Winter Park, FL Real Estate Search

Winter Park, FL Properties between $4,000,000 and $5,000,000 for Sale

Our website features the best real estate search for between $4,000,000 and $5,000,000 properties available in Winter Park, FL and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Winter Park, FL Properties between $4,000,000 and $5,000,000 for Sale

1631 Hillcrest Avenue, Winter Park
$4,500,000
5 Beds ⋅ 6 Baths ⋅ Ellno Willo SubDv. ⋅ 32789 Zip Code
Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, abundant natural light, and premium finishes throughout. Every bedroom features its own en-suite bath. Resort-style pool and putting green anchor the outdoor living space, perfect for Florida's year-round lifestyle. Detached garage offers flexible storage, workshop space, plus room for a private home gym. Minutes from Park Avenue's shops, dining, and top-rated schools. Top quality construction and unbeatable location. Schedule your private showing today.

1631 Hillcrest Avenue, Winter Park
617 N Interlachen Avenue, Winter Park
$4,695,000
11 Beds ⋅ 8 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code
Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision. From the moment you arrive, the classic Spanish Revival influence and established setting offer a sense of history and individuality rarely found in newer construction. The multiple buildings create exciting possibilities for guest accommodations, private home offices, studios, hobby spaces, entertaining areas, or other uses permitted by applicable zoning and regulations. The residence offers an opportunity to preserve its distinctive architectural character while updating and personalizing the interiors and amenities for today's lifestyle. For buyers who appreciate homes with a story, architectural distinction, and the potential to make a property uniquely their own, this estate stands apart from the typical Winter Park offering. Even more compelling is the location. The property is within walking distance of Winter Park's famous Park Avenue, renowned for its restaurants, boutiques, cafes, galleries, cultural attractions, and unmistakable charm. Enjoy the rare opportunity to leave the car at home and stroll to one of Central Florida's most celebrated dining, shopping, and entertainment destinations. Rollins College is also nearby, while convenient access to downtown Orlando combines the charm and sophistication of Winter Park with easy connectivity to the greater Orlando area. The property is not individually listed on the Winter Park Register of Historic Places and is not located within a locally designated historic district, an important consideration for buyers exploring future renovation and personalization plans. Buyers should independently verify applicable zoning, permitting, building, and preservation requirements for any intended improvements or uses. With its James Gamble Rogers II design, 1929 origins, Spanish Revival character, approximately half-acre setting, substantial combined square footage, three accessory buildings, and an outstanding location within walking distance of famous Park Avenue, 617 N Interlachen Ave is far more than a conventional home purchase. It is an opportunity to take a distinctive piece of Winter Park architecture and shape its next chapter. Bring your vision and discover the possibilities where history, architecture, location, and potential come together in a truly one-of-a-kind Winter Park estate.

