ceilings in the main living areas have been removed and replaced with a clean knockdown finish, giving the home a fresh and updated feel. The bathroom updates are a major highlight: one bathroom has been fully renovated with a walk-in shower, while the second bathroom features a new countertop, new cabinetry, and soft-close cabinets. Additional updates include a 2021 roof, HVAC system from 2016, new water heater, washer and dryer, energy-efficient double-pane windows, energy-efficient French doors, LED fixtures, and solar tubes that fill the home with natural light. There is also attic space for convenient extra storage. The primary suite offers a bonus sunroom/flex space that is insulated and equipped with plexiglass sliders and a mini-split unit hook-up, making it perfect for a home office, greenhouse, playroom, sitting room, or creative space. French doors with built-in blinds lead out to the screened lanai, creating an easy indoor-outdoor flow. Outside, enjoy a beautifully landscaped, fully fenced backyard with a utility shed that has its own breaker—perfect for storage, hobbies, or the handy person in the house. The pavers in the front courtyard and back patio add even more charm and function to the exterior spaces. Aloma Park is a small, quaint Winter Park community with only two cul-de-sac streets, 42 duplex homes, and no through traffic. Residents enjoy access to a community pool, tennis courts, basketball courts, and a clubhouse available to rent for gatherings. Zoned for excellent A-rated Winter Park schools and conveniently located near UCF, Full Sail University, Rollins College, downtown Winter Park, Oviedo, shopping, dining, and major roadways, this home offers the perfect blend of comfort, convenience, and affordability. Hurry to see this Winter Park gem — there’s nothing to do here but bring your furniture!

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

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

Remarks: Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Brian Hyser (407-951-2472)

Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the desirable neighborhoods of Winter Park within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining. Step inside to discover a spacious, light-filled floor plan featuring generous living areas, well-sized bedrooms, and a thoughtfully designed layout ideal for families or guests. Out back, you’ll find your own private oasis. The freshly resurfaced sparkling pool and expansive backyard provide the perfect setting for weekend barbecues, gatherings with friends, or simply relaxing under the Florida sunshine. With plenty of room to entertain, play, or unwind, this outdoor space truly sets the home apart. The property also features a metered irrigation system, helping maintain the lush landscaping efficiently and economically. Conveniently located near top-rated schools, shopping, dining, and major roadways, this exceptional property combines comfort, convenience, and the charm that makes Winter Park such a wonderful place to call home. Recent updates include: Pool resurfaced – April 2026 Roof replaced – 2022 New electrical panel – 2025

Listing is courtesy of: BHHS FLORIDA REALTY (407-406-5300)

Listing Agent: Nancy Morales (321-747-7448)

Remarks: Under Construction. Introducing the newest showpiece from LUIH Luxury Homes, perfectly positioned in the heart of Winter Park. Set on an oversized homesite along a quiet, tree-lined street, this residence immediately captivates with its expansive front lawn and timeless architectural presence. Inside, the home unfolds with a thoughtfully designed and highly functional floor plan that balances refined living with effortless entertaining. The spacious family room serves as the heart of the home, anchored by a sleek electric fireplace and framed by open sightlines into the kitchen and main living spaces, creating a warm yet sophisticated gathering environment. At the center of it all is a chefs kitchen designed to impress, featuring striking Calacatta quartz countertops, a full suite of Thermador appliances, custom cabinetry, an oversized center island, and an expansive walk-in pantry. Just beyond, the dining area is intentionally set apart to create a more intimate atmosphere, enhanced by a beautifully appointed wet bar with a wine refrigerator and floating shelving illuminated by elegant LED underlighting. The first-floor primary suite offers a true private retreat, with sliding glass doors opening directly to the pool and outdoor living areas. The spa-inspired bathroom is finished in exquisite marble tile and features a freestanding soaking tub, an oversized walk-in shower, dual vanities, and a generous custom walk-in closet designed for seamless organization. A rare and highly desirable feature for Winter Park living, the main level also includes a private guest suite along with a dedicated office, providing flexibility for hosting guests or working from home in comfort and style. Upstairs, a spacious loft-style living area creates the perfect setting for a media room, lounge, or secondary gathering space. Three additional bedrooms offer generous accommodations, each thoughtfully designed to provide comfort and privacy. Outdoor living is equally impressive. A large covered lanai with a fully equipped summer kitchen sets the stage for year-round entertaining and elegant alfresco dining. The backyard feels both expansive and secluded, highlighted by a resort-style pool and spa and complemented by ample green space for relaxation and recreation. Ideally located just minutes from the iconic shops, restaurants, and cafes of Park Avenue, the home offers the perfect balance of tranquility and connectivity. Residents are also moments from Cady Way Park and Winter Park High School, placing some of the area's best amenities right at your doorstep.

