Homes For Sale in Winter Park 32789 - 160 homes

Remarks: Welcome to this beautifully remodeled two story home in one of Winter Park’s most desirable upscale neighborhoods, offering timeless charm, modern upgrades, and no HOA restrictions. Completely renovated in 2019, this property features a newer roof, windows, A/C system, electrical, plumbing, driveway, and a fully fenced yard with a private entry gate, along with fresh exterior & interior repaint completed in 2025. Inside, you will find bright, open living spaces and a modern kitchen designed for both everyday living and entertaining. Upstairs, a spacious family room opens to a covered balcony with serene lake views, creating an ideal space to relax or entertain. The flexible layout also allows for two separate living areas, making it well suited for multi-generational living or rental income. Step outside to enjoy the expansive gated yard with plenty of room for gatherings along with ample parking. Conveniently located just minutes from shopping, dining, Downtown Orlando, Downtown Winter Park, Full Sail University, and Rollins College, this home offers an exceptional location. The seller is offering 1% closing cost Buyer credit with a full price offer. Do not miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location. Contact us today to schedule your private showing!

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

Listing Agent: Jill Healey (407-797-1420)

Remarks: Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom. Durable vinyl flooring with cozy carpeted bedrooms with a spacious walk in in closet in the primary bedroom. You will get a private balcony — perfect for morning coffee or evening relaxation and the convenience of your our laundry with washer and dryer hookups included. This condo is perfectly located in a desirable area with lots of nearby shopping, restaurants, and amenities

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Brandy Ray (949-449-5652)

Remarks: Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat, complete with a walk-in closet and an en-suite bathroom featuring dual sinks, and a separate soaking Jacuzzi. Step outside to enjoy the covered patio—perfect for entertaining or unwinding. The backyard a outdoor escape with a sparkling in-ground pool and a fenced area for added versatility. Inside, the home has been refreshed with new interior paint and partial flooring updates, giving it a clean, updated feel. Don’t miss the opportunity to make this beautiful property your next home. 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: 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: Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views from the second level. Designer LED ambient lighting is integrated throughout — including illuminated floating stair treads and custom feature shelving — creating a dramatic yet inviting atmosphere. The kitchen is both refined and functional, featuring an oversized island, premium appliances, expansive prep space, and a generous walk-in pantry. The open layout flows seamlessly into the living and dining areas, anchored by a striking fireplace feature wall and wide-plank wood flooring. The primary suite offers a spa-level retreat with a dedicated wet area and freestanding soaking tub, delivering a luxurious, architectural bathroom experience. Designed for entertaining, the outdoor living space includes a private pool and a fully equipped summer kitchen — ideal for Florida living year-round. Additional features include: • Spray foam insulation for superior efficiency • Deeded access to a private boat ramp on Lake Killarney • No HOA dues Located in one of Central Florida’s most desirable neighborhoods, this home is just a short walk or drive to Park Avenue dining, shopping, and entertainment. A rare opportunity to own new construction with architectural character in Winter Park.

Listing is courtesy of: CLASSIC HOMES (407-493-8553)

Listing Agent: Randy Lazarus (407-247-9337)

Remarks: Exquisite new construction 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: Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main house has a flexible floor plan that includes four bedrooms and four and one half baths, a sunroom ideal for home office, formal dining room, oversized family room and charming sitting area with fireplace. The kitchen is a chef's delight with six burner gas range, large center island, plentiful l space for gatherings and a separate breakfast room. Other notable features include gleaming wood floors, double pane windows offering abundant natural light, adorable laundry room/mud room. French doors from many rooms open to a classic front porch that is a perfect place for relaxing and enjoying picturesque grounds with towering oaks. Step outside to a private heated pool. Detached garage includes Tesla charging station. This gated compound situated on .42 acres is one block from Lake Osceola and a easy walk to Park Avenue.

