28,232

Winter Park, FL Homes

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  • /20

    $426,000

    $74K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,376 Sq Ft

    501 Heritage Blvd, Winter Park, FL 32792

    Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality.A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights

    Bernardo Carrasquel B EXP REALTY LLC

    501 Heritage Blvd, Winter Park, FL 32792
  • /50

    Starting at $1,107 Per Month

    • 1 - 3 Beds

    349 Scottsdale Square, Winter Park, FL 32792

    This community boasts a prime location that effortlessly combines charm with convenience. Nestled in a well established neighborhood, it offers residents easy access to an array of amenities, including local shops, cafes, and restaurants, all just a short stroll away. The mature landscaping creates a tranquil atmosphere, inviting residents to take leisurely walks and enjoy the scenery.

    Winter Park Woods Apartments

    349 Scottsdale Square, Winter Park, FL 32792
  • /2

    $1,590,000

    Sold Mar 06, 2026

    1166 Oaks Blvd, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,860 Sq Ft
    • Built 2018

    Last Sold Summary

    • 12% Below List Price
    • $556/SF
    • 153 Days On Market

    Current Estimated Value $1,620,787

    Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

    1166 Oaks Blvd, Winter Park, FL 32789
    • /2

      Est $664,737

      Not Listed For Sale

      402 Saint Dunstan Way, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,779 Sq Ft
      • Built 1964
      402 Saint Dunstan Way, Winter Park, FL 32792

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  • /86

    $739,000

    • 2 Beds
    • 2 Baths
    • 1,311 Sq Ft

    250 Carolina Ave Unit 205B, Winter Park, FL 32789

    Discover the ease of Winter Park living in the highly desirable gated community of Park West, ideally located just steps from Park Avenue. From this exceptional location, charming boutiques, sidewalk cafés, award-winning restaurants, and the popular weekly farmers market are all within easy reach—giving you the freedom to leave the car behind and enjoy everything Park Avenue has to offer. This

    Troy Hensley BHHS FLORIDA REALTY

    250 Carolina Ave Unit 205B, Winter Park, FL 32789
  • /17

    Starting at $1,399 Per Month

    • 1 - 3 Beds

    1743 Semoran Cir N, Winter Park, FL 32792

    Sapphire Winter Park offers the ultimate luxury oasis as a sanctuary of good living tucked away on 26-acres of lush landscaping. Located in the city of Winter Park, Florida, select apartments offer washer & dryer, modern white shaker cabinets, quartz countertops, contemporary light & utility fixtures, stainless-steel appliances and vinyl wood floors in main areas with carpet in each bedroom. Our

    Sapphire Winter Park

    1743 Semoran Cir N, Winter Park, FL 32792
  • /2

    $390,000

    Sold Jun 11, 2026

    7517 Laurel Springs Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • Built 1972

    Last Sold Summary

    • 2% Below List Price
    • $232/SF
    • 4 Days On Market

    Current Estimated Value $394,430

    Last Listing Agent Jay Patterson KELLER WILLIAMS ADVANTAGE REALTY

    7517 Laurel Springs Dr, Winter Park, FL 32792
    • /2

      Est $462,553

      Not Listed For Sale

      2151 Conifer Ave, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,806 Sq Ft
      • Built 1970
      2151 Conifer Ave, Winter Park, FL 32792

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Denise Korrey KORR REALTY CORP

  • /49

    $1,049,900

    $149K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,652 Sq Ft

    1448 Lake Florence Way, Winter Park, FL 32792

    Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in builder and custom upgrades. Ideally located just 2 miles from Target and Costco, near the 417, and next to highly regarded private schools including Trinity Preparatory School, this home offers luxury and convenience in an

    Abby Nelson RE/MAX 200 REALTY

    1448 Lake Florence Way, Winter Park, FL 32792
  • /35

    Starting at $1,279 Per Month

    • 1 - 3 Beds

    3207 Rosebud Ln, Winter Park, FL 32792

    These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

    Summerlin at Winter Park Apartments

    3207 Rosebud Ln, Winter Park, FL 32792
  • /2

    $321,000

    Sold Jul 08, 2026

    5894 Shale Ct, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Built 1985

    Last Sold Summary

    • 2% Above List Price
    • $313/SF
    • 11 Days On Market

    Current Estimated Value $280,005

    Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    5894 Shale Ct, Winter Park, FL 32792
    • /2

      Est $331,409

      Not Listed For Sale

      7642 Glenmoor Ln, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,217 Sq Ft
      • Built 1984
      7642 Glenmoor Ln, Winter Park, FL 32792