617 N Interlachen Avenue, Winter Park
702 Via Bella, Winter Park
$4,250,000
4 Beds ⋅ 6 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code
Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmanship to one of Winter Park’s coveted residential corridors. Encompassing 3,720 square feet, the four-bedroom, five-and-one-half-bath home blends sophisticated interiors with contemporary systems and inviting spaces designed for both everyday living and entertaining. "OPTION TO PURCHASE HOME TURN-KEY": Owner has just finished a ~ $500,000 complete furnishings install thru Brianna Michelle Interior Design! A solid mahogany front door opens to interiors defined by Botticino limestone flooring with a distinctive textured finish, bespoke millwork, and generous gathering spaces. Coffered ceilings and recessed WAC lighting add architectural dimension, while insulated casement windows fill the home with natural light. The expansive central living area flows seamlessly into the dining space and beautifully appointed kitchen, featuring custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite countertops, and a remarkable collection of professional-grade appliances, including a 43-inch La Cornue gas range with McGurken hood, Thermador refrigerator and freezer columns, and Bosch dishwasher. A generously sized walk-in pantry continues the custom cabinetry and quartzite finishes while incorporating dual refrigeration drawers and a dedicated ice maker. The adjacent mudroom is outfitted with substantial hardwood built-ins, providing exceptional organization and storage. The first-floor primary suite occupies a private wing and showcases wide-plank European white oak flooring by Forrest Accents, a customized walk-in closet, and an elegant spa-inspired bath. Natural stone countertops, Rohl polished nickel fixtures, marble flooring and shower surfaces, and a frameless glass enclosure create a polished yet inviting retreat. Throughout the home, solid-core doors are complemented by Emtek hardware. Positioned near the front entry, the library offers a sophisticated setting for work or quiet reflection, with matching oak flooring and custom casement windows. A solid wood staircase ascends to a second living area with an adjoining lounge or flex space. Three additional bedroom suites provide private accommodations, each with en-suite baths featuring porcelain flooring, frameless glass showers, brushed quartz and dolomite vanities, designer lighting, and integrated closet systems. Modern infrastructure includes CAT-5/6 wiring, Sonos-integrated speakers, Lutron RA-3 smart lighting controls, and pre-wiring for home security with digital camera ports strategically located at key entry points. Multiple access points from the primary suite and kitchen wing extend to a beautifully enclosed outdoor environment framed by mature landscaping designed by Signature Landscape. A Roman-inspired cabana with soaring ceilings and exposed beams serves as the centerpiece for outdoor entertaining. The fully tiled saltwater pool, representing a $50,000 upgrade, features therapy jets, LED-lit bubblers, a dual-skimmer system, Jandy heat-pump automation, and a Paramount self-cleaning system. Minutes to vibrant shopping, restaurants, sidewalk cafes of Park Avenue, and all that downtown Winter Park has to offer.

702 Via Bella, Winter Park
2403 Euston Road, Winter Park
$4,299,000
Justamere Camp Rep SubDv. ⋅ 32789 Zip Code
Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres across two combined lots (2401 & 2403 Euston Ave), you'll have the space—and the freedom—to design an architectural masterpiece or a serene retreat that blends seamlessly with the natural beauty of this exclusive setting. Lake Killarney is a hidden 234-acre gem, beloved for its tranquility, paddleboarding and watersports, abundant wildlife, and lakeside dining. Locals savor moments like scenic seaplane lunches at Hillstone and cozy evenings around fire pits under starlit skies. With no public access, the lake offers unmatched privacy, and its pristine waters are maintained year-round by a thoughtful system of two drainage wells. Just minutes away, enjoy the vibrant lifestyle Winter Park is known for—Rollins College, Park Avenue, Winter Park Village, Whole Foods, the Farmers Market, and a rich cultural scene are all at your fingertips. Whether you’re dreaming of a peaceful sanctuary or a showstopping entertainer’s paradise, this property offers the ultimate trifecta: land, luxury, and lifestyle.

2403 Euston Road, Winter Park
857 Brock Street, Winter Park
$4,350,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured grounds, dual porte cochere’s, and a motor court leading to a two-car garage. Every element has been thoughtfully considered to create a residence that feels as though it has always belonged in Winter Park. Inside, exceptional craftsmanship takes center stage. A marble mosaic entry introduces interiors defined by chevron-pattern hardwood flooring, refined millwork, natural stone, and carefully curated finishes. The floor plan is equally impressive, balancing grand entertaining spaces with an effortless sense of livability. The main level features a dedicated library/home office, formal dining room, and expansive gathering room overlooking the private courtyard. At the heart of the home, the chef’s kitchen pairs Calacatta marble countertops with a full suite of Thermador appliances, a statement ILVE range, and an oversized butler’s pantry offering exceptional prep and storage space. The first-floor primary suite is a private retreat with direct access to the courtyard and an incredible spa-inspired bath finished in marble. Dual vanities, Perrin & Rowe fixtures, a freestanding soaking tub, walk-in shower, and an expansive dressing room elevate the suite to another level. Upstairs, four generously proportioned bedrooms each feature an ensuite bath and walk-in closet, surrounding a spacious central loft ideal for an additional living or entertaining space. Continuing to the third level, a fully finished attic space provides an unexpected bonus room perfectly suited for a private gym or a game room. The outdoor living experience is just as remarkable. At the center of the home is a spectacular courtyard-style pool, creating a private resort atmosphere framed by the residence and lush landscaping. An expansive covered cabana provides multiple areas for dining and lounging, complemented by a fireplace and full summer kitchen for year-round entertaining. Beyond the courtyard, ample yard space adds another layer of usability rarely found with such an intimate outdoor design. This home also offers the rare opportunity to enjoy one of Winter Park’s most desirable residential settings while remaining within walking distance of the boutiques, acclaimed restaurants, cafés, and vibrant atmosphere of Park Avenue. Hannibal Square and Winter Park Village are also just moments away, placing some of the city’s best dining, shopping, and entertainment within effortless reach. Timeless in its architecture and uncompromising in its execution, this home is destined to become one of Winter Park’s most distinguished residences. Renderings are artistic interpretations. Features and finishes may vary from final construction.

