Homes For Sale in Winter Park 32789 - 206 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: 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: 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: One or more photo(s) has been virtually staged. NESTLED IN THE HEART OF HISTORIC WINTER PARK, THIS CHARMING RESIDENCE AT 518 SHOREVIEW AVE OFFERS TIMELESS CHARCTER. JUST STEPS FROM BEAUTIFUL LAKE KILARNEY. INSIDE, YOU WILL FIND STUNNING HARDWOOD FLOORS THAT ADD WARMTH AND ELEGANCE THROUGHOUT, ALONG WITH AN UPDATED PRIMARY BATHROOM FEATURING A RELAXING GARDEN TUB.THE INVITING FLORIDA ROOM PROVIDES THE PERFECT SPACE TO UNWIND OR ENTERTAIN WHILE ENJOYING THE NATURAL SURROUNDINGS. THE KITCHEN FEATURES A REVERSE OSMOSIS SYSTEM TO FILTER THE DRINKING WATER. THIS PROPERTY IS A RARE OPPORTUNITY TO OWN A PIECE OF WINTER PARK HISTORY IN AN UNBEATABLE LOCATION NEXT TO FABULOUS SHOPPING AND DINING EXPERIENCES. ** SELLER HAS PLANS FOR ATTIC EXPANSION AVAILABLE.

Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)

Listing Agent: Kendra Wallace (407-457-7069)

Remarks: Under Construction. Spectacular new LUIH Luxury Home in the heart of Winter Park! Clean architectural lines, a bold façade, and curated exterior detailing set the tone for what unfolds inside. Beyond the entry, the home opens into a dramatic, light-filled living space featuring a sleek electric fireplace, framed by custom built-ins with ambient LED underlighting, while a glass-enclosed wine display serves as a stunning architectural detail. The kitchen is a true centerpiece, designed to impress at every level. Outfitted with a full suite of premium Thermador appliances, striking Calacatta quartz countertops, custom cabinetry, and a spacious walk-in pantry. Privately positioned, the primary suite is a sanctuary of calm and sophistication. The spa-inspired bath evokes a boutique hotel experience, featuring floating mirrors, a freestanding soaking tub, an expansive glass-enclosed walk-in shower, and refined finishes that create a sense of understated luxury. The custom walk-in closet is equally impressive, offering both scale and thoughtful organization. A rare and highly sought-after feature in Winter Park, the home offers two bedrooms on the first floor, ideal for guests. Upstairs, a spacious loft creates an additional living area perfect for relaxing or entertaining, complemented by a dedicated office and three generously sized bedrooms. The outdoor living experience is nothing short of amazing. As you step through the expansive sliders, the interior flows seamlessly to a covered lanai designed for true indoor-outdoor living. A fully equipped summer kitchen anchors the space, ideal for hosting, while the expansive backyard is transformed into a private retreat with a sparkling pool and spa, offering both tranquility and the perfect backdrop for entertaining. Perfectly positioned for the Winter Park lifestyle, you’re a short golf cart ride from the shops and dining of Park Avenue, with Cady Way Park, the YMCA, and Winter Park Village also just moments away. In a market where true quality is rare, this residence stands apart, an exceptional blend of design, craftsmanship, and livability that defines what luxury should feel like in Winter Park.

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

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

Remarks: Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors, every detail reflects a refined, cohesive aesthetic. Step inside to warm oak wood floors and a light-filled open-concept layout ideal for both everyday living and upscale entertaining. The chef’s kitchen is a true statement, featuring custom oak cabinetry, sleek quartz countertops with a dramatic waterfall island, and an expansive breakfast bar. Top-of-the-line appliances include a Sub-Zero refrigerator, Wolf 6-burner gas professional range with grill and double ovens, Wolf microwave, Miele dishwasher with PowerDisk system, and a built-in Miele coffee station. The kitchen flows effortlessly into both a breakfast nook and a separate dining area, while the designer bar serves as a stunning focal point—complete with two Sub-Zero dual zone wine refrigerators accommodating more than 200 bottles, along with additional Sub-Zero refrigerator and freezer drawers. Downstairs all blinds are motorized and have gorgeous custom drapes. Upstairs, all three bedrooms are en suite, offering a private retreat for family and guests. A versatile loft area features a custom-designed laundry space concealed behind built-in cabinetry for a clean, streamlined aesthetic. One bedroom has been thoughtfully designed as a home office with a built-in Murphy bed, providing flexibility without compromising luxury. The outdoor space is equally refined, featuring low-maintenance turf, a beautifully designed pool, and a covered lanai perfect for relaxing or entertaining. A built-in grill area and lush privacy hedging create a serene backyard oasis, with landscaping professionally designed and maintained by Signature Landscaping. Additional highlights include a 2-car garage and a Sonos sound system in the living room and lanai, enhancing the home’s elevated lifestyle experience. Most furnishings are available for purchase separately, offering a truly turnkey, designer-furnished opportunity. Ideally located just minutes from Park Avenue, top-rated schools,Rollins College, fine dining, and boutique shopping, this exceptional home represents the very best of Winter Park luxury living. Perfect lock and leave home with the perfect location!

