Homes For Sale in Winter Park 32789 - 191 homes

Remarks: Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical, windows, recessed lighting, a/c unit, and more. Natural sunlight flows throughout the home reflecting off the refinished wood floors creating an inviting and cozy environment. The open kitchen features quartz countertops, glass crafted tile backsplash, custom cabinets, breakfast bar and stainless steel appliances. Feel refreshed and relaxed as you step into the primary suite with barn doors leading into the spa-inspired bathroom, complete with dual vanities and a large walk-in tiled shower. The backyard is fully fenced and the outdoor patio is screened-in and covered. Extra storage space can be used in the outdoor shed or the one car attached garage. No HOA and not in a flood zone. The property’s exceptional location offers close proximity to I-4 East and West, upscale award-winning Winter Park restaurants and boutiques, Winter Park Village, WP9 Golf Course, Park Ave, and the upcoming state-of-the-art Lifetime Fitness center which features over 85,000 SqFt and 5 acres of the best that wellness amenities have to offer. Nearby EV charging stations located within 2 miles away make sustainable living effortless. Rare opportunity to settle into or invest in a peaceful updated retreat located in the highly desirable and vibrant community of Winter Park.

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

Listing Agent: Michael Domi (407-212-8841)

Remarks: Elegant 1922 Mission Revival home, located in popular College Quarter is a registered historic place in Winter Park, FL. Lifestyle is neighborly/relaxed/pet friendly/enhanced by proximity to Lake Virginia/lakeshore sidewalks/Rollins College campus/downtown Winter Park/Central Park/museums/shops/restaurants/cultural events, most walking distance. College Quarter residents enjoy exclusive use of Park/Dock on Lake Virginia to kayak/paddleboard/motor through Chain of Lakes or meet up for holiday fireworks/once-in-a-lifetime or yearly celestial events. College Quarter is one of the oldest/most architecturally diverse neighborhoods. This 1922 home represents the Florida Mission Revival vernacular through a timeless blend of stucco exterior walls/asymmetrical façade/prominent arches above doors/large windows/a flat roof/barrel red tiles/a distinctive parapet and walled courtyard with wrought-iron gate designed by local master ironworker. True to Mission Revival style, home connects to nature and surrounding College Quarter landscape through above architectural details that embody poetics of Mission Revival style. Builder used sensitive siting, placed home at highest elevation on street & it remains responsive to prevailing lake breezes/paths of rising sun & moon 104 years later. Lake light/sunlight/moonlight take centerstage in every room. Whether through window or door, each part of house has relationship with its surroundings. Mission Revival style accomplishes what homeowners often seek—a home’s ability to surprise. Airiness/lightness, beautiful atmosphere/ambience that Mission Revival architecture creates is notable that way. Mission Revival layout is key to that effect. Home’s modified Great Room layout combines roles of several traditional rooms--family/kitchen/living/dining rooms into 1 expansive space ideal for families/entertaining guests/enjoying natural light/views. Open layout in house is conducive to spending quality time together/socializing/entertaining. Proximity of kitchen/dining/living & outdoor spaces allow for easy interaction/conversation & creates sense of togetherness. Great Room dominates first floor living/dining room areas. One interior archway frames foyer, another leads to family room. Left of fireplace in Great Room are French Doors to enclosed porch/walled courtyard/plunge pool. Ceiling is 10 ft exposed rafters, 2 large, arched windows, one on East wall, one on West, face each other across 4 interior spaces. Changing light seen through handblown windowpanes in Great Room illuminate first floor & exterior environment. When moon rises over lake's cypress trees it appears in Great Room east window, travels thru sky, peeps into 2nd floor windows before moving ever higher in the sky. Kitchen’s center island is gleaming butcher block & divides food prep area from pantry/laundry/guest bathroom/living/dining areas. Kitchen counter imported tile/oak cabinets/small eat-in breakfast nook. French Doors open to brick courtyard/garden area/plunge pool. Kitchen/Pantry/Guest Bathroom have heart of pine floors. Laundry new ceramic tile, built-in wood cabinets/shelves, new washer/dryer, stainless-steel sink. Great Room floors original oak. Staircase/second story floors original heart of pine. Bedroom 1 ensuite Bathroom/Linen Closet/Balcony. Bedroom 2 beautiful views/2 closets/built-in drawers/. Bedroom 3 best water views during day. Single-family ownership 45 years. Roof & 2 balconies 5 yrs old. Major renovations 2021- to present

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

Listing Agent: Wendy Brandon (407-435-9009)

Remarks: Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This flows effortlessly into a gorgeous gourmet kitchen with high-end appliances featuring a Wolf range, Sub-Zero refrigerator, Euro-style cabinetry, oversized island, and walk-in pantry. The downstairs primary suite overlooks the pool and includes a spa-like bath with soaking tub and rain showers. An additional ensuite bedroom on the first floor works perfectly as a guest room or office. Upstairs you’ll find a large loft and media area with private balcony, along with three ensuite bedrooms including walk-in closets. Step outside and enjoy year-round living under the covered lanai featuring a summer kitchen overlooking the saltwater pool surrounded by mature landscaping. An outdoor bath adds extra convenience, and the oversized lot provides abundant space to relax, entertain or dine al fresco. This home comes complete with a spacious three-car garage with EV charging. Minutes to Interlachen Country Club, Winter Park Racquet Club, and Park Ave shopping. Don’t miss this beautiful custom modern home in one of Winter Park’s most sought-after neighborhoods! Ask about the new landscaping package, and driveway installation.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Tab Bish Llc (855-450-0442)