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

  • /44

    $925,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 2,093 Sq Ft

    1927 S Lakemont Ave, Winter Park, FL 32792

    Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter Park's premier builder, Meridian Homes. Nestled between the peaceful shores of Lake Spier and Lake Compton, this intimate enclave of just 10 luxury townhomes offers architecturally distinctive modern contemporary design and low maintenance living in one of Winter Park's most

    Abby Green IAD REAL ESTATE

    1927 S Lakemont Ave, Winter Park, FL 32792
  • /18

    Starting at $1,330 Per Month

    • Studio - 2 Beds

    311 N Knowles Ave, Winter Park, FL 32789

    Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

    Park East - Park Knowles Apartments

    311 N Knowles Ave, Winter Park, FL 32789
  • /2

    $2,050,000

    Sold Apr 30, 2026

    1205 Mayfield Ave, Winter Park, FL 32789

    • Land
    • 23,958 Sq Ft
    • $3,727,273 per Acre

    Last Sold Summary

    • 18% Below List Price
    • 89 Days On Market

    Current Estimated Value $2,147,768

    Last Listing Agent Abby Nelson RE/MAX 200 REALTY

    1205 Mayfield Ave, Winter Park, FL 32789
    • /2

      Est $369,602

      Not Listed For Sale

      2008 Nottingdale Ln, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,278 Sq Ft
      • Built 1980
      2008 Nottingdale Ln, Winter Park, FL 32792

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Robert Bretz, PA EXP REALTY LLC

  • /71

    $685,000

    $15K PRICE DROP Under Contract
    • 4 Beds
    • 3 Baths
    • 2,702 Sq Ft

    3114 Heartleaf Place, Winter Park, FL 32792

    Under contract-accepting backup offers. Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection

    Nadia Kurakin CHAMPION HOMES

    3114 Heartleaf Place, Winter Park, FL 32792
  • /36

    Starting at $1,349 Per Month

    • Studio - 3 Beds

    2000 Village Ln, Winter Park, FL 32792

    5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

    The Taylor at Winter Park

    2000 Village Ln, Winter Park, FL 32792
  • /2

    $261,000

    Sold May 13, 2026

    1500 Gay Rd Unit 8D, Winter Park, FL 32789

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

    Last Sold Summary

    • 2% Below List Price
    • $254/SF
    • 19 Days On Market

    Current Estimated Value $260,275

    Last Listing Agent Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

    1500 Gay Rd Unit 8D, Winter Park, FL 32789
    • /2

      Est $665,171

      Not Listed For Sale

      1536 Golfside Dr, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,888 Sq Ft
      • Built 1980
      1536 Golfside Dr, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  • /54

    $1,300,000

    • 3 Beds
    • 2.5 Baths
    • 1,873 Sq Ft

    1922 Hammerlin Ave, Winter Park, FL 32789

    WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end design, high-end finishes and an exceptional lifestyle location near East End Market, Baldwin Park, Audubon Park and all of Winter Parks charm. Behind the private gated courtyard and modern fencing, discover a thoughtfully

    Felicia Donateli PALM PROPERTIES OF CF, INC.

    1922 Hammerlin Ave, Winter Park, FL 32789
  • /23

    Starting at $1,324 Per Month

    • 1 - 2 Beds

    3935 Sutton Place Blvd, Winter Park, FL 32792

    Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

    Alvista Winter Park

    3935 Sutton Place Blvd, Winter Park, FL 32792
  • /2

    $440,000

    Sold Jan 29, 2026

    1621 Puritan Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,765 Sq Ft
    • Built 1963

    Last Sold Summary

    • 12% Below List Price
    • $249/SF
    • 342 Days On Market

    Current Estimated Value $434,472

    Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

    1621 Puritan Ave, Winter Park, FL 32792
    • /2

      Est $670,779

      Not Listed For Sale

      1640 Cypress Point Ln, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,704 Sq Ft
      • Built 1980
      1640 Cypress Point Ln, Winter Park, FL 32792

      Last Sold Summary

      • 23 Days On Market

      Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  • /22

    $180,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792

    PRICE IMPROVEMENT! TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. A NEW A/C SYSTEM INSTALLED IN 2026 adds extra peace of mind for the next owner. Step inside to find a bright and airy living and dining area with sliding

