Winter Park, FL Homes

• 

  

  

  /51

  $1,595,000

  • 5 Beds
  • 3.5 Baths
  • 3,292 Sq Ft

  1453 Lyndale Blvd, Winter Park, FL 32789

  Welcome to this updated and architecturally unique 5-bedroom, 3.5-bathroom custom home, offering 3,292 square feet of luxury living in the heart of Winter Park. Step inside and you’re immediately greeted by gleaming porcelain tile floors, smooth modern non-textured walls, and soaring ceilings that create a light and airy feel. The spacious living room features custom wall details, crown molding,

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1453 Lyndale Blvd, Winter Park, FL 32789
• 

  

  

  /19

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  1509 Springtime Loop, Winter Park, FL 32792

  This beautiful 3 bedroom, 2 bath home is located in the desirable Autumn Glen neighborhood in Winter Park. Newly Renovated bathrooms, ceramic tile floors for the whole house and freshly painted interior. The entire house has new rooms doors, closets doors and new blinds. Vaulted ceilings throughout the home with skylights. Nice recently renovated kitchen with Stainless steel appliances. Beautiful

  1509 Springtime Loop, Winter Park, FL 32792
• 

  

  /2

  $2,550,000 Sold Aug 15, 2025

  • 4,338 Sq Ft
  • $588/SF
  • 82 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2008

  1400 Place Picardy, Winter Park, FL 32789

  1440 Place Picardy, Winter Park, FLCustom-Built Elegance with Timeless FinishesA custom-built residence completed in 2008 that blends classic craftsmanship with luxurious, modern living. From the moment you step inside, the superior millwork, solid hardwood floors, and elegant design details make a lasting impression.The gourmet kitchen is a chef’s dream, featuring marble

  Jennifer King CORCORAN PREMIER REALTY

  1400 Place Picardy, Winter Park, FL 32789
• 

  

  /2

  Est $458,930 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  2719 Bright Bird Ln, Winter Park, FL 32792

  2719 Bright Bird Ln, Winter Park, FL 32792
• 

  

  

  /29

  $455,000

  • 5 Beds
  • 3 Baths
  • 1,945 Sq Ft

  3642 Periwinkle Dr, Winter Park, FL 32792

  Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income.The main home features a freshly painted interior and exterior, new LVP flooring

  John Hwangbo HONEST REAL ESTATE COMPANY

  3642 Periwinkle Dr, Winter Park, FL 32792
• 

  

  /30

  $2,250 per month

  • 1 Bed
  • 1.5 Baths
  • 915 Sq Ft
  • Condo for Rent

  690 Osceola Ave Unit 407, Winter Park, FL 32789

  Welcome to breathtaking waterfront living at Lake Virginia Condo community in Winter Park. Gorgeous water views from every room in this fourth floor, 915 sqft, 1-bedroom, 1.5-bathroom end unit overlooking Lake Virginia and the Lake Virginia-Osceola Canal. Step inside and immediately you’re greeted by Lake Virginia through the large floor to ceiling sliders. The roomy bedroom and bathroom provide

  Delaney Heidenescher CREEGAN GROUP

  690 Osceola Ave Unit 407, Winter Park, FL 32789
• 

  /2

  $100,000 Sold Aug 15, 2025

  • 1,356 Sq Ft
  • $74/SF
  • 156 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  7340 Daniel Webster Dr Unit 7, Winter Park, FL 32792

  Price Reduction-Stop by and view this condo located in a prime location. First floor unit-No CARPET-Tile and newer laminate flooring (installed in 2021) that adds a sleek, modern touch throughout. The kitchen comes fully equipped with updated appliances, including a microwave and dishwasher, both replaced in 2021, making meal prep and clean-up a breeze.Recent upgrades include a brand-new

  Marina Heath EXP REALTY LLC

  7340 Daniel Webster Dr Unit 7, Winter Park, FL 32792
• 

  

  /18

  Est $461,627 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2790 Bright Bird Ln, Winter Park, FL 32792

  2790 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /25

  $339,000

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

  1920 Carrigan Ave, Winter Park, FL 32792

  Welcome home to 1920 Carrigan Avenue! Located in the highly desirable Winter Park section of Seminole County, this beautifully updated 3-bedroom, 2-bathroom home sits on an oversized 0.22-acre lot with mature trees and no HOA. Inside, you’ll find a modern and inviting space featuring remodeled bathrooms, an updated kitchen with stainless steel appliances, stylish laminate flooring, and fresh

  Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
• 

  

  /11

  $4,350 per month

  • 4 Beds
  • 3.5 Baths
  • 2,503 Sq Ft
  • House for Rent

  2804 Dike Rd, Winter Park, FL 32792

  This house centrally located between Winter Park, Winter Springs and very accessible but secluded at the same time. The main areas featured in section 1 is the house which is for rent and section 2 could additionally be rented as needed.

