Winter Park, FL Homes

• 

  

  

  /60

  $2,345,000

  • 4 Beds
  • 3.5 Baths
  • 3,986 Sq Ft

  2299 Via Tuscany, Winter Park, FL 32789

  Stunning 4-bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardwood oak floors, two fireplaces, and a chef’s kitchen offering premium appliances including SubZero Refrigeration and Viking 6-Burner Gas Cooktop. The private backyard features a large pool, covered

  Vincent Scarlatos CORCORAN PREMIER REALTY

  2299 Via Tuscany, Winter Park, FL 32789
• 

  

  

  /28

  $2,350 per month

  • 3 Beds
  • 2 Baths
  • 1,334 Sq Ft
  • House for Rent

  1005 Bradford Dr, Winter Park, FL 32792

  Welcome to your new home in the desirable Winter Park, FL! This 3-bedroom single-family home is a perfect blend of comfort and convenience. The open floor plan is complemented by tile and wood floors, creating a warm and inviting atmosphere. Each bedroom is oversized, offering ample space for relaxation, and features walk-in closets for all your storage needs. The updated bathrooms, including a

  Justin Recca INNOVATIVE REALTY, LLC

  1005 Bradford Dr, Winter Park, FL 32792
• 

  

  /2

  $538,500 Sold May 16, 2025

  2855 Cady Way, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • $310/SF
  • 76 Days On Market

  Current Estimated Value $533,536

  Last Listing Agent Joe Cremonese GLOBAL PROPERTIES SALES & MGMT

  2855 Cady Way, Winter Park, FL 32792
• 

  

  

  /7

  Est $90,498 Not Listed For Sale

  • Studio
  • 1 Bath
  • 590 Sq Ft

  7309 Daniel Webster Dr Unit B, Winter Park, FL 32792

  7309 Daniel Webster Dr Unit B, Winter Park, FL 32792
• 

  

  

  /30

  $155,000

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  151 Lewfield Cir Unit 4, Winter Park, FL 32792

  Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new

  Susan Tamlin KELLER WILLIAMS REALTY AT THE PARKS

  151 Lewfield Cir Unit 4, Winter Park, FL 32792
• 

  

  /19

  $2,300 per month

  • 4 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • House for Rent

  7284 Abbey Ln, Winter Park, FL 32792

  This 4 Bedroom/2 Bathroom home, located in beautiful Winter Park, hosts an open floor plan, granite countertops in the kitchen, stainless appliances, expansive Living Room and a sliding glass doorway in to the large fenced backyard. 2 car attached garage. NO PETS

  Courtney Davis ABSOLUTE REALTY GROUP, LLC

  7284 Abbey Ln, Winter Park, FL 32792
• 

  /2

  $284,000 Sold May 23, 2025

  2539 Antilles Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $249/SF
  • 50 Days On Market

  Current Estimated Value $284,112

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

  2539 Antilles Dr, Winter Park, FL 32792
• 

  

  /36

  Est $1,439,935 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,950 Sq Ft

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  1405 Chapman Cir Unit OR, Winter Park, FL 32789
• 

  

  /19

  $355,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,214 Sq Ft

  3117 Shady Pine Ave, Winter Park, FL 32792

  Under contract-accepting backup offers. PRICE JUST REDUCED! A true Winter Park gem in a quiet, tree-lined neighborhood with no HOA! This 3-bed, 2-bath home is well maintained and upgraded, featuring a fully paid 2021 Tesla solar roof, keeping energy costs low. The paver driveway, 2-car garage, and ample street parking offer convenience and curb appeal. Recent updates include new luxury vinyl

  Alistair Baxter EXP REALTY LLC

  3117 Shady Pine Ave, Winter Park, FL 32792
• 

  

  /33

  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • House for Rent

  1622 Arbor Park Dr, Winter Park, FL 32789

  Offering a $500 move-in incentive if moved in by the end of December! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  1622 Arbor Park Dr, Winter Park, FL 32789
• 

  /2

  $730,000 Sold Dec 27, 2024

  1102 Wildmeadow Run, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • Built 2020

  Last Sold Summary

  • 3% Below List Price
  • $282/SF
  • 55 Days On Market

  Current Estimated Value $749,156

  Last Listing Agent Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  1102 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /33

  Est $435,131 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2003 Canny Cove, Winter Park, FL 32792

  2003 Canny Cove, Winter Park, FL 32792
• 

  

  /54

  $950,000

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  668 Overspin Dr, Winter Park, FL 32789

