28,231

Winter Park, FL Homes

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  • /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
  • /14

    $2,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,923 Sq Ft
    • House for Rent

    1956 Japonica Rd, Winter Park, FL 32792

    Welcome to 1956 Japonica Road, Winter Park, FL 32792! This beautifully updated 3-bedroom, 2-bathroom single-family home offers approximately 1,923 square feet of living space, a 2-car garage, and a spacious fenced backyard in the established Winter Woods neighborhood.Step inside to a bright, open floor plan featuring luxury vinyl plank and tile flooring throughout for a clean, modern look and

    1956 Japonica Rd, Winter Park, FL 32792
  • /2

    $510,000

    Sold Jul 21, 2026

    641 W Lyman Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2003

    Last Sold Summary

    • $455/SF
    • 12 Days On Market

    Current Estimated Value $547,708

    Last Listing Agent Ted Moseley REAL BROKER, LLC

    641 W Lyman Ave, Winter Park, FL 32789
    • /2

      Est $224,533

      Not Listed For Sale

      7468 Swallow Run Unit 38, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,578 Sq Ft
      • Built 1974
      7468 Swallow Run Unit 38, Winter Park, FL 32792

      Last Sold Summary

      • 52 Days On Market

      Last Listing Agent Chris Creegan CREEGAN GROUP

  • /66

    $3,265,000

    • 5 Beds
    • 5.5 Baths
    • 4,924 Sq Ft

    1761 Legion Dr, Winter Park, FL 32789

    One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was

    Harry Pool, III COLDWELL BANKER REALTY

    1761 Legion Dr, Winter Park, FL 32789
  • /33

    $9,900 Per Month

    • 5 Beds
    • 6 Baths
    • 2,735 Sq Ft
    • House for Rent

    1442 Palm Ave, Winter Park, FL 32789

    Gorgeous 5-bedroom /6-bathroom Luxury Estate with Guest House & Pool in Winter ParkThis stunning two-story home offers the perfect blend of luxury and comfort right in the heart of Winter Park. At the center of the home is a beautiful open kitchen outfitted with high-end appliances, solid wood cabinets, and granite countertops . A true chef’s layout that flows into the living spaces. You'll

    Magdalena Cuprys KELLER WILLIAMS REALTY AT THE PARKS

    1442 Palm Ave, Winter Park, FL 32789
  • /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 $3,087,570

    Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

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

      Not Listed For Sale

      3000 George Mason Ave Unit 1, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,108 Sq Ft
      • Built 1974
      3000 George Mason Ave Unit 1, Winter Park, FL 32792

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Nathalie Charles PREMIUM PROPERTIES R.E SERVICE

  • /45

    $205,000

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

    3371 River View Way Unit 46, Winter Park, FL 32792

    Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved

    Safiya Bourne REALTY ONE GROUP EVOLVE

    3371 River View Way Unit 46, Winter Park, FL 32792
  • /14

    $2,095 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,550 Sq Ft
    • House for Rent

    2577 Galliano Cir, Winter Park, FL 32792

    This two story 2/2.5 townhouse is in a securely located, private, gated Winter Park community and includes a private attached 1 car garage. This home features wood floors, carpet, and tile. All appliances are also included, including washer and dryer. For convenience, the laundry room is upstairs with the bedrooms. Strategically located in Winter Park, just minutes from 436, I-4, and the posh

    2577 Galliano Cir, 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 $1,068,939

    Last Listing Agent Troy Hensley BHHS FLORIDA REALTY

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

      Est $284,177

      Not Listed For Sale

      218 Balfour Dr Unit 12, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,256 Sq Ft
      • Built 1985
      218 Balfour Dr Unit 12, Winter Park, FL 32792

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Dawn Romance FANNIE HILLMAN & ASSOCIATES

  • /46

    $775,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft

    1369 Blue Stem Ln, Winter Park, FL 32792

    Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer

    He Gao U S GLORY REALTY

    1369 Blue Stem Ln, Winter Park, FL 32792
  • /17

    $2,095 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,514 Sq Ft
    • House for Rent

    2028 Albert Lee Pkwy, Winter Park, FL 32789

    This charming 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy the best of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area, a lovely kitchen, dining room, large bedrooms, a cozy

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    2028 Albert Lee Pkwy, Winter Park, FL 32789
  • /2

    $2,150,000

    Sold Aug 13, 2026

    2361 Mulbry Dr, Winter Park, FL 32789

    • 4 Beds
    • 4 Baths
    • 3,130 Sq Ft
    • Built 2026

    Last Sold Summary

    • 10% Below List Price
    • $687/SF
    • 77 Days On Market

    Current Estimated Value $2,089,254

    Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC

    2361 Mulbry Dr, Winter Park, FL 32789
    • /2

      Est $294,888

      Not Listed For Sale

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

      • 1 Bed
      • 1 Bath
      • 482 Sq Ft
      • Built 1960
      311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.

