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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.

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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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1411 Via Tuscany Winter Park FL 32789

Winter Park, FL1411 Via Tuscany

Price$15,900,000

Est. Mortgage: $/month

MLS Number O5949590

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 9,092
  • Year Built 1926

Elevated and overlooking extraordinary grounds this magnificent, one-of-a-kind, Private Resort Estate is sited directly on Lake Maitland, one of the Winter Park Chain of Lakes. Built in 1926, on the National Register of Historic Places and thought to be a Mizner Spanish Revival style, the estate underwent a multi-year extensive renovation and addition by Pellegrini Homes with eminent Architect Dailey Janssen. Known as a preeminent area The Vias in Winter Park is the perfect location for this well-designed and extremely high-quality custom residence. A central foyer greets you and flows naturally into grand rooms for living and entertaining. The special finishes this home has to offer include amenities well-planned for entertaining family intimately or on a grander scale with guests. The two-story dwelling consists of flex spaces featuring exquisite finishes; Bourgien stone flooring, French heart oak flooring, 100 year old Pecky Cypress beams and ceilings, custom designed Hope windows and doors. The kitchen features custom Turkish wood cabinetry, a La Cornue range, Sub-zero refrigerators, Dacor warming drawer, a working island, and more. Opening naturally to the family room with custom designed built-ins and gas fireplace. This smart plan includes two offices featuring Pecky Cypress ceilings and French baked White Oak floors. The separate private Casita with kitchen is perfect for guests with views of the estate (square footage not included in total). From the hand selected antique rolled barrel tiles on roof and ancient Pecky Cypress interiors to the solid marble and copper tubs, there are too many gorgeous features to name. The incredible outdoor landscaping, designed by well known Mario Nievera, terracing down, with a cascading rivulet, to the lake and boathouse, creates the perfect backdrop for outdoor living and entertaining. Imported custom designed Italian hand painted glass tile defines the stunning pool next to the cabana with a full kitchen, wood burning pizza oven, & changing rooms with showers. The huge basement hosts the media room, laundry room, wine grotto, and two mechanical rooms. Enjoy the true Florida lifestyle with a heated spa, outdoor fire pit, and boathouse with dock, balcony, and two baths. Exceptional features include; wine grotto, electric shades in most rooms, home theatre, air-conditioned garage with caterers kitchen, hand carved Italian sinks and tub, elevator, gazebo, whole house generator, top of the line water filtration system, Lutron technology, gas lanterns and more...

Listing Courtesy of CORCORAN PREMIER REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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1000 Genius Drive Winter Park FL 32789

Winter Park, FL1000 Genius Drive

Price$12,495,000

Est. Mortgage: $/month

Pending

MLS Number O5937062

  • Residential
  • Area Winter Park
  • Mls Status Pending
  • Square Feet 13,855
  • Year Built 1925

Perfectly positioned along the shores of Lake Virginia and Lake Mizell on the Winter Park Chain of Lakes, this majestic Mediterranean estate rests on approximately two acres with water frontage on three sides of the property and is truly a sight to behold. Originally built in 1925, but underwent an extensive, complete interior/exterior renovation and expansion, completed in October 2018. Gorgeous gates greet you upon entry, with a circular driveway leading to the front door. Beauty abounds from the moment you enter, as the gracious interior is comprised of generous living spaces and attention to detail throughout. Owned by Rollins College in the mid-20th century, the home's total renovation encompasses phenomenal features that include a large chef's island kitchen and separate caterer's kitchen, an all-glass, walk-in wine room, two master suites on the first and second floor, a full gym, elevator, an incredible air-conditioned 18-car garage with hydraulic lifts and pneumatics. The outside encompasses an opulent oasis with sprawling manicured grounds, a summer kitchen for alfresco dining and a resort-like pool and spa for soaking up the summer sun. A sports court welcomes friendly competition for athletic aficionados, while synthetic turf adds to the landscaping perfection. Panoramic sunrise and sunset views enhance the stunning scenery, as the home faces Lake Mizell to the front and Lake Virginia in the back. Two boat docks, one fitted for a boat and the other for wave runners, allow you to explore all that the Winter Park Chain of Lakes has to offer. Ideally situated just moments from Park Avenue, Rollins College and more, this lakefront masterpiece is truly one-of-a-kind.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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 W Fairbanks Avenue Winter Park FL 32789