  2804 Dike Rd, Winter Park, FL 32792
• 

  /2

  $1,050,000 Sold Aug 14, 2025

  • 1,492 Sq Ft
  • $704/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  2250 Forrest Rd, Winter Park, FL 32789

  Incredible location in the heart of Winter Park, situated on an oversized lot, on a brick street, close to Park Avenue.

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  2250 Forrest Rd, Winter Park, FL 32789
• 

  

  /39

  Est $852,901 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1770 Mondrian Cir, Winter Park, FL 32789

  1770 Mondrian Cir, Winter Park, FL 32789
• 

  

  /48

  $689,000

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

  1174 Wildmeadow Run, Winter Park, FL 32792

  Welcome to Hawks Crest – Winter Park’s premier gated, resort-style community! This beautifully appointed home features a timeless terracotta tile roof, elegant plantation shutters, and durable tile flooring throughout the main living areas and carpet in the bedrooms. Designed with comfort and convenience in mind, the home is wheelchair accessible and already prepped for solar panels and security

  Jen Marks EXP REALTY LLC

  1174 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /9

  $3,500 per month

  • 6 Beds
  • 3 Baths
  • 2,722 Sq Ft
  • House for Rent

  1288 Michigan Ave, Winter Park, FL 32789

  5 bedrooms, 3 bathrooms super close to Winter Park Village and conveniently located close to all Winter Park activities. Lots of remodeling!! No garage, large treed backyard!

  Eric Weigand CQ ORLANDO REALTY INC

  1288 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $690,000 Sold Aug 14, 2025

  • 1,841 Sq Ft
  • $375/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  2433 Whitehall Cir, Winter Park, FL 32792

  FANTASTIC UPDATED AND EXPANDED WINTER PARK HOME JUST LISTED! Tucked away in a quiet, highly sought-after neighborhood and zoned for desired Winter Park schools, this home is one of the nicest and most rare opportunities to hit the market in some time! Beautifully and tastefully re-imagined, renovated and expanded in 2022! Located in one of the best specific locations in the neighborhood!

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2433 Whitehall Cir, Winter Park, FL 32792
• 

  

  /44

  Est $1,052,224 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1768 Mondrian Cir, Winter Park, FL 32789

  1768 Mondrian Cir, Winter Park, FL 32789
• 

  

  /57

  $749,900

  • 4 Beds
  • 3.5 Baths
  • 2,582 Sq Ft

  1465 Lone Feather Trail, Winter Park, FL 32792

  Stunning 4-Bedroom Taylor Morrison Home in a Premier Winter Park Community! Welcome to this beautifully appointed 4-bedroom, 3.5-bath, 2,582 sq. ft., nestled in one of Winter Park’s most desirable gated communities with resort-style amenities. Built just 4 years ago, this residence blends modern elegance with comfort and convenience.Step inside to find an open-concept design with luxury

  Chris Watts THE TEAM REAL ESTATE GROUP INC

  1465 Lone Feather Trail, Winter Park, FL 32792
• 

  

  /25

  $1,201 - $2,977 per month

  ARIUM Winter Park

  1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
• 

  /2

  $1,575,000 Sold Aug 14, 2025

  • 2,958 Sq Ft
  • $532/SF
  • 5 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2002

  1394 Grove Terrace, Winter Park, FL 32789

  Beautiful Sylvan Lake Shores Mediterranean home. Ideally located in quintessential Old Winter Park with its tree lined, brick streets that surround Lake Mizell. This 4 bedroom 3 1⁄2 bath, plus office home features timeless architectural features such as classic wide molding, repeated archways and a custom ironwork stairway. The soaring 10 foot ceilings accentuate the classic feel of this elegant

  Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
• 

  

  /32

  Not Listed For Sale

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792
• 

  

