Winter Park Homes For Sale & Real Estate - 416 homes

Remarks: Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.

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

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

Remarks: Under Construction. A refined expression of new construction by LUIH Homes, this exceptional two-story residence blends timeless architecture with thoughtfully curated modern living in one of Central Florida’s desirable locations. From moment of arrival, the home impresses with beautiful curb appeal, a welcoming presence and a design that balances elegance with everyday comfort. Inside, gorgeous oak floors extend throughout the main living areas, complementing an open-concept floor plan designed for entertaining and relaxed living. The spacious chef’s kitchen serves as the heart of the home, featuring premium quartz countertops, custom cabinetry, a stylish wine bar with beverage refrigerator, and a high-end Thermador appliance package including a gas range, built-in oven and microwave. Overlooking the inviting family room with fireplace, a wall of glass sliders seamlessly connects the interior to the expansive covered lanai, creating an effortless indoor-outdoor lifestyle. The outdoor living space is equally impressive, offering generous room for lounging and dining, along with a fully equipped summer kitchen complete with a 32-inch built-in grill and beverage cooler. Beyond, a sparkling pool and spa are set within a meticulously landscaped, fenced backyard, an ideal setting for entertaining and quiet enjoyment. The first-floor primary suite provides a private retreat, featuring a large walk-in closet with a custom organization system and a spa-inspired bath with dual vanities, a soaking tub and an oversized glass-enclosed shower. A secondary bedroom suite with a private bath is also on the main level, offering flexibility for guests or multi-generational living. A spacious laundry room with Samsung washer and dryer and a well-appointed powder bath complete the first floor. Upstairs, the home continues to impress with three additional bedrooms, including one with an en-suite bath and two connected by a Jack and Jill bath. A dedicated office and a generous gathering or bonus room provide additional space for work, recreation or relaxation. Additional highlights include a two-car garage with epoxy flooring and an electric vehicle charger. Ideally just minutes from boutiques and dining of Park Avenue, as well as the vibrant restaurant scenes of Baldwin Park and Audubon Park, the home also offers convenient access to major roadways, downtown Orlando, leading hospitals, and Orlando International and executive airports. In a highly regarded A-rated public school district (Audubon K-8 and Winter Park High), this residence presents an exceptional opportunity to enjoy luxury, location and lifestyle in harmony.

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

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

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.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

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

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

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 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: Virtually Staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience. This ultra-private corner unit boasts one of the community’s most desirable floor plans—perfectly positioned in a peaceful enclave just steps from the vibrant heart of Winter Park Village and mere minutes from I4, offering seamless access to downtown Orlando and beyond. Designed for the modern lifestyle, this stunning residence features an open-concept layout with soaring ceilings, oversized windows, and luxury finishes throughout. The sleek chef’s kitchen anchors the space, showcasing dramatic gray cabinetry, a bold black center island, and a high-end Samsung appliance package, complete with a natural gas cooktop and built-in wall oven. Quartz countertops and a full-height backsplash give a seamless, refined look, while a spacious walk-in pantry adds everyday convenience. Upstairs, three generously sized bedrooms each pair with a spa inspired bathroom deliver elevated comfort. Each bath is thoughtfully designed with floating vanities, designer porcelain tile, and custom closet systems—bringing a boutique hotel aesthetic to your personal retreat. Enjoy quiet mornings or golden-hour gatherings on the expansive private terrace, framed by glass railings and pre-plumbed for a future summer or cocktail kitchen—perfect for effortless indoor-outdoor entertaining. Residents enjoy exclusive access to lakefront pavilion, and an array of watersport amenities including kayak, paddleboard, and canoe storage. With everything Winter Park has to offer just moments away, this location offers the perfect blend of serenity and connectivity.