Listing is courtesy of: OLDE TOWN BROKERS INC (407-425-5069)

Listing Agent: Noelle Leblanc (407-491-2744)

Remarks: Grand Southern charm and architectural elegance define this stately residence in one of Winter Park’s most desirable neighborhoods, set along a quiet brick-lined street just steps from Lake Chelton. Positioned on nearly half an acre, the home spans over 5,200 square feet, offering 5 bedrooms, 4.5 baths, a designated office, a large, versatile media/game room, a 3-car garage, and an expansive lanai with summer kitchen and resort style pool— all brought together in a smart well-planned layout ideal for effortless everyday living and exceptional entertaining. Step inside to a beautifully curated interior where rich architectural detail and livable design come together. Extensive custom millwork—seen in detailed moldings, trim work, and built-ins—adds depth and character throughout. The entry opens to gracious living and dining spaces, complemented by an impressive 550+ bottle temperature-controlled wine room. At the heart of the home, a beautifully appointed Kitchen, featuring white wood cabinetry, a six-burner gas range, an oversized quartz island, and a delightful breakfast nook that seamlessly connects to the family room featuring custom built-ins and fireplace—creating a natural gathering space. Tucked away, the first-floor primary suite offers a spacious sitting area, a beautifully customized closet with dressing area, and a luxurious bath with marble flooring, a large double-head walk-in shower, dual vanities, a free -standing tub, and built-in linen cabinetry—designed as a calming and private sanctuary. The first level also features a private guest bedroom with en-suite bath, creating an ideal setup for friends & family. A generously sized laundry room offers abundant cabinetry and exceptional storage, making everyday tasks feel effortless. Upstairs, three spacious bedrooms and two full baths provide comfortable accommodations, with two bedrooms opening through French doors to the front double balcony—perfect for enjoying peaceful treetop views. The back of the home unfolds around a beautiful pool and spa, with French doors from multiple rooms opening to the lanai and creating a natural indoor-outdoor connection. Retractable screens allow for year-round enjoyment of the well-appointed summer kitchen, making it ideal for both relaxed evenings and easy entertaining. Other notable highlights: a whole house natural gas generator, extensive brick paver driveway & motor court, automated driveway gate, integrated sound system, security cameras and new roof 2024. Lastly, this profound property offers top rated Winter Park schools and easy access to Park Ave, Downtown Orlando, Audubon Park Garden District and Baldwin Park.

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

Listing Agent: Mary Colton (407-222-7388)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to one of the most affordable opportunities to own in the highly sought-after Winter Park High School district. This well-maintained community is tucked into a beautiful setting and is extremely convenient to everything that makes Winter Park one of Central Florida's top lifestyle destinations. This end-unit two bedroom / two-and-a-half bath condo in Sandlewood Creek combines a hip retro-classic style with comfort, functionality, and peace of mind with a long list of recent improvements. Solid knotty-pine wood accent paneling is featured throughout and compliments the freshly painted walls in designer colors. The kitchen has been partially renovated and has a nice clean and modern vibe, complemented by granite countertops and updated bathrooms for a clean, modern feel. The roof was replaced in 2021. Major system upgrades include an A/C (2019) and a brand-new water heater (2026), while the entire interior has just been freshly painted, carpets professionally cleaned, and a final detailed cleaning completed—making this home truly move-in ready. Whether you're looking for a primary residence, a low-maintenance lifestyle, or a smart investment in one of Central Florida’s most consistently in-demand areas, this property checks all the boxes. Enjoy easy living in a quiet, established community just minutes from everything that makes Winter Park special—top-rated schools, dining, shopping, and parks. Pre-approved for FHA financing and recent updates that your insurance company will like - this is a rare opportunity in this market. Don't miss it!. Sellers have this priced to sell, so don't delay. Call today to make your appointment for your private viewing.

