Winter Park, FL Homes

• 

  

  

  /56

  $315,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,027 Sq Ft

  5894 Shale Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. **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.** Talk about location, location, location! Welcome to this beautifully updated and well-maintained 2-bedroom, 2-bathroom, 1-car garage home in Winter Park, perfectly situated in the

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  5894 Shale Ct, Winter Park, FL 32792
• Explore Winter Park

• 

  

  

  /23

  $2,450 Per Month

  • 2 Beds
  • 2 Baths
  • 1,137 Sq Ft
  • Townhouse for Rent

  1440 Michigan Ave, Winter Park, FL 32789

  Live in the heart of Winter Park, just steps from the city’s most loved restaurants, cafés, yoga studios, and boutique shops. This beautifully renovated unit offers the perfect blend of walkability, comfort, and style. Zoned for top-rated Winter Park schools and within walking distance to a renowned private school, the location alone makes this an exceptional find. Inside, the home features a

  

  Farzana Zalil

  CHARLES RUTENBERG REALTY ORLANDO

  1440 Michigan Ave, Winter Park, FL 32789
• 

  

  /2

  $400,000

  Sold Jun 24, 2026

  721 Dunbar St, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1950

  Last Sold Summary

  • $393/SF
  • 4 Days On Market

  Current Estimated Value $475,488

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  721 Dunbar St, Winter Park, FL 32789
• 

  

  /2

  Est $594,188

  Not Listed For Sale

  2310 Cady Way, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft
  • Built 1961

  2310 Cady Way, Winter Park, FL 32792

  Last Sold Summary

  • 68 Days On Market
• 

  

  

  /46

  $475,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft

  3641 Oak Vista Ln, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to Winter Park. VIEW VIRTUAL TOUR! The Original Owner has meticulously cared for this home and the pride of ownership shines through. The real showstopper is your private outdoor oasis! Enjoy Florida’s endless sunshine in the expansive, screened-in back porch and pool area—perfect for year-round gatherings, pool parties, and quiet weekends at home.

  

  Laurie Cain

  CHARLES RUTENBERG REALTY ORLANDO

  3641 Oak Vista Ln, Winter Park, FL 32792
• 

  

  /131

  Starting at $1,295 Per Month

  • 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,

  Oak Reserve at Winter Park

  

  541 Oak Reserve Ln, Winter Park, FL 32792
• 

  /2

  $217,000

  Sold Jun 22, 2026

  2400 Dominica Run, Winter Park, FL 32792

  • 2 Beds
  • 1 Bath
  • 854 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $254/SF
  • 48 Days On Market

  Current Estimated Value $218,637

  Last Listing Agent Laura Toppin FLORIDA HOME TEAM REALTY LLC

  2400 Dominica Run, Winter Park, FL 32792
• 

  /2

  Est $2,209,076

  Not Listed For Sale

  301 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,694 Sq Ft
  • Built 1958

  301 Rippling Ln, Winter Park, FL 32789

  Last Sold Summary

  • 98 Days On Market
• 

  

  /31

  $380,000

  Pending

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  440 Cambridge Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. **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 to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  440 Cambridge Blvd, Winter Park, FL 32789
• 

  

  /34

  $1,650 Per Month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Condo for Rent

  625 Trinidad Ct Unit 625, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Move right into this CLEAN & WELL-MAINTAINED 2 BEDROOM / 2 BATH ONE-STORY CONDO offering 1,037 SF OF COMFORTABLE LIVING SPACE in the heart of WINTER PARK! This MOVE-IN READY home features a SPACIOUS LAYOUT, NATURAL LIGHT, and a functional floor plan perfect for comfortable everyday living. Enjoy a SMALL & COZY BACKYARD PATIO AREA, perfect for

  

  Nydia Marrero

  ZEN LIVING HOMES LLC

  625 Trinidad Ct Unit 625, Winter Park, FL 32792
• 

  /2

  $710,000

  Sold Jun 23, 2026

  1108 Fairway Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $423/SF
  • 82 Days On Market

  Current Estimated Value $704,612

  Last Listing Agent Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

  1108 Fairway Dr, Winter Park, FL 32792
• 

  /2

  Est $87,341

  Not Listed For Sale

  185 Scottsdale Square Unit F185, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Built 1974

  185 Scottsdale Square Unit F185, Winter Park, FL 32792

  Last Sold Summary

  • 13 Days On Market
• 

  

  /36

  $419,900

  Open Fri 2:30PM - 3PM $60K PRICE DROP

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

  3463 Arnel Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. DO NOT MISS THIS OPPORTUNITY! PRICE IMPROVEMENT + Pool Home + Paid-Off Solar Panels + No HOA in Winter Park! Welcome to this move-in-ready 3-bedroom, 2-bathroom home with approximately 1,770 square feet of living space, a 2-car garage, and a private pool, all located in the established Eastbrook community. Roof replaced in 2018, fully paid-off solar

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  3463 Arnel Dr, Winter Park, FL 32792
• 

  

  /75

  Starting at $1,443 Per Month

  • 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.