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

Listing Agent: Brandon Geers (941-928-5152)

Remarks: Virtually Staged. This move-in-ready classic ranch-style pool home offers a relaxed 60’s retro vibe with vaulted ceilings, 4 bedrooms, 2 full bathrooms, and light-filled living spaces. Newer manufactured wood flooring flows throughout the main living spaces, complementing the spacious layout that includes a formal living room, dining area, breakfast nook, and a large free-flowing kitchen designed for both everyday living and entertaining. The kitchen features an open space concept, island, solid wood cabinets, granite countertops, over-range hood, and stainless-steel appliances. All four bedrooms are positioned just off the main hallway, creating a practical and functional layout. The 4th bedroom features French doors and offers exceptional flexibility for use as a home office, creative studio, workout space, or playroom, with a view of the pool and backyard. The primary bedroom includes an ensuite with a tiled shower. Additional features include an indoor laundry area, two-car carport with 2 storage rooms, and a large lot that adds to the home’s overall sense of space and privacy. Situated on a quiet street with limited through traffic, this home offers a peaceful setting while remaining close to everything Winter Park has to offer. The private, fully fenced backyard is a standout feature, offering a beautifully landscaped setting with a sparkling pool, Tiki Bar and plenty of space for outdoor entertaining or relaxing. Whether enjoying a quiet morning coffee, relaxing with a good book, or unwinding with a glass of wine in the gazebo, this outdoor space is designed to embrace the Florida lifestyle. Bonus features include a well-water irrigation system and newly sodded yard. Recent updates provide added peace of mind, including a roof installed in 2015, along with a new HVAC heat pump system installed 2026 with (10-year Warranty) and water heater installed in 2026. The home has been well maintained both inside and out, offering true move-in-ready convenience. Located in the sought-after Brookshire Elementary, Glenridge Middle, and Winter Park High School zones, the home is also close to Rollins College, Full Sail University, AdventHealth Winter Park, and the Orlando VA Medical Center. Outdoor enthusiasts will appreciate nearby Cady Way Trail, Blue Jacket Park, and Lake Baldwin, along with close proximity to Lake Berry and the neighborhood boat ramp and fishing dock. Buyer should verify any access rights or neighborhood use details.

Listing is courtesy of: ADAIR REALTY INC (407-476-1453)

Listing Agent: Michael Rains, Pa (407-325-8414)

Remarks: Under contract-accepting backup offers. Enjoy the best of living in this beautifully renovated well maintained 2-bedroom, 2-bath condominium located in the highly desirable gated Park West Condominiums. Perfectly positioned just steps from the renowned Park Avenue, this exceptional residence offers walking distance access to award-winning restaurants, charming boutiques, sidewalk cafés, and the popular weekly farmer’s market. This rare 3rd-floor corner unit which enhances privacy was completely remodeled in 2019 with quality upgrades throughout. The interior features are engineered wood flooring, updated tile, modern ceiling lighting, and a bright open-concept floor plan filled with natural light from expansive sliding glass doors leading to three private walk-out balconies. The redesigned kitchen in 2019 includes new cabinetry, countertops, a complete suite of kitchen appliances, including washer and dryer. Both bathrooms have also been tastefully renovated, creating a clean and contemporary feel throughout the home. Additional improvements include a brand-new HVAC system installed in July 2024, offering peace of mind and energy efficiency for years to come. Spacious bedrooms, generous storage, and seamless indoor-outdoor living make this condo ideal for both everyday living and entertaining. Park West residents enjoy beautifully maintained grounds along with community amenities including a sparkling swimming pool and tennis courts. The community is also conveniently located to Rollins College and Full Sail College. Whether you are searching for a full-time residence or seasonal retreat, this exceptional condo combines timeless Winter Park charm with modern updates and an unbeatable location.

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

Listing Agent: Kevin Mcclanahan (407-491-8509)

Remarks: Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

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

Listing Agent: Drew Henner (407-406-0662)

Remarks: Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

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

Listing Agent: Cathy Sawruk Williams (407-489-3921)

Remarks: Under contract-accepting backup offers. Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready. But what truly sets this property apart is the location and land. With new construction and beautifully updated homes all around, this is the perfect spot for anyone looking to build something special. Enjoy the home as it is, rent it out for steady income, or start planning your future build in a prime Winter Park setting. A property with this kind of potential doesn’t come around often.