MLS Number O5898942

  • CommercialSale
  • Property SubType Office
  • Subdivision Killarney Estates
  • Square Feet 20,384
  • Acreage 1.05

Winter Park, FL Iconic, Landmark, Trophy Property. Fully leased with long term credit tenant history. High Visibility Prime Corner location at Fairbanks Avenue and 17-92 (Orlando Avenue) in Affluent Winter Park, an affluent sub-market of the Orlando Florida area. Extremely stable investment with minimal landlord responsibilities. Recently Modernized Elevators, Each Elevator opens directly to each full floor office suite. Recent Fire System Devices replaced throughout the building. Recent lobby and bathroom renovations. Truly a unique investment and 1031 Exchange opportunity for investment. Ample Surface Parking. Free Standing 3 lane Bank Drive Through. Full Financials are available upon request to a qualified buyer investor. 1031 Exchange Opportunity. Thank you for looking.

Listing Courtesy of FLORIDA PREMIER REALTY GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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101 S New York Avenue Winter Park FL 32789

MLS Number O5963443

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 7,425
  • Acreage 0.04

This Commercial Condo is a second generation office space located on the second floor and has abundant sunlight. The space is designed with interior perimeter offices and conference rooms, beautiful reception area, and open work space to meet any users need. Tech users, Marketing Firms, Law Firms, Real Estate Offices, and really any professional user will love calling this building home. The open floor concept allows for collaboration but still provides enough offices for executives and top producers. (11 Offices, Conference room, and Breakroom).

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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101 S New York Avenue Winter Park FL 32789

MLS Number O5963472

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 7,425
  • Acreage 0.04

This Commercial Condo is a second generation office space located on the second floor and has abundant sunlight. The space is designed with interior perimeter offices and conference rooms, beautiful reception area, and open work space to meet any users need. Tech users, Marketing Firms, Law Firms, Real Estate Offices, and really any professional user will love calling this building home. The open floor concept allows for collaboration but still provides enough offices for executives and top producers. (11 Offices, Conference room, and Breakroom).

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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101 S New York Avenue Winter Park FL 32789

MLS Number O5963473

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 7,425
  • Acreage 0.04

This Commercial Condo is a second generation office space located on the second floor and has abundant sunlight. The space is designed with interior perimeter offices and conference rooms, beautiful reception area, and open work space to meet any users need. Tech users, Marketing Firms, Law Firms, Real Estate Offices, and really any professional user will love calling this building home. The open floor concept allows for collaboration but still provides enough offices for executives and top producers. (11 Offices, Conference room, and Breakroom).

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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101 S New York Avenue Winter Park FL 32789

MLS Number O5963474

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 7,425
  • Acreage 0.04

This Commercial Condo is a second generation office space located on the second floor and has abundant sunlight. The space is designed with interior perimeter offices and conference rooms, beautiful reception area, and open work space to meet any users need. Tech users, Marketing Firms, Law Firms, Real Estate Offices, and really any professional user will love calling this building home. The open floor concept allows for collaboration but still provides enough offices for executives and top producers. (11 Offices, Conference room, and Breakroom).

