Winter Park, FL Homes

• 

  

  

  /25

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft

  3425 Ferndell Dr, Winter Park, FL 32792

  Fully Renovated Gem in Winter Park!Welcome to your dream home in one of Central Florida’s most sought-after neighborhoods—Winter Park. This beautifully renovated 3-bedroom, 2-bathroom residence blends timeless charm with modern updates, offering the perfect move-in-ready sanctuary for today’s lifestyle.Step inside and fall in love with the light-filled open layout, anchored by a stunning

  Ivanhoe Alvarez LOKATION

  3425 Ferndell Dr, Winter Park, FL 32792
• 

  

  

  /15

  $2,020 per month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  1407 Chilean Ln, 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

  1407 Chilean Ln, 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
• 

  

  

  /43

  Est $811,016 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
• 

  

  

  /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
• 

  

  /26

  $2,600 per month

  • 2 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • House for Rent

  1513 Harmon Ave, Winter Park, FL 32789

  Lawn and Security System included with this fantastic 2/2 plus office Orwin Manor home. Home features hardwood flooring throughout with tile in kitchen and Florida Room/Sunroom areas. Florida Room/sunroom is perfect light and bright area for home office/workspace/flex/fitness room. Great Room is a generous space for larger modular or L-couch layout. Newer interior paint throughout. Primary suite

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1513 Harmon Ave, Winter Park, FL 32789
• 

  /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
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  /40

  Est $812,209 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
• 

  

  /77

  $689,900

  • 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
• 

  

  /15

  $2,090 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  5335 N Orange 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

  5335 N Orange Ave, Winter Park, FL 32792
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  /2

  $850,000 Sold Jun 24, 2025

  • 2,910 Sq Ft
  • $292/SF
  • 25 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1954

  1832 Magnolia Ave, Winter Park, FL 32789

  Stunning fully remodeled Winter Park bungalow featuring a 500 square foot detached guest house. This charming residence is perfectly positioned on a rare oversized .41-acre double lot and has been completely transformed, offering a harmonious blend of modern luxury and timeless elegance. The main house features 4 bedrooms and 2.5 baths while the guest house features a living room, bedroom,

  Christopher Christensen COMPASS FLORIDA LLC

  1832 Magnolia Ave, Winter Park, FL 32789
• 

  

  /25

  Est $251,000 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
• 

  

  /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
• 

  

  /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
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  /2

  $400,000 Sold Jun 24, 2025

  • 2,124 Sq Ft
  • $188/SF
  • 47 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  4991 Tangerine Ave, Winter Park, FL 32792

  Welcome to 4991 Tangerine Ave in the heart of Winter Park! This charming 4-bedroom, 2-bathroom home offers comfortable living with no carpet throughout—perfect for easy maintenance. The spacious family and dining room combination provides an open and inviting layout, ideal for gatherings. A large, air-conditioned Florida room adds even more flexibility, ensuring plenty of space for entertaining.

  Darein Washington KELLER WILLIAMS ADVANTAGE REALTY

  4991 Tangerine Ave, Winter Park, FL 32792
• 

  

  /16

  Est $1,053,096 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
• 

  

  /74

  $1,750,000 Open Sun 11AM - 3PM

  • 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
• 

  /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
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  /2

  $72,000 Sold Jun 24, 2025

  • 785 Sq Ft
  • $92/SF
  • 4 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  Located on the First Floor, this single-story condo features a one bedroom and one bathroom layout with a Foyer, Formal Dining and Living room with laminate flooring, Quaint Kitchen, Updated Bathroom and a Spacious Primary Bedroom with laminate flooring. In addition this condo includes a covered front porch and covered outdoor patio space with views of greenery. The unit has a private Laundry

  Erin Tompkins COLDWELL BANKER RESIDENTIAL RE

  273 Scottsdale Square Unit 273, Winter Park, FL 32792
• 

  

