28,401

Winter Park, FL Homes

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  • /25

    $1,350,000

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1881 Lake Spier Dr, Winter Park, FL 32789

    Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier.Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy,

    Rafael Zenke Pinhao NOVA REAL ESTATE SERVICES INC

    1881 Lake Spier Dr, Winter Park, FL 32789
  • /30

    $2,750 Per Month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 238, Winter Park, FL 32789

    Experience lakefront living at its finest in this exceptional Winter Park condo overlooking beautiful Lake Killarney. Enjoy breathtaking sunset views from your private waterfront retreat, complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers

    Alex Scures COLONIALTOWN REALTY

    151 N Orlando Ave Unit 238, Winter Park, FL 32789
  • /2

    $800,200

    Sold Oct 03, 2025

    4107 Gabriella Ln, Winter Park, FL 32792

    • 4 Beds
    • 3.5 Baths
    • 3,074 Sq Ft
    • Built 1998

    Last Sold Summary

    • 33% Below List Price
    • $260/SF
    • 112 Days On Market

    Current Estimated Value $1,014,949

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    4107 Gabriella Ln, Winter Park, FL 32792
    • /2

      Est $214,864

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 1,219 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

      Last Sold Summary

      • 44 Days On Market

  • /26

    $185,000

    $25K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft

    3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

    Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own

    Qing Lin SPRINGHILL PROPERTIES LLC

    3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
  • /12

    $1,825 Per Month

    • 2 Beds
    • 2.5 Baths
    • 960 Sq Ft
    • Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!

    303 Sandlewood Trail, Winter Park, FL 32789

    Welcome home to this beautifully renovated two-story condo in desirable Sandlewood Trails. This 2-Bedroom, 2.5 Bath condo home is ideally located in Winter Park and is one of the few condo communities where residents are close enough to bike or walk to Dommerich Elementary and Maitland Middle School.As you enter, you are welcomed by a spacious Great Room and attractive gray-toned laminate

    303 Sandlewood Trail, Winter Park, FL 32789
  • /2

    $405,500

    Sold May 28, 2026

    2834 Bright Bird Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Built 2024

    Last Sold Summary

    • 7% Below List Price
    • $213/SF
    • 108 Days On Market

    Current Estimated Value $398,920

    Last Listing Agent Irene Navarro LIFESTYLE INTERNATIONAL REALTY

    2834 Bright Bird Ln, Winter Park, FL 32792
    • /2

      Est $179,041

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 2703, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,127 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 2703, Winter Park, FL 32792

      Last Sold Summary

      • 276 Days On Market

  • /76

    $2,199,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,330 Sq Ft

    525 S Lakemont Ave, Winter Park, FL 32792

    Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfectblend of elegance, comfort, and modern design. Featuring 4 spacious bedrooms and 4 beautifully appointed bathrooms, this masterpieceshowcases custom cabinetry and closets throughout, ensuring every space is both functional and refined. The chef’s kitchen is a true

    Nicole D. Cates KELLER WILLIAMS ADVANTAGE III

    525 S Lakemont Ave, Winter Park, FL 32792
  • /44

    $2,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,312 Sq Ft
    • Townhouse for Rent

    2233 Shadowland Loop, Winter Park, FL 32792

    Welcome home to this spacious and beautifully maintained 3-bedroom, 2.5-bath townhome residence in Winter Park. Featuring modern fixtures and an open-concept layout, this home offers both comfort and functionality. The well-appointed kitchen overlooks generous living and dinning spaces, making it ideal for everyday living and entertaining. Separate sitting or living space as you enter the home.

    Yarmmys Vargas ZEN LIVING HOMES LLC

    2233 Shadowland Loop, Winter Park, FL 32792
  • /2

    $3,020,000

    Sold Oct 02, 2025

    1820 Englewood Rd, Winter Park, FL 32789

    • 5 Beds
    • 5.5 Baths
    • 4,263 Sq Ft
    • Built 2015

    Last Sold Summary

    • 8% Below List Price
    • $708/SF
    • 70 Days On Market

    Current Estimated Value $3,037,611

    Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

    1820 Englewood Rd, Winter Park, FL 32789
    • /2

      Est $398,980

      Not Listed For Sale

      620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 1,214 Sq Ft
      • Built 1986
      620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

      Last Sold Summary

      • 188 Days On Market

  • /47

    $2,800,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 3,286 Sq Ft

    660 W Morse Blvd, Winter Park, FL 32789

    Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking

    Jennifer Sloan COMPASS FLORIDA LLC

    660 W Morse Blvd, Winter Park, FL 32789
  • /19

    $2,400 Per Month

    • 3 Beds
    • 3 Baths
    • 1,471 Sq Ft
    • Townhouse for Rent

    7542 Cranes Creek Ct, Winter Park, FL 32792

    The first month’s rent is 50% off with an approved lease. This beautifully upgraded end‑unit townhome in the Cranes Creek community offers 1,471 sq ft of thoughtfully laid‑out living space with 3 bedrooms and 3 baths across two stories. Built in 2006, the home features a one‑car attached garage, vaulted ceilings, tile and carpet flooring, ceiling fans,

