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$674,900
3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code
**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true new construction quality in an established neighborhood. Located steps from Winter Park Village, Park Avenue, Whole Foods, Starbucks, Publix, cinema, restaurants, and more. Arrive home to a grand 51' custom driveway flanked by mature Italian cypress trees, sculptural landscaping, and elegant iron railing — pulling directly to your covered front porch entry. No garage means no wasted space — just a clean, architectural arrival experience designed to impress. Inside, light-filled interiors with soaring 6" baseboards, full custom tile flooring, and an abundance of natural light create a gallery-like aesthetic that feels curated, not cookie-cutter. Custom liner windows in the dining room and primary suite flood the home with natural light while adding unmistakable architectural character. **The Kitchen:** - Designer floating shelves - Smart range and under-counter built-in microwave - Under-cabinet and island LED lighting - Decorative pendants and ambient lighting throughout **The Primary Suite:** A private retreat with ceiling-mounted rain shower and spa-like finishes designed to decompress after a walkable night out on Park Avenue. **Smart Home Ready:** - New AC system (inside and out) with smart thermostat - Tankless water heater and fully new plumbing - Smart lock entry - Google Nest doorbell with two-way audio - Smart soffit exterior lighting - Weather-monitored smart irrigation **Out Back:** A fully private PVC-fenced backyard sanctuary — spacious enough for pets, entertaining, and room to roam. A covered porcelain tile patio plus a separate fire pit slab make this an outdoor living extension you'll actually use year-round in the Florida lifestyle. Over 300 sq ft of additional space was added to accommodate two additional bathrooms, interior laundry, and a layout built for real life — including a new stacked washer and dryer. Properties combining true gut-renovation quality, luxury designer touches, smart technology, and this rare walkable Winter Park address don't last. Move-in ready — and built to last for decades.

860 N Denning Drive, Winter Park
$624,444
3 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the highly sought-after Winter Park 32789 zip code, just moments from scenic Lake Killarney. Situated on an oversized 0.27-acre lot with no HOA, this exceptional property offers endless possibilities, including ample space to add a pool, guest house/ADU, or create the custom outdoor living space of your dreams. Full of charm and warmth, the home features bright and spacious living areas designed for both everyday comfort and entertaining, highlighted by a cozy wood-burning fireplace. The recently renovated kitchen showcases updated cabinetry, new countertops, newer appliances, and stylish tile flooring throughout the entire first floor. The kitchen flows seamlessly into the breakfast area overlooking the expansive fenced backyard, creating the perfect indoor-outdoor lifestyle. Upstairs, you’ll find wood flooring throughout the staircase and second floor, along with three light-filled bedrooms, two full bathrooms, and a versatile flex space ideal for a home office, playroom, or study area. Additional upgrades include a renovated downstairs half bath, updated secondary bathroom, professionally cleaned and sanitized AC ducts, new ceiling fans in all bedrooms, a newly installed garage door, a new garage roof, new irrigation system and a main roof replacement completed in 2018. Relax on the inviting front porch swing and enjoy peaceful lake breezes with your morning coffee or evening glass of wine. Ideally located near Park Avenue, Winter Park Village, premier dining, shopping, entertainment, and major highways with easy access to Downtown Winter Park and Orlando. Move-in ready and filled with modern updates, timeless character, and unbeatable potential, this property also presents an incredible opportunity to live in while your custom dream home is being built.