  /39

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft

  5346 Cypress Dr, Winter Park, FL 32792

  Impeccably cared for and ready for its next chapter, this Winter Park home blends timeless charm with essential modern updates. The property features a premium paver driveway, double-pane windows, offering both curb appeal and efficiency. Inside, the home has been kept in clean original condition, reflecting years of consistent maintenance and pride of ownership. Major systems have been

  Kristy Kesterson KELLER WILLIAMS ADVANTAGE REALTY

  5346 Cypress Dr, Winter Park, FL 32792
• 

  

  /15

  $1,850 per month

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

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

  Welcome to your dream home in the heart of Winter Park! This beautifully updated 2-bedroom, 2-bath condo offers the perfect blend of style, comfort, and convenience. Just steps away from Mead Gardens, fantastic restaurants, cozy coffee shops, vibrant cocktail bars, and so much more, you’ll love the walkable and bikeable lifestyle. Park Avenue is only minutes away, making it easy to enjoy

  Joe Devlin DEVLIN INVESTORS & ASSOCIATES

  1250 S Denning Dr Unit 105, Winter Park, FL 32789
• 

  /2

  $2,800,000 Sold Aug 14, 2025

  • 3,932 Sq Ft
  • $712/SF
  • 57 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2024

  1891 Lake Spier Dr, Winter Park, FL 32789

  Welcome to a rare opportunity to embrace the Winter Park lakefront lifestyle in this custom-built masterpiece that blends timeless architecture with relaxed coastal sophistication. Crafted by Hanson Custom Homes and thoughtfully curated by Kate Voss Interiors, this modern coastal residence offers the perfect setting for those who value both refined living and a vibrant, connected lifestyle. With

  Mike Derenthal LPT REALTY, LLC

  1891 Lake Spier Dr, Winter Park, FL 32789
• 

  /2

  Est $112,206 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 786 Sq Ft

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792
• 

  

  /39

  $320,000

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

  1871 Casselwood St, Winter Park, FL 32792

  Welcome home to this charming townhouse with great potential, offering the perfect blend of comfort and convenience. Featuring a spacious open floor plan, and private patio perfect for gatherings. This residence is ideal for both relaxing and entertaining. Located close to shopping, dining, this home provides easy access to everything you need. A MUST SEE... MAKE YOUR APPOINTMENT TODAY!!!

  Nicholas Zervos ERA GRIZZARD REAL ESTATE

  1871 Casselwood St, Winter Park, FL 32792
• 

  

  /20

  $4,945 per month

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Condo for Rent

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

  Welcome to this cozy and inviting 2-bedroom, 1-bathroom home, perfect for couples, small families, or solo travelers eager to explore Central Florida. Situated just 3 miles from Downtown Orlando, 12 miles from Universal Studios, and 8 miles from Disney, this location is unbeatable.This charming property features two spacious queen bedrooms, a full bathroom with a walk-in shower, and a working

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
• 

  /2

  $493,000 Sold Aug 14, 2025

  • 1,191 Sq Ft
  • $414/SF
  • 67 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1952

  2327 Mulbry Dr, Winter Park, FL 32789

  Charming Mid-Century Ranch in Prime Winter Park Location – Steps from Blue Jacket Park. Ideally situated in the heart of Winter Park and just a stone’s throw from Baldwin Park’s beloved Blue Jacket Park, this tastefully updated 3 BEDROOM, PLUS OFFICE, 1.5 BATHROOM home blends timeless character with modern touches. Enjoy a freshly painted interior, stainless steel appliances, indoor laundry, and

  Charlie Peterson KELLER WILLIAMS HERITAGE REALTY

  2327 Mulbry Dr, Winter Park, FL 32789
• 

  

  /18

  Est $444,430 Not Listed For Sale

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

  2778 Bright Bird Ln, Winter Park, FL 32792

  2778 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /45

  $440,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 2,179 Sq Ft

  1362 Tierra Cir, Winter Park, FL 32792

  Welcome to this unique 4-bedroom ranch-style home in the heart of Winter Park! This residence offers flexibility and comfort for today’s lifestyle. The converted two-car garage has been transformed into an additional bedroom with separate entrance, perfect for guests or an in-law suite. Inside, the kitchen flows seamlessly into the bright family room. Entertain with ease in the large dining and

  John Muccigrosso RE/MAX 200 REALTY

  1362 Tierra Cir, Winter Park, FL 32792
• 

  

