28,402

Winter Park, FL Homes

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  • /22

    $190,000

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

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

    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. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax and enjoy the

    Steven Pugh EXP REALTY LLC

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
  • /6

    $3,000

    Total Monthly Price

    • 2 Beds
    • 2.5 Baths
    • 1,100 Sq Ft
    • Townhouse for Rent

    1144 Washington Ave, Winter Park, FL 32789

    Fully remodeled 2 BR, 2.5 BA townhouse in a wonderful location of Winter Park. 1 block from the Winter Park Tennis Center, walking distance to Rollins College and Park Ave. The townhouse is tucked into a quiet neighborhood known as The Quarters. New Kitchen, Appliances, cabinets and fixtures. New carpeting, and hard wood floors throughout. All three bathrooms have been remodel with new vanities

    1144 Washington Ave, Winter Park, FL 32789
  • /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 $883,096

    Last Listing Agent Jenn Carlisle LPT REALTY, LLC

    737 N Capen Ave, Winter Park, FL 32789
    • /32

      Est $203,071

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,119 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792

      Last Sold Summary

      • 35 Days On Market

  • /42

    $598,000

    $26K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,620 Sq Ft

    1822 Yorkshire Dr, Winter Park, FL 32792

    Virtually Staged. PRICE REDUCTION...priced to move! Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the

    MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

    1822 Yorkshire Dr, Winter Park, FL 32792
  • /35

    Starting at $1,058 Per Month

    • Studio - 3 Beds

    300 Jamestown Dr, Winter Park, FL 32792

    Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

    Carlton Arms of Winter Park

    300 Jamestown Dr, 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 $631,911

    Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

    352 Cambridge Blvd, Winter Park, FL 32789
    • /42

      Est $691,474

      Not Listed For Sale

      311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,574 Sq Ft
      • Built 1960
      311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

      Last Sold Summary

      • 75 Days On Market

  • /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
  • /30

    Starting at $1,972

    Total Monthly Price

    • 1 - 2 Beds

    3045 Aloma Ave, Winter Park, FL 32792

    Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar-all with an attentive team at your

    Rosalia Winter Park 55+ Active Adult Community

    3045 Aloma Ave, Winter Park, FL 32792
  • /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 $327,985

    Last Listing Agent Kim Goldin KELLER WILLIAMS ADVANTAGE REALTY

    7529 Village Green Dr, Winter Park, FL 32792
    • /30

      Est $1,308,458

      Not Listed For Sale

      345 W Welbourne Ave Unit 104, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,734 Sq Ft
      • Built 2009
      345 W Welbourne Ave Unit 104, Winter Park, FL 32789

      Last Sold Summary

      • 3 Days On Market

  • /59

    $695,000

    $55K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,968 Sq Ft

    744 Cornwall Rd, Winter Park, FL 32792

    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 recreational opportunities, including a refreshing

    Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

    744 Cornwall Rd, Winter Park, FL 32792
  • /27

    Starting at $1,154

    Total Monthly Price

    • Studio - 3 Beds

    1701 Lee Rd, Winter Park, FL 32789

    There's no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the

    Westmount at Winter Park

    1701 Lee Rd, Winter Park, FL 32789
  • /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 $1,084,074

    Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

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

      Est $972,329

      Not Listed For Sale

      1245 Wisconsin Ave, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 2,610 Sq Ft
      • Built 2013
      1245 Wisconsin Ave, Winter Park, FL 32789

      Last Sold Summary

      • 51 Days On Market

  • /51

    $2,650,000

    New Construction $150K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,553 Sq Ft

    541 W Canton Ave, Winter Park, FL 32789

    Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

    Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

    541 W Canton Ave, Winter Park, FL 32789
  • /30

    Starting at $1,275 Per Month

    • 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

    Signal Pointe

    2500 Howell Branch Rd, Winter Park, FL 32792
  • /2

    $223,000

    Sold Oct 30, 2025

    1378 Chilean Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1960

    Last Sold Summary

    • $168/SF

    Current Estimated Value $363,791

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

    1378 Chilean Ln, Winter Park, FL 32792
    • /36

      Est $189,976

      Not Listed For Sale

      2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,018 Sq Ft
      • Built 1984
      2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /31

    $474,000

    $21K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,596 Sq Ft

    2803 Banchory Rd, Winter Park, FL 32792

    Located in Winter Park Pines, this 4-bedroom, 2-bath home offers a warm, flexible layout with comfortable living spaces and everyday functionality throughout. With 1,596 square feet, the home provides room to gather, relax, entertain, and adapt to changing needs over time. Inside, the floor plan includes both a living room and a separate family room, creating useful separation for daily life. One

