Winter Park, FL Homes

• 

  

  

  /23

  $265,000

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, 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

  $1,025,000 Sold Jun 27, 2025

  • 2,546 Sq Ft
  • $403/SF
  • 55 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2019

  2680 Oglesby Ave, Winter Park, FL 32789

  Welcome to your Winter Park dream home—a modern farmhouse masterpiece blending timeless design with contemporary comforts. Built in 2019, this single-family home offers four spacious bedrooms, two and a half baths, and luxurious finishes you'll cherish for years.Nestled between the highly coveted areas and school zones of College Park and Winter Park, this property is an opportunity you

  Kris Kennedy COMPASS FLORIDA LLC

  2680 Oglesby Ave, Winter Park, FL 32789
• 

  

  

  /29

  Est $567,632 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
• 

  

  

  /10

  $109,000

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

  What an opportunity !! A 2 bedroom 2 bath Condo located in Winter Park. Fantastic opportunity-priced to sell! 2 bedroom, 2 bath condo in The Colonies ready for new owner. Light and bright First floor unit features Eat-kitchen, tile floors throughout - no carpet! French doors with built-in blinds lead to spacious balcony. Both bedrooms have large Walk-In closets! *Inside laundry *A/C 2017 -

  Pedro Ramos ROCKER'S REAL ESTATE, LLC

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792
• 

  

  /29

  $3,700 per month

  • 3 Beds
  • 2 Baths
  • 2,102 Sq Ft
  • House for Rent

  1946 Strathaven Rd, Winter Park, FL 32792

  $100 OFF THE FIRST 6 MONTHSFor Rent – Spacious 3BR Home in Prime Winter Park Location!LOCATION, LOCATION, LOCATION! This spacious 3-bedroom, 2-bath home with a large den and cozy wood-burning fireplace sits on an oversized lot in Kenilworth Shores – Sec 7, with deeded access to Lake Berry.Zoned for Winter Park High, Glenridge Middle, and Brookshire Elementary, and just

  Youbel Montesino LPT REALTY, LLC

  1946 Strathaven Rd, Winter Park, FL 32792
• 

  /2

  $100,000 Sold Jun 27, 2025

  • 130 Sq Ft
  • $769/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  336 Scottsdale Square, Winter Park, FL 32792

  Welcome to this three bedroom, two bathroom townhouse, perfectly situated just minutes from Downtown Winter Park, Full Sail University, and UCF—offering a prime location for both convenience and lifestyle. The spacious floor plan features a downstairs kitchen, living room, and dining room, along with a bedroom and full bathroom, making it ideal for guests. Upstairs, you'll find two additional

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  336 Scottsdale Square, Winter Park, FL 32792
• 

  

  /16

  Est $205,353 Not Listed For Sale

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

  3378 Cedar Springs Place Unit 154, Winter Park, FL 32792

  3378 Cedar Springs Place Unit 154, Winter Park, FL 32792
• 

  

  /36

  $5,800,000

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft

  1221 Richmond Rd, Winter Park, FL 32789

  An Award-Winning Architectural Masterpiece built by Chris Salhab with Valdara Custom HomesCompleted 2024Parade of Homes Showcase Home – Grand Award WinnerAurora Awards – Custom Home Grand Award5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Deeded Lake AccessWelcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of

  Audra Wilks KELLER WILLIAMS WINTER PARK

  1221 Richmond Rd, Winter Park, FL 32789
• 

  

  /9

  $2,699 per month

  • 4 Beds
  • 2 Baths
  • 2,288 Sq Ft
  • House for Rent

  3330 Coleus Ct, 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 $2963.90. That covers your base rent, $2699.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  3330 Coleus Ct, 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
• 

  

  /10

  Est $460,544 Not Listed For Sale

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

  2726 Bright Bird Ln, Winter Park, FL 32792

  2726 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /41

  $1,200,000

  • 6 Beds
  • 4 Baths
  • 4,277 Sq Ft

  2080 Wood Thrush Ln, Winter Park, FL 32792

  Exceptional Living Awaits in the Heart of Winter ParkNestled in the sought-after community of Waters Edge at Hawks Crest, this stunning4268 square-foot energy-efficient home offers an exquisite blend of classic eleganceand modern comfort. This Kerville II model, built by Meritage Homes in 2020, has beenthoughtfully designed to be both welcoming and refined.From the moment you

  Nate Klutznick LOKATION

  2080 Wood Thrush Ln, Winter Park, FL 32792
• 

  

  /18

  $4,900 per month

  • 4 Beds
  • 2.5 Baths
  • 1,856 Sq Ft
  • House for Rent

  2952 de Brocy Way, Winter Park, FL 32792

  Step inside and be amazed by this fully renovated Winter Park Pines home, where modern luxury, stylish finishes, and everyday comfort come together seamlessly. With spacious bedrooms, an open, airy layout, and designer touches throughout, this home is ideal for entertaining or simply enjoying peaceful living. Step out to a screened-in patio overlooking a sprawling backyard and private pool, your

  Summer Hornburg BELMONT REALTY

  2952 de Brocy Way, Winter Park, FL 32792
• 

  /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
• 

  

  /25

  Est $2,019,248 Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789
• 

  