  Modern Elegance Meets Custom Craftsmanship in the Heart of Winter ParkWelcome to your dream home — a custom-built Winter Park masterpiece blending modern luxury with thoughtful design. With over 2,500 sq/ft of stunning living space, this 4-bedroom, 3-bathroom home was built to impress and designed to entertain.Step inside and be captivated by the seamless open layout, drenched in natural

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  668 Overspin Dr, Winter Park, FL 32789
• 

  

  /18

  $1,350 per month

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft
  • Condo for Rent

  200 St Andrews Blvd Unit 606, Winter Park, FL 32792

  Welcome to this beautifully updated 1-bedroom, 1-bathroom condo located at 200 St. Andrews Blvd, Unit 606, Winter Park, FL 32792. Step inside to find stunning wood flooring throughout and a modern kitchen featuring stainless steel appliances and granite countertops, perfect for cooking and entertaining. Enjoy a comfortable and spacious bedroom with plenty of natural light, and unwind in the

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  200 St Andrews Blvd Unit 606, Winter Park, FL 32792
• 

  /2

  $290,000 Sold Sep 22, 2025

  7102 Easter St, Winter Park, FL 32792

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 67 Days On Market

  Current Estimated Value $287,506

  Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

  7102 Easter St, Winter Park, FL 32792
• 

  

  /55

  Est $1,071,972 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1772 Mondrian Cir, Winter Park, FL 32789

  1772 Mondrian Cir, Winter Park, FL 32789
• 

  

  /45

  $399,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price of $399,000. This fully renovated one-bedroom, one-bathroom condo spans 900 square feet and offers single-story, ground-floor, corner-unit living just steps from Park Avenue. The 2018 full renovation was extensive and included new electrical

  Padgett McCormick KELLY PRICE & COMPANY LLC

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
• 

  

  /29

  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Townhouse for Rent

  2349 Inagua Way, Winter Park, FL 32792

  Well maintained townhome in Winter Park. This home features updated bathrooms, ceramic tile, dining area and kitchen. The atrium has been enclosed making an excellent computer area. All major systems are routinely serviced. This home also has private backyard that is fully fenced. The community neighborhood features 2 large pools and tennis court. Convenient to major shopping center, fitness

  Laura Forty-Garcia RE/MAX CENTRAL REALTY

  2349 Inagua Way, Winter Park, FL 32792
• 

  /2

  $805,000 Sold Jul 01, 2025

  1795 Walker Ave, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 1958

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 143 Days On Market

  Current Estimated Value $785,487

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1795 Walker Ave, Winter Park, FL 32789
• 

  

  /19

  Est $224,580 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792
• 

  

  /55

  $1,599,000 Pending

  • 3 Beds
  • 4 Baths
  • 2,964 Sq Ft

  1270 Arlington Place, Winter Park, FL 32789

  Modern Elegance in the Heart of Winter Park! Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste. A long paver driveway welcomes you with ample

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
• 

  

  /21

  $1,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Townhouse for Rent

  7473 Belle River Ct Unit 16, Winter Park, FL 32792

  OWNER OFFERING ONE MONTH RENT CREDIT!!Spacious 3 Bed / 2.5 Bath Townhome-Style Condo in Hidden Oaks, Winter Park Welcome to this beautiful 3-bedroom, 2.5-bath townhome-style condo featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your

  Michael Barr PREMIUM PROPERTIES R.E SERVICE

  7473 Belle River Ct Unit 16, Winter Park, FL 32792
• 

  /2

  $567,500 Sold Dec 09, 2025

  1010 Aragon Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft
  • Built 1949

  Last Sold Summary

  • 1% Below List Price
  • $391/SF
  • 2 Days On Market

  Last Listing Agent Devin Loh COLDWELL BANKER RESIDENTIAL RE

  1010 Aragon Ave, Winter Park, FL 32789
• 

  

  /43

  Est $795,447 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7984 Pleasant Pine Cir, Winter Park, FL 32792

  7984 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /19

  $510,000

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft

  2627 Ambergate Rd, Winter Park, FL 32792

  Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!Investors -- You will love the cash flow upside with this property.Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for

  Ryan Minadie COLDWELL BANKER RESIDENTIAL RE

  2627 Ambergate Rd, Winter Park, FL 32792
• 

  

  /31

  $2,399 per month

  • 3 Beds
  • 2 Baths
  • 1,603 Sq Ft
  • House for Rent

  1734 Willa Cir, Winter Park, FL 32792

  Beautifully Upgraded Home in Winter Park’s Desirable Willa Grove Community Discover this beautifully maintained 3-bedroom, 2-bath single-family home offering 1,603 sq. ft. of comfortable living space in one of Winter Park’s most sought-after neighborhoods. Step inside and enjoy a bright, open split-bedroom floor plan with a modern kitchen featuring a breakfast bar, stainless steel appliances, and

  Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

  1734 Willa Cir, Winter Park, FL 32792
• 

  

  /32

  $380,000 Sold Mar 07, 2025

  830 Overspin Dr, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1952

  Last Sold Summary

  • 3% Below List Price
  • $330/SF
  • 30 Days On Market

  Current Estimated Value $371,986

  Last Listing Agent Richard Bavec TOLARIS REALTY GROUP LLC

  830 Overspin Dr, Winter Park, FL 32789
• 

  

  /40

  Est $818,149 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,706 Sq Ft

  2035 Soaring Oak Way, Winter Park, FL 32792

  2035 Soaring Oak Way, Winter Park, FL 32792
• 

  

  /9

  $177,000

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792

  *** SELLER WILL PAY SPECIAL ASSESSMENT AT CLOSING BRING MONTHLY ASSESSMENT TO $420****Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community. 1,031 sq. ft. newer roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes

  Abranette Lopez LPT REALTY, LLC

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792
• 

  

  /26

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792

  This rental townhouse-style condo in the Hidden Oaks community of Winter Park offers both comfort and convenience. It features 2 bedrooms and 2.5 bathrooms, with an inviting open-concept living and dining area on the main floor. Enjoy the convenience of a guest half bath and a fully equipped kitchen with updated appliances, a breakfast nook or flexible space, and an indoor laundry room with a

  Kerry Jeffcoat-Squeteri COMPASS FLORIDA LLC

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792
• 

  /2

  $925,000 Sold Feb 19, 2025

  223 Page St, Orlando, FL 32806

  • 4 Beds
  • 3.5 Baths
  • 2,685 Sq Ft
  • Built 2024

  Last Sold Summary

  • 5% Below List Price
  • $345/SF
  • 143 Days On Market

  Current Estimated Value $875,485

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  223 Page St, Orlando, FL 32806
• 

  

  /25

  Est $302,000 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft

  5408 Peaco Place, Winter Park, FL 32792

  5408 Peaco Place, Winter Park, FL 32792
• 

  

  /34

  $2,499,000

  • 4 Beds
  • 5 Baths
  • 4,875 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  "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 Maitland/Winter Park CHAIN OF LAKES! This custom modern/contemporary 2008 build, derives it's over 4800 sq/ft of essence and uniqueness by fusing vibrant colors and eloquence with

  Brian Rotenberger COMPASS FLORIDA LLC

  2550 Venetian Way, Winter Park, FL 32789
• 

  

  /90

  $16,550 per month

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft
  • House for Rent

  1860 Via Contessa, Winter Park, FL 32789

  Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Viasneighborhood,offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcomingatmosphere.Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

  Sylvester Harding SIERRA REALTY GROUP LLC

  1860 Via Contessa, Winter Park, FL 32789
• 

  /2

  $118,000 Sold Dec 30, 2024

  114 Scottsdale Square Unit 114, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • 9% Below List Price
  • $109/SF
  • 7 Days On Market

  Current Estimated Value $113,399

  Last Listing Agent Jeffrey Filegar VIVA ORLANDO REALTY INC.

  114 Scottsdale Square Unit 114, Winter Park, FL 32792
• 

  

  /16

  Est $1,025,582 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  2400 Roxbury Rd, Winter Park, FL 32789

  2400 Roxbury Rd, Winter Park, FL 32789
• 

  

  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez AGENT TRUST REALTY CORPORATION

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
• 

  

  /25

  $9,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • House for Rent

  1530 Via Tuscany, Winter Park, FL 32789

  Newly Remodeled Pool home located on premier street in Winter Park. This 4 bedroom home has just been totally updated with very tasteful upgrades. Notable items include: new paint in and out, new flooring in foyer, kitchen, baths. All baths remodeled, new light fixtures, new pavers on rear patio and pool, new landscaping package. The kitchen features new stone counters and backsplash. Also there

  Dan Haber CORCORAN PREMIER REALTY

  1530 Via Tuscany, Winter Park, FL 32789
• 

  /2

  $2,078,500 Sold Dec 11, 2025

  715 Via Bella, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 4,328 Sq Ft
  • Built 1976

  Last Sold Summary

  • 12% Below List Price
  • $480/SF
  • 70 Days On Market

  Last Listing Agent Adam Roark COMPASS FLORIDA LLC

  715 Via Bella, Winter Park, FL 32789
• 

  

  /19

  Est $2,518,922 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft

  350 Beloit Ave, Winter Park, FL 32789

  350 Beloit Ave, Winter Park, FL 32789

Showing Results 521 - 560, Page 14 of 18