Winter Park, FL Homes

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  $260,000

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft

  151 N Orlando Ave Unit 101, Winter Park, FL 32789

  Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops,

  

  Elizabeth Fowler

  THE FLORIDA PROPERTY SHOP SALE

  (321) 463-4625

  151 N Orlando Ave Unit 101, Winter Park, FL 32789
• Explore Winter Park

• 

  

  

  /15

  $1,300 per month

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

  3060 George Mason Ave Unit 10, Winter Park, FL 32792

  Welcome to this beautifully updated 1-bedroom, 1-bath condo located in the highly desirable community of Winter Park. This charming unit features an open and inviting layout with abundant natural light, creating a warm and comfortable living space. The kitchen offers modern cabinetry and ample counter space, flowing nicely into the living and dining areas—perfect for both relaxing and

  

  Juliana Garcia Moraes

  PRISTINE INTERNATIONAL REALTY LLC

  (321) 463-7744

  3060 George Mason Ave Unit 10, Winter Park, FL 32792
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  /2

  $517,000 Sold Nov 07, 2025

  1628 Lawndale Cir, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $301/SF
  • 6 Days On Market

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  1628 Lawndale Cir, Winter Park, FL 32792
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  /2

  Est $466,838 Not Listed For Sale

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

  1596 Little Wren Ln, Winter Park, FL 32792

  1596 Little Wren Ln, Winter Park, FL 32792
• 

  

  

  /19

  $174,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  Well maintained 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The main living areas have wood laminate tile flooring and granite countertops in the kitchen. The bathrooms have been updated with sleek fixtures, modern design elements and newly painted. Nearby, you will find top rated schools and

  

  Monica Perlas

  COLDWELL BANKER REALTY

  (321) 449-2749

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
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  /26

  $1,475 per month

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

  2500 Lee Rd Unit 244, Winter Park, FL 32789

  Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

  

  Rustina Gibson

  RE/MAX VANTAGE

  (321) 252-2868

  2500 Lee Rd Unit 244, Winter Park, FL 32789
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  /2

  $130,000 Sold May 09, 2025

  1695 Lee Rd Unit E205, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  Last Sold Summary

  • 10% Below List Price
  • $148/SF
  • 25 Days On Market

  Current Estimated Value $138,534

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY

  1695 Lee Rd Unit E205, Winter Park, FL 32789
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  /2

  Est $621,236 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,790 Sq Ft

  2364 Kestrel Perch Place, Winter Park, FL 32792

  2364 Kestrel Perch Place, Winter Park, FL 32792
• 

  

  /26

  $80,000 Pending

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  7341 Daniel Webster Dr Unit 2, Winter Park, FL 32792

  Under contract-accepting backup offers. Affordable living in Winter Park. This 1-bedroom, 1-bath condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated, the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport.

  

  Rob Aponte

  REAL BROKER, LLC

  (321) 321-8355

  7341 Daniel Webster Dr Unit 2, Winter Park, FL 32792
• 

  

  /22

  $2,800 per month

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft
  • House for Rent

  3326 Young St, Winter Park, FL 32792

  Available to view and rent Sept. 7th. Adorable, Newly Renovated 4 Bedroom, 2 Bathroom home with a large fenced yard. Fresh paint and brand-new vinyl flooring throughout. All new energy-efficient windows and doors. Lots of natural light with brand and new cabinets and quartz countertops in the kitchen along with Stainless Steel Appliances. Split bedroom floor plan. The primary bedroom features a

  

  Shelley Davis

  REMI EMERSON RESIDENTIAL

  (321) 250-5179

  3326 Young St, Winter Park, FL 32792
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  /2

  $2,144,000 Sold Aug 21, 2025

  1077 N Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft
  • Built 2004

  Last Sold Summary

  • $619/SF
  • 0 Days On Market

  Current Estimated Value $2,125,651

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  Est $237,436 Not Listed For Sale