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

Listing Agent: Nicole Seybold (407-808-9374)

Remarks: A masterfully crafted custom residence in the heart of Winter Park, this 2014 Barefoot Brothers home blends timeless architecture with modern functionality just moments from Park Avenue and the Audubon Park Garden District. Designed for both refined entertaining and active everyday living, this 5-bedroom + office home offers a flexible, family-focused floor plan plus an expansive second floor bonus room, ideal for recreation, media, or study. A formal dining room and oversized great room with 11.5’ ceilings create the perfect balance of comfort and sophistication. The first-floor primary suite features a private, attached office space and a spa-inspired ensuite with marble floors, marble-topped double vanity, freestanding cast iron soaking tub with gooseneck filler, double walk-in shower, Kohler fixtures, and a statement chandelier over the tub. The chef’s kitchen showcases marble countertops, a walnut center island, a large walk-in pantry, 10’ ceilings, GE gas range, new Samsung refrigerator, and Bosch dishwasher — all opening seamlessly to the living area anchored by a gas fireplace with custom built-ins and double French doors leading outside. Designed with connection in mind, the breezeway links the main home to the detached garage and opens to a charming river rock paved patio — perfect for gatherings and outdoor dining. A recently repainted timber-framed front porch welcomes guests with timeless curb appeal, complemented by a circular driveway, irrigation system, and landscape lighting. Built with longevity and energy efficiency in mind, this home features insulated concrete form (ICF) construction, vinyl double-pane Low-E windows, two tankless water heaters, natural gas connections (fireplace, range, dryer, outdoor grill), Cat 6 ethernet wiring, surround sound, and ceiling fans throughout. Spend your mornings biking to coffee in Audubon Park and your evenings enjoying dinner on the Park Avenue — all while coming home to a thoughtfully constructed retreat designed for modern family living. With roof, electrical, and plumbing completed in 2014, this home offers peace of mind, architectural character, and an exceptional lifestyle in one of Winter Park’s most desirable corridors. Schedule your private showing today!

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

Listing Agent: Jill Healey (407-797-1420)

Remarks: Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The primary suite and family room both feature tall ceilings and an abundance of natural light, creating a bright and inviting wing of the home. The kitchen opens to the casual dining area and family room, creating a central gathering space. French doors from the family room lead to a peaceful, southern-inspired screened patio overlooking a spacious yard on nearly half an acre. At the front of the home, a separate living room provides a quieter setting, while the formal dining room is complemented by a butler’s kitchen for added functionality when hosting. Upstairs includes four additional bedrooms with classic charm, featuring original hardwood floors and generously sized rooms, offering flexibility for guests, family, or office space. Just steps from Park Avenue and the Winter Park 9, this home offers an ideal location with easy access to shopping, dining, and golf.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Jennifer King (407-595-3272)

Remarks: Walk in and feel instantly at home in this stunning 5-bedroom, 3-bath POOL home with a 3-car garage, offering over 3,600 square feet of living space on more than ¾ of an acre in the highly desirable Sevilla neighborhood of Winter Park. Backing directly to Howell Creek and Mead Gardens, this property offers the rare luxury of no rear neighbors and exceptional privacy. Upon entry, you’re welcomed by beautiful wood floors and versatile spaces to the left that can serve as a formal living room, dining room, office, or playroom. Continue into the impressive family room, featuring vaulted ceilings, skylights, and a wood-burning fireplace, creating a light-filled and inviting atmosphere. To the right wing of the home are four bedrooms and two bathrooms, including the primary suite. One secondary bedroom connects to the primary, making it ideal for a nursery, home office, or sitting room. The spacious primary retreat offers large walk-in closets, dual vanities, a soaking tub, separate shower, and French doors that open directly to the pool and backyard oasis. The kitchen, located just off the family room, features travertine flooring and flows seamlessly into a huge pantry, oversized laundry room, drop zone, and a second primary suite with ensuite bath—perfect for guests or multigenerational living. Outside, the home has been meticulously maintained, showcasing a new roof (2023), exterior paint (2018), pavered circular driveway, well, and lush tropical landscaping that enhances the home’s curb appeal. Additional features include a three-car side-entry garage, pool heater, designer lighting, engineered hardwood floors, and crown molding throughout. Located within the highly sought-after Winter Park School District (Audubon K-8 and Winter Park High School) and just minutes from Park Avenue, Central Park, Rollins College, SunRail, the Winter Park Farmer’s Market, and world-class shopping and dining. Schedule your private showing today—this exceptional home won’t last long!

