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Winter Park Homes for Sale

Winter Park, FL is a family friendly, upscale suburban community. The city is located just seven miles northeast of Orlando. Park Avenue has a variety of upscale shops, restaurants, and art galleries. Winter Park Village offers outdoor shopping and restaurants. Popular nightlife attractions include Luma, Prato, Cocina 214, and Boca. Central Park has beautiful fountains, a rose garden, and seasonal events. Homes in Winter Park include condos, townhomes, and single family homes. The city is home to Rollins College, a private coed liberal arts school founded in 1885.

View Winter Park Properties

Explore all properties for sale in Winter Park, FL in the greater Orlando area listed below. As you search through listings please be sure to contact us with any questions or to schedule a viewing.

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1120 Preserve Point Drive Winter Park FL 32789

MLS Number O6269585

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 11,255
  • Year Built 2009

Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate is a true private oasis. With over 11,000 square feet of living area and a beautifully landscaped...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
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$63,593/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2661 Via Tuscany Winter Park FL 32789

Winter Park, FL2661 Via Tuscany

Price$10,999,999

Est. Mortgage: $57,581/month

MLS Number O6260493

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,564
  • Year Built 2024

Introducing a stunning modern European-style home, blending contemporary design with timeless elegance. This property offers luxurious finishes, open-concept living spaces, Located in the heart of Historic Winter Park...

Listing Courtesy of PV LUXURY GROUP PA

$
$
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$57,581/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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654 W Morse Boulevard Winter Park FL 32789
Pending

MLS Number O6240628

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 8,752
  • Year Built 2022

Under contract-accepting backup offers. Distinctive. Inspirational. Timeless. Casa K is the ultimate in luxury and location. Designed by internationally respected architect, Kamal Rizk and constructed in 2022, it is a...

Listing Courtesy of KELLY PRICE & COMPANY LLC

$
$
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$30,694/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1400 Alabama Drive Winter Park FL 32789

MLS Number O6212012

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 7,916
  • Year Built 1996

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland - the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes luxury and...

Listing Courtesy of IRON VALLEY REAL ESTATE CENTRAL FLORIDA

$
$
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$30,527/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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541 Virginia Drive Winter Park FL 32789

MLS Number O6268853

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,725
  • Year Built 2008

Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury...

Listing Courtesy of HOMEVEST REALTY

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$
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$25,851/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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210 Chelton Circle Winter Park FL 32789

MLS Number O6239351

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,264
  • Year Built 2024

This gorgeous, new-construction FG Schaub custom home is the epitome of stunning contemporary design by architect, Michael Weinrich. As you enter this sprawling residence, with views of both Lake Sue and Lake Chelton...

Listing Courtesy of CORCORAN PREMIER REALTY

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$
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$22,144/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2228 Azalea Place Winter Park FL 32789

Winter Park, FL2228 Azalea Place

Price$5,400,000

Est. Mortgage: $20,173/month

MLS Number O6250411

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,072
  • Year Built 2008

Gorgeous Winter Park home beautifully curated with designer details and recently featured in June's “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This...

Listing Courtesy of COMPASS FLORIDA LLC

$
$
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$20,173/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2161 Sharon Road Winter Park FL 32789

Winter Park, FL2161 Sharon Road

Price$4,985,000

Est. Mortgage: $17,401/month

MLS Number O6263091

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 6,338
  • Year Built 2023

Nestled in the esteemed The Vias area and near the WPRC, resides a home signifying the essence of sophistication and luxury. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive...

Listing Courtesy of LA ROSA REALTY HORIZONS LLC

$
$
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$17,401/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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421 Lakewood Drive Winter Park FL 32789

Winter Park, FL421 Lakewood Drive

Price$4,500,000

Est. Mortgage: $0/month

Pending

MLS Number O6153641

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 5,847
  • Year Built 1957

This elegant Winter Park lakefront residence offers luxury lakeside living, situated on the picturesque shores of Lake Osceola. This exquisite home invites you in with a grand circular driveway and meticulous...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$0/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1231 Via Salerno Winter Park FL 32789

Winter Park, FL1231 Via Salerno

Price$4,275,000

Est. Mortgage: $22,545/month

Pending

MLS Number O6234338

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 5,633
  • Year Built 2005

Experience the pinnacle of luxury living in this stunning five-bedroom estate situated on an oversized 120-foot wide lot on a tranquil and premier Vias brick street. This elegant Tuscan Mediterranean enjoys over 5,600...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$22,545/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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571 Lake Front Boulevard Winter Park FL 32789

MLS Number O6220284

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,500
  • Year Built 1967

Pre-Construction. To be built. Welcome to Winter Park lakefront living at its finest. In the heart of Winter Park, this new construction residence promises to be a masterpiece of luxury and modern living. Spanning over...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$22,044/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1751 Glencoe Road Winter Park FL 32789

Winter Park, FL1751 Glencoe Road

Price$4,100,000

Est. Mortgage: $21,376/month

MLS Number O6255877

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,520
  • Year Built 2025

Under Construction. Exquisite new construction residence nestled in the heart of Winter Park, walking distance to Park Ave. This luxurious home boasts over 4,000 square feet of meticulously designed living space...

Listing Courtesy of COMPASS FLORIDA,LLC

$
$
%
$21,376/month over 360 payments
Federal 30-year interest rate: 7.04% last updated on Jan 16, 2025
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Based on information submitted to StellarMLS as of January 19, 2025 . All data is obtained from various sources and has not been, and will not be, verified by broker or StellarMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.