    Steven Pugh EXP REALTY LLC

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
  • /35

    Starting at $1,592

    Total Monthly Price

    • 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

    Stonecastle Apartment Homes

    2015 New Stonecastle Terrace, Winter Park, FL 32792
  • /2

    $800,000

    Sold Apr 30, 2026

    737 N Capen Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft
    • Built 2021

    Last Sold Summary

    • 13% Below List Price
    • $415/SF
    • 99 Days On Market

    Current Estimated Value $832,601

    Last Listing Agent Jenn Carlisle LPT REALTY, LLC

    737 N Capen Ave, Winter Park, FL 32789
    • /2

      Est $840,270

      Not Listed For Sale

      1421 Sunset Dr, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 1,672 Sq Ft
      • Built 1977
      1421 Sunset Dr, Winter Park, FL 32789

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  • /26

    $249,900

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

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792

    Under contract-accepting backup offers. THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESSELED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES

    Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792
  • /16

    Starting at $1,599 Per Month

    • 2 Beds

    4704 Lucier Ct, Winter Park, FL 32792

    *Restricted units only*App and Admin special for only $175!Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

    The Vista at Winter Park

    4704 Lucier Ct, Winter Park, FL 32792
  • /2

    $640,000

    Sold Jun 05, 2026

    352 Cambridge Blvd, Winter Park, FL 32789

    • 5 Beds
    • 3 Baths
    • 1,917 Sq Ft
    • Built 1920

    Last Sold Summary

    • 2% Below List Price
    • $334/SF
    • 46 Days On Market

    Current Estimated Value $639,165

    Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

    352 Cambridge Blvd, Winter Park, FL 32789
    • /2

      Est $386,744

      Not Listed For Sale

      1041 Manchester Cir, Winter Park, FL 32792

      • 4 Beds
      • 2 Baths
      • 1,678 Sq Ft
      • Built 1977
      1041 Manchester Cir, Winter Park, FL 32792

      Last Sold Summary

      • 147 Days On Market

      Last Listing Agent Bob Paulson COLDWELL BANKER REALTY

  • /26

    $520,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,774 Sq Ft

    1905 Bonanza Ct, Winter Park, FL 32792

    Florida living at its best! Welcome to this beautifully appointed single-story home, ideally situated on a quiet roundabout and offering the perfect blend of comfortable living and standout outdoor space. Inside, you’ll find a stylish modern kitchen featuring QUARTZ COUNTERTOPS, sleek cabinetry, STAINLESS STEEL APPLIANCES, and a beautiful backsplash, complemented by luxury vinyl flooring and

    Bailey Briscoe ORCHARD BROKERAGE, LLC

    1905 Bonanza Ct, Winter Park, FL 32792
  • /35

    Starting at $1,642 Per Month

    • Studio - 3 Beds

    1874 Harmon Ave, Winter Park, FL 32789

    Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

    Berkshire Winter Park

    1874 Harmon Ave, Winter Park, FL 32789
  • /2

    $340,000

    Sold May 15, 2026

    7529 Village Green Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,575 Sq Ft
    • Built 1972

    Last Sold Summary

    • 5% Above List Price
    • $216/SF
    • 4 Days On Market

    Current Estimated Value $340,444

    Last Listing Agent Kim Goldin KELLER WILLIAMS ADVANTAGE REALTY

    7529 Village Green Dr, Winter Park, FL 32792
    • /2

      Est $916,185

      Not Listed For Sale

      3011 Temple Trail, Winter Park, FL 32789

      • 5 Beds
      • 2.5 Baths
      • 2,406 Sq Ft
      • Built 1965
      3011 Temple Trail, Winter Park, FL 32789

      Last Sold Summary

      • 83 Days On Market

      Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  • /59

    $630,000

    $120K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 1,968 Sq Ft

    744 Cornwall Rd, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by

    Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

    744 Cornwall Rd, Winter Park, FL 32792
  • /11

    Starting at $1,504

    Total Monthly Price

    • 1 - 2 Beds

    7502 Sun Key Blvd, Winter Park, FL 32792

    Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

    Solis at Winter Park

    7502 Sun Key Blvd, Winter Park, FL 32792
  • /2

    $1,088,000

    Sold Jan 30, 2026

    1092 Wading Waters Cir, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 3,057 Sq Ft
    • Built 2019

    Last Sold Summary

    • 9% Below List Price
    • $356/SF
    • 60 Days On Market

    Current Estimated Value $1,092,563

    Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

    1092 Wading Waters Cir, Winter Park, FL 32792
    • /2

      Est $393,114

      Not Listed For Sale

      5234 Ohio St, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,226 Sq Ft
      • Built 1973
      5234 Ohio St, Winter Park, FL 32792

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

Showing Results 81 - 120, Page 3 of 18

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