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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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1341 College Point Winter Park FL 32789

MLS Number O6257650

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,279
  • Year Built 2005

This custom lakefront home on Winter Park's Chain of Lakes offers stunning views of Lake Virginia and is in the historic Virginia Heights neighborhood, just a short walk from Rollins College and downtown Park Avenue...

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

$
$
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$21,349/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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850 Georgia Avenue Winter Park FL 32789

MLS Number O6236795

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,627
  • Year Built 1987

Welcome to an exquisite 3-bedroom, 5.5-bath plus office pool home in the heart of Winter Park. Set back 150 feet from the picturesque brick street, this stunning residence offers unparalleled privacy and elegance...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
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$21,109/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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1391 Richmond Road Winter Park FL 32789

MLS Number O6246352

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,635
  • Year Built 2001

Welcome to 1391 Richmond Road-a true work of art and a surreal living experience now on the market. The most discerning buyer will fall in love with the optimal location, an unusually private lot right in the heart of...

Listing Courtesy of STOCKWORTH REALTY GROUP

$
$
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$20,799/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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2810 Lake Howell Lane Winter Park FL 32792
Pending

MLS Number O6260116

  • Residential
  • Area Winter Park/Aloma
  • Mls Status Pending
  • Square Feet 4,900
  • Year Built 1996

Under contract-accepting backup offers. This extraordinary estate, on approximately 2.5-3 acres of meticulously maintained grounds, offers the ultimate in Florida lakefront living. on the serene shores of private...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
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$18,698/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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1821 Summerland Avenue Winter Park FL 32789
Pending

MLS Number O6248611

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 5,097
  • Year Built 2014

Under contract-accepting backup offers. Stunning Winter Park residence.

Listing Courtesy of COMPASS FLORIDA,LLC

$
$
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$18,650/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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2550 Venetian Way Winter Park FL 32789

Winter Park, FL2550 Venetian Way

Price$3,299,000

Est. Mortgage: $17,630/month

MLS Number O6258445

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,875
  • Year Built 2008

"The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Park, accessing the...

Listing Courtesy of COMPASS FLORIDA LLC

$
$
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$17,630/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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1730 Winchester Drive Winter Park FL 32789

MLS Number O6235073

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,080
  • Year Built 2024

Under Construction. Welcome to this exquisite 5-bedroom, 5.5-bathroom home built by Lundev, perfectly situated in the highly sought-after Timberlane Shores neighborhood of Winter Park. Spanning 4,080 square feet, this...

Listing Courtesy of KELLER WILLIAMS WINTER PARK

$
$
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$17,608/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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1900 W Fawsett Road Winter Park FL 32789

MLS Number O6251960

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,600
  • Year Built 1969

Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As...

Listing Courtesy of KELLY PRICE & COMPANY LLC

$
$
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$17,368/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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1618 Holts Grove Circle Winter Park FL 32789
Pending

MLS Number O6220012

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 4,807
  • Year Built 2014

Under contract-accepting backup offers. ACCEPTING BACK UP OFFERS. Please review photos...some painting inside and out was completed this month (Dec). Custom masterpiece! 5 bedrooms, 5 full baths, and 3 half baths. The...

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

$
$
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$17,234/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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425 Alberta Drive Winter Park FL 32789

Winter Park, FL425 Alberta Drive

Price$3,000,000

Est. Mortgage: $16,032/month

Pending

MLS Number O6263168

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 2,310
  • Year Built 1938

Under contract-accepting backup offers. 425 Alberta Drive is a Gamble Rogers-designed lakefront home with a boathouse built in 1938 that has not been registered historical and is being sold as is. Bring your builder to...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$16,032/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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585 Via Lugano Winter Park FL 32789

Winter Park, FL585 Via Lugano

Price$2,999,999

Est. Mortgage: $16,032/month

Pending

MLS Number O6265823

  • Land
  • Area Winter Park
  • Mls Status Pending
  • Acreage 0.63

Presenting a once-in-a-lifetime opportunity to own a prime piece of property on one of Winter Park's most prestigious streets in the Via's, surrounded by multimillion-dollar homes. This oversized 0.63-acre lot...

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

$
$
%
$16,032/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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585 Via Lugano Winter Park FL 32789

Winter Park, FL585 Via Lugano

Price$2,999,999

Est. Mortgage: $16,032/month

Pending

MLS Number O6265815

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 4,390
  • Year Built 1961

Presenting a once-in-a-lifetime opportunity to own a prime piece of property on one of Winter Park's most prestigious streets in the Via's, surrounded by multimillion-dollar homes. This oversized 0.63-acre lot, located...

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

$
$
%
$16,032/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.