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

Listing Agent: Gary Cohl (321-277-8671)

Remarks: Under contract-accepting backup offers. Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate Flooring Flows Throughout, and the Split Floor Plan Offers Ideal Privacy. Down One Hallway, You Will Find Two Well-Sized Bedrooms and a Shared Full Bathroom with a Shower/Tub Combo. Off The Family Room, The Master Suite Is Generously Sized and Includes Two Separate Sinks. A Large Walk-In Closet Provides Excellent Storage, and the Sliding Glass Door Leads to Your Own Private Fenced-In Yard, Perfect for Plants, Gardening, or Extra Seating When Entertaining. Just A Short Walk from Your Reserved Parking Spaces, You'll Find the Clean and Refreshing Community Pool, Making Relaxation Effortless. Don’t Miss This Opportunity—Call Today to Schedule Your Showing! Lease Must Be Honored Until 11/30/26 with a Rental Rate of $1,850.00 Monthly

Listing is courtesy of: OUTLET REALTY (407-353-5518)

Listing Agent: Ivan Tobon (407-353-5518)

Remarks: Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC system (2023), new water heater (2026), providing peace of mind for years to come. Enjoy Florida living at its finest on the private screened patio - perfect for relaxing or entertaining. Ideally situated 25 minutes from Downtown Orlando, 30 min from OIA, and 40 min from world-class attractions, this home is also just 6 minutes from Full Sail University, 12 minutes from the prominent Rollins College, and 19 minutes from UCF - making it an ideal choice for families and investors alike. A true must-see - schedule your showing today.

Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)

Listing Agent: Hugo Hernandez (407-716-5594)

Remarks: Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

Listing is courtesy of: GALLOWAY REAL ESTATE (407-421-9990)

Listing Agent: Sidney Galloway (407-421-9990)

Remarks: PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!

Listing is courtesy of: FLORIDA INVESTMENT REALTY GRP (407-937-8450)

Listing Agent: Yuleisy Marquez (407-937-8450)

Remarks: Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of comfortable living space in the Stratford A Winter Park Condo community. This 2-bed townhouse in Winter Park features an open floorplan with a large living and dining area, updated wood-look flooring throughout the main living spaces and bedrooms, recessed lighting, ceiling fans, and sliding glass doors that bring in natural light. The kitchen offers ample cabinet storage, stainless steel appliances, tile flooring, and a functional pass-through breakfast bar that opens to the main living area, creating a seamless layout for everyday living and entertaining. Upstairs, the oversized primary suite includes a walk-in closet, private en-suite bathroom, and generous floor space, while the secondary bedroom also features wood-look flooring, natural light, and easy access to the second full bathroom. Additional highlights include inside laundry, updated lighting fixtures, open parking, and plenty of storage throughout. Residents enjoy access to community amenities including a pool, fitness center, tennis courts, sidewalks, and maintained grounds, with HOA dues covering water, exterior maintenance, recreational facilities, and grounds maintenance. Conveniently located near Howell Branch Rd and SR 436, this Winter Park townhome provides quick access to shopping, dining, Downtown Winter Park, Maitland, Full Sail University, UCF, and Downtown Orlando. Located near highly rated Seminole County schools, parks, restaurants, and everyday conveniences, this property offers low maintenance living in a well-connected Central Florida location.