2418 Euston Road, Winter Park
$3,150,000
3 Beds ⋅ 5 Baths ⋅ South Interlachen Place SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to South Interlachen Place, an exceptional luxury townhome ideally positioned in the heart of downtown Winter Park. Just steps from Park Avenue, this sophisticated residence offers an unparalleled lifestyle defined by elegance, convenience, and access to the area’s finest dining, shopping, and cultural experiences. Thoughtfully designed with 3 bedrooms, 3 full bathrooms, and 2 half baths, this nearly brand-new residence is filled with natural light and refined architectural details throughout. Extensive upgrades include new roof, new exterior doors, new windows, new HVAC systems, new tankless water heater, new private elevator, and more—all with included warranties for added peace of mind and long-term value. A private front patio and double glass entry doors set the tone for the home’s elevated design. Inside, expansive floor-to-ceiling windows, an interior atrium, and skylights create a bright, airy ambiance throughout the main living spaces. The open-concept living and dining areas are ideal for both intimate gatherings and grand entertaining. At the heart of the home, the chef’s kitchen is a true statement of style and function, appointed with premium appliances including a Wolf gas cooktop and Sub-Zero refrigerator. A stunning quartz waterfall island anchors the space, while a dedicated bar and coffee station—complete with a Sub-Zero wine refrigerator and dual beverage drawers—adds a layer of sophistication for effortless entertaining. The second level is a private sanctuary, dedicated to the luxurious primary suite. The spa-inspired bath features dual vanities, a freestanding soaking tub, and an expansive walk-in shower, complemented by a generous custom closet. A refined loft with built-in cabinetry offers a flexible space for a home office or lounge, enhanced by a mini built-in Sub-Zero refrigerator for added comfort and convenience. On the third level, two well-appointed guest suites each feature en-suite baths, with one offering access to a serene open-air atrium—bringing a unique architectural element and tranquil outdoor connection into the home. Seamlessly blending luxury and functionality, the residence is equipped with Lutron lighting and a new private interior elevator providing effortless access from the secure garage to every level, including the rooftop. The crown jewel of this home is the private rooftop terrace, an extraordinary urban retreat designed for elevated living. Complete with a full outdoor kitchen, BBQ, beverage refrigerator, half bath, and fireplace, this space offers multiple lounge and dining areas—perfect for entertaining under the stars or enjoying quiet evenings above the city. Additional features include a secure private garage with storage, guest parking, and the added benefit of a concierge service included in the HOA fee, enhancing convenience and elevating the overall lifestyle experience. This is a rare opportunity to own a truly exceptional, move-in-ready luxury townhome in one of Winter Park’s most coveted locations—where design, quality, and lifestyle converge.

125 S Interlachen Avenue Unit 2, Winter Park
$710,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to Park West Condominiums — one of Winter Park’s most coveted and rarely available condominium communities, ideally located just one block from the boutiques, dining, and charm of Park Avenue. This unique 4th floor residence offers an exceptional combination of space, privacy, and potential. Featuring 3 bedrooms and 2 bathrooms, the expansive floor plan has been enlarged by enclosing two patios, creating generous living spaces rarely found in condominium living. Vaulted ceilings, skylights, and abundant natural light enhance the open, airy feel throughout the home, while the top-floor location provides remarkable tranquility and privacy. The spacious kitchen offers ample counter space, a breakfast bar, and excellent cabinet space, while the living area is anchored by a fireplace — another uncommon feature in condo living. Large bedrooms, a sizable in-unit laundry room with extensive storage, and an oversized attic provide an extraordinary amount of storage seldom seen in comparable properties. The primary suite features vaulted ceilings, a walk-in closet, and a spacious bathroom layout. For maximum flexibility, the second bedroom, featuring a bright Sun Room alcove, connects to the primary bedroom so it could also be utilized as a private den. Recent unit improvements include a NEW HVAC system, a NEW Water Heater, and Plumbing updates. A reserved covered parking space is included, along with plentiful guest parking for visitors. Residents of Park West enjoy a secure gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements completed. Association fees include water, sewer, and trash service, creating a truly low-maintenance “lock-and-leave” lifestyle ideal for travelers or seasonal residents. While this condo presents an exciting opportunity for personalization, the location, floor plan, and features make this an exceptional offering with tremendous potential. Opportunities in Park West are exceedingly rare — this is your chance to create something truly special in the heart of Winter Park.

300 Carolina Avenue Unit 402C, Winter Park
$989,500
1 Beds ⋅ 2 Baths ⋅ Village Winterset Inc SubDv. ⋅ 32789 Zip Code
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.