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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1106 Palmer Avenue Winter Park FL 32789

Winter Park, FL1106 Palmer Avenue

Price$4,350,000

Est. Mortgage: $/month

MLS Number A4508883

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 6,500
  • Year Built 2001

One of a kind on a private lane providing total privacy! A walk to Park Ave lifestyle. Details of the finishes are a must see! Venetian plaster and custom window treatments. 4 gas fireplaces. Recent updated kitchen boasts SubZero fridge Gaggenau oven and steamer & Wolf range with custom cabinets. Full carriage house apartment with adjoining art studio. Total home air purification, dehumidifier and water purification. Owners upstairs bedroom includes spacious private ladies bath suite with free standing tub and ample closets just for the lady of the Manor Separate gentleman's bath and closet are designed for him. Garage has large A/C'd storage room. Rear porch has retractable screens, fireplace and summer kitchen sub

Listing Courtesy of KEYS REALTY REDEFINED LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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690 N New York Avenue Winter Park FL 32789

Winter Park, FL690 N New York Avenue

Price$3,850,000

Est. Mortgage: $/month

MLS Number O5935400

  • Residential
  • Area Winter Park
  • Mls Status Active
  • Square Feet 4,901
  • Year Built 2021

Pre-Construction. To be built. Greens at Park. This address says it all…690 N. New York Avenue, where unparalleled luxury meets quintessential Winter Park lifestyle. Iconic English cottage architecture. This is a once in a lifetime opportunity to own a single family (fee simple) luxury real estate home in the heart of Winter Park. Located just steps from Park Avenue's upscale shops and restaurants while providing stunning views of the famous Winter Park golf course. The 6 estate lots will be built by the distinguished, FG Schaub Custom Homes known for his Grand open space which has become synonymous with him and his architect David Larson, Ltd. These homes will be fully customizable yet offering several luxury features: -Energy-efficient homes with the latest in smart home technology -Interior features include 11'4'' ceilings on the first floor and 9'4” on the second floor -Transitional room with a retractable screen and custom pool -Sub-Zero/Wolf appliance package including the washer and dryer -Fitness room with rubberized flooring, and many more high-end finishes -Each home will be equipped with a customized elevator As part of this exclusive community the exterior maintenance will be handled by the association, making the Greens at Park truly a sanctuary to call home. *Photos are not actual and are intended for inspirational purposes.

Listing Courtesy of THE HOPE GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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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101 S New York Avenue Winter Park FL 32789

MLS Number O5963494

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 5,559
  • Acreage 0.04

This Unit is by far the nicest Commercial Condo Unit for Sale in Winter Park. The space is mainly an open concept with premiter glass offices, beautiful conference room complete with barnstyle doors, and beautiful finishes throughout the suite. The former user was a tech group that converted the walls into highend dry erase allowing every single wall the ability to be breakout collaborative space, no mater where you are seated in your office. (3 Glass offices, Conference Room, 2 Call Booths, and Breakroom).

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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

101 S New York Avenue Winter Park FL 32789

MLS Number O5963496

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 5,559
  • Acreage 0.04

This Unit is by far the nicest Commercial Condo Unit for Sale in Winter Park. The space is mainly an open concept with premiter glass offices, beautiful conference room complete with barnstyle doors, and beautiful finishes throughout the suite. The former user was a tech group that converted the walls into highend dry erase allowing every single wall the ability to be breakout collaborative space, no mater where you are seated in your office. (3 Glass offices, Conference Room, 2 Call Booths, and Breakroom)

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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

101 S New York Avenue Winter Park FL 32789

MLS Number O5963500

  • CommercialSale
  • Property SubType Office
  • Subdivision Winter Park Comm
  • Square Feet 5,559
  • Acreage 0.04

This Unit is by far the nicest Commercial Condo Unit for Sale in Winter Park. The space is mainly an open concept with premiter glass offices, beautiful conference room complete with barnstyle doors, and beautiful finishes throughout the suite. The former user was a tech group that converted the walls into highend dry erase allowing every single wall the ability to be breakout collaborative space, no mater where you are seated in your office. (3 Glass offices, Conference Room, 2 Call Booths, and Breakroom).

Listing Courtesy of 4 ACRE REALTY LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.09% last updated on Oct 21, 2021
* 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 MFRMLS as of October 26, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MFRMLS. 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.