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

Listing Agent: Efrain Reyes (407-575-4226)

Remarks: Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a surprisingly flexible layout. The current owner has creatively configured the space with separate living and dining areas, while the enclosed porch serves as a bedroom. The updated kitchen features decorative tile flooring, stainless steel appliances, and solid wood cabinetry. Sliding glass doors lead to a bonus room that can easily function as a home office, guest space, workout room, or additional living area. The bathroom includes a single vanity and tub/shower combination, and you'll appreciate the abundance of storage throughout the unit. One of the biggest advantages of this property is the peace of mind that comes with a monthly HOA fee that covers nearly everything—including electric, water, sewer, trash, building insurance, landscaping, pool maintenance, and on-site management. . Whispering Waters recently passed its structural integrity inspection and reserve study with excellent results, reflecting the care and quality of this well-managed community. Residents also enjoy access to beautiful Lake Osceola, where you can launch a kayak, relax by the water, or take in breathtaking sunset views. Whether you're looking for a full-time residence or a seasonal retreat this condo offers an unbeatable Winter Park location and true lock-and-leave convenience.

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

Listing Agent: Andrea Parra Chopite, Pa (407-515-0097)

Remarks: Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation. One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare expansion (subject to licensing and approvals)—a unique value-add opportunity for growing operators. The property is already configured for childcare use with existing operations in place, making this an ideal turn-key opportunity for families looking to step into business ownership or operators seeking to expand their footprint. Sale includes real estate. Business goodwill, licensing, and operations may be included or negotiated separately. Convenient location with strong demand for childcare services. Please do not disturb staff or business operations. Showings by appointment only.

Listing is courtesy of: RE/MAX INNOVATION (407-281-1053)

Listing Agent: Ronald Trotter (321-331-1585)

Remarks: Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive, you’ll notice the peaceful ambiance—towering trees, lush greenery, and the soothing backdrop of untouched landscape. Inside, the home features a spacious and inviting layout with approximately 4 bedrooms and 3 bathrooms, designed for both comfortable living and effortless entertaining. Large windows frame picturesque views of the wooded backdrop, filling the home with natural light and bringing the outdoors in. The kitchen flows seamlessly into the main living areas, while the split floor plan offers privacy for the primary suite, complete with tranquil views of the conservation area. Step outside to your backyard oasis where you can unwind, host gatherings, or simply enjoy the sights and sounds of nature along Howell Creek. Opportunities like this are incredibly rare—nearly an acre of protected land, no rear neighbors, and a location just minutes from everything Winter Park has to offer. Experience the perfect balance of privacy, space, and convenience in this truly special home.

Listing is courtesy of: CHAMPION HOMES (863-420-0007)

Listing Agent: Nadia Kurakin (509-981-9819)

Remarks: One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly crafted masterpiece by Urban Perch, a boutique home builder. In downtown Winter Park, this stunning new construction home offers 3,421 square feet of elegant, efficient living area. The primary residence features four bedrooms plus a generous flex space, the perfect office, home gym or playroom and 4.5 baths with designer fixtures and finishes. A separate casita with a full bath provides additional space for multigenerational living or as a private guesthouse. Upon entering, you are greeted by an expansive open-plan living area with soaring ceilings that effortlessly blends sophisticated style with indulging comfort. The kitchen is a culinary dream, equipped with Le Cornue and Monogram appliances, marble and quartzite countertops and a separate scullery with plenty of storage and ample prep space. The kitchen opens to one of the main living areas, featuring a precast concrete fireplace surround with exquisite millwork details, forming a focal point leading up to the angular ceiling and overhead beams. Engineered hardwood floors throughout and curated specialty tiles in wet spaces ensure the home maintains a clean, classic and modern feel. Floor-to-ceiling French doors and oversized sliders invite natural light and offer views of the beautifully landscaped grounds, including a sparkling heated saltwater pool and fully equipped outdoor kitchen. This wellness home incorporates advanced features to ensure a healthy living environment, from air and water purification systems to specialty lighting, all designed to promote a balanced lifestyle. Just moments from charming parks, highly rated restaurants and boutique shopping, 1627 Mizell Avenue is more than just a home, it’s a sanctuary. With excellent accessibility and a vibrant community, this is an ideal setting for those seeking a blend of suburban tranquility and urban convenience.

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

Listing Agent: Bianca Khoury (407-797-1121)