Winter Park, FL Homes

• 

  

  

  /29

  $390,000

  • 2 Beds
  • 1 Bath
  • 1,028 Sq Ft

  1516 Pinewood Dr, Winter Park, FL 32789

  PINEWOOD SUB N/9 LOT 12 BLK AWell-maintained, modest 2-1 home in College Park with carport, deck, and porch. Home materials include laminate and tile flooring, granite kitchen countertops, energy efficient windows, vinyl siding, and metal roof. All appliances included (washer, dryer, refrigerator, dishwasher, oven/stove with range hood, microwave). Also includes backyard garden, working

  Matt Buttner LIST NOW REALTY, LLC

  1516 Pinewood Dr, Winter Park, FL 32789
• 

  

  

  /13

  $2,325 per month

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • House for Rent

  5351 Cypress Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2469.90. That covers your base rent, $2325.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5351 Cypress Dr, Winter Park, FL 32792
• 

  

  /2

  $440,000 Sold Jun 27, 2025

  • 1,572 Sq Ft
  • $280/SF
  • 93 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  5359 Lanyard Ct, Winter Park, FL 32792

  MOTIVATED SELLER. Meticulously Maintained Corner-Lot Pool Home with Modern Upgrades & No HOA!Pride of ownership shines throughout this beautifully maintained corner-lot home, offering privacy, space, and modern comfort on over a quarter-acre of professionally landscaped grounds—all with NO HOA! Every detail has been thoughtfully cared for, ensuring a move-in-ready retreat for its next

  Nicole Dege REDFIN CORPORATION

  5359 Lanyard Ct, Winter Park, FL 32792
• 

  

  

  /35

  Est $309,320 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  228 Balfour Dr Unit 17, Winter Park, FL 32792
• 

  

  

  /77

  $689,900 Open Sat 1AM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,251 Sq Ft

  3759 Kinsley Place, Winter Park, FL 32792

  EXPECT TO BE IMPRESSED! Tucked away in a quaint and quiet Winter Park neighborhood, this beautifully maintained two-story 4-bedroom, 2.5-bath pool home sits on a lushly landscaped conservation lot with a charming paver walkway and inviting curb appeal. From the moment you step inside, you’ll appreciate the thoughtful updates and timeless character that make this home truly special.The newly

  Drew Belani COMPASS FLORIDA LLC

  3759 Kinsley Place, Winter Park, FL 32792
• 

  

  /18

  $4,340 per month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • House for Rent

  332 N Phelps Ave, Winter Park, FL 32789

  Discover the allure of this Winter Park retreat! Nestled in a prime location, this delightful 3 bedroom, 2 bathroom abode boasts a sunlit open floor plan that invites comfort and relaxation. Adorned with warm wood flooring and custom millwork, the home exudes charm at every turn. The heart of this residence is its inviting kitchen, complete with ample counter space, abundant storage, and a

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  332 N Phelps Ave, Winter Park, FL 32789
• 

  /2

  $280,000 Sold Jun 27, 2025

  • Land
  • 0.17 Acre
  • $1,647,059 per Acre

  • 123 Days On Market

  2446 Lotafun Ave, Winter Park, FL 32789

  Who wouldn’t want to live on a street called LOTAFUN? This is your opportunity to build your dream home on a quiet street with convenient access to Winter Park, Maitland and Orlando as well as Interstate 4 either from Lee Road or Fairbanks Avenue. This beautiful vacant lot has 75-feet of frontage and is 100-feet deep. This has a Winter Park address but is located in Orange County. An

  David Francetic COLDWELL BANKER RESIDENTIAL RE

  2446 Lotafun Ave, Winter Park, FL 32789
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  /80

  Est $1,215,734 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,307 Sq Ft

  1999 Soaring Oak Way, Winter Park, FL 32792

  1999 Soaring Oak Way, Winter Park, FL 32792
• 

  

  /27

  $307,000

  • 2 Beds
  • 2 Baths
  • 1,362 Sq Ft

  638 Warrenton Rd, Winter Park, FL 32792

  Welcome to this charming 2-Bedroom, 2-Bathroom duplex located in desirable Winter Park. This duplex offers a range of amenities that will surely enhance your living experience. This duplex has tile flooring throughout, for ease of care. The kitchen boasts one year new stainless steel appliances and an eat-in area space with wonderful natural light from the window looking to the backyard, perfect

  Nicholas Musashe SUN PROPERTIES, INC.