857 Brock Street, Winter Park
231 Chelton Circle, Winter Park
$4,700,000
4 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury living. Showcasing his signature aesthetic, the home emphasizes sleek architectural lines, refined finishes, and a seamless connection between indoor and outdoor spaces. Expansive walls of glass flood the interior with natural light and create a striking façade that embodies its contemporary elegance. The main living areas are designed for both entertaining and everyday living. A dramatic two-story living room is anchored by designer furnishings, which extend throughout the home, while the spacious dining area comfortably accommodates large gatherings. The adjacent family room continues the modern aesthetic with a built-in media wall, sleek fireplace, textured design elements, and a triple sliding door connecting the indoor and outdoor spaces. Ready for any caliber of chef, the kitchen boasts Thermador appliances, along with extensive cabinetry and countertop space, soft-close drawers, a waterfall edge island, generously sized pantry, and reverse osmosis water filtration. A private home theater on the main level offers a true cinematic experience with surround sound, custom seating, and blackout shades, along with a stylish wet bar, providing additional space for entertaining. The home’s Crestron automation system is discreetly integrated, allowing full control of lighting, climate, and technology from a single interface. Upstairs, a striking floating staircase leads to a gallery-style landing overlooking the living space below. For those exhausting days, you can instead take a ride on the elevator. The expansive primary suite features a sitting area, a custom closet, and terrace access. The spa-inspired primary bath includes dual rain showers with body sprays, a soaking tub, and dual vanities with elegant finishes. Additional second-floor amenities include a fitness room with steam shower and sauna, an additional en-suite bedroom, one of the two laundry rooms, and access to an upper-level terrace overlooking the landscaped grounds and pool. Two en-suite guest bedrooms are conveniently tucked away on the first floor for maximum privacy. Offering four bedrooms, five full bathrooms, and two half baths, the home delivers both comfort and sophistication at every turn. Thoughtfully integrated automated shades provide effortless privacy, while the advanced air purification systems and whole-home water softener complement the home's advanced smart features. This residence is offered fully furnished with curated Restoration Hardware pieces, including custom-selected furniture, lighting, rugs, and artwork that enhance its cohesive design. Outdoor living is equally impressive, with covered lanai spaces enhanced by automated roll-down screens, designer furnishings, a summer kitchen with gas grill and ventilation, and tranquil poolside views. The property also includes a split, three-car garage with a large driveway protected by a gated entrance. Completing this extraordinary dwelling is its location in the heart of Winter Park. This lakeside residence sits minutes from Park Ave Shopping, Rollins College, AdventHealth, multiple Botanical Gardens and Museums, well-rated grade schools, and highway access. Schedule your private showing today and experience the Winter Park lifestyle firsthand.

231 Chelton Circle, Winter Park
503 N Interlachen Avenue, Winter Park
$4,500,000
Winter Park SubDv. ⋅ 32789 Zip Code
RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses. Future residents will enjoy picturesque walks along Winter Park's famous brick streets just off the shores of the chain of lakes. Nearby attractions like the Winter Park Farmer's Market, the Winter Park Golf Course, a highly rated 9-hole gem in the center of town, Casa Feliz, Central Park, and more are all within just a few minutes stroll.

503 N Interlachen Avenue, Winter Park
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