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

  1920 Woodcrest Dr Unit 10, Winter Park, FL 32792

  1920 Woodcrest Dr Unit 10, Winter Park, FL 32792
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  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
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  /15

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • House for Rent

  1891 Oglesby Ave, Winter Park, FL 32789

  Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus

  

  Paul Jimenez

  URBANISTA BROKERS

  (321) 977-5674

  1891 Oglesby Ave, Winter Park, FL 32789
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  /2

  $1,450,000 Sold Feb 27, 2025

  1101 Kenwood Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,955 Sq Ft
  • Built 2024

  Last Sold Summary

  • 23% Below List Price
  • $491/SF
  • 363 Days On Market

  Current Estimated Value $1,471,545

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1101 Kenwood Ave, Winter Park, FL 32789
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  /2

  Est $396,485 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft

  535 N Interlachen Ave Unit 101, Winter Park, FL 32789

  535 N Interlachen Ave Unit 101, Winter Park, FL 32789
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  /7

  $567,000

  • 5 Beds
  • 3 Baths
  • 2,615 Sq Ft

  7502 Waunaqua Dr, Winter Park, FL 32792

  Welcome home to Lake Waunatta Cove subdivision in Orange County. This attractive, beautifully decorated, very spacious 5 bedrooms, 3 full bathrooms, with a family room, and a very rare Basement. This roomy home is open and airy with vaulted ceilings, skylights, newer lighted ceiling fans in all bedrooms, living room, and family room, a wood burning fireplace in the living room, and a fantastic

  

  Carmen Vazquez

  REALTY TECH INC

  (689) 319-9633

  7502 Waunaqua Dr, Winter Park, FL 32792
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  /110

  $1,395 - $2,075 per month

  Oak Reserve at Winter Park

  1 - 3 Beds

  541 Oak Reserve Ln, Winter Park, FL 32792

  Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

  541 Oak Reserve Ln, Winter Park, FL 32792
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  /2

  $620,000 Sold Jul 21, 2025

  2855 Lion Heart Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,727 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $359/SF
  • 62 Days On Market

  Current Estimated Value $590,658

  Last Listing Agent Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
• 

  /2

  Est $282,797 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft

  700 Melrose Ave Unit M33, Winter Park, FL 32789

  700 Melrose Ave Unit M33, Winter Park, FL 32789
• 

  

  /38

  $299,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft

  2804 Whispering Way, Winter Park, FL 32792

  The PERFECT size!! 2 bedroom/2 bath home with an OPEN & SMART floorplan! 2025 FRESH PAINT INSIDE & OUT! 2023 NEW ROOF Beautiful vinyl floors in common areas and FRESH carpet in the bedrooms. Charming screened back porch is perfect for relaxing evenings or slow morning coffee. Or take a walk to the private LAKE to enjoy the breeze and birds. Paddleboards, kayaks, and canoes are welcome. NO

  

  Robin Leedom-Hafen

  TOP VALUE PROPERTIES LLC

  (321) 461-5800

  2804 Whispering Way, Winter Park, FL 32792
• 

  

  /18

  $1,550 per month

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

  3651 N Goldenrod Rd Unit 106, Winter Park, FL 32792

  Recently renovated first floor 2-bedroom, 2 bathroom, 840sqft condominium is located in Lancelot at Winter Park just off of University Blvd and Goldenrod Road. It's been beautifully updated with brand new 42" cabinets and new counter tops, vinyl plank floors throughout, new bathroom vanities, high efficiency AC system, window blinds and fresh paint. The newly renovated kitchen is expansive and

  Justin Recca INNOVATIVE REALTY, LLC

  3651 N Goldenrod Rd Unit 106, Winter Park, FL 32792
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  /2

  $675,000 Sold Jul 10, 2025

  1511 Chestnut Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1960

  Last Sold Summary

  • $529/SF
  • 1 Day On Market

  Current Estimated Value $659,068

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
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  /2

  Est $334,871 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft

  500 N Pennsylvania Ave Unit E, Winter Park, FL 32789

  500 N Pennsylvania Ave Unit E, Winter Park, FL 32789
• 

  