Listing is courtesy of: VOSS REALTY INC (407-456-0777)

Listing Agent: Lindsay Kaye Voss (407-456-0777)

Remarks: Tucked behind towering hedges on a coveted brick-lined street, this estate sits on an approximately ½-acre corner lot and has been enhanced with thoughtful improvements, delivering a rare combination of modern functionality, Old World charm, and a fabulous lifestyle. Notable updates include newer HVAC systems (2020 and 2025), a tankless gas water heater, a fully renovated laundry room with new LG stackable washer and dryer, newer kitchen appliances, new copper gutters and downspouts, fresh exterior paint (2025), a newly designed primary bathroom, and much more. The main residence spans over 3,600+ SF with an attached 2-car garage and is complemented by a detached, fully equipped 700+ SF studio apartment located above an additional 2-car garage, as well as an air-conditioned outdoor bar. With two dwellings, a four-car garage, expansive outdoor entertaining space on ½ acre, and surrounded by tall podocarpus hedges, this home is a true private compound. This is not just a home—it’s a destination! Enter the main residence into a dramatic living space featuring 12-foot ceilings, a 30-foot span, a gas fireplace, and walls of windows and doors. With a rear southern exposure, natural light pours in through five sets of French doors, offering views of the brick-paver pool deck and lush, fenced grounds beyond. The family room flows seamlessly into the open kitchen, elevated by newer luxury appliances including a Sub-Zero refrigerator, Wolf gas range, and dual Miele dishwashers. At the center, a copper-topped island anchors the space, complemented by a wood-stained beadboard ceiling and a spacious dinette for casual dining. Just beyond the kitchen, a large dining room and adjacent den (currently used as a library & office) offers flexible living options. A side entrance opens to a covered porch overlooking a generous side yard framed by tall privacy hedges—ideal for a dog run or discreet boat storage. Downstairs, three additional bedrooms feature vaulted ceilings and access to three well-appointed full baths, creating a functional layout for family and guests. Privately positioned upstairs, the expansive primary suite offers a quiet retreat, highlighted by a recent full-scale luxury bathroom renovation with elegant custom finishes. Features include a large glass shower with three showerheads, dual vanities, a Toto washlet, designer mood lighting, and custom cabinetry with linen storage. French doors from both the bedroom and bath open to a covered balcony overlooking the backyard and pool, while three custom walk-in closets create a true dressing room experience with additional flexible space for an office or hobby room. Designed for entertaining, the outdoor living is equally impressive. A sprawling lawn surrounds the large saltwater pool and expansive paver patio for lounging and dining. A covered, air-conditioned bar is outfitted with custom cabinetry, exquisite lighting, a copper sink, dishwasher, wine fridge, and beverage fridge—all secured by an electronic storm shutter. The extended bar seamlessly serves the adjacent tent-covered lounge area, complete with a pool bath and outdoor shower. The detached studio apartment, positioned above the second 2-car garage, features a private entry along with a full kitchen and bath, making it ideal for extended stays or flexible living arrangements. Located just minutes from vibrant Park Avenue, this distinctive Winter Park compound blends curated finishes, meaningful upgrades, and exceptional privacy.

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

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

Remarks: Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the heart of City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers plenty of exquisite interior features. The home welcomes you with a beautifully designed 16 ft wide circular driveway wrapped in upgraded pavers, offering both elegance and functionality. A very rare 4-car garage in Winter Park with two in the rear and two in the front of the home. Starting with entering through massive 10 ft. double iron doors flowing into the foyer with 11ft high ceiling beginning with the flex/office room and formal dining to your left and right. Followed by entering the gallery that leads to the great room. The Chef’s Kitchen, a culinary dream featuring an oversized center island, quartz countertops throughout, custom 42"+15" wood cabinetry, a custom walk-in pantry, and top-of-the-line Thermador professional series. That Includes a 48' refrigerator, 48" gas cooktop, custom hood, dishwasher, built-in microwave, double convection ovens and built in coffee station. On your way to the formal dining, you pass by the show-stopping, Tempered glass wine room. Its crystal-clear glass enclosure offers a striking view of your curated collection, while the built-in wine chiller ensures each bottle is perfectly preserved. This elegant transition creates a seamless blend of function and sophistication, setting the tone for unforgettable dining experiences just steps away. The primary suite offers tranquility peace of mind, and the primary bath has a spa-like oasis with a spacious shower stand-alone tub. Followed by a custom closet thoughtfully design with plenty of room and storage. The guest retreat area has a huge bedroom, access to a full bath including private access to the Lania and pool. Tucked away with its own private entrance attached to the rear garage, the in-law suite above the garage offers the perfect blend of comfort and independence. This thoughtfully designed space includes a full bath, a cozy living area, and a convenient space with a kitchenette—ideal for extended stays or multi-generational living. Make your way to the second floor that has 11ft ceilings as well. As you reach the top the space opens into a massive game room with a wet bar, perfect for entertainment retreat with a balcony. All second-floor bedrooms have a thoughtfully design with a full bath for privacy. As you make your way back downstairs to outside, step through the oversized sliding glass doors and into your private outdoor oasis. Effortlessly extending your living space into the open air. Just beyond, the sparkling gas heated/saltwater pool and spa framed by lush landscaping and designed for both relaxation and recreation. Also, the fully equipped summer kitchen features gas grille, beverage refrigerator and ample counter space—perfect for alfresco dining and effortless entertaining. This seamless indoor-outdoor flow creates the ultimate setting for enjoying the Florida lifestyle in style and comfort. This masterpiece is equipped with a full irrigation system around the home, exterior lighting, exterior cameras for security. Smart home system ready for lighting, music and security controlled by Control 4 system for your convenience. Interlachen Golf community less than 5 min, Phelps Park walking distance, Park Ave 10 min and restaurant and retail minutes away.