  Bainbridge Winter Park

  

  1400 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /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 $2,128,691

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  Est $510,987

  Not Listed For Sale

  2607 Verde Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,953 Sq Ft
  • Built 1968

  2607 Verde Ln, Winter Park, FL 32792

  Last Sold Summary

  • 68 Days On Market
• 

  

  /65

  $995,000

  Open Sat 12AM - 2PM $155K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  Virtually Staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. With soaring 10-foot ceilings throughout and a stately

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  1800 Magnolia Ave, Winter Park, FL 32789
• 

  

  /65

  $6,700 Per Month

  • 5 Beds
  • 4 Baths
  • 2,918 Sq Ft
  • House for Rent

  2075 Jewell Ave, Winter Park, FL 32789

  FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a

  

  Paul Jimenez

  URBANISTA BROKERS

  2075 Jewell Ave, 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

  Current Estimated Value $290,933

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
• 

  /2

  Est $900,086

  Not Listed For Sale

  1832 Magnolia Ave, Winter Park, FL 32789

  • 5 Beds
  • 3.5 Baths
  • 2,910 Sq Ft
  • Built 1954

  1832 Magnolia Ave, Winter Park, FL 32789

  Last Sold Summary

  • 25 Days On Market
• 

  

  /24

  $134,900

  $5K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the

  

  Jason Price

  RE/MAX SELECT GROUP

  1695 Lee Rd Unit E103, Winter Park, FL 32789
• 

  

  /28

  Starting at $1,599 Per Month

  • 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

  Elon Winter Park

  

  712 Nicolet 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 $609,863

  Last Listing Agent Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
• 

  /2

  Est $2,242,686

  Not Listed For Sale

  7849 Georgeann St, Winter Park, FL 32792

  • 6 Beds
  • 8 Baths
  • 4,860 Sq Ft
  • Built 2012

  7849 Georgeann St, Winter Park, FL 32792

  Last Sold Summary

  • 63 Days On Market
• 

  

  /38

  $259,900

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 17D, Winter Park, FL 32789

  Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates include: Water Heater in

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 17D, Winter Park, FL 32789
• 

  

  /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

  2500 Lee Rd Unit 244, 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 $681,645

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  Est $97,910

  Not Listed For Sale

  197 Scottsdale Square, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Built 1974

  197 Scottsdale Square, Winter Park, FL 32792

  Last Sold Summary

  • 1 Day On Market
• 

  

  /28

  $199,900

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 220, Winter Park, FL 32789

  **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 to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 220, Winter Park, FL 32789
• 

  

  /43

  Starting at $1,196 Per Month

  • 1 - 2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  Seabrook

  

  3114 Terry Brook Dr, Winter Park, FL 32792
• 

  /2

  $955,000

  Sold Feb 24, 2026

  512 Clarendon Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $338/SF
  • 21 Days On Market

  Current Estimated Value $965,643

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
• 

  /2

  Est $77,243

  Not Listed For Sale

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft
  • Built 1974

  273 Scottsdale Square Unit 273, Winter Park, FL 32792

  Last Sold Summary

  • 4 Days On Market
• 

  

  /29

  $229,000

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

  7454 Wynnewood Square Unit 188, Winter Park, FL 32792

  Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of this

  

  Manoj Patel

  APPLE REALTY

  7454 Wynnewood Square Unit 188, Winter Park, FL 32792
• 

  

  /81

  Starting at $1,877

  Total Monthly Price

  • 1 - 3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  Vintage Winter Park Apartments

  

  7490 Dwell Well Way, Winter Park, FL 32792
• 

  /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 $285,523

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

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

  /2

  Est $207,111

  Not Listed For Sale

  4944 Tangerine Ave, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft
  • Built 1973

  4944 Tangerine Ave, Winter Park, FL 32792

  Last Sold Summary

  • 97 Days On Market
• 

  

  /37

  $419,900

  $5K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  1871 Casselwood St, Winter Park, FL 32792

  Under contract-accepting backup offers. BRAND NEW ROOF 2026. Beautifully updated and move-in ready home in Winter Park featuring a BRAND NEW 2026 A/C system and Brand new 2026 water heater to be installed before closing. This 4-bedroom, 2.5-bath home with a 2-car garage offers waterproof luxury vinyl flooring, recessed lighting, updated fixtures, fireplace, screened patio, and a bright,

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  1871 Casselwood St, Winter Park, FL 32792
• 

  

  /54

  Starting at $1,294 Per Month

  • 1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

  Cranes Landing Apartments

  

  3440 N Goldenrod Rd, Winter Park, FL 32792
• 

  /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 $1,279,216

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
• 

  

  /42

  Est $1,597,726

  Not Listed For Sale

  1805 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft
  • Built 2014

  1805 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 12 Days On Market

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