    Melissa Johnson EXP REALTY LLC

    2803 Banchory Rd, Winter Park, FL 32792
  • /35

    Starting at $1,141 Per Month

    • 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,

    Golden Oaks

    7701 Acorn Woods Cir, Winter Park, FL 32792
  • /2

    $1,575,000

    Sold Aug 14, 2025

    1394 Grove Terrace, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 2,958 Sq Ft
    • Built 2002

    Last Sold Summary

    • $532/SF
    • 5 Days On Market

    Current Estimated Value $1,595,861

    Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

    1394 Grove Terrace, Winter Park, FL 32789
    • /2

      Est $139,967

      Not Listed For Sale

      289 Lewfield Cir, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 678 Sq Ft
      • Built 1973
      289 Lewfield Cir, Winter Park, FL 32792

      Last Sold Summary

      • 58 Days On Market

  • /77

    $1,995,000

    • 4 Beds
    • 3 Baths
    • 3,696 Sq Ft

    2261 Mulbry Dr, Winter Park, FL 32789

    Welcome to this extraordinary, better-than-new residence in the heart of Winter Park, a thoughtfully designed and impeccably upgraded custom, one-owner home built in 2020 that effortlessly blends timeless elegance with today’s most sought-after luxury features. Situated on a wonderfully deep, private lot with no HOA, this remarkable two-story home was crafted for elevated everyday living,

    Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

    2261 Mulbry Dr, Winter Park, FL 32789
  • /24

    Starting at $1,481 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

    $625,000

    Sold Sep 29, 2025

    3759 Kinsley Place, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 2,251 Sq Ft
    • Built 1988

    Last Sold Summary

    • 11% Below List Price
    • $278/SF
    • 50 Days On Market

    Current Estimated Value $645,881

    Last Listing Agent Drew Belani COMPASS FLORIDA LLC

    3759 Kinsley Place, Winter Park, FL 32792
    • /39

      Est $222,506

      Not Listed For Sale

      220 Lewfield Cir, Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,300 Sq Ft
      • Built 1973
      220 Lewfield Cir, Winter Park, FL 32792

      Last Sold Summary

      • 109 Days On Market

  • /50

    $1,800,000

    $200K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,065 Sq Ft

    723 Symonds Ave, Winter Park, FL 32789

    Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    723 Symonds Ave, Winter Park, FL 32789
  • /20

    Starting at $1,357 Per Month

    • 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

    ARIUM Winter Park

    3250 Bishop Park Dr, Winter Park, FL 32792
  • /2

    $285,000

    Sold Sep 24, 2025

    7777 Fernbrook Way, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1985

    Last Sold Summary

    • 4% Above List Price
    • $261/SF
    • 3 Days On Market

    Current Estimated Value $287,744

    Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

    7777 Fernbrook Way, Winter Park, FL 32792
    • /21

      Not Listed For Sale

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

      • 2 Beds
      • 2 Baths
      • 1,267 Sq Ft
      • Built 1974
      7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

      Last Sold Summary

      • 81 Days On Market

  • /22

    $184,900

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 222, Winter Park, FL 32789

    Stop searching—your ultimate lifestyle upgrade is here. Perfectly positioned on the tranquil waters of Lake Killarney, this stunning residence offers the rare opportunity to secure a premier waterfront address in the heart of coveted Winter Park. This home is defined by an open, airy layout and sleek, durable engineered wood flooring that flows throughout the living space, creating a seamless

    Christine Bouchard HOMESMART

    2500 Lee Rd Unit 222, Winter Park, FL 32789
  • /13

    Starting at $3,200 Per Month

    • 2 Beds

    1886 Demetree Dr, Winter Park, FL 32789

    Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter ParkWelcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals.This thoughtfully

    Waterbridge Subdivision

    1886 Demetree Dr, Winter Park, FL 32789
  • /2

    $675,000

    Sold Mar 16, 2026

    620 Darcey Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 2,075 Sq Ft
    • Built 1967

    Last Sold Summary

    • 9% Below List Price
    • $325/SF
    • 14 Days On Market

    Current Estimated Value $685,935

    Last Listing Agent Jason Asa LPT REALTY, LLC

    620 Darcey Dr, Winter Park, FL 32792
    • /24

      Est $195,320

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 987 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 2210, Winter Park, FL 32792

      Last Sold Summary

      • 0 Days On Market

  • /28

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,872 Sq Ft

    7522 Aloma Pines Ct, Winter Park, FL 32792

    Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along

    Vildan Nigro RIVA REALTY GROUP LLC

    7522 Aloma Pines Ct, Winter Park, FL 32792
  • /20

    $2,445 Per Month

    • 5 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    3628 Datura Ct, 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 $2589.90. That covers your base rent, $2445.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    3628 Datura Ct, Winter Park, FL 32792
  • /2

    $315,000

    Sold Jan 01, 2026

    615 Warrenton Rd, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,221 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $258/SF
    • 50 Days On Market

    Current Estimated Value $315,457

    Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

    615 Warrenton Rd, Winter Park, FL 32792
    • /2

      Est $1,529,956

      Not Listed For Sale

      101 S New York Ave Unit 303, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,174 Sq Ft
      • Built 2009
      101 S New York Ave Unit 303, Winter Park, FL 32789

      Last Sold Summary

      • 129 Days On Market

Showing Results 121 - 160, Page 4 of 18

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