Listing is courtesy of: DERENTHAL REALTY (321-662-8014)

Listing Agent: Mike Derenthal (321-662-8014)

Remarks: A New Standard of Modern Sophistication in Winter Park In a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living. Step through the striking 10-foot glass pivot doors into a world defined by light and scale. The soaring foyer gives way to an expansive open-concept floor plan, where the boundary between indoors and out begins to blur. Sleek Italian wood flooring guides you through the main level to the heart of the home: a grand living area anchored by a statement fireplace. It is a space designed for the quiet morning coffee just as much as the vibrant evening gala. A Symphony of Intelligence. This home lives and breathes with you. Equipped with a fully integrated Control4 automation system, the environment responds to your touch. From your device, you can orchestrate the perfect atmosphere—adjusting custom lighting scenes, streaming high-fidelity music, or setting the climate before you even arrive. This "invisible concierge" extends to the water’s edge, allowing you to manage pool temperatures and lighting with effortless precision. The kitchen is a masterclass in culinary elegance, blending European minimalism with professional-grade power. Light-toned cabinetry hides clever storage solutions, while premium Sub-Zero and Wolf appliances sit beneath striking Neolith double countertops. It is a space that invites creativity, whether you are hosting an intimate chef-led dinner or enjoying a slow Sunday brunch. The commitment to "pride of ownership" is felt most deeply in the private quarters. Each of the four bedrooms is a dedicated en suite retreat, featuring voluminous walk-in closets and spa-inspired baths. Custom vanities, Neolith surfaces, and soft, indirect lighting create a hotel-level sense of calm, ensuring every guest or family member feels a sense of total seclusion. The Backyard Resort. The transition to the outdoors is seamless, revealing a private oasis designed for the quintessential Florida lifestyle. A Brazilian IPE wood deck surrounds a shimmering, heated mini-pebble pool in French gray. Beyond the water, the lushly landscaped grounds lead to a premier summer kitchen clad in sintered stone. Here, under the Florida stars, the integrated grill and sink provide the ultimate setting for al-fresco entertaining. Experience the pinnacle of Winter Park living. You are situated just moments from the refined energy of Park Avenue, the prestigious Interlachen Country Club, and the scenic beauty of Phelps Park. With zoning for the area’s top-rated schools the location is as strategic as it is beautiful. Notable Refinements: • Whole-home generator ensuring absolute peace of mind. • Finished garage floors and a circular driveway accented with salt and pepper gravel. • Full-home Control4 integration for music, light, and climate. Experience the art of living well—connect with us today for an exclusive private tour **Unique financial opportunities available: The seller is open to owner financing and Bitcoin (Digital Asset/ Crypto) as a medium of exchange. Please reach out to discuss how we can facilitate a transaction tailored to your needs.**

Listing is courtesy of: ROI AVE LLC (321-663-7276)

Listing Agent: Mark Anthony Buot (407-925-1716)

Remarks: Under contract-accepting backup offers. Amazing location near Park Ave! Completely reimagined and rebuilt from the studs, this exceptional one-story 3-bedroom, 2-bath residence offers the perfect blend of modern luxury and timeless charm in one of Winter Park’s most coveted locations—just a short stroll to the boutiques, dining, and cultural attractions of Park Avenue. Every inch of this home has been thoughtfully renovated in 2026 with no detail overlooked. Enjoy peace of mind with all-new electrical, plumbing, HVAC, windows, and garage door, ensuring efficiency and reliability for years to come. Roof 2021. A beautifully designed paver driveway enhances the home's curb appeal, creating a warm and welcoming first impression. Inside, the open and inviting floor plan is enhanced by premium tile flooring, designer finishes, and an abundance of natural light. The stunning, fully updated kitchen serves as the heart of the home, featuring sleek cabinetry, quartz counters, high-end finishes, and center island with bar seating. The kitchen flows seamlessly into the living and dining spaces—perfect for both everyday living and entertaining. Both bathrooms have been beautifully redesigned with modern fixtures and elegant touches. The spacious first floor primary suite offers a serene retreat with en-suite bath featuring a stunning walk in shower. Enjoy the convenience of the indoor laundry room with extra storage space. Step outside to the screened in back porch to enjoy the Florida lifestyle. Situated in a highly desirable Winter Park neighborhood, this turnkey home combines walkability, luxury upgrades, and an unbeatable location. A rare opportunity to own a like-new home just moments from the very best of Park Avenue living.