  638 Warrenton Rd, Winter Park, FL 32792
• 

  

  /15

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,611 Sq Ft
  • Condo for Rent

  7475 Canford Ct Unit 21, Winter Park, FL 32792

  Discover the charm of this spacious 2-bedroom, 2.5-bathroom condo nestled in the heart of Winter Park. The beautifully maintained community at 7475 Canford Ct offers a peaceful retreat with easy access to top-rated schools, shopping, and dining. Presented by Renters Warehouse, this home boasts 1,611 sq ft of comfortable living space.Step inside to find a bright, open floor plan with

  7475 Canford Ct Unit 21, Winter Park, FL 32792
• 

  /2

  $2,500,000 Sold Jun 26, 2025

  • 4,860 Sq Ft
  • $514/SF
  • 63 Days On Market

  • 6 Beds
  • 8 Baths
  • Built 2012

  7849 Georgeann St, Winter Park, FL 32792

  BACK ON THE MARKET DUE TO BUYER FINANCING. BELOW Appraised Value! Lakefront Luxury in Winter Park. This CUSTOM gated estate feels like living at a resort. Situated on the beautiful 72-acre PRIVATE, spring-fed Lake Waunatta, this property has it ALL. Completely rebuilt in 2012, featuring six OVERSIZED bedrooms, six full bathrooms and two half-baths, home office, primary spa bath retreat,

  Angela McCloskey KELLER WILLIAMS REALTY AT THE PARKS

  7849 Georgeann St, Winter Park, FL 32792
• 

  

  /11

  Est $464,991 Not Listed For Sale

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

  2770 Bright Bird Ln, Winter Park, FL 32792

  2770 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /74

  $1,750,000 Open Sun 1PM - 4PM

  • 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

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
• 

  

  /29

  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,152 Sq Ft
  • House for Rent

  957 Dupont Ave, Winter Park, FL 32789

  Nestled in the heart of Winter Park's most desirable zip code, this beautifully maintained 3-bedroom, 2.5-bath home is a rare find. Located at 957 Dupont Ave, Winter Park, FL 32789, this charming residence offers 1,289 sq. ft. of living space on a generous 7,875 sq. ft. lot, complete with a 1-car attached garage. This home is move-in ready and brimming with updates. Step inside to discover an

  Stephanie Barber HOME & HIVE REALTY

  957 Dupont Ave, Winter Park, FL 32789
• 

  /2

  $515,000 Sold Jun 26, 2025

  • 2,197 Sq Ft
  • $234/SF
  • 58 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  2819 Scarlet Rd, Winter Park, FL 32792

  Welcome to Winter Park Pines, a community known for its tree-lined streets, friendly neighbors, and the rare charm of front-door mail delivery! This spacious 2,000+ sq. ft. home presents an incredible opportunity to invest in a neighborhood where property values are soaring.Nestled on a picturesque street, this home boasts fantastic curb appeal and a lush, private backyard oasis—perfect for

  Amy Turner KELLER WILLIAMS WINTER PARK

  2819 Scarlet Rd, Winter Park, FL 32792
• 

  

  /46

  Est $997,429 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft

  1913 S Lakemont Ave, Winter Park, FL 32792

  1913 S Lakemont Ave, Winter Park, FL 32792
• 

  

  /53

  $3,400,000

  • 5 Beds
  • 5.5 Baths
  • 4,296 Sq Ft

  473 Fletcher Place, Winter Park, FL 32789

  Experience the perfect blend of luxury, lifestyle, and location in this completely custom 2017 Lundev build, just one mile from the boutiques and dining of Park Avenue and less than 100 feet from access to Lake Osceola, perfect for paddleboarding or launching a canoe.Tucked away on a quiet, tree-lined street, this residence makes a striking first impression with it's stunning elevation

  Brandon Geers COMPASS FLORIDA LLC

  473 Fletcher Place, Winter Park, FL 32789
• 

  

  /16

  $2,285 per month

  • 3 Beds
  • 2 Baths
  • 1,992 Sq Ft
  • House for Rent

  7423 Antietam Ct E, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2429.90. That covers your base rent, $2285.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7423 Antietam Ct E, Winter Park, FL 32792
• 