  /19

  Est $2,663,145 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
• 

  

  /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
• 

  

  /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
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  /2

  $468,470 Sold Jun 20, 2025

  • 1,724 Sq Ft
  • $272/SF
  • 25 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1977

  1026 Manchester Cir, Winter Park, FL 32792

  Welcome to your private oasis—where thoughtfully designed living spaces and beautiful upgrades come together in one incredible home. Whether it’s poolside afternoons, entertaining under the lanai, or cozy nights inside, this property delivers the Florida lifestyle you’ve been searching for. Step inside this well-maintained split floor plan home and enjoy a spacious family room that flows

  David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, 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
• 

  

  /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
• 

  

  /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

  $82,000 Sold Jun 20, 2025

  • 1,020 Sq Ft
  • $80/SF
  • 13 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  185 Scottsdale Square Unit F185, Winter Park, FL 32792

  Beautifully maintained and updated 2 Bedroom and 2 Bath condo in Winter Park! Easy to care for tile floors flow through the kitchen, living, and dining areas. The kitchen features a tile backsplash, newer stainless steel appliances, and cabinets with decorative glass inserts. An open concept living and dining area is bright with a large slider that opens to a private patio. Each bedroom features

  Erin Baker FANNIE HILLMAN & ASSOCIATES

  185 Scottsdale Square Unit F185, Winter Park, FL 32792
• 

  

  /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
• 

  

  /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
• 

  

  /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

  $205,000 Sold Jun 20, 2025

  • 1,059 Sq Ft
  • $194/SF
  • 97 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  4944 Tangerine Ave, Winter Park, FL 32792

  Welcome to this delightful 2-bedroom, 2-bath end-unit condominium, offering the perfect blend of comfort and style! As you enter, you’re greeted by a charming foyer with a convenient coat closet, setting the tone for this spacious and inviting home. The expansive living/dining area is perfect for both everyday living and entertaining guests. A newer sliding glass door leads to a peaceful screened

  Christine David WATSON REALTY CORP

  4944 Tangerine Ave, 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
• 

  

  /40

  $419,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

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

  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 Integrity

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

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

  

  /17

  $2,349 per month

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  324 Lake Fair Ln, Winter Park, FL 32789

  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 $2493.90. That covers your base rent, $2349.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  324 Lake Fair Ln, Winter Park, FL 32789
• 

  /2

  $850,000 Sold Jun 20, 2025

  • 2,085 Sq Ft
  • $408/SF
  • 282 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1919 S Lakemont Ave, Winter Park, FL 32792

  Special financing or closing cost credits available for qualified buyers!Introducing the 2024 PARADE OF HOMES ORLANDO WINNER - BEST IN CLASS! This exceptional, move-in ready residence is perfectly situated between the serene shores of Lake Spier and Lake Compton in the exclusive Lake Spier Crossing community of Winter Park.Discover modern luxury with 10 impeccably designed two-story townhomes,

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1919 S Lakemont Ave, 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
• 

  

  /51

  $865,000 Open Sun 1AM - 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
• 

  

  /14

  $2,300 per month

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

  641 S Lakemont Ave, Winter Park, FL 32792

  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 tastefully modernized with new fixtures. Throughout the main

  Alisa Hildebrand WEICHERT REALTORS HALLMARK PROPERTIES

  641 S Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $530,000 Sold Jun 18, 2025

  • 817 Sq Ft
  • $649/SF
  • 0 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  2525 Lafayette Ave, Winter Park, FL 32789

  Investor / Builder special!! Prime land opportunity located just minutes from Park Avenue. Don't miss your chance to build your custom home in this highly desirable area, surrounded by multi-million dollar homes. Value is in the land. Schedule your showing today!

  Blaike Gill KELLER WILLIAMS WINTER PARK

  2525 Lafayette Ave, Winter Park, FL 32789
• 

  

  /11

  Not Listed For Sale

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

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