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

Listing Agent: Ingrid Livingston (407-595-5972)

Remarks: Discover this generously sized 3-bedroom, 3.5-bath townhome offering 2,083 square feet of flexible living space in one of Winter Park's most coveted locations. This two-story residence features a semi-attached 2-car garage and thoughtful room layouts perfect for today's lifestyle. The main level welcomes you with formal living and dining rooms, ideal for entertaining. The separate family room showcases a wood-burning fireplace and flows seamlessly to the heart of the home—the kitchen. French doors open from the family room to a vaulted screened lanai, creating the perfect Florida indoor-outdoor living experience for year-round enjoyment. Upstairs, you'll find three oversized bedrooms, each with its own full bathroom for ultimate privacy and convenience. The second-floor interior laundry adds everyday ease between the bedroom suites. This home presents wonderful potential for personalization and updating to match your vision. The location simply can't be beat—moments from the shops and dining of Park Avenue, beautiful Rollins College, and the tree-lined streets of the historic College Quarter neighborhood. HOA fees of $691/month include lawn maintenance for carefree living. Easy to show—schedule your private showing today and envision the possibilities!Retry

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

Listing Agent: Kelly Price (407-645-4321)

Remarks: A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

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

Listing Agent: Thomas Bonner (407-401-3748)

Remarks: Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park!  This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and  Structural Integrity Reserve Study with flying colors. Enjoy all of these activities nearby including the award winning restaurants, boutique shops and museums.  There is walkability to the Alfond Inn, Rollins College, the Sunrail / Amtrak Station, Farmer's Market and all things the Park Avenue area has offers including beautiful parks and lakes to explore.  Just outside your door and on the shore of Lake Osceola you will find the historic Winter Park Boat Tour.  At Whispering Waters the lush community grounds and shared patios are a tropical oasis of flowering plants and charming decorative ponds.  This highly sought after ground floor corner unit comes with an abundance of natural light and has just been freshly painted as well as new energy efficient windows installed.  It features neutral colors, easy care ceramic tile in the kitchenette & bathroom, with laminate flooring in the main living area.  The low monthly HOA fee includes electricity, gas, heat, water, sewer, trash, grounds care, pool service and all building exterior maintenance. The owner pays for Cable & Internet. Association approval is required for all new owners.  One assigned & deeded exterior parking space comes with this unit. Drop your groceries off in the covered and gated parking garage in the basement, with a short elevator ride to the ground floor.  Amenities include an onsite manager, pool, clubroom, covered boathouse with boat slips (Docks may become available for lease or purchase). Whether you are seeking a full-time residence, a winter retreat or mother/father in-law suite, this home offers effortless, low-maintenance living-just lock and leave!l Schedule your showing soon as this gem is sure to go quickly! Professional photographs coming soon!

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

Listing Agent: Jeff Dodds (407-937-9521)

Remarks: Welcome to one of Winter Park's most sought-after addresses — a beautifully updated 2-bedroom, 2-bath condo that perfectly blends timeless Florida charm with modern finishes. Just a stroll from Park Avenue's boutiques and restaurants, the iconic Rollins College campus, the location is truly unmatched. Inside, the open-concept kitchen flows effortlessly into the living area — ideal for entertaining or relaxed everyday living. Rich wood-look ceramic tile floors run throughout, offering the warmth of hardwood with the durability of tile. Both bathrooms have been tastefully updated with fresh, contemporary finishes. The crown jewel of this home is the stunning sunroom, where floor-to-ceiling windows frame sweeping views of the community's lush 8+ acres of private gardens and a sparkling pool. Whether you're sipping your morning coffee or winding down at sunset, this serene retreat offers a daily connection to nature that feels worlds away from the city — while keeping you right in the heart of it. This is a 55+ community with room for younger owners. Call agent for details

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

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

Remarks: Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction, MJS Designers, and Collins & Co. From concept to completion, every detail is thoughtfully orchestrated, allowing the future owner to tailor finishes, layout, and architectural style to match their vision. Ideally positioned just minutes from Park Avenue’s renowned dining, boutique shopping, and vibrant lifestyle, the property also offers convenient access to I-4, College Park, and Downtown Orlando—delivering both prestige and connectivity. The proposed residence spans approximately 2,500 square feet and is designed with intentional flow, abundant natural light, and refined modern finishes. The layout allows for elevated indoor-outdoor living, with the option to incorporate a private pool and outdoor entertaining space. Located within close proximity to major medical centers, including AdventHealth Winter Park (approximately 2.5 miles), AdventHealth Orlando (approximately 4 miles), and Orlando Health Orlando Regional Medical Center (approximately 5 miles), this location offers both lifestyle and practical convenience for medical professionals and those seeking proximity to top-tier healthcare. Opportunities like this are increasingly limited in Winter Park—secure your homesite and begin designing a one-of-a-kind residence in one of Central Florida’s most desirable zip codes.