  /2

  $245,000 Sold Jun 26, 2025

  • 1,295 Sq Ft
  • $189/SF
  • 84 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  2471 Tahoe Cir, Winter Park, FL 32792

  Welcome to this beautifully renovated 2-bedroom, 2-bathroom condo located in the desirable Cedarwood Village community of Winter Park. This 1,295 sq ft home seamlessly blends modern updates with classic charm, offering a comfortable and stylish living space. The heart of this home boasts a brand-new kitchen equipped with modern appliances, sleek countertops, and ample cabinet space, perfect for

  Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

  2471 Tahoe Cir, Winter Park, FL 32792
• 

  

  /11

  Not Listed For Sale

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792
• 

  

  /41

  $170,000

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  Location, location, location!! And priced to sell!! This 3 bedroom 2 bathroom corner unit condo is conveniently located within a short drive distance to Rollins College, UCF, Valencia College, hospitals, shopping, dining, and entertainment! The unit is located on the first floor and has an open floor plan, spacious kitchen with plenty of cabinet space (all appliances are included) 3 well

  Madalay Fleming LA ROSA REALTY KISSIMMEE

  1695 Lee Rd Unit D116, Winter Park, FL 32789
• 

  

  /19

  $2,595 per month

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • House for Rent

  3976 Waterview Loop, Winter Park, FL 32792

  3 bedrooms, 2 bathrooms and a two car garage offering 1,444 square feet. Open floor plan with neutral colors, high ceilings. This home has a nice and open kitchen with an over abundance of cabinets, plenty of counter space granite and stainless steel appliances. Open to the kitchen you’ll find a large eat in nook and a family room/ dining room combination floor plan with sliding glass doors

  Courtney Davis ABSOLUTE REALTY GROUP, LLC

  3976 Waterview Loop, Winter Park, FL 32792
• 

  /2

  $335,000 Sold Jun 26, 2025

  • 1,408 Sq Ft
  • $238/SF
  • 120 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1986

  3131 Ash Park Loop, Winter Park, FL 32792

  Under contract Taking back up offers!! Welcome to your next home located at 3131 Ash Park Loop in the serene Hyde Park community. This inviting 2-bedroom, 2-bathroom house offers a clean, open split floor plan that’s perfect for both living and entertaining. Move-in ready, this home also presents a unique chance for creative renovations, making it a blank canvas for your personal

  Amanda Binns STRICKLAND REALTY GROUP INC

  3131 Ash Park Loop, Winter Park, FL 32792
• 

  

  /11

  Est $480,467 Not Listed For Sale

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

  2737 Bright Bird Ln, Winter Park, FL 32792

  2737 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /68

  $670,777

  • 4 Beds
  • 3 Baths
  • 2,846 Sq Ft

  3115 Heartleaf Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to your dream home in Winter Park, FL! This stunning 4-bedroom, 3-bathroom residence is situated on a desirable corner lot, offering ample space and privacy. This home was recently updated with a brand new HVAC system installed (May 2025), and a roof that’s only 4 years old (2021), complete plumbing repipe done in (2020). This home boasts

  Selby Turnbull EXP REALTY LLC

  3115 Heartleaf Place, Winter Park, FL 32792
• 

  /2

  $2,780 per month

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft
  • House for Rent

  630 N Lakemont Ave, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  630 N Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $515,000 Sold Jun 25, 2025

  • 1,953 Sq Ft
  • $264/SF
  • 68 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  2607 Verde Ln, Winter Park, FL 32792

  Welcome home! This COMPLETELY REMODELED 4 bedrooms, 2 baths, 1,953 sq ftcul-de-sac home is nestled in the highly desirable Casa Aloma community. As you walkthrough the front door, you are greeted by a bright open concept living /dining roomspace. The turn-key property includes the following updates: brand new roof (2025),new hot water tank (2025), luxury vinyl plank flooring

  David Wald FOUNDERS REALTY GROUP

  2607 Verde Ln, Winter Park, FL 32792
• 

  

  /21

  Est $449,597 Not Listed For Sale

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

  2861 Clever Ln, Winter Park, FL 32792

  2861 Clever Ln, Winter Park, FL 32792
• 

  