  /19

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

  7706 Country Place Unit A8, Winter Park, FL 32792
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  /75

  $1,553 - $3,581 per month

  Bainbridge Winter Park

  1 - 3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  1400 Morgan Stanley Ave, Winter Park, FL 32789
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  /2

  $280,000 Sold Jul 30, 2025

  700 Melrose Ave Unit A22, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Below List Price
  • $261/SF
  • 130 Days On Market

  Current Estimated Value $288,492

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  /2

  Est $349,575 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,204 Sq Ft

  647 Huntington Ave Unit 8, Winter Park, FL 32789

  647 Huntington Ave Unit 8, Winter Park, FL 32789
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  /44

  $386,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  1531 Lawndale Cir, Winter Park, FL 32792

  Natural light in EVERY Room!! This beautiful 3 bedroom/2 bath home features an updated kitchen finished in WALNUT-stained cabinets and GRANITE counter tops, black appliances, and a mosaic glass backsplash to catch the sunshine. Harmonious wood- look tile is both beautiful and durable. Elevated bathrooms with GRANITE countertops and updated vanities. Primary bath has dual sinks and a glass block

  

  Robin Leedom-Hafen

  TOP VALUE PROPERTIES LLC

  (321) 638-5705

  1531 Lawndale Cir, Winter Park, FL 32792
• 

  

  /11

  $1,700 per month

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Townhouse for Rent

  2523 Alexa Ct, Winter Park, FL 32792

  Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

  Jaleel Smith LA ROSA REALTY LLC

  2523 Alexa Ct, Winter Park, FL 32792
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  /2

  $1,300,000 Sold Aug 28, 2025

  1500 Mizell Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft
  • Built 1957

  Last Sold Summary

  • $564/SF
  • 2 Days On Market

  Current Estimated Value $1,270,234

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
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  /2

  Est $87,193 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft

  173 Scottsdale Square, Winter Park, FL 32792

  173 Scottsdale Square, Winter Park, FL 32792
• 

  

  /15

  $134,900

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

  1695 Lee Rd Unit B216, Winter Park, FL 32789

  Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. The end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a

  

  Martha Grasty

  RE/MAX ASSURED

  (321) 516-0992

  1695 Lee Rd Unit B216, Winter Park, FL 32789
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  /85

  $1,470 - $4,940 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
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  /2

  $374,900 Sold Oct 10, 2025

  2028 Leanne Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 1968

  Last Sold Summary

  • $244/SF
  • 9 Days On Market

  Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

  2028 Leanne Ct, Winter Park, FL 32792
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  /2

  Est $524,958 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft

  721 Roughbeard Rd, Winter Park, FL 32792

  721 Roughbeard Rd, Winter Park, FL 32792
• 

  

  /51

  $1,199,900

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome home to this beautifully renovated 4-bedroom, 2-bathroom home nestled on a desirable corner lot in the heart of Winter Park’s Timberlane Shores community. Boasting

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 599-3889

  1981 Blue Ridge Rd, Winter Park, FL 32789
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  /16

  $1,950 per month

  • 2 Beds
  • 2.5 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  7765 Fernbrook Way, Winter Park, FL 32792

  Come and see your new home!! In a great area. There are lots of updates they make this rental beautiful!! Come see all new bathrooms, new ceramic floors and completely new paint. Large rear yard for entertaining. Call today to see your new home!!!

  Jodi Nielsen OVER THE TOP REALTY LLC

  7765 Fernbrook Way, Winter Park, FL 32792
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  /2

  $750,000 Sold Jun 09, 2025

  2756 Summerfield Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Above List Price
  • $431/SF
  • 4 Days On Market

  Current Estimated Value $736,992

  Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

  2756 Summerfield Rd, Winter Park, FL 32792
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  /2

  Est $301,299 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2423 Dominica Run, Winter Park, FL 32792

  2423 Dominica Run, Winter Park, FL 32792

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