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

Listing Agent: Vinny Lay (407-756-4255)

Remarks: Under contract-accepting backup offers. Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right, the living room features built-in shelving and a bay window that fills the space with natural light. It flows into the formal dining room, also with hardwood floors, plantation shutters, and plenty of room to host. A conveniently located powder bath serves this side of the home. To the left is the heart of the house - a generously sized kitchen with abundant white cabinetry, stone countertops, a center island, double ovens, a built-in pantry with pull-out storage, and a breakfast bar. The separate eat-in area overlooks the backyard and opens to the screened porch through French doors. The kitchen connects to a large family room with coffered ceilings, a gas fireplace, built-ins, and additional French doors leading outside. The home offers a three-way split floor plan for privacy. The primary suite sits on its own wing and is very spacious, featuring crown molding, a bay window, and French doors to the patio. The en-suite bath includes double vanities, large "His & Hers" walk-in closets with custom closet systems, a soaking tub, separate shower, and private water closet. On the opposite side of the home, you’ll find a generously sized secondary bedroom with its own en-suite bathroom and walk-in closet. Toward the back of the house is a third bedroom with a built-in desk, French doors to the exterior, and an en-suite Jack-and-Jill bath that also serves the family room. The first floor also includes an indoor laundry room with ample cabinetry and a utility sink. Upstairs, a huge bonus room offers incredible flexibility - game room, media room, office, or potential fourth bedroom. There is also space to add a bathroom if desired. Out back, a large screened porch with high ceilings overlooks a peaceful, lushly landscaped yard with plenty of room to enjoy Florida living. Additional features include plantation shutters throughout, a spacious two-car garage, and an unbeatable location just minutes from Park Avenue’s shopping and dining. Zoned for highly rated Dommerich Elementary, Maitland Middle, and Winter Park High. Call today to schedule your private showing!

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

Listing Agent: Maria Van Warner (407-256-8066)

Remarks: Located in the heart of Winter Park, this beautifully fully renovated 2-bedroom, 2.5-bath condominium: New Roof, New Hot Water Heater, New Plumbing, New Maytag Washer & Drier offers the perfect blend of modern design and walkable lifestyle. The open-concept floor plan creates a bright and airy living space ideal for both everyday living and entertaining. The completely updated kitchen features all-new appliances, contemporary finishes, and seamless flow into the dining and living areas. Both bedrooms are generously sized and include private en-suite bathrooms, providing comfort and privacy, while the additional half bath is perfect for guests. Every detail has been thoughtfully updated, making this home truly move-in ready. Enjoy being just minutes from the acclaimed restaurants, shops, and cafés along Park Avenue, with easy access to parks, recreation, and the charm that defines Winter Park living. The property is zoned for highly regarded Dommerich Elementary School and Winter Park High School, making it an excellent option for both homeowners and investors.

Listing is courtesy of: NOELKE REALTY (407-607-7166)

Listing Agent: Tom Noelke (407-607-7166)

Remarks: Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to everything Winter Park, a pedestrian village of delight! Natural light fills the central courtyard which features an iron water fountain. Private pool with heated spa and outdoor grilling and entertaining area. Interior features include fireplaces in living room, 2 Southwest facing covered outdoor walkout balconies, accessed by living room, den, master bedroom and one directly over looking the pool. Master bathroom includes separate tub and shower, dual closets, split vanities and plenty of storage space. 4 full bath- 1 half bath (5). Two specified parking spaces also have large storage closets with security gate and elevator access to your floor. K-8 Audubon School district! Unit / building “horseshoe” configuration provides no neighbors on any of the 4 sides, courtyard interior, Private Luxury Living all on ONE floor!

Listing is courtesy of: HELLOSOLD LLC (954-778-5300)

Listing Agent: Dan Farber (954-778-5300)