Winter Park, FL Homes

• 

  

  

  /65

  $2,295,000

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  Update! ALL NEW Black Steel doors installed 11/2025 and windows with low e-dual pane glass to be installed 12/25 ($150k value!). Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
• 

  

  

  /30

  $1,295 - $2,690 per month

  Signal Pointe

  1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
• 

  

  

  /19

  $172,000 Sold May 23, 2025

  700 Melrose Ave Unit E24, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft
  • Built 1964

  Last Sold Summary

  • 14% Below List Price
  • $219/SF
  • 164 Days On Market

  Current Estimated Value $179,813

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
• 

  

  /2

  Est $204,344 Not Listed For Sale

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

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792
• 

  

  

  /35

  $269,000

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft

  2009 Cornell Ave, Winter Park, FL 32789

  Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Perfect as a long-term rental, short-term investment, or a future flip with strong resale appeal. Live

  Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
• 

  

  /41

  $8,500 per month

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • House for Rent

  300 Killarney Dr, Winter Park, FL 32789

  Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

  Kelly Price KELLY PRICE & COMPANY LLC

  300 Killarney Dr, Winter Park, FL 32789
• 

  /2

  $266,000 Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
• 

  /2

  Est $970,479 Not Listed For Sale

  • 3 Beds

  2726 Lake Howell Ln, Winter Park, FL 32792

  2726 Lake Howell Ln, Winter Park, FL 32792
• 

  

  /26

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  1007 Early Ave, Winter Park, FL 32789

  Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is perfect for entertaining, gardening, or simply relaxing under the Florida sun. With plenty of room

  Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789
• 

  

  /35

  $1,244 - $2,202 per month

  Venue At Winter Park

  1 - 3 Beds

  5 Autumn Breeze Way, Winter Park, FL 32792

  Come home to Venue—a community nestled in the heart of Winter Park. Venue is designed to make your living experience better than it has ever been before.When it comes to finding the perfect floor plan for your lifestyle, we have you covered. Choose from our newly renovated 1, 2, and 3-bedroom residences offering refined interior finishes and premier features that are sure to fit all of your

  5 Autumn Breeze Way, Winter Park, FL 32792
• 

  /2

  $600,000 Sold Apr 10, 2025

  7531 Lodge Pole Trail, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,141 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $280/SF
  • 20 Days On Market

  Current Estimated Value $584,509

  Last Listing Agent Austin Cummings NEXTDWELL

  7531 Lodge Pole Trail, Winter Park, FL 32792
• 

  /2

  Est $308,514 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft

  5879 Marble Ct, Winter Park, FL 32792

  5879 Marble Ct, Winter Park, FL 32792
• 

  

  /22

  $298,000

  • 2 Beds
  • 2 Baths
  • 893 Sq Ft

  609 Gallery Dr Unit 204, Winter Park, FL 32792

  IMMACULATE !!!!! Close to everything from this quiet 2nd floor 2/2 condo at THE GALLERY in Winter Park! Safe 3-minute walk to Publix, restaurants, movies and Crealde Art Center via gated back entrance to complex, Starbucks just outside the other way. Stainless steel and granite, dishwasher, built-in microwave. High ceilings in LR/DR and master. Walk-in closet in master. Screened balcony overlooks

  Olga Ray A2Z REALTY GROUP

  609 Gallery Dr Unit 204, Winter Park, FL 32792
• 

  

  /29

  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft
  • House for Rent

  2809 Bower Rd, Winter Park, FL 32792

  Step into timeless style and everyday comfort in this beautifully maintained mid-century modern home, featuring 3 spacious bedrooms, 2 updated bathrooms, and an inviting backyard heated pool perfect for relaxing or entertaining.Inside, you’ll find stunning terrazzo floors that flow throughout the living spaces, adding both durability and classic charm. The cozy wood-burning fireplace creates

  Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

  2809 Bower Rd, Winter Park, FL 32792
• 

  /2

  $245,900 Sold Aug 11, 2025

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,132 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $217/SF
  • 2 Days On Market

  Current Estimated Value $250,811

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
• 

  

  /8

  Est $951,243 Not Listed For Sale

  • 1 Bed

  470 W Comstock Ave, Winter Park, FL 32789

  470 W Comstock Ave, Winter Park, FL 32789
• 

  

  /26

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
• 

  

  /27

  $1,236 - $2,799 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
• 

  /2

  $725,000 Sold May 13, 2025

  1570 Grove Terrace, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft
  • Built 1991

  Last Sold Summary

  • $436/SF

  Current Estimated Value $732,584

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1570 Grove Terrace, Winter Park, FL 32789
• 

  

  /41

  Est $1,562,041 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,287 Sq Ft

  1005 S Pennsylvania Ave, Winter Park, FL 32789

  1005 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /33

  $150,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

  Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

  SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
• 

  

  /9

  $2,100 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  367 Holt Ave, Winter Park, FL 32789

  Live steps away from everything Winter Park and all it has to give! Ideally located just around the corner from Rollins College and two blocks from the shops, restaurants, and cafes of Park Avenue. Perfect for College, professionals, or anyone who wants to enjoy the walkable lifestyle of this sought-after neighborhood. The owner is responsible for landscaping, the water bill, and pest control.

  Michelle Ingrassia LPT REALTY, LLC

  367 Holt Ave, Winter Park, FL 32789
• 

  

  /49

  $1,650,000 Sold Mar 12, 2025

  1781 Goodrich Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,701 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $611/SF
  • 88 Days On Market

  Current Estimated Value $1,662,226

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  1781 Goodrich Ave, Winter Park, FL 32789
• 

  /2

  Est $746,510 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1166 Wildmeadow Run, Winter Park, FL 32792

  1166 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /27

  $380,000

  • 3 Beds
  • 2.5 Baths
  • 1,787 Sq Ft

  7506 Aloma Pines Ct, Winter Park, FL 32792

  Aloma Trails is a gated townhome community, built by Ryan Homes, located in Winter Park. Conveniently you'll find it's location between UCF and Rollins College. Seminole County is known for its highly rated public schools. Only minutes from Park Avenue shopping and restaurants. This END UNIT townhome features 3 bedrooms, 2 1/2 bathrooms, and a TWO car garage. Granite countertops, 42” upper

  Corey Van Dyke HOMEVEST REALTY

  7506 Aloma Pines Ct, Winter Park, FL 32792
• 

  

  /35

  $976 - $1,373 per month

  Golden Oaks

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
• 

  /2

  $1,300,000 Sold Sep 22, 2025

  1371 Lyndale Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $479/SF
  • 8 Days On Market

  Current Estimated Value $1,283,867

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
• 

  /2

  Est $440,077 Not Listed For Sale

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

  1935 Canny Cove, Winter Park, FL 32792

  1935 Canny Cove, Winter Park, FL 32792
• 

  

  /57

  $999,950

  • 4 Beds
  • 2.5 Baths
  • 3,121 Sq Ft

  1444 Pelican Bay Trail, Winter Park, FL 32792

  Seller Financing Available--Attractive Terms--Potentially Below Market Rate. A True Gem on the Lake! If you've been dreaming of owning a lakefront property with a Winter Park address, this is your chance! This stunning 4-bedroom, 2.5-bathroom home in the tranquil Pelican Bay Subdivision is move-in ready and full of charm. As you approach, you'll be greeted by lush landscaping. Step through the

  Jacob Hara TRANSCEND REALTY

  1444 Pelican Bay Trail, Winter Park, FL 32792
• 

  

  /34

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,763 Sq Ft
  • House for Rent

