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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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2040 Venetian Way Winter Park FL 32789

Winter Park, FL2040 Venetian Way

Price$9,995,000

Est. Mortgage: $52,341/month

MLS Number O6249727

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 8,082
  • Year Built 2002

Majestic lakefront estate fully renovated in 2021 located in the beautiful Winter Park, Florida. Nestled on sprawling acreage, this breathtaking 6-bedroom, 7.5 bathroom lakefront mansion offers unparalleled luxury and...

Listing Courtesy of COLDWELL BANKER RESIDENTIAL RE

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$52,341/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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1245 Howell Point Winter Park FL 32792

Winter Park, FL1245 Howell Point

Price$7,000,000

Est. Mortgage: $32,736/month

Pending

MLS Number O6247174

  • Residential
  • Area Winter Park/Aloma
  • Mls Status Pending
  • Square Feet 6,540
  • Year Built 1989

Under contract-accepting backup offers. South Carolina "Low Country" style manor home situated on 10.52 luxurious lake front acres just 10 minutes from the heart of downtown Winter Park! From the moment you enter the...

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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$32,736/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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

MLS Number O6240628

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

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 sanctuary in the heart of our city. The...

Listing Courtesy of KELLY PRICE & COMPANY LLC

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$32,572/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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$32,409/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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$24,194/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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698 N New York Avenue Winter Park FL 32789

MLS Number O6211406

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,096
  • Year Built 2025

Pre-Construction. To be built. Custom design and build your dream home or use the plan that we have permitted! Rare, new construction opportunity in the heart of Winter Park, just 1 block from Park Avenue being built...

Listing Courtesy of CORCORAN PREMIER REALTY

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$
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$24,194/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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1660 Palmer Avenue Winter Park FL 32789

MLS Number O6209613

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 5,636
  • Year Built 2024

Welcome to this new 2024 elegant Hampton's style residence, the epitome of luxury and sophistication. As you enter through the remote-operated gated entrances, a grand circular driveway welcomes you to a private motor...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$22,917/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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: $22,263/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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$
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$22,263/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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
Pending

MLS Number O6153641

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

Under contract-accepting backup offers. 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...

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

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$16,371/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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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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$
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$14,735/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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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985 Lincoln Circle Winter Park FL 32789

MLS Number O6193386

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 3,660
  • Year Built 2024

One or more photo(s) has been virtually staged. Pre-Construction. To be built. THIS HOME IS CURRENTLY UNDER CONSTRUCTION. TO BE COMPLETED MAY 2025. Some finishes may still be available for Buyer selection. This home...

Listing Courtesy of UNITED REAL ESTATE PREFERRED

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$
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$14,735/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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

$
$
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$14,408/month over 360 payments
Federal 30-year interest rate: 6.84% last updated on Nov 21, 2024
* 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 November 25, 2024 . 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.