Remarks: Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and contemporary luxury. From the moment you step through the elegant foyer, you're greeted by sun-drenched interiors showcasing gleaming hardwood floors, soaring coffered ceilings, and designer details at every turn. The thoughtful floor plan reveals a private home office with custom built-ins and fireplace to the right, and a gracious formal dining room to the left—perfect for hosting memorable gatherings. The heart of this home is the spectacular kitchen, a true chef's masterpiece featuring custom cabinetry, pristine marble countertops, statement pendant lighting, and top-tier appliances. This culinary haven flows seamlessly into the light-filled family room, where expansive windows frame views of your private outdoor sanctuary. The first-floor primary retreat is a haven of tranquility, featuring an expansive walk-in dressing room with exceptional storage and a spa-inspired ensuite bath. Luxuriate in the freestanding soaking tub, refresh in the walk-in shower, or prepare for your day at the generous double vanity—all appointed with elegant finishes befitting this caliber of home. Three generously proportioned guest bedrooms upstairs offer optimal comfort and privacy, complemented by a Jack-and-Jill bath and additional hall bath. A spacious bonus room with backyard views provides versatility for a media room, playroom, or home gym. Above the garage, an additional 260-square-foot bonus room with wet bar and wine fridge creates the ideal entertainer's lounge or game room. Step through French doors to your private resort-style backyard—a meticulously landscaped oasis featuring a sparkling pool and spa surrounded by lush greenery, stately palms, and thoughtful lighting. Whether gathering around the firepit, lounging poolside, or dining alfresco under the stars, this outdoor retreat elevates everyday living to an art form. No detail has been overlooked in this complete renovation: designer light fixtures and custom window treatments throughout, first-floor laundry convenience, elevated trim and baseboard, fresh paint, recessed lighting, and three HVAC units ensuring year-round comfort. The location is simply unparalleled—a leisurely stroll to the Winter Park Racquet Club, zoned for A-rated public schools, and just moments from the world-renowned shops and restaurants of Park Avenue. This is more than a home; it's a lifestyle of distinction in Central Florida's most desirable address.

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

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

Remarks: Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. The side entry two-car garage was once converted into a 425 sq ft air-conditioned bonus room—perfect as a media room, home gym, or additional living space. This could easily be converted back if the next owner requires more living space. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park, and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to own this exceptional home in the heart of Winter Park!

Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)

Listing Agent: Sue Silberbusch (407-252-3157)

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: This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet, downstairs main and additional guest suite, and upstairs includes remaining beds and baths. An inviting foyer welcomes you with volume ceilings, wood floors and a large transom window that allows beautiful natural light in. The family room is spacious with a marble wrap electric fireplace with lighting detail and niche for a flat screen TV. Clear glass doors across the back of the house lead you to the outside covered porch for ease of entertainment. The kitchen is open, light and bright with 42-inch shaker double stack cabinetry, large pantry and great workspace, a peninsula with bar seating as well as an eat-in kitchen area for large gatherings. Stainless appliances, granite counters and creative backsplash round it all out. The oversized laundry room includes an extra refrigerator and a second pantry for added convenience. The dining with tray ceiling, designer fixture and textured wallpaper add to the style of the home as well as dedicated office or flex space. Luxury continues into a primary suite with built-ins, large spa-like bath with sleek finishes, soaking tub, large dual-head shower and spacious walk-in closet. The primary suite overlooks backyard and opens to an outdoor oasis with open-air lanai with generous covered porch to gather or enjoy a night of alfresco dining. State-of-the-art modern resort-style pool with heated spa, sun shelf with fountain feature, a fire feature runs along edge of pool and transforms the backyard into a luxurious tropical oasis particularly at night. Hardscaping elements include pathways trimmed with turf grass, professional landscape lighting that enhances and elevates the home. Don’t wait to tour this special home in the heart of Winter Park, close to the best schools with Lakemont Elementary, Glenridge Middle and Winter Park High. A mile from Park Avenue, close to hospital and walkable to the YMCA, Phelps Park and fantastic restaurants.