  2862 Kings Deer Rd, Winter Park, FL 32792

  Discover this beautifully fully renovated 3-bedroom, 2-bathroom home in the heart of Winter Park. Every detail has been thoughtfully updated, offering modern finishes, an open layout, and comfortable living spaces perfect for both relaxing and entertaining. Enjoy an unbeatable location just minutes from UCF, Full Sail University, and the highly sought-after Park Avenue shopping and dining

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  2862 Kings Deer Rd, Winter Park, FL 32792
• 

  /2

  $525,000 Sold Dec 26, 2024

  5111 Lake Howell Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,278 Sq Ft
  • Built 1957

  Last Sold Summary

  • 12% Below List Price
  • $230/SF
  • 94 Days On Market

  Current Estimated Value $531,348

  Last Listing Agent Don Sprenkel 1ST CLASS REAL ESTATE LEGACY GROUP

  5111 Lake Howell Rd, Winter Park, FL 32792
• 

  /2

  Est $750,668 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft

  1421 Wooddale Ave, Winter Park, FL 32789

  1421 Wooddale Ave, Winter Park, FL 32789
• 

  

  /34

  $550,000

  • 3 Beds
  • 3 Baths
  • 1,602 Sq Ft

  7641 Village Green Dr, Winter Park, FL 32792

  Welcome to this inviting single-family home at 7641 Village Green Dr in desirable Winter Park, FL. This well-maintained residence features 3 bedrooms and 3 full bathrooms across approximately 1,958 square feet of living space -- perfect for comfortable daily living and entertaining. Set on a generous lot of nearly 0.30 acres, the property includes a private fenced-in backyard with an in-ground

  Jannett Marten Compass Florida, LLC

  7641 Village Green Dr, Winter Park, FL 32792
• 

  

  /35

  $1,325 - $2,620 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
• 

  /2

  $421,700 Sold May 29, 2025

  1189 Lazy Hollow Place, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft
  • Built 1984

  Last Sold Summary

  • $277/SF
  • 7 Days On Market

  Current Estimated Value $421,930

  Last Listing Agent Virginia Silberstein ORLANDO EXPERT REALTY LLC

  1189 Lazy Hollow Place, Winter Park, FL 32792
• 

  /2

  Est $319,383 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft

  5804 Shale Ct, Winter Park, FL 32792

  5804 Shale Ct, Winter Park, FL 32792
• 

  

  /27

  $145,000

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792

  Townhouse 2 bedroom 2.5 bath, both bathrooms on the second floor are remodeled. The Townhome is rent $1,600. The unit is located in Winter Park Area and is close to the shopping and dining. It is also close to public transportation. HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

  Daiana Garcia Medrano LA ROSA REALTY ORLANDO LLC

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792
• 

  

  /49

  $9,000 per month

  • 4 Beds
  • 5 Baths
  • 3,478 Sq Ft
  • House for Rent

  1350 Lyndale Blvd, Winter Park, FL 32789

  Gorgeous, Custom & recently renovated! This home features 4 bedrooms, 3 full baths & 2 half baths. Spacious, light & bright with 10’ ceilings, Brazilian cherry floors, and a gourmet kitchen. The kitchen is a chef's dream and perfect for entertaining. It boasts natural wood cabinets, large center island, dual fuel six-burner range, wine fridge and a built-in refrigerator. It overlooks a casual

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1350 Lyndale Blvd, Winter Park, FL 32789
• 

  /2

  $279,000 Sold Aug 11, 2025

  Unlisted Address

  • 2 Beds
  • 2.5 Baths
  • 1,186 Sq Ft
  • Built 1981

  Last Sold Summary

  • $235/SF
  • 4 Days On Market

  Current Estimated Value $278,337

  Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

  Unlisted Address
• 

  

  /15

  Est $120,870 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  192 Scottsdale Square Unit 192, Winter Park, FL 32792

  192 Scottsdale Square Unit 192, Winter Park, FL 32792

Showing Results 281 - 320, Page 8 of 18