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

Listing Agent: Prentice Williams (321-438-8955)

Remarks: Welcome to an exceptional opportunity in the highly desirable Park Grove community—an impeccably updated one-story residence ideally situated just moments from the vibrant shops and dining of Park Avenue and all that downtown Winter Park has to offer. With charming curb appeal, pristine landscaping, and timeless architectural appeal, this home makes a stunning first impression. Inside, a thoughtfully designed floor plan offers seamless flow, perfectly suited for both everyday living and effortless entertaining. Beautiful wood flooring spans the main living areas, while the Florida room showcases distinctive Mexican tile, adding warmth and character. Designer lighting, curated tile selections, and stylish wallpaper accents create a bright, inviting aesthetic throughout. The formal sitting room, complete with custom built-ins, and an elegant dining room provide refined gathering spaces. At the heart of the home, a light-filled kitchen opens to the spacious family room, where a cozy wood-burning fireplace serves as a focal point. The adjacent Florida room is lined with windows, offering serene views of the sparkling pool and lush, private backyard. The generously sized primary suite is thoughtfully positioned for privacy, featuring its own wood-burning fireplace, a large walk-in closet, and a beautifully appointed ensuite bath with dual vanities and an oversized walk-in shower. Four additional bedrooms are located on the opposite side of the home, two of which include ensuite baths—ideal for guests or multi-generational living. Outdoor living is equally impressive, with a beautifully pavered lanai overlooking the pool and ample space for al fresco dining, entertaining, and relaxing poolside. Tucked away in one of Winter Park’s most sought-after neighborhoods, this home offers both tranquility and convenience, with easy access to downtown Orlando, major hospitals, top-rated public and private schools, and key roadways. A rare blend of style, comfort, and location—this is Florida living at its finest.

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

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

Remarks: Luxury Lakeview Townhome in Winter Park! Experience elevated living in this newly built 3-bedroom, 3.5-bath residence with over 2,300 sq ft and breathtaking direct views of Lake Killarney. A dramatic 17-ft foyer welcomes you into a bright, open-concept great room featuring 11-ft ceilings and floor-to-ceiling windows that capture stunning water and nature views. The designer kitchen is built for entertaining with quartz countertops, Wolf and Sub-Zero appliances, double-stacked soft-close cabinetry, a walk-in pantry, and custom lighting. Motorized window shades add comfort and convenience throughout. Step outside to the 22-ft oversized lanai surrounded by lush landscaping—perfect for outdoor living. Upstairs, a versatile loft/office space leads to a private balcony with cocktail kitchen and panoramic lake views. The luxurious primary suite features floor-to-ceiling windows, dual closets, and a spa-inspired bath with designer tile, dual vanities, private water closet, and oversized frameless glass shower. Two additional bedrooms each include private en-suite baths, with a conveniently located laundry room. Additional highlights include a two-car garage with epoxy floor, EV charging plug, and extra storage. BONUS OPTION - Impossible to find boat slip on Lake Killarney available for purchase with this unique townhome. Located in one of Central Florida’s most sought-after communities, this exceptional home combines modern luxury, scenic lake views, and an unbeatable Winter Park location. Schedule your private showing today and experience luxury lakefront living at its finest.