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

Listing Agent: Alison Mosley (407-304-6458)

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

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

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

Remarks: Discover unparalleled luxury at The Douglas Grand, a distinguished location just a stone’s throw from Park Ave in Downtown Winter Park. This expansive 2-Story unit boasts 3,174 sq/ft of living space with your private elevator. From the moment you step inside, you’ll be captivated by the exquisite craftmanship and modern comforts that define this exceptional residence. This stunning condo boast three spacious ensuite bedrooms and abundance of storage. The heart of this home is the gourmet kitchen, custom-designed and built to fulfill every chef's dream complemented by top-of-the-line appliances that include a wall-mounted convection/microwave oven and a cutting-edge Wolfe induction stove top. The kitchen is not only functional but also perfect for entertaining, featuring a spacious breakfast bar where culinary creativity knows no bounds. As you move through this exceptional residence, in the living room, dining room, and entrance, creating an inviting ambiance that welcomes you home. Indulge in the spa-like sanctuary of the master bathroom, where luxury knows no bounds with a charming fireplace in the primary suite. Here, you'll find a sumptuous bathtub, separate vanity areas. With three generously appointed bedrooms, featuring custom closets, you'll have ample space to organize your wardrobe and storage needs effortlessly. Step onto the private balcony upstairs and be captivated by the breathtaking views. This secluded outdoor space is an ideal setting for unwinding with an evening cocktail, savoring a family dinner, or starting your day with a tranquil cup of morning coffee. The Douglas Grand enjoys a central location that places you within a lifestyle that defines this charming community. In addition to its unmatched location, this building offers a quiet, private, and secure environment—making it the perfect choice for those seeking a "lock and leave" second home or a luxurious vacation retreat. Don't miss this opportunity to experience the height of elegance and y reach of Downtown Winter Park's award-winning restaurants, cultural museums, upscale shopping boutiques, and the vibrant sophistication. Contact me today to schedule a private viewing of this remarkable residence.

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Julie Scott (407-497-3492)

Remarks: One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just one mile from Park Avenue, SunRail, and Rollins College, and only half a mile from Hannibal Square, local parks, and the Winter Park Library, this property offers an unbeatable blend of convenience, walkability, and lifestyle. As you step inside, you are greeted by a modern open floor plan enhanced with luxury vinyl plank flooring that flows seamlessly throughout the home. The spacious living and dining areas create an inviting environment ideal for both everyday living and entertaining. The updated kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and timeless white shaker cabinetry. Its thoughtful layout allows for easy conversation and connection while preparing meals, making it as functional as it is stylish. The oversized great room provides flexibility for relaxing, hosting guests, or creating a dedicated workspace. Both bedrooms are generously sized, offering comfort and versatility. The owner’s bedroom is especially appealing, complete with a custom closet organizer and direct access to a private paver patio—an ideal setting to enjoy Florida’s year-round sunshine. The bathroom has been tastefully updated with granite countertops and a shower/tub combination accented by classic white subway tile, creating a clean and timeless aesthetic. Outdoors, the secluded backyard offers privacy and future potential, with room to expand or customize according to your vision. Whether you are searching for a primary residence, a downsizing opportunity, or an investment in the heart of Winter Park, this property presents a rare chance to own a beautifully updated home in a prime location. Experience the charm, convenience, and lifestyle that 1036 Aragon Avenue has to offer. Schedule your private showing today.

Listing is courtesy of: WATSON REALTY CORP (407-359-2300)

Listing Agent: Tim Veigle (407-399-0879)

Remarks: Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a formal dining room, which connects to a secondary living area perfect for entertaining. The open kitchen features granite countertops, stainless steel appliances, and a casual eat-in area, while refinished terrazzo floors run throughout the home adding character and easy-care durability that's quintessentially Florida. 2021 roof and HVAC mean the big-ticket items are already done. Step outside to a large screened-in patio overlooking a spacious backyard with plenty of room to add a pool or expand. Minutes from Park Avenue and Downtown Winter Park's incredible restaurants and fantastic shopping, Rollins College, UCF, AdventHealth Winter Park, Downtown Orlando, and more. At $460,000 in 32789, this one won't last.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Caroline Fiore (407-538-2381)

Remarks: One or more photo(s) has been 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: This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home’s refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef’s kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home’s commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park’s most sought-after neighborhoods.

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

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

Remarks: Under contract-accepting backup offers. Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new windows (2019) a renovated primary bedroom and bath (2019), new septic drainfield (2023), tankless water heater (2019), new refrigerator (2024) and in ground pool converted to saltwater in 2023. A rare opportunity to own a classic Winter Park home in beautiful condition with modern improvements and exceptional outdoor living. Walk to Hunger Street Tacos, Lombardi’s Seafood and Creative Jane Art Studio while being conveniently located near 1-4, College Park and Winter Park. Come see this gem!

Listing is courtesy of: ANNE ROGERS REALTY GROUP INC (407-649-4141)

Listing Agent: Arden Magee (407-276-1698)

Remarks: Under contract-accepting backup offers. Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

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

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

Remarks: Charming 3-bedroom, 2-bath home in the heart of desirable Winter Park. Bright and inviting layout with comfortable living spaces and plenty of natural light. Enjoy a private backyard perfect for relaxing or enteraining. Conveniently located near shopping and dinning.

Listing is courtesy of: INT'L PROFESSIONAL REALTY INC (407-699-7718)

Listing Agent: Lorena Ortega (407-256-3631)

Remarks: This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

Listing is courtesy of: PRIMESTATE REALTY, INC. (407-850-9494)

Listing Agent: Hoover Yap (407-342-9395)

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 of Winter Park close to tons of and amenities. Currently being rented for $1550/month

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

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

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)