    7542 Cranes Creek Ct, Winter Park, FL 32792
  • /2

    $1,120,000

    Sold Jan 08, 2026

    5236 Lake Howell Rd, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 3,710 Sq Ft
    • Built 2025

    Last Sold Summary

    • 23% Below List Price
    • $302/SF
    • 129 Days On Market

    Current Estimated Value $1,066,409

    Last Listing Agent Troy Hensley BHHS FLORIDA REALTY

    5236 Lake Howell Rd, Winter Park, FL 32792
    • /2

      Est $544,293

      Not Listed For Sale

      875 Miles Ave Unit 4, Winter Park, FL 32789

      • 18 Beds
      • 18 Baths
      • 1,852 Sq Ft
      • Built 2005
      875 Miles Ave Unit 4, Winter Park, FL 32789

      Last Sold Summary

      • 123 Days On Market

  • /36

    $649,000

    $16K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,749 Sq Ft

    3135 Heartleaf Place, Winter Park, FL 32792

    Tucked away along the tree-lined streets of the desirable Lost Creek community, this beautifully updated two-story residence is truly move-in ready. Major updates include a new roof in 2022 and a new water heater in 2026, offering peace of mind for years to come. Ideally situated in sought-after Winter Park, this exceptional home also includes exclusive creek-to-lake access leading to the

    Shirley Jones COLDWELL BANKER REALTY

    3135 Heartleaf Place, Winter Park, FL 32792
  • /29

    $5,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,940 Sq Ft
    • Townhouse for Rent

    784 S Pennsylvania Ave, Winter Park, FL 32789

    Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The

    Steven Koleno BEYCOME OF FLORIDA LLC

    784 S Pennsylvania Ave, Winter Park, FL 32789
  • /2

    $423,000

    Sold Aug 07, 2025

    2812 Bright Bird Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft
    • Built 2024

    Last Sold Summary

    • 8% Below List Price
    • $222/SF
    • 87 Days On Market

    Current Estimated Value $433,720

    Last Listing Agent Jessica Snyder LPT REALTY, LLC

    2812 Bright Bird Ln, Winter Park, FL 32792
    • /2

      Est $441,067

      Not Listed For Sale

      2931 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2931 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 32 Days On Market

  • /46

    $1,725,000

    $175K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    1840 Bryan Ave, Winter Park, FL 32789

    This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    1840 Bryan Ave, Winter Park, FL 32789
  • /20

    $3,995 Per Month

    • 3 Beds
    • 3 Baths
    • 1,715 Sq Ft
    • House for Rent

    1667 Mizell Ave, Winter Park, FL 32789

    Minimum Deposit $3995. Monthly Rent $3995. Available June 1st!Contact Polina at or email to schedule your private showing. Showings are not confirmed until you speak directly with the Property Manager and a mutually agreed upon showing day/time has been established.Welcome to your dream Winter Park home! This charming 3-bedroom, 3 full bathroom gem is the epitome of comfort and

    1667 Mizell Ave, Winter Park, FL 32789
  • /2

    $760,000

    Sold Jul 17, 2025

    2159 Marsh Sedge Ln, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 2,192 Sq Ft
    • Built 2019

    Last Sold Summary

    • 4% Below List Price
    • $347/SF
    • 42 Days On Market

    Current Estimated Value $770,776

    Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

    2159 Marsh Sedge Ln, Winter Park, FL 32792
    • /2

      Est $448,761

      Not Listed For Sale

      2939 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      2939 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 8 Days On Market

  • /26

    $144,500

    $31K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 749 Sq Ft

    3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

    What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real

    Kelly Flores COLDWELL BANKER REALTY

    3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
  • /19

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1942 Conifer Ct, Winter Park, FL 32792

    Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a table with 4 chairs - picnic in your own park

    Scott Banta BLACKFIN REALTY LLC

    1942 Conifer Ct, Winter Park, FL 32792
  • /2

    $450,000

    Sold Jul 22, 2025

    1624 Little Wren Ln, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 2,308 Sq Ft
    • Built 2019

    Last Sold Summary

    • 5% Below List Price
    • $195/SF
    • 23 Days On Market

    Current Estimated Value $473,984

    Last Listing Agent Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

    1624 Little Wren Ln, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      3065 George Mason Ave Unit B, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 525 Sq Ft
      • Built 1974
      3065 George Mason Ave Unit B, Winter Park, FL 32792

      Last Sold Summary

      • 168 Days On Market

  • /36

    $450,000

    Open Sat 1PM - 4PM $30K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,669 Sq Ft