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

Listing Agent: Lisa Gould (407-721-7612)

Remarks: Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design, ideal for both relaxed living and effortless entertaining. The kitchen serves as a focal point, appointed with leathered granite countertops, a generous center island with seating and a seamless connection to the inviting family room, where a gas fireplace adds warmth and charm. Walls of sliding glass doors extend the living space outdoors to a beautifully designed lanai, complete with a gas-heated pool and a fully equipped summer kitchen featuring a grill, sink, beverage refrigerator and additional seating area. The main level also includes a well-appointed guest suite with a private bath, offering comfort and privacy for visitors, along with a dedicated office or study space. Upstairs, a spacious bonus room provides flexibility for a media room, playroom or lounge, while two additional bedrooms accompany the expansive primary suite. The primary retreat is designed for relaxation, showcasing dual walk-in closets and a luxurious bath with a freestanding soaking tub, oversized shower and separate vanities. High-end finishes are showcased throughout, including travertine flooring across the main living areas and rich wood floors that continue through the bedrooms, staircase, upper hallway and bonus room. As a resident of Windsong, you’ll enjoy access to exceptional community amenities, including resort-style pools, a splash pad, playground and access to the scenic Winter Park Chain of Lakes, creating a lifestyle that is both vibrant and serene in one of Central Florida’s most desirable settings.

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

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

Remarks: Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. In one of Winter Park’s established neighborhoods, residents enjoy access to top-rated schools, tree-lined streets, and proximity to Park Avenue’s renowned dining and shopping, as well as the area’s scenic Chain of Lakes. Originally built in 2012, this four-bedroom, 3.5-bath home offers over 3,200 square feet of thoughtfully designed living space, enhanced by a comprehensive series of recent upgrades. The fully renovated 2025 kitchen serves as centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink, refinished cabinetry and designer hardware, all anchored by an expansive island ideal for gathering and entertaining. The first-floor primary suite provides a private retreat, complemented by a completely renovated spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and an upgraded walk-in shower. Additional 2025 renovations include the powder bath and laundry room, along with new lighting, fresh interior paint, plantation shutters and custom built-ins throughout. Designed for comfort and versatility, the home also features a dedicated office and a spacious upstairs loft with a custom built-in dry bar and beverage refrigerator. Outdoor living is equally inviting, with a private backyard oasis featuring a saltwater pool and spa with sun shelf, travertine decking, and a fully equipped outdoor kitchen with quartzite countertops and custom cabinetry. Electronic roll-down screens and updated landscaping, including a Clusia hedge, provide enhanced privacy and year-round enjoyment. Additional improvements include a new downstairs HVAC system, updated irrigation and sod, exterior paint and a whole-home security system. Move-in ready and ideally located, this home offers a seamless blend of modern upgrades and timeless design.

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

Listing Agent: Michelle Hochfelder (407-221-5073)

