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Newest Winter Park Real Estate Listings

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Newest Winter Park Real Estate Listings

1830 Gladiolas Drive, Winter Park image
1830 Gladiolas Drive, Winter Park $375,000

Welcome to 1830 Gladiolas Drive, a beautiful 3 bedroom, 2 bathroom home in Winter Park’s Garden Lake Estates community. This move-in ready home features a 2023 AC, a 2022...

  • 3 Beds
  • 2 Baths
  • Garden Lake Estates Unit 1 SubDv.
  • 32792 Zip Code
1021 Princess Gate Boulevard, Winter Park image
1021 Princess Gate Boulevard, Winter Park $410,000

Welcome to this 3-bedroom, 2-bath pool home in the established Howell Estates neighborhood of Winter Park! Situated on a spacious 0.31-acre lot, this single-story residen...

  • 3 Beds
  • 2 Baths
  • Howell Estates Rep SubDv.
  • 32792 Zip Code
7463 Canford Court Unit 15, Winter Park image
7463 Canford Court Unit 15, Winter Park — Whisperwood Condo $270,000

Welcome to this beautifully updated corner home in the Whisperwood community of Winter Park! Featuring 3 bedrooms and 2.5 bathrooms, this property offers an open-concept ...

  • 3 Beds
  • 3 Baths
  • Whisperwood Condo SubDv.
  • 32792 Zip Code
1940 Magnolia Avenue, Winter Park image
1940 Magnolia Avenue, Winter Park $1,190,000

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This s...

  • 4 Beds
  • 4 Baths
  • Temple Terrace Annex SubDv.
  • 32792 Zip Code
1401 Pelham Road, Winter Park image
1401 Pelham Road, Winter Park $650,000

Welcome home to this charming 1940's bungalow in Orwin Manor, one of Winter Park’s most sought-after neighborhoods. The single-story home has 3 bedrooms, 2 full baths and...

  • 3 Beds
  • 2 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
1200 Via Salerno, Winter Park image
1200 Via Salerno, Winter Park $5,995,000

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live...

  • 5 Beds
  • 6 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
1735 Demetree Drive, Winter Park image
1735 Demetree Drive, Winter Park $1,050,000

Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of estab...

  • 4 Beds
  • 3 Baths
  • Waterbridge SubDv.
  • 32789 Zip Code
603 Carnation Drive, Winter Park image
603 Carnation Drive, Winter Park $419,900

Welcome to 603 Carnation Dr in Winter Park! This 4-bedroom, 2-bathroom home offers 1,427 square feet of living space with an updated kitchen and inviting living and dinin...

  • 4 Beds
  • 2 Baths
  • Eastbrook Sub SubDv.
  • 32792 Zip Code
506 Lander Road, Winter Park image
506 Lander Road, Winter Park $450,000

Investor or renovation opportunity in the Winter Park High school district! This solid block home features a great location for the buyer with vision. Opportunity await...

  • 3 Beds
  • 2 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
2330 Westminster Ct., Winter Park image
2330 Westminster Ct., Winter Park $985,000

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigne...

  • 5 Beds
  • 3 Baths
  • Glencoe Sub SubDv.
  • 32789 Zip Code
1030 Bonita Drive, Winter Park image
1030 Bonita Drive, Winter Park $1,100,000

Exceptional opportunity to build on beautiful Bonita Drive, one of Winter Park’s most picturesque brick-lined streets, with this 0.18-acre (approximately 8,014-square-foo...

  • Comstock Park SubDv.
  • 32789 Zip Code
624 Dunraven Drive, Winter Park image
624 Dunraven Drive, Winter Park $620,000

Welcome to this charming Winter Park home, featuring classic terrazzo floors and wonderful natural light. This home boasts a cozy wood-burning fireplace that serves as a...

  • 3 Beds
  • 2 Baths
  • Kenilworth Shores Sec 05 SubDv.
  • 32792 Zip Code
808 Densmore Drive, Winter Park image
808 Densmore Drive, Winter Park $509,999

Welcome to 808 Densmore Drive, a beautifully updated 3-bedroom, 2-bathroom pool home tucked into the established Winter Park Estates neighborhood! Blending modern farmhou...

  • 3 Beds
  • 2 Baths
  • Winter Park Estates SubDv.
  • 32792 Zip Code
1884 Jessica Court, Winter Park image
1884 Jessica Court, Winter Park $699,900

Enjoy bright, inviting living and your own screened pool retreat in Winter Park! This 3-bedroom, 2-bath home offers 1,666 square feet with vaulted ceilings, abundant natu...

  • 3 Beds
  • 2 Baths
  • Waterbridge SubDv.
  • 32789 Zip Code
1631 Hillcrest Avenue, Winter Park image
1631 Hillcrest Avenue, Winter Park $4,500,000

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, ab...

  • 5 Beds
  • 6 Baths
  • Ellno Willo SubDv.
  • 32789 Zip Code
4832 Tangerine Avenue Unit 4832, Winter Park image
4832 Tangerine Avenue Unit 4832, Winter Park — 4832 Tangerine Ave $188,800

Welcome to comfortable living in desirable East Winter Park. This beautifully maintained condominium offers a spacious and inviting floor plan in a quiet, established com...

  • 2 Beds
  • 2 Baths
  • Wrenwood Condo SubDv.
  • 32792 Zip Code
1825 Whitehall Drive, Winter Park image
1825 Whitehall Drive, Winter Park $3,195,000

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed natural stone, a stately brick entry, and striking black-framed windows define its European-ins...

  • 4 Beds
  • 6 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
4786 Tangerine Avenue Unit 4786, Winter Park image
4786 Tangerine Avenue Unit 4786, Winter Park — 4786 $220,000

Discover comfort, style, and convenience in the heart of Winter Park! This beautifully updated 2-bedroom, 1.5-bathroom, two-story condominium offers approximately 1,281 s...

  • 2 Beds
  • 2 Baths
  • Wrenwood Condo SubDv.
  • 32792 Zip Code
239 Orange Terrace Drive, Winter Park image
239 Orange Terrace Drive, Winter Park $450,000

Welcome to 239 Orange Terrace Drive! This charming 4 bedroom, 2.5 bath home offers 1,866 square feet of living space in a convenient Winter Park location. Situated on a s...

  • 4 Beds
  • 3 Baths
  • Orange Terrace SubDv.
  • 32789 Zip Code
2887 Temple Trail, Winter Park image
2887 Temple Trail, Winter Park $695,000

Some homes stand out because of their finishes. Others because of their location. Rarely do you find one that brings both together so beautifully. Nestled alongside an 8...

  • 2 Beds
  • 3 Baths
  • Temple Trail Village SubDv.
  • 32789 Zip Code
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