  /30

  $765,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  620 Darcey Dr, Winter Park, FL 32792

  New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heights neighborhood. This home features four bedrooms, two baths, over 2,076 square feet of natural sunlight flowing throughout, enclosed back porch and a fully fenced backyard. Beautiful curb appeal with a long extended driveway, great for large gatherings, parking your boat, RV

  Michael Domi PREMIER SOTHEBY'S INTL. REALTY

  620 Darcey Dr, Winter Park, FL 32792
• 

  

  /17

  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  641 S Lakemont Ave, Winter Park, FL 32792

  Property has been updated and is move in ready for you! This delightful Winter Park home could be the perfect fit for you! Conveniently located near excellent public schools, shopping centers, and essential healthcare facilities, this remodeled 1450 square foot residence features 3 bedrooms and 2 full baths. The kitchen is brand new, boasting updated appliances, while the bathrooms have been

  Alisa Hildebrand WEICHERT REALTORS HALLMARK PROPERTIES

  641 S Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $2,250,000 Sold Jun 25, 2025

  • 3,694 Sq Ft
  • $609/SF
  • 98 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 1958

  301 Rippling Ln, Winter Park, FL 32789

  Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access. Featuring a private boat lift, dock, and spacious outdoor entertaining areas, this property is perfect for boating enthusiasts and nature

  Cynthia Fernandez XCLUSIVE HOMES LLC

  301 Rippling Ln, Winter Park, FL 32789
• 

  

  /23

  Est $335,916 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3197 Crown Jewel Ct, Winter Park, FL 32792

  3197 Crown Jewel Ct, Winter Park, FL 32792
• 

  

  /40

  $399,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789
• 

  

  /6

  $2,275 per month

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • House for Rent

  7457 Blue Jacket Place E, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2539.90. That covers your base rent, $2275.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7457 Blue Jacket Place E, Winter Park, FL 32792
• 

  /2

  $100,000 Sold Jun 25, 2025

  • 1,020 Sq Ft
  • $98/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  197 Scottsdale Square, Winter Park, FL 32792

  Featuring a functional floor plan, this property is perfect for investors or buyers looking to customize their new home. Located in a convenient and central location, you’ll be close to shopping, dining, major highways, and the vibrant charm of Winter Park. Whether you’re looking for a project to create your dream space or an investment opportunity, this property is a blank canvas waiting for

  Edward Lee LA ROSA REALTY ORLANDO LLC

  197 Scottsdale Square, Winter Park, FL 32792
• 

  

  /32

  Est $619,968 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  1178 Wildmeadow Run, Winter Park, FL 32792

  1178 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /51

  $840,000 Open Sat 2PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789

  Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious,

  Lois Rawson COLDWELL BANKER RESIDENTIAL RE

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789
• 

  

  /21

  $1,695 per month

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

  7449 Wynnewood Square Unit 182, Winter Park, FL 32792

  Come home to this charming townhome in Winter Park! This beautifully maintained 2 bedroom, 2.5 bath home offers the perfect blend of comfort, convenience, and privacy. Step inside to an inviting open floor plan ideal for entertaining or simply relaxing at home. The spacious kitchen features a cozy eating area, perfect for casual meals or morning coffee. Upstairs you will find two generously sized

  Annette Ortega KELLER WILLIAMS ADVANTAGE 2 REALTY

  7449 Wynnewood Square Unit 182, Winter Park, FL 32792
• 

  /2

  $550,000 Sold Jun 24, 2025

  • 1,856 Sq Ft
  • $296/SF
  • 68 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  2310 Cady Way, Winter Park, FL 32792

  Welcome home to the sought after neighborhood of Brookshire Heights with in the Greater Winter Park Pines Community, where tree-lined streets and the friendly touch of a neighborhood where the mailman still delivers to your door await you! This spacious and updated 3-bedroom, 2-bathroom home is an entertainer’s dream, offering a perfect blend of modern updates, cozy living spaces, and serene

  Amy Turner KELLER WILLIAMS WINTER PARK

  2310 Cady Way, Winter Park, FL 32792
• 

  

  /18

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft

  1411 Miller Ave, Winter Park, FL 32789

  1411 Miller Ave, Winter Park, FL 32789

Showing Results 401 - 440, Page 11 of 18