  • /26

    $399,000

    $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    1995 Canny Cove, Winter Park, FL 32792

    Welcome to Grayson Square at Winter Park by Pulte Homes. This Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe and

    Rosemary Siegler KELLER WILLIAMS ELITE PARTNERS III REALTY

    1995 Canny Cove, Winter Park, FL 32792
  • /10

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Grdyn House

    1855 Eastbrook Blvd Unit 1, Winter Park, FL 32792

    Beautiful one bedroom studio apartment for rent in Winter Park. This unit comes fully furnished and ready to move in. Rent includes water, electricity, and internet. This home is centrally located within minutes from UCF, Fullsail, restaurants, Costco, grocery stores and major highways.

    1855 Eastbrook Blvd Unit 1, 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 $377,531

    Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

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

      Est $321,334

      Not Listed For Sale

      3251 Crown Jewel Ct, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,408 Sq Ft
      • Built 2019
      3251 Crown Jewel Ct, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Erin Fang FLORIDA REALTY INVESTMENTS

  • /10

    $1,749,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,715 Sq Ft

    2525 Lafayette Ave, Winter Park, FL 32789

    Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brings contemporary design and elevated living to one of Winter Park's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and 2,715 square feet of thoughtfully designed living space, the home blends clean architectural

    Matt Tomaszewski CORCORAN PREMIER REALTY

    2525 Lafayette Ave, Winter Park, FL 32789
  • /50

    $4,677 Per Month

    • 4 Beds
    • 3 Baths
    • 2,267 Sq Ft
    • House for Rent

    350 N Phelps Ave, Winter Park, FL 32789

    Beautifully updated home in the heart of Winter Park - available November 1! Welcome to 350 North Phelps Avenue. This move-in-ready home offers four bedrooms, three full bathrooms, an open split floor plan, a bonus room with French doors, and a large fenced backyard, blending modern elegance with timeless charm. The house has a Tesla Level 2 fast charger and a state-of-the-art reverse osmosis

    AJ Lash GOYAL & DECOSTER REALTY

    350 N Phelps Ave, Winter Park, FL 32789
  • /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 $556,535

    Last Listing Agent Janie Harris UNITED REAL ESTATE PREFERRED

    1018 Bradford Dr, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      2609 Holly Rd Unit 2611, Winter Park, FL 32792

      • 4 Beds
      • 4 Baths
      • 2,382 Sq Ft
      • Built 1972
      2609 Holly Rd Unit 2611, Winter Park, FL 32792

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Natalie Rudnitsky FLORIDA CAPITAL REALTY

  • /17

    $279,900

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,197 Sq Ft

    3302 Royal St, Winter Park, FL 32792

    Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen countertops. Eat in area in kitchen.Kitchen bar opens to great room. Huge corner lot great for handyman with trailer, boat, RV or truck to park in backyard.Easy access to add on garage in backyard. Cathedral ceilings great room. NO HOA.

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    3302 Royal St, Winter Park, FL 32792
  • /15

    $1,650 Per Month

    • 2 Beds
    • 1 Bath
    • 974 Sq Ft
    • House for Rent

    2704 Tortoise Cove, Winter Park, FL 32792

    * 2 bedroom 1 bath with a 1 car garage * 924 sq. ft. * custom paint* all tile floors* stove and fridge* custom cabinets* blinds and ceiling fans* washer and dryer * large fenced in back yard* lawn care included* pet friendly homeclose to shopping, 436 and Howell Branch areaRentSmartUSA• Applications are per adult ($90). Applicant(s) must

    2704 Tortoise Cove, Winter Park, FL 32792
  • /2

    $260,000

    Sold Apr 03, 2026

    3580 Wilde Ave, Winter Park, FL 32792

    • Land
    • 35,283 Sq Ft
    • $320,988 per Acre

    Last Sold Summary

    • 340 Days On Market

    Current Estimated Value $261,729

    Last Listing Agent Gwendolen Flynn COLDWELL BANKER REALTY

    3580 Wilde Ave, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      104 Moyses Rd, Winter Park, FL 32792

      • 4 Beds
      • 4 Baths
      • 1,872 Sq Ft
      • Built 1985
      104 Moyses Rd, Winter Park, FL 32792

