Winter Park, FL Homes

• 

  

  

  /11

  $440,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft

  1909 Edwin Blvd, Winter Park, FL 32792

  The house is located in great location and features 3 bedrooms, 2 bathrooms. It sits on a corner lot and offers high ceilings throughout.

  Thu Nguyen CHARLES RUTENBERG REALTY ORLANDO

  1909 Edwin Blvd, Winter Park, FL 32792
• 

  

  

  /20

  $1,850 per month

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 2903, Winter Park, FL 32792

  *Move-In Special*$100 OFF FIRST MONTH RENT if lease is signed by February 10th. Experience the best of Winter Park living in this highly sought-after 2-bedroom, 1.5-bathroom 2-story condo located in the Four Seasons community! This beautiful unit features modern light fixtures, stainless steel appliances, and upgraded flooring throughout. Enjoy the convenience of an included washer and dryer.

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  200 Saint Andrews Blvd Unit 2903, 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 $373,916

  Last Listing Agent Richard Bavec TOLARIS REALTY GROUP LLC

  830 Overspin Dr, Winter Park, FL 32789
• 

  

  

  /18

  Est $434,522 Not Listed For Sale

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

  2796 Bright Bird Ln, Winter Park, FL 32792

  2796 Bright Bird Ln, Winter Park, FL 32792
• 

  

  

  /58

  $1,725,000 Pending

  • 3 Beds
  • 4.5 Baths
  • 3,164 Sq Ft

  1630 Chestnut Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets." This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets a relaxed tone throughout, blending timeless design

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1630 Chestnut Ave, Winter Park, FL 32789
• 

  

  /22

  $1,350 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 104, Winter Park, FL 32792

  Great location in Winter Park! This 2-bedroom, 2-bath apartment offers comfortable living with easy access to everything you need. Open Parking in front and located close to Full Sail University, UCF, Valencia College, and major roads like University Blvd and SR-436 (Semoran Blvd). Enjoy being just minutes from shopping centers, grocery stores, coffee shops, and restaurants, including Publix,

  Julio Lopez JCL REALTY INC

  3651 N Goldenrod Rd Unit 104, 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 $895,515

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  223 Page St, Orlando, FL 32806
• 

  

  /88

  Est $1,928,597 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft

  1661 Hillcrest Ave, Winter Park, FL 32789

  1661 Hillcrest Ave, Winter Park, FL 32789
• 

  

  /64

  $449,900

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

  1951 Canny Cove, Winter Park, FL 32792

  Discover comfortable Winter Park living in this bright and stylish 3-bedroom, 2.5-bathroom corner-unit townhome located in the gated Grayson Square community. Abundant natural light fills the open-concept living area, which flows seamlessly to a covered lanai that’s perfect for relaxing mornings or quiet evenings. The modern kitchen includes stainless steel appliances, quartz countertops, and

  Denise Del Castillo LPT REALTY, LLC

  1951 Canny Cove, Winter Park, FL 32792
• 

  

  /18

  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1148 Park Green Place, Winter Park, FL 32789

  Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

  Linda Baez DON ASHER & ASSOCIATES, INC.

  1148 Park Green Place, 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
• 

  /2

  Est $426,509 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  2719 Bright Bird Ln, Winter Park, FL 32792

  2719 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /58

  $1,999,000

  • 5 Beds
  • 3.5 Baths
  • 3,423 Sq Ft

  1540 Palm Ave, Winter Park, FL 32789

  Welcome to this stunning SINGLE STORY five-bedroom home with high ceilings, in one of Winter Park’s most desirable neighborhoods, where charming restorations and luxury new builds create a vibrant community feel. Designed with both beauty and comfort in mind, this open-concept home offers bright, welcoming living spaces and thoughtful upgrades throughout. Completely rebuilt in 2014 and tons of

  John McDade FANNIE HILLMAN & ASSOCIATES

  1540 Palm Ave, 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

  $602,500 Sold May 09, 2025

  777 S Denning Dr Unit B, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,762 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 37 Days On Market

  Current Estimated Value $603,584

  Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

  777 S Denning Dr Unit B, Winter Park, FL 32789
• 

  

  /18

  Est $426,907 Not Listed For Sale

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

  2790 Bright Bird Ln, Winter Park, FL 32792

  2790 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /41

  $255,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 229, Winter Park, FL 32789

  Million Dollar Lakefront View of Lake Killarney from Private Balcony and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has been improved with raised Ceilings and expansive Wood

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  2500 Lee Rd Unit 229, Winter Park, FL 32789
• 

  

  /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 February! 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

  $445,000 Sold Mar 20, 2025

  1663 Meadowgold Ct, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,851 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $240/SF
  • 173 Days On Market

  Current Estimated Value $446,346

  Last Listing Agent Dallas Wittish ORLANDO REALTY & PROPERTY MGNT

  1663 Meadowgold Ct, Winter Park, FL 32792
• 

  