269 E Canton Avenue Unit 269, Winter Park
$2,500,000
5 Beds ⋅ 6 Baths ⋅ Osceola Shores Sec 03 SubDv. ⋅ 32789 Zip Code
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within walking distance of the world-class dining and boutiques of Park Avenue, views of Lake Osceola with easy lake access, with a coveted Winter Park location and top notch schools. This 5-bedroom, 4-full and 2-half-bath pool home residence offers an enviable blend of timeless architecture and modern refinement. The interior has been updated and maintained to the highest standards. The home’s open-concept floor plan is anchored by rich, newer solid wood flooring and elegant plantation shutters throughout. At the heart of the home, the chef’s kitchen is a culinary masterpiece featuring, pristine quartz countertops, high-end stainless steel Bosch appliances, natural gas range, double ovens, and a walk-in pantry. A sophisticated entertainer’s bar area off the kitchen is equipped with a 100+ bottle dual-zone wine cooler, beverage cooler, ice maker, and service sink. This area is open to the kitchen an living areas for easy entertaining or catering. The newly reimagined primary retreat is a spa-like sanctuary, showcasing white marble tile, a frameless glass shower with dual rainfall heads, a deep garden soaking tub, double vanity areas with new quartz counter tops, new mirrors and lighting and a bespoke walk-in closet. The primary walk in closet was just updated with a top of the line shelving and storage system for easy organization. The home's floor plan is thoughtfully designed for flexibility, featuring a second primary suite on the main level. Back upstairs, you will find three additional guest bedrooms and two additional full bathrooms, a versatile bonus/flex room over the garage and a private balcony offering serene lake views. The bonus room has endless possibilities and can be used as a recreation room, movie theatre, exercise room, play room, or in-law/nanny quarters as the second back staircase could be a private entry. Outdoor Oasis & Infrastructure Designed for seamless indoor-outdoor living, the rear grounds feature a covered lanai over looking the pool. The covered lanai offers a living and dining area, a newly built-in outdoor kitchen with a professional grill, and a paver-lined patio surrounding a sparkling pool and gas fire pit gazebo sitting area on the other side of pool area. Plenty of yard space to throw the football, practice soccer skills or throw the frisbee with fido!! Exceptional Features Include: Mechanical Integrity: Roof replaced in 2020; updated A/C systems (2016/2019); Rinnai tankless natural gas water heater, brand new primary bathroom, all bathrooms have been refreshed, recently updated kitchen, newer solid wood floors throughout. Storage & Utility: 3-car garage with extended bays for extra storage, oversized closets throughout, and two convenient staircases. Cozy Accents: 2 fireplaces with one being wood-burning and one gas. Three distinct breakfast/dining areas within the kitchen plus formal dining. This is more than a home; it is an invitation to the quintessential Winter Park lifestyle you have been dreaming of living!

450 Lakewood Drive, Winter Park
$1,525,000
4 Beds ⋅ 2 Baths ⋅ Virginia Heights Rep SubDv. ⋅ 32789 Zip Code
A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park
$529,000
3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code
In the sought-after Orwin Manor neighborhood, this beautifully updated one-story residence offers a seamless blend of comfort, style and convenience. Featuring three bedrooms and two baths, the home showcases an open-concept floor plan enhanced by engineered wood flooring that extends throughout every room, creating a cohesive and inviting living environment. The kitchen is thoughtfully updated with quartz countertops, refreshed cabinetry, newer appliances and a charming breakfast nook, ideal for casual dining. The living spaces flow effortlessly to a wonderful enclosed porch, providing additional year-round enjoyment, with direct access to an open brick-paver patio complete with a firepit, all set in a fully fenced backyard ideal for entertaining or relaxing in privacy. Both baths have been tastefully updated, and a new roof installed in 2021 that adds to the home’s overall appeal and peace of mind. Ideally just minutes from vibrant shopping and dining of downtown Winter Park and College Park, with convenient access to major roadways and the AdventHealth Orlando campus, this home offers exceptional accessibility to all metro Orlando has to offer. Whether as a primary residence or an investment opportunity, this property presents an exceptional offering in a prime, established location.

1741 Westchester Avenue, Winter Park
$3,995,000
4 Beds ⋅ 6 Baths ⋅ Winflor Court Pt Rep SubDv. ⋅ 32789 Zip Code
Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious gourmet kitchen overlooks the main living areas and pool, and is equipped with premium Wolf appliances and a separate chef’s kitchen for added convenience. Enjoy seamless indoor-outdoor living with a covered lanai featuring motorized screens, heaters, and a mosquito misting system. The outdoor space also includes a summer kitchen, gas fire pit, and a pool equipped with a swim jet system that creates a continuous current, effectively transforming it into an endless lap pool. A detached fitness studio with a steam shower provides a private wellness retreat. Additional highlights include custom built-ins, engineered hardwood floors and surround sound throughout. The oversized two-car garage offers epoxy flooring, custom storage, and a dog wash station. Irrigation is supplied by a private well, and the home also features underground utilities and a full security system. The exterior is designed for both beauty and low maintenance, with manicured landscaping and artificial turf that stays lush year-round. With no HOA, added privacy, and exceptional attention to detail throughout, this home offers a rare opportunity to experience luxury living at its finest. This home is conveniently located near the Enzian Theater and less than a mile from Winter Park Village, with top-rated schools nearby, this home combines comfort, style and an unbeatable location. Schedule your private showing today.

1441 Cardinal Court, Winter Park
$1,350,000
3 Beds ⋅ 2 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier. Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy, nature, and long-term value. Located in one of Winter Park’s most established areas, just minutes from Park Avenue, top-rated schools, and everyday conveniences, this is a unique canvas for those looking to create something truly exceptional. No HOA. No CDD.