  /31

  $2,000 per month

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

  640 N Park Ave Unit 4, Winter Park, FL 32789

  MORE PICTURES TO COME! Welcome to the heart of Winter Park! This beautiful first floor condo is located in one of the town’s most iconic buildings, Park Aire. Nestled between the famous Winter Park Golf Course and downtown area where shopping and dining are a must! Other close by attractions include, the Morse Museum, Central Park, Hannibal Square and Scenic Boat Tours. This updated condo

  Flory Clark UNITED REAL ESTATE PREFERRED

  640 N Park Ave Unit 4, Winter Park, FL 32789
• 

  /2

  $749,000 Sold Aug 13, 2025

  • 2,509 Sq Ft
  • $299/SF
  • 52 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1967

  627 Darcey Dr, Winter Park, FL 32792

  Nestled in the heart of sought-after Winter Park, this beautifully updated 4-bedroom, 2-bathroom home offers 2,509 square feet of versatile living space designed for comfort, functionality, and style. Perfect for families or anyone needing room to grow, the home features multiple living areas including a formal living room with a bay window and elegant shutters, a cozy family room, a bright

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  627 Darcey Dr, Winter Park, FL 32792
• 

  

  /29

  Est $560,352 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
• 

  

  /31

  $210,000

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

  7457 Belle River Ct Unit 12, Winter Park, FL 32792

  Location, Location, Location! Welcome to this charming Winter Park townhome. The first floor features a convenient half bath and an in-unit laundry area. Upstairs, you’ll find two spacious primary suites, each with its own private bathroom. Enjoy outdoor living with a private back patio and take advantage of the community pool just steps away. Perfectly situated for comfort and lifestyle! Enjoy

  Jasmin Cabral LIFESTYLE INTERNATIONAL REALTY

  7457 Belle River Ct Unit 12, Winter Park, FL 32792
• 

  

  /13

  $3,425 per month

  • 3 Beds
  • 2 Baths
  • 1,416 Sq Ft
  • House for Rent

  5351 Cypress Dr, 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 $3569.90. That covers your base rent, $3425.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5351 Cypress Dr, Winter Park, FL 32792
• 

  /2

  $391,250 Sold Aug 13, 2025

  • 2,096 Sq Ft
  • $187/SF
  • 71 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  1985 Japonica Rd, Winter Park, FL 32792

  JUST REDUCED!!! Move-In Ready Evergreen Park Home with 4 Bedrooms 2 Bathrooms and a 2 Car Garage with a Pool on an Oversized Lot in this much Sought-After Quiet Neighborhood. Home has a NEW ROOF and a NEW AC (2023). Home has a wonderful layout with a split floorplan, separate family and living rooms, dual fireplace with engineered wood and ceramic tile throughout. Kitchen has plenty of countertop

  Aaron Mighty MIGHTY REALTY INC

  1985 Japonica Rd, Winter Park, FL 32792
• 

  

  /16

  Est $196,728 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
• 

  

  /25

  $215,000

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

  607 Saint Johns Ct Unit 607, Winter Park, FL 32792

  This stylish condo lives more like a townhouse, offering two stories, a private patio, and a fenced yard for added privacy and outdoor enjoyment.Inside, you’ll find an open floor plan with vaulted ceilings and a cozy wood-burning fireplace. The updated kitchen and bathrooms pair perfectly with ceramic tile and luxury vinyl flooring throughout—no carpet in sight! A versatile first-floor

  Allison Day RE/MAX TOWN & COUNTRY REALTY

  607 Saint Johns Ct Unit 607, Winter Park, FL 32792
• 

  

  /15

  $2,050 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
• 

  /2

  $145,000 Sold Aug 13, 2025

  • 802 Sq Ft
  • $181/SF
  • 68 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  7352 Swallow Run, Winter Park, FL 32792

  Spacious 2nd floor condo in quiet community! You will absolutely fall in love with this newly renovated 2 bedroom 2 bathroom condo retreat! The open floor plan is great for entertaining family and friends, while the split bedroom layout offers privacy. The modern kitchen features white shaker cabinetry, stainless steel appliances, pendant lighting, built-in wine storage with wine glass rack,

  Ashley Quandt LEERDAM PROPERTIES INC.

  7352 Swallow Run, Winter Park, FL 32792
• 

  

  /10

  Est $443,244 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

Showing Results 321 - 360, Page 9 of 18