Winter Park, FL Homes

• 

  

  

  /42

  $440,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 2,308 Sq Ft

  2224 Shadowland Loop, Winter Park, FL 32792

  **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.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 450-7733

  2224 Shadowland Loop, Winter Park, FL 32792
• Explore Winter Park

• 

  

  

  /26

  $1,465 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) 336-5615

  2500 Lee Rd Unit 244, Winter Park, FL 32789
• 

  

  /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
• 

  

  /2

  Est $2,974,896 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 4,807 Sq Ft

  1618 Holts Grove Cir, Winter Park, FL 32789

  1618 Holts Grove Cir, Winter Park, FL 32789
• 

  

  

  /35

  $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
• 

  

  /57

  $2,900 per month

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • House for Rent

  2128 Sycamore Dr, Winter Park, FL 32789

  MOVE-IN READY! Don’t miss this fantastic opportunity to rent a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to the home’s longevity.

  

  Luis Perez Garcia

  EXP REALTY LLC

  (321) 492-0489

  2128 Sycamore Dr, Winter Park, FL 32789
• 

  /2

  $299,000 Sold Jan 15, 2026

  2804 Whispering Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1986

  Last Sold Summary

  • $277/SF
  • 4 Days On Market

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  2804 Whispering Way, Winter Park, FL 32792
• 

  /2

  Est $322,750 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789
• 

  

  /51

  $1,180,000

  • 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
• 

  

  /16

  $1,600 per month

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

  3044 Antique Oaks Cir Unit 177, Winter Park, FL 32792

  Welcome home to this fantastic 1-bedroom, 1-bath residence, conveniently located in the desirable Winter Park - Parkview Village Condo community. The home offers a comfortable and functional layout with well-proportioned living spaces, a charming kitchen with ample counter and cabinet space, and many appealing features throughout. Don’t miss this opportunity—this home won’t last long! All

  

  Robert Michael

  ROBERT MICHAEL & COMPANY INC.

  (321) 462-5169

  3044 Antique Oaks Cir Unit 177, Winter Park, FL 32792
• 

  /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 $137,112

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY

  1695 Lee Rd Unit E205, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  667 Montego Bay Ct Unit S, Winter Park, FL 32792

  667 Montego Bay Ct Unit S, Winter Park, FL 32792
• 

  

  /26

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  1952 Spring St, Winter Park, FL 32792

  Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store.The interior features

  

  Bethanne Baer

  BEAR TEAM REAL ESTATE

  (321) 517-0753

  1952 Spring St, Winter Park, FL 32792
• 

  

  /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
• 

  /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 $1,483,681

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1101 Kenwood Ave, Winter Park, FL 32789
• 

  /2

  Est $206,047 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792
• 

  

  /87

  $774,900

  • 5 Beds
  • 2.5 Baths
  • 2,646 Sq Ft

  2215 Marsh Sedge Ln, Winter Park, FL 32792

  NEW PRICE – Preserve-View Pool Retreat in a Gated, Family-Friendly Winter Park Community This is the one buyers wait for — and it’s finally here at a new price. Perfectly positioned on a premium preserve lot with no rear neighbors, this beautifully upgraded 2,645 sq ft Winter Park home offers rare privacy, peaceful green views, and your own screened in-ground pool — a combination that almost

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 463-5067

  2215 Marsh Sedge Ln, Winter Park, FL 32792
• 

  

  /131

  $1,295 - $2,025 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
• 

  /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 $2,131,857

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  Est $381,328 Not Listed For Sale

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

  7632 Aloma Pines Ct, Winter Park, FL 32792

  7632 Aloma Pines Ct, Winter Park, FL 32792
• 

  

  /33

  $200,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
• 

  

  /25

  $5,500 per month

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • House for Rent

  1815 Barker Dr, Winter Park, FL 32789

  Available for Monthly Rentals | Furnished or UnfurnishedWelcome to your luxury lake-view home in Winter Park where comfort meets style. This beautifully designed 4-bedroom / 2-bath residence features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. ( for shorter terms only 3 bedrooms, a fourth bedroom is

  Cliff Glansen FLATFEE.COM

  1815 Barker Dr, Winter Park, FL 32789
• 

  /2

  $290,000 Sold Feb 06, 2026

  1920 Carrigan Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1954

  Last Sold Summary

  • 14% Below List Price
  • $233/SF
  • 141 Days On Market

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
• 

  /2

  Est $1,135,863 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,510 Sq Ft

  1571 Oneco Ave, Winter Park, FL 32789

  1571 Oneco Ave, Winter Park, FL 32789
• 

  

  /34

  $249,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft

  2432 Barbados Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. *ACCEPTING BACKUP OFFERS* Welcome to 2432 Barbados Dr, Winter Park! This beautifully updated 2-bedroom, 2-bath home that delivers the perfect blend of comfort, privacy, and that easy Florida lifestyle. From the moment you arrive, you’ll appreciate the peace of mind that comes with a BRAND NEW roof, along with a layout that feels both functional and

  

  Robert Cozzone

  KOKOMO REALTY LLC

  (321) 467-7900

  2432 Barbados Dr, Winter Park, FL 32792
• 

  

  /75

  $1,332 - $3,469 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
• 

  /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 $593,822

  Last Listing Agent Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
• 

  /2

  Est $451,856 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,438 Sq Ft

  2112 Staunton Ave, Winter Park, FL 32789

  2112 Staunton Ave, Winter Park, FL 32789
• 

  

  /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
• 

  

  /12

  $1,400 per month

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

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
• 

  /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 $670,419

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  Est $263,836 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  2634 Cayman Way, Winter Park, FL 32792

  2634 Cayman Way, Winter Park, FL 32792
• 

  

  /19

  $225,000

  • 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
• 

  

  /28

  $1,589 - $1,609 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
• 

  /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 $281,032

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
• 

  /2

  Est $191,429 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  7420 Woodburn Ct Unit 25, Winter Park, FL 32792

  7420 Woodburn Ct Unit 25, Winter Park, FL 32792
• 

  

  /31

  $359,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  1690 Viburnum Ln, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to 1690 Viburnum Lane, a classy, 3 Bed, 2 Bath home in the heart of Winter Park! *NEW* Roof (2024), Driveway (2025), Water Heater (2026), HVAC & Double-Pane Windows (2019)! The spacious & open layout is highlighted by the large windows allowing natural light to flood in the living room area through to the kitchen. The kitchen features ample storage

  

  Julie Boyd-Elrod

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 483-3150

  1690 Viburnum Ln, Winter Park, FL 32792
• 

  

  /25

  $3,000 per month

  • 3 Beds
  • 2.5 Baths
  • 1,659 Sq Ft
  • Townhouse for Rent

  1278 Miller Ave, Winter Park, FL 32789

  Bright and beautiful END UNIT townhome in a very desirable, centrally located, WINTER PARK community. This bright, open floor plan features hardwood floors throughout the first floor, stairs and second floor hallway. Gourmet eat-in kitchen with granite countertops, center island, cherry cabinets and stainless appliances including a gas range. The enclosed patio courtyard is private and great for

  Susan Tamlin KELLER WILLIAMS REALTY AT THE PARKS

  1278 Miller Ave, Winter Park, FL 32789
• 

  /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 $1,277,442

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
• 

  /2

  Est $1,025,331 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,610 Sq Ft

  627 N Interlachen Ave Unit B, Winter Park, FL 32789

  627 N Interlachen Ave Unit B, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 18