      Last Sold Summary

      • 43 Days On Market

      Last Listing Agent Georgina O'Bryan SIGNATURE BROKERS REALTY LLC

  • /35

    $435,000

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

    3740 Hawthorne Ln, Winter Park, FL 32792

    This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in all the bedrooms.The screened in pool is also heated and has a Heated Spa. It is conveniently located in Seminole County with a Winter Park address. It also features a ROOF that is only two years old ! You can cool off in the

    John Crea FLORIDA REALTY INVESTMENTS

    3740 Hawthorne Ln, Winter Park, FL 32792
  • /46

    $7,250 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,394 Sq Ft
    • House for Rent

    1368 Hibiscus Ave, Winter Park, FL 32789

    Discover refined living in the heart of Winter Park in this beautifully appointed 4-bedroom, 2.5-bathroom single-family pool home. Immediately to the right of the entryway, a beautiful private office provides a convenient and quiet space for working from home or studying.Filled with natural light, the home features an inviting open layout, and a spacious living area centered around a cozy

    Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

    1368 Hibiscus Ave, Winter Park, FL 32789
  • /2

    $417,100

    Sold Nov 24, 2025

    690 Osceola Ave Unit 502, Winter Park, FL 32789

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 1969

    Last Sold Summary

    • 26% Below List Price
    • $298/SF
    • 196 Days On Market

    Current Estimated Value $425,764

    Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

    690 Osceola Ave Unit 502, Winter Park, FL 32789
    • /2

      Est $449,587

      Not Listed For Sale

      1323 Merrydale Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,964 Sq Ft
      • Built 2021
      1323 Merrydale Way, Winter Park, FL 32792

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Melissa Johnson EXP REALTY LLC

  • /18

    $130,000

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 143, Winter Park, FL 32789

    It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239

    Carol Wittman PALMANO GROUP RE BROKERAGE LLC

    2500 Lee Rd Unit 143, Winter Park, FL 32789
  • /29

    $2,985 Per Month

    • 4 Beds
    • 2 Baths
    • 2,228 Sq Ft
    • House for Rent

    7606 Waunatta Ct, Winter Park, FL 32792

    Welcome to this 4-bedroom, 2-bathroom home nestled on a quiet, tree-lined cul-de-sac in Winter Park. This beauty offers a spacious and functional layout with multiple living areas and a versatile flex space that can be used as an office, playroom, or additional living area. A wood-burning fireplace adds a cozy touch to the living space too. The kitchen features granite countertops, stainless

    7606 Waunatta Ct, Winter Park, FL 32792
  • /2

    $435,800

    Sold Apr 27, 2026

    5418 Ardmore Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1980

    Last Sold Summary

    • 3% Below List Price
    • $279/SF
    • 5 Days On Market

    Current Estimated Value $436,346

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5418 Ardmore Dr, Winter Park, FL 32792
    • /2

      Not Listed For Sale

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

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

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Denise McKinley RE/MAX TOWN & COUNTRY REALTY

  • /38

    $650,000

    $49K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    1009 Lake Bell Dr, Winter Park, FL 32789

    Under contract-accepting backup offers. Rarely does a property offer this combination of waterfront living, privacy, and walkable convenience in the heart of Winter Park. Situated on nearly half an acre at the end of a quiet dead-end street, this unique property features approximately 133 feet of waterfront frontage with direct access to private Lake Bell. Adding to the property's distinctive

    Padgett McCormick KELLY PRICE & COMPANY LLC

    1009 Lake Bell Dr, Winter Park, FL 32789
  • /14

    $2,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft
    • Townhouse for Rent

    1326 Merrydale Way, Winter Park, FL 32792

    Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood. The corner townhouse has huge living room one and half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and shopping center.

    He Gao U S GLORY REALTY

    1326 Merrydale Way, Winter Park, FL 32792
  • /2

    $1,200,000

    Sold Mar 20, 2026

    950 Aragon Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,592 Sq Ft
    • Built 2020

    Last Sold Summary

    • $463/SF
    • 5 Days On Market

    Current Estimated Value $1,197,659

    Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

    950 Aragon Ave, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      3015 Aaron Burr Ave Unit 7, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,088 Sq Ft
      • Built 1974
      3015 Aaron Burr Ave Unit 7, Winter Park, FL 32792

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Liza Figueroa CONTINENTAL INVT INT'L NETWORK

Showing Results 361 - 400, Page 10 of 18

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