  /56

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,070 Sq Ft

  2517 Windward Way, Winter Park, FL 32792

  Welcoming townhome on cul-de-sac with no rear neighbors. Step out ontoyour roomy 16 x 12 screened porch and take in the peaceful views of thetennis courts and green space—it’s the perfect spot to relax with your morningcoffee or unwind after a long day. Inside, you’ll love the bright, open feelthanks to clerestory windows in the living room, freshly painted walls, andbrand-new

  Sheila Mathews COLDWELL BANKER RESIDENTIAL RE

  2517 Windward Way, Winter Park, FL 32792
• 

  

  /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

  $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
• 

  

  /25

  Est $398,290 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7494 Aloma Pines Ct, Winter Park, FL 32792

  7494 Aloma Pines Ct, Winter Park, FL 32792
• 

  

  /44

  $1,100,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,826 Sq Ft

  512 Clarendon Ave, Winter Park, FL 32789

  Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for Audubon K-8! This spacious 2,826 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood like tile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen

  Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
• 

  

  /36

  $5,600 per month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst 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
• 

  

  /7

  Est $94,962 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
• 

  

  /20

  $295,000

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft

  1920 Woodcrest Dr Unit 15, Winter Park, FL 32792

  Gorgeous, fully renovated 2-bedroom / 2-bathroom condominium nestled in the heart of Winter Park along a beautiful and quiet tree lined street! The unit has new premium vinyl plank floors throughout. Living and dining room are open concept, perfect for entertaining! The updated kitchen features quartz counter tops, stainless appliances with new light and bright cabinetry. Bedrooms are a split

  Shirley Jones COLDWELL BANKER RESIDENTIAL RE

  1920 Woodcrest Dr Unit 15, Winter Park, FL 32792
• 

  /2

  $2,899 per month

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

  881 Julian St, Winter Park, FL 32789

  This home is currently undergoing exciting renovations and will be ready for you soon. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

  881 Julian St, Winter Park, FL 32789
• 

  /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
• 

  

  /36

  Est $1,444,075 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
• 

  

  /42

  $749,000

  • 4 Beds
  • 2 Baths
  • 1,891 Sq Ft

  346 Elkhorn Ct, Winter Park, FL 32792

  Welcome to your next chapter in Winter Park Pines, tucked within the most sought-after school district in all of Orlando, Florida, just minutes from everything. This 4-bedroom, 2-bath, 1,891 sq ft home with an expansive 500 sq ft lanai, oversized pool, has only had two owners — and now it’s ready to welcome the third. Transformed over time, this is not a flip.From the moment you step

  Ryan Everroad 407 PROPERTIES

  346 Elkhorn Ct, Winter Park, FL 32792
• 

  

  /23

  $1,450 per month

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

  3651 N Goldenrod Rd Unit B109, Winter Park, FL 32792

  Welcome home! This fantastic 2 bedroom, 2 bath Condo is available for move in on July 8th, 2025! You will love this fabulous condo in the charming and great central location of Winter Park /East Orlando. The 2 bedroom, 2 bath condo offers a spacious living and dining combo, with an open floor paln, large kitchen with lots of cabinet and storage space!! There are Sizable closet space in both

  Steve Simpson 407 PROPERTIES

  3651 N Goldenrod Rd Unit B109, 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
• 

  

  /33

  Est $448,160 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
• 

  

  /56

  $629,777

  • 4 Beds
  • 3 Baths
  • 2,672 Sq Ft

  3102 Heartleaf Place, Winter Park, FL 32792

  Tucked away on the tree-lined streets of the Lost Creek community, this contemporary two-story residence offers a rare blend of serenity and sophistication. Ideally located in sought-after Winter Park, this exceptional property offers exclusive creek-to-lake access leading to the sparkling waters of Lake Howell—just minutes away from vibrant city life and top-tier amenities.From the

  Karen Arbutine RE/MAX CENTRAL REALTY

  3102 Heartleaf Place, Winter Park, FL 32792
• 

  

  /15

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • House for Rent

  1381 Viburnum 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

  1381 Viburnum Ln, 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
• 

  

  /55

  Est $1,108,621 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
• 

  

  /50

  $469,000

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft

  2405 Firstlight Way, Winter Park, FL 32792

  Experience refined living in the sought-after gated community of Hawks Crest. This elegant 3-bedroom, 2.5-bathroom home offers 1,964 sq ft of thoughtfully designed living space with a 2-car garage featuring a sleek epoxy finish.As you enter, natural light floods the spacious living room, highlighting the modern finishes and open layout. The gourmet kitchen is a chef’s dream—equipped with

  Carmen Acosta EXP REALTY LLC

  2405 Firstlight Way, Winter Park, FL 32792
• 

  

  /31

  $1,450 per month

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

  614 Grenadine Ct Unit 614, Winter Park, FL 32792

  Beautiful 1 Bedroom 1 Bath, corner unit. Light and bright with plenty of windows. This condo has a fantastic layout with a very efficient use of space and floor plan. New paint throughout with tile in the living areas and new carpet in the bedroom. Beautiful open kitchen with plenty of space for prepping and cooking your favorite meals and a breakfast bar. A huge master bedroom with large walk-in

  Fabian Berastegui P & C PROPERTIES

  614 Grenadine Ct Unit 614, 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
• 

  

  /19

  Est $251,737 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

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