    5530 S Lake Burkett Ln, Winter Park, FL 32792

    "Price Improvement" This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story

    Mostafa Boulhanna MNT INTERNATIONAL

    5530 S Lake Burkett Ln, Winter Park, FL 32792
  • /23

    $2,300 Per Month

    • 3 Beds
    • 2 Baths
    • 1,371 Sq Ft
    • House for Rent

    2441 Fifeshire Dr, Winter Park, FL 32792

    Welcome to this charming 3BR/2BA Single Family Home in Winter Park! This cozy home is located in the heart of Winter Park, FL, and boasts a range of amenities that make it a perfect place to call home. The house features three generously sized bedrooms and two full bathrooms, with stand-in showers. The living area is enhanced with a fireplace and ceiling fans for added comfort. The fully equipped

    2441 Fifeshire Dr, Winter Park, FL 32792
  • /2

    $389,900

    Sold Mar 18, 2026

    700 Melrose Ave Unit M4, Winter Park, FL 32789

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

    Last Sold Summary

    • 1% Below List Price
    • $363/SF
    • 7 Days On Market

    Current Estimated Value $381,081

    Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

    700 Melrose Ave Unit M4, Winter Park, FL 32789
    • /2

      Est $205,758

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,120 Sq Ft
      • Built 1981
      608 Montego Bay Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 5 Days On Market

  • /29

    $399,000

    Pending
    • 4 Beds
    • 3 Baths
    • 1,359 Sq Ft

    610 Ellendale Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Discover timeless charm and modern comfort in this beautifully maintained 4-bedroom, 3-bath home built in 1957, located in one of the most highly desirable areas of Winter Park. Nestled along picturesque, tree-lined streets, this property offers the perfect blend of classic character and thoughtful updates. Step inside to find a recently remodeled kitchen

    Amy Fouraker 4 ACRE REALTY LLC

    610 Ellendale Dr, Winter Park, FL 32792
  • /22

    $2,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,674 Sq Ft
    • House for Rent

    2028 Sussex Rd, Winter Park, FL 32792

    Welcome home to Winter Park living at its finest in this beautifully updated one-story home where comfort, convenience, and charm come together. From the moment you enter, you'll notice the bright, freshly painted interior, spacious layout, and modern touches throughout—including new updated bathrooms, landscaping enhancements and brand-new stainless-steel appliances. The attached two-car garage

    Kevan Patel CENTRAL FLORIDA REALTY MANAGEMENT LLC

    2028 Sussex Rd, Winter Park, FL 32792
  • /2

    $605,000

    Sold Dec 22, 2025

    2478 Whitehall Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,256 Sq Ft
    • Built 1965

    Last Sold Summary

    • 19% Below List Price
    • $268/SF
    • 123 Days On Market

    Current Estimated Value $614,793

    Last Listing Agent Erica Magtira LPT REALTY, LLC

    2478 Whitehall Cir, Winter Park, FL 32792
    • /89

      Est $1,266,669

      Not Listed For Sale

      3629 Midiron Dr, Winter Park, FL 32789

      • 5 Beds
      • 4.5 Baths
      • 3,252 Sq Ft
      • Built 2024
      3629 Midiron Dr, Winter Park, FL 32789

      Last Sold Summary

      • 13 Days On Market

  • /27

    $114,000

    $16K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 881 Sq Ft

    1695 Lee Rd Unit E204, Winter Park, FL 32789

    Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

    Brandy Ray LOKATION

    1695 Lee Rd Unit E204, Winter Park, FL 32789
  • /19

    $1,595 Per Month

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Newly Renovated Small 2BR w/Den Guest House

    7004 Mills Rd, Winter Park, FL 32792

    This Guest house is in great condition. Just renovated last year. Rent includes Electric & Water. Unincorporated, Orange Co, Winter Park address. Shared driveway and 1 designated carport.New Stainless Steel Gas Range/Oven, Refrigerator, & Dishwasher. New Luxury Vinyl Plank Flooring and LED lighting throughout!

    7004 Mills Rd, Winter Park, FL 32792
  • /2

    $565,000

    Sold Jun 04, 2026

    1018 Bradford Dr, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 2,513 Sq Ft
    • Built 1974

    Last Sold Summary

    • 3% Above List Price
    • $225/SF
    • 4 Days On Market

    Current Estimated Value $520,231

    Last Listing Agent Janie Harris UNITED REAL ESTATE PREFERRED

    1018 Bradford Dr, Winter Park, FL 32792
    • /38

      Est $754,337

      Not Listed For Sale

      1477 Lone Feather Trail, Winter Park, FL 32792

      • 5 Beds
      • 3.5 Baths
      • 2,894 Sq Ft
      • Built 2021
      1477 Lone Feather Trail, Winter Park, FL 32792

      Last Sold Summary

      • 30 Days On Market

Showing Results 401 - 440, Page 11 of 18

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