1881 Lake Spier Drive, Winter Park
$1,649,000
4 Beds ⋅ 4 Baths ⋅ Twin Acres SubDv. ⋅ 32789 Zip Code
Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home features floor-to-ceiling glass, a wraparound terrace, and a bold two-story façade. The quartz river rock and concrete drive leads to dual frosted glass garage doors, pre-wired for an EV charger. Inside, a dramatic floating staircase is framed by a 17’ window, anchoring the open-concept living space with views of the private backyard. The modern kitchen includes light gray touch-open cabinetry, soft-close drawers, black stainless appliances, and a Calacatta quartz waterfall island. The outdoor space is designed for entertaining, with a covered lanai, expansive marble terrace, and a mini-pebble pool with sun shelf and water features. Lush podocarpus hedging and a masonry wall provide privacy. The first floor offers a dedicated office and full pool bath. Upstairs features four bedrooms with Italian frameless doors and three European-inspired bathrooms. The primary suite includes a custom walk-in closet and private access to the wraparound terrace overlooking the pool. Surrounded by beautiful tree-lined streets ideal for strolling and golf-cart rides to nearby shops, restaurants, and friends’ homes, this property offers the best of the Winter Park lifestyle. The home is also zoned for top-rated Winter Park schools. A rare modern home in one of Winter Park’s most desirable locations. Call today for your private showing.

1903 N Park Avenue, Winter Park
$3,275,000
4 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code
Looking for a home with character, sophistication, and a design that feels completely unique? This Winter Park residence delivers a truly custom home build with nearly all of the living space on one level. Completely rebuilt in 2018 by Posada Homes, a member of the Master Custom Builders Council, the home sits on a rare 0.39 acres lot along a picturesque, tree-lined street within walking distance to Park Avenue. Beyond the beautifully manicured grounds, expansive windows fill the interiors with natural light, highlighting hardwood floors, intricate millwork, and crisp architectural lines. Each space reveals thoughtful details, from the hidden wine room just off the foyer to the custom built-ins and gas fireplace that lend warmth to the family room. The kitchen brings together custom cabinetry, quartz countertops, premium Thermador appliances, and a generous center island. Open to the expansive great room, it creates a natural gathering place for everything from quiet mornings to lively evenings with friends. High ceilings and designer lighting complement the architecture while keeping the atmosphere inviting. Privately positioned off the family room, the primary suite offers room to truly unwind, with a sitting area, private coffee bar, and a spacious bath featuring dual vanities, a soaking tub, and an oversized walk-in shower. A second main-level primary suite adds flexibility for hosting overnight guests or accommodating multigenerational living. Upstairs, a private office, half bath, and bonus room provide dedicated space for work, media, or recreation. Outside, a covered lanai overlooks the sparkling pool and expansive grounds, extending the home’s gathering spaces into a peaceful outdoor setting. A detached, 252-square-foot studio, currently used as a gym, offers additional space for fitness, creative pursuits, or a private escape. Park Avenue’s boutiques, restaurants, and cafés are within walking distance, with Rollins College and the Winter Park Chain of Lakes close by. Here, custom craftsmanship, a predominantly single-level layout, and a coveted Winter Park setting come together in a home designed to be enjoyed every day. For buyers who envision a lighter interior palette, the seller is open to providing a credit toward flooring updates and coordinating installation, an opportunity to personalize the home’s aesthetic with added convenience.

1581 Forest Avenue, Winter Park
$1,595,000
3 Beds ⋅ 2 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code
Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue’s renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted “Vias” of Winter Park, a collection of streets long regarded as one of the city’s most established and desirable residential enclaves. The existing residence is perfectly livable and has benefited from numerous upgrades, offering flexibility for immediate occupancy while planning a future custom build. The home also presents excellent rental potential. Please note the interior is currently being utilized for storage and does not reflect its full presentation potential, providing an opportunity for cosmetic refresh or personalization. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end¦users alike — a rare chance to secure one of Winter Park’s most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park
$680,000
4 Beds ⋅ 4 Baths ⋅ Swoope Park SubDv. ⋅ 32789 Zip Code
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.

432 W Swoope Avenue, Winter Park
$299,999
2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix, Trader Joe's, Regal Movie Theater, and a variety of restaurants and bars. Join this vibrant community and make this beautiful condo your new investment property or dream home!

151 N Orlando Avenue Unit 118, Winter Park