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

Listing Agent: Christopher Christensen (407-312-8003)

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: Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

Listing is courtesy of: CEPEDA REAL ESTATE LLC (407-900-1792)

Listing Agent: Brandi Cepeda (407-900-1565)

Remarks: Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff of Native Homes, every detail has been thoughtfully curated to impress even the most discerning buyer. The expansive floor plan encompasses 5 bedrooms, 6 full baths, and 1 half bath, blending sophistication and comfort across multiple living spaces. Highlights include a dramatic great room, inviting family room, private study, downstairs guest suite, a full bar featuring a 56-bottle wine refrigerator, and an upstairs game room ideal for both everyday living and elegant entertaining. A grand entry reveals the great room with soaring floor-to-ceiling windows and elegant Italian porcelain tile, all overlooking the serene pool and patio. The chef’s kitchen seamlessly connects to the family room and features Canadian-crafted European-style cabinetry, Wolf, Sub-Zero & Fisher & Paykel appliances (dual ovens, dual dishwashers, built-in coffee maker, wine cooler, and beverage center), quartzite countertops, a large island with bar seating, hidden walk-in pantry, plus whole house water softener and filtration systems for premium convenience. The first-floor primary suite is a true retreat with spa-inspired amenities and a custom-built walk-in closet complete with cabinetry and a spacious island. Also on the main level: a private guest suite and dedicated home office/study. Upstairs, a generous game room and three additional en suite bedrooms provide comfort and privacy for family and guests alike. Designed for seamless indoor-outdoor living, the residence boasts two covered lanais finished in Turkish Marble, disappearing screens, a summer kitchen with Urban Bonfire Cabinetry, refrigerator, and ice maker, along with a freestanding fire pit and lush tropical landscaping. The saltwater pool with sun shelf and heated gas spa ensures year-round enjoyment. Built to the highest standards, the home features R-14 block walls with core 500 insulation, open cell foam insulation in attic, Andersen windows, a flat concrete tile roof, and tongue-and-groove ceilings on all lanais. Additional luxuries include: Select European white oak wood floors and Italian porcelain flooring throughout 12’ ceilings on the main level, 10’ ceilings upstairs Cutting-edge construction for efficiency and durability

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

Listing Agent: John Mcdade (407-721-7275)

Remarks: Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs. There's abundant storage throughout, including coat, linen, patio, and under-stair space that could be converted into a small office or workout nook. The kitchen comes fully equipped with all appliances, ample cabinet space, and a breakfast bar, while the dining area overlooks the pond and opens to the patio with an additional storage closet. Upstairs, the primary suite includes an en-suite bath, a large walk-in closet, and corner windows that brings in great natural light. The second bedroom is located downstairs and offers dual closets and a ceiling fan. Updated luxury vinyl flooring runs through most of the home, and there is also an in-unit washer/dryer for convenience. Located in the highly desirable Winter Park Villas community, residents enjoy a wide array of amenities including a sparkling pool, clubhouse with fitness center, tennis courts, car wash station, scenic ponds, pet stations. The HOA provides exceptional value by covering roof & exterior maintenance, lawn service, water, trash, sewer, pest control—ensuring truly low-maintenance living. Conveniently located just minutes from Full Sail University, Rollins & Valencia Colleges, approximately 10 minutes from downtown Winter Park. Top-rated schools nearby, this property is an excellent opportunity for both homeowners & investors. Outdoor enthusiasts will also appreciate easy access to the nearby Cady Way Trail, perfect for walking, jogging, or cycling.

Listing is courtesy of: PLATINUM REALTY GROUP FLORIDA INC (407-270-7378)

Listing Agent: Adam Eisen (407-808-6967)

Remarks: Under contract-accepting backup offers. Virtually Staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

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

Listing Agent: James Ferngren (407-739-3433)

Remarks: Under contract-accepting backup offers. Exceptional opportunity to build new in one of Winter Park’s most desirable and established areas on the north shore of Lake Killarney. Situated on a spacious 0.34-acre lot, this property offers over one-third of an acre—providing ample room to design and construct a substantial custom home in a neighborhood known for its longtime charm, mature surroundings, and unbeatable location. With some homes nearby enjoying water access and lakefront settings, the area continues to be highly sought after for both renovation and new construction opportunities. Originally built in 1957, the existing ranch home is being offered for land value, presenting an ideal opportunity for builders, investors, or buyers looking to create their dream home in a prime Winter Park location. Perfectly positioned near Lee Road and I-4, the property offers quick access to downtown Winter Park, Park Avenue, Maitland, Orlando, top dining, shopping, entertainment, and everyday conveniences. Opportunities for oversized homesites in this location are becoming increasingly rare, especially in such a well-established and centrally located community. Whether you are a builder searching for your next project or a buyer looking to secure premium land in Winter Park, this property represents exceptional potential in a highly sought-after location.

Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)

Listing Agent: William Wygle (407-375-9005)