Homes for Sale in Winter Park, FL with 5-Bedrooms

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  $4,199,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,891 Sq Ft

  1417 Williams Dr, Winter Park, FL 32789

  Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1417 Williams Dr, Winter Park, FL 32789
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  $3,590,000 New Construction

  • 5 Beds
  • 7 Baths
  • 4,520 Sq Ft

  1751 Glencoe Rd, Winter Park, FL 32789

  Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed Davila Homes masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication.

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1751 Glencoe Rd, Winter Park, FL 32789
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  $6,895,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  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

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
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  $4,995,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  $1,634,900 Open Sat 1PM - 4PM

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  1510 Miller Ave, Winter Park, FL 32789

  New Construction – JUST COMPLETED! Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1510 Miller Ave, Winter Park, FL 32789
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  $3,650,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  $1,499,000 New Construction

  • 5 Beds
  • 4 Baths
  • 2,895 Sq Ft

  1473 Berkshire Ave, Winter Park, FL 32789

  Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue -- a newly completed residence on a peaceful, tree-lined street. This two-story home offers 5 bedrooms, 4 bathrooms, and nearly 2,900 sq ft of living space. Features include 10-ft ceilings, 8-ft solid-core doors,

  Crystal Canina Golden Group Realty LLC

  1473 Berkshire Ave, Winter Park, FL 32789
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  $3,135,000 Open Sat 2PM - 4PM

  • 5 Beds
  • 5.5 Baths
  • 3,863 Sq Ft

  1821 Englewood Rd, Winter Park, FL 32789

  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

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1821 Englewood Rd, Winter Park, FL 32789
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  $4,950,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 6,406 Sq Ft

  1660 Palmer Ave, Winter Park, FL 32789

  New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
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  $1,195,000

  • 5 Beds
  • 3.5 Baths
  • 3,490 Sq Ft

  2035 Lake Sue Dr, Orlando, FL 32803

  Welcome to Lake Sue Drive – A Rare Gem located in Beeman Park right in the heart of the Audubon Park Garden District. Situated on an oversized 0.49 lot (21,148 sf), this property has been owned by the same family for over 80 years. This charming home offers 4 bedrooms and 2.5 bathrooms in the main residence, along with a detached guest house (704 sq ft) complete with a full kitchen and

  Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2035 Lake Sue Dr, Orlando, FL 32803
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  $2,740,000

  • 6 Beds
  • 5 Baths
  • 4,001 Sq Ft

  1411 Nottingham St, Orlando, FL 32803

  This one-of-a-kind, top-tier custom contemporary home in coveted Beverly Shores/Rose Isle delivers true turnkey luxury with exceptional finishes, premium cabinetry, high-end appliances, and fully integrated smart features throughout. The six-bedroom, three-and-a-half-bath main home—featuring one bedroom currently used as a private office—plus a detached 384 SF casita (seventh bedroom) sits on a

  Gwyn Clark FANNIE HILLMAN & ASSOCIATES

  1411 Nottingham St, Orlando, FL 32803

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