Remarks: Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV lights (2025), FRESH INTERIOR PAINT, NEWER WATER HEATER (2021), double-pane windows, and the aerobic septic system was recently serviced (2022). All that is left is to move in and enjoy the lifestyle! This home’s flexible floor plan delivers TWO PRIMARY SUITES – one on the first floor and another upstairs – making it ideal for multi-generational living, in-laws, long-term guests, or simply room to grow. The downstairs suite features a spa-like en-suite bath with dual sinks, a SOAKING TUB, large glass shower, and a WALK-IN/THROUGH CLOSET that connects directly to the main floor laundry. Upstairs, the second suite offers a private bath and direct access to a balcony. The SECOND LAUNDRY ROOM upstairs and huge 30x11 BONUS/UTILITY ROOM provide even more convenience and space. At the heart of the home you will find a GOURMET KITCHEN, crafted with the home chef in mind offering an LG STUDIO REFRIGERATOR, INDUCTION COOKTOP, DOUBLE WALL OVEN, sleek stone counters and a complementary backsplash, upgraded cabinetry, and a large ISLAND with bar seating and chic pendant lighting. The kitchen flows seamlessly into the OPEN LIVING AND DINING AREAS, making everyday living or hosting family and friends a breeze. The LOFT at the top of the stairs delivers additional flexible living space and includes a wet bar with fridge, perfect for a casual hangout space, movie room, office space or anything else you or your family might need. TILE AND WOOD FLOORS, crown molding, and an abundance of natural light give the interior a modern yet timeless feel. Outside you will enjoy stylish curb appeal with a paver driveway – plus a COVERED LANAI overlooking a FENCED BACKYARD, and the spacious lot offers plenty of room for outdoor living. From golf, fine and casual dining to shopping, top-rated schools like Princeton Elementary, and easy access to I-4, 426, and 436, everything you love about Winter Park is right at your fingertips! This home offers the upgrades, the space, and the location you have been waiting for. Call today to schedule a tour and fall in love with your new HOME SWEET HOME!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Back on the market—an exceptional opportunity in Winter Park. Now offered below appraised value, this residence has been thoughtfully refreshed with new carpet, interior paint, and thoughtful enhancements. Presented for the first time, this beautifully appointed 2014 David Weekley home is tucked away on a large corner lot within a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. Featuring 5 bedrooms and 5 bathrooms, the home is designed for both refined living and effortless entertaining, this home includes a private office and expansive bonus spaces. A standout feature of this property is its exceptional and highly sought-after parking flexibility. In addition to the 3-car garage, a newly added driveway (2024) provides additional space for guests and everyday convenience. Beyond that, a gated parking area—discreetly tucked behind an accessible double gate—offers secure storage for a boat, jet skis, or additional vehicles, eliminating the need for off-site storage and enhancing both lifestyle and practicality. Inside, the home showcases a curated collection of upgrades, including custom built-ins throughout the living spaces, office, flex areas, and dining room; custom built closets in every room; and a thoughtfully redesigned pantry with pull-out shelving. Unique touches such as under-stair storage with a hidden “secret door,” custom barn doors, and a LaCantina slider elevate both function and design. Outside is an entertainer’s paradise. There is a covered custom-built summer kitchen with metal roof featuring a built-in LP Grill, Primo Kamodo Smoker, stainless steel storage drawers and cabinets, counter storage ice bucket and plenty of island space for dining. The large pool and adjoining hot tub provide ample space for hours of fun and entertainment. The backyard putting green adds a fun distinctive, resort-style touch. Additional enhancements include brand new luxurious Berber carpet, attic flooring, overhead garage storage, plantation shutters, landscape lighting, updated exterior paint and interior paint, a tankless gas water heater, updated designer lighting through the home and multiple bathroom updates. The roof was replaced in 2021 for added peace of mind. The kitchen is a cooks dream with abundant storage, ample counter space and two ovens. A GE Monogram Dual Fuel Range was added to the kitchen in 2023. The 2021 dining room renovation introduces a custom bar, added storage and striking raw-edge floating shelves—perfectly blending modern sophistication with everyday livability. With its prime location, elevated finishes, and rare combination of luxury and utility—particularly its unmatched parking and storage capabilities, this move-in-ready Winter Park home is truly a standout offering! Inspection report available upon request.

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

Listing Agent: Sarah Tomlinson (407-721-7823)

Remarks: One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized 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. Inside, soaring 10-foot ceilings and a stately wood-burning fireplace set a welcoming tone 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 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. 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)

Remarks: Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of the design has been meticulously curated to evoke a sense of refined tranquility, where clean lines, natural textures, and warm tones create a timeless yet inviting atmosphere. Inside, expansive open concept living spaces are bathed in natural light, showcasing designer lighting, custom millwork, and seamless indoor-outdoor integration. The chef’s kitchen is a true centerpiece, anchored by dramatic quartz countertops, sleek custom cabinetry, and top-tier stainless steel appliances, complemented by a hidden walk-in pantry that enhances both style and function. The main living area opens effortlessly to the pool creating a fluid connection between indoor elegance and alfresco entertaining. The primary suite is a private retreat defined by calm sophistication offering a spa-inspired bath with a massive walk-in shower featuring multiple shower heads, a freestanding soaking tub, dual vanities, and a custom closet that feels like a boutique dressing room. Upstairs, a loft serves as a serene media or lounge area, while three spacious ensuite bedrooms provide comfort and privacy for family and guests. A dedicated home office continues the home’s minimalist aesthetic, fostering focus in a tranquil setting. Outdoors, the property unfolds into a private resort-like sanctuary with a sparkling pool, lush landscaping, and a fully equipped summer kitchen designed for seamless entertainment. A newly added rooftop deck serves as an architectural statement piece, connected by a spiral staircase that descends to the backyard below. The detached gym offers flexibility as a fitness studio, guest suite, game room, or creative workspace. From its sleek modern lines to its spa-like finishes, this home captures the essence of elevated Winter Park Living. A short walk to Winter Park Village and downtown WP puts you right in the middle of everything.

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

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