  /39

  Est $863,539 Not Listed For Sale

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

  1770 Mondrian Cir, Winter Park, FL 32789

  1770 Mondrian Cir, Winter Park, FL 32789
• 

  

  /53

  $2,575,000

  • 5 Beds
  • 5 Baths
  • 4,026 Sq Ft

  2503 Versailles Ave, Winter Park, FL 32789

  Beautifully updated and offered for the first time, this 2015 David Weekley home sits on a rare cul-de-sac in the heart of Winter Park, zoned for Dommerich Elementary and Winter Park schools. This 5-bedroom, 5-bath home features an office, large bonus room, covered lanai with full summer kitchen, and a backyard putting green. Additional highlights include a 3-car garage, a gated parking pad ideal

  Sarah Tomlinson COMPASS FLORIDA LLC

  2503 Versailles Ave, Winter Park, FL 32789
• 

  

  /21

  $1,895 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

  $434,000 Sold Sep 12, 2025

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,556 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Above List Price
  • $279/SF
  • 55 Days On Market

  Current Estimated Value $443,572

  Last Listing Agent Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
• 

  

  /44

  Est $1,061,720 Not Listed For Sale

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

  1768 Mondrian Cir, Winter Park, FL 32789

  1768 Mondrian Cir, Winter Park, FL 32789
• 

  

  /46

  $1,495,000

  • 4 Beds
  • 4 Baths
  • 3,237 Sq Ft

  1408 Chapman Cir, Winter Park, FL 32789

  Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in the Elizabeth’s Walk subdivision in the highly coveted Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023),

  Jennifer Sloan COMPASS FLORIDA LLC

  1408 Chapman Cir, Winter Park, FL 32789
• 

  

  /90

  $15,500 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

  $505,000 Sold Aug 01, 2025

  715 Roughbeard Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1968

  Last Sold Summary

  • 12% Below List Price
  • $224/SF
  • 60 Days On Market

  Current Estimated Value $528,542

  Last Listing Agent Christine Gerardi NEXTHOME DIAMOND PROPERTIES

  715 Roughbeard Rd, Winter Park, FL 32792
• 

  

  /32

  Not Listed For Sale

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792
• 

  

  /5

  $995,000 Pending

  • Land
  • 0.45 Acre
  • $2,211,111 per Acre

  2260 Hawick Ln, Winter Park, FL 32792

  Under contract-accepting backup offers. This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property is currently vacant as the home and trees were recently demo'ed. The future development of three (3) fee simple single family lots (50’ wide) is the highest and best use of this land. The lot split process is complete with

  Michael Rasmussen DAVEN REAL ESTATE INC

  2260 Hawick Ln, Winter Park, FL 32792
• 

  

  /25

  $8,500 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

  $252,500 Sold Jul 17, 2025

  2309 Sun Valley Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,669 Sq Ft
  • Built 1985

  Last Sold Summary

  • 11% Below List Price
  • $151/SF
  • 65 Days On Market

  Current Estimated Value $257,987

  Last Listing Agent Kristin Vogt CENTURY 21 INTEGRA

  2309 Sun Valley Cir, Winter Park, FL 32792
• 

  /2

  Est $107,263 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 786 Sq Ft

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792
• 

  

  /57

  $2,900,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 7 Baths
  • 5,483 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7 versatile bonus rooms, including a private

  Adriana Oyarce ANCHOR REAL ESTATE

  1401 Green Cove Rd, Winter Park, FL 32789
• 

  

  /15

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
• 

  /2

  $458,000 Sold Feb 25, 2025

  3455 Athena Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,161 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $212/SF
  • 135 Days On Market

  Current Estimated Value $471,905

  Last Listing Agent Stephanie Kovats KELLER WILLIAMS ADVANTAGE REALTY

  3455 Athena Dr, Winter Park, FL 32792
• 

  

  /18

  Est $412,763 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2778 Bright Bird Ln, Winter Park, FL 32792

  2778 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /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
• 

  

  /15

  $2,000 per month

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave, Winter Park, FL 32789

  Charming 3-Bedroom Home for Rent in Winter Park This charming 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. The main home offers a functional and comfortable layout, ideal for everyday living. The property also includes a separate efficiency unit and a rear unit, both currently rented and featuring independent entrances, providing

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave, Winter Park, FL 32789
• 

  /2

  $660,000 Sold Apr 14, 2025

  1037 Fairway Dr, Winter Park, FL 32792

  • 3 Beds
  • 3 Baths
  • 2,145 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $308/SF
  • 29 Days On Market

  Current Estimated Value $656,994

  Last Listing Agent Skip Juma LEGACY REALTY & BROKERS LLC

  1037 Fairway Dr, Winter Park, FL 32792
• 

  

  /29

  Est $520,798 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,003 Sq Ft

  8097 Pleasant Pine Cir, Winter Park, FL 32792

  8097 Pleasant Pine Cir, Winter Park, FL 32792

Showing Results 561 - 600, Page 15 of 18