28,232

Winter Park, FL Homes

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  • /51

    $2,495,000

    New Construction $305K 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
  • /29

    Starting at $1,209

    Total Monthly Price

    • 1 - 3 Beds

    3733 N Goldenrod Rd, Winter Park, FL 32792

    Welcome home to Atlas at Winter Park!

    Atlas at Winter Park

    3733 N Goldenrod 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 $363,220

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

    1378 Chilean Ln, Winter Park, FL 32792
    • /2

      Est $397,566

      Not Listed For Sale

      7602 Glenmoor Ln, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,687 Sq Ft
      • Built 1984
      7602 Glenmoor Ln, Winter Park, FL 32792

      Last Sold Summary

      • 126 Days On Market

      Last Listing Agent Uzi Husain KELLER WILLIAMS REALTY AT THE PARKS

  • /5

    $138,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 776 Sq Ft

    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792

    Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
  • /35

    Starting at $1,475 Per Month

    • Studio - 3 Beds

    433 W New England Ave, Winter Park, FL 32789

    We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

    Hannibal Square

    433 W New England Ave, Winter Park, FL 32789
  • /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 $645,484

    Last Listing Agent Drew Belani COMPASS FLORIDA LLC

    3759 Kinsley Place, Winter Park, FL 32792
    • /2

      Est $592,757

      Not Listed For Sale

      236 N Ranger Blvd, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,844 Sq Ft
      • Built 1963
      236 N Ranger Blvd, Winter Park, FL 32792

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Ramses Misel Trillos EXP REALTY LLC

  • /31

    $474,000

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

    2803 Banchory Rd, Winter Park, FL 32792

    Under contract-accepting backup offers. 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,

    Melissa Johnson EXP REALTY LLC

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

    Starting at $1,067 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

    $475,000

    Sold Jul 17, 2026

    3641 Oak Vista Ln, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,645 Sq Ft
    • Built 1981

    Last Sold Summary

    • $289/SF
    • 7 Days On Market

    Current Estimated Value $473,714

    Last Listing Agent Laurie Cain CHARLES RUTENBERG REALTY ORLANDO

    3641 Oak Vista Ln, Winter Park, FL 32792
    • /2

      Est $1,250,134

      Not Listed For Sale

      171 Cortland Ave, Winter Park, FL 32789

      • 2 Beds
      • 2 Baths
      • 1,683 Sq Ft
      • Built 1940
      171 Cortland Ave, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jerry Oller FANNIE HILLMAN & ASSOCIATES

  • /35

    $295,000

    Open Sat 10AM - 12PM
    • 2 Beds
    • 2 Baths
    • 1,544 Sq Ft

    2302 Barbados Dr, Winter Park, FL 32792

    Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment and major roadways. This spacious end-unit home offers 2 bedrooms, 2 full bathrooms and approximately 1,544 square feet of living space, plus an enclosed 260-square-foot sunroom, providing nearly 1,800 square feet of usable living area.Originally designed as a 3-bedroom

    George Freelove KELLER WILLIAMS REALTY AT THE PARKS

    2302 Barbados Dr, Winter Park, FL 32792
  • /12

    $4,354

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • House for Rent

    1915 Taylor Ave, Winter Park, FL 32792

    This probably looks like one of those Miami-style inflated listings; except the home is in Orlando.You may be thinking, "This isn't exactly a mansion with every luxury amenity under the sun."You may be thinking, "For this kind of rent, shouldn't I be in some luxury condo with a resort-style pool, full gym, concierge, clubhouse, bar, pool tables, cabanas, fire pits, restaurants

    1915 Taylor Ave, 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 $285,035

    Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

    7777 Fernbrook Way, Winter Park, FL 32792
    • /2

      Est $371,209

      Not Listed For Sale

      1767 Meadowgold Ln, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1987
      1767 Meadowgold Ln, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kyle Clark RE/MAX TOWN & COUNTRY REALTY

  • /50

    $1,700,000

    $300K 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
  • /30

    Starting at $2,097

    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

    $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 $323,975

    Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

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

      Est $270,451

      Not Listed For Sale

      2517 Windward Way, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,070 Sq Ft
      • Built 1975
      2517 Windward Way, Winter Park, FL 32792

      Last Sold Summary

      • 15 Days On Market

      Last Listing Agent Sheila Mathews COLDWELL BANKER REALTY

  • /2

    $180,000

    • 1 Bed
    • 1 Bath
    • 638 Sq Ft

    1695 Lee Rd Unit D107, Winter Park, FL 32789

    Don't miss out the great opportunity to own a unit in the heart of Winter Park Area. A perfect primary or secondary residence or investment home. Waterfall Cove is a great community with spacious pool, playground and lots of lush landscaping. Easy access to Major Highways a minute from I-4, bike away from Downtown Winter Park, close to major theme parks, major shopping area, restaurant, movie

    Hoover Yap PRIMESTATE REALTY, INC.

    1695 Lee Rd Unit D107, Winter Park, FL 32789
  • /27

    Starting at $1,276

    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

    $699,000

    Sold Jul 09, 2026

    676 Dunblane Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,827 Sq Ft
    • Built 1962

    Last Sold Summary

    • 7% Below List Price
    • $383/SF
    • 172 Days On Market

    Current Estimated Value $689,250

    Last Listing Agent Emma Kaplan BALDWIN PARK REALTY LLC

    676 Dunblane Dr, Winter Park, FL 32792
    • /2

      Est $241,333

      Not Listed For Sale

      2480 Tahoe Cir, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,173 Sq Ft
      • Built 1980
      2480 Tahoe Cir, Winter Park, FL 32792

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Michael Wood UNITED REAL ESTATE PREFERRED

  • /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
  • /30

    Starting at $1,225 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

    $875,000

    Sold Sep 10, 2026

    1600 Oneco Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,538 Sq Ft
    • Built 1969

    Last Sold Summary

    • $345/SF
    • 0 Days On Market

    Current Estimated Value $867,046

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

    1600 Oneco Ave, Winter Park, FL 32789
    • /2

      Est $270,469

      Not Listed For Sale

      2426 Windward Way, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 932 Sq Ft
      • Built 1976
      2426 Windward Way, Winter Park, FL 32792

      Last Sold Summary

      • 50 Days On Market

      Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY

  • /10

    $1,250,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,525 Sq Ft

    1870 Staunton Ave, Winter Park, FL 32789

    Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction,

    Vinny Lay COMPASS FLORIDA LLC

    1870 Staunton Ave, Winter Park, FL 32789
  • /35

    Starting at $925 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

    $325,000

    Sold Dec 30, 2025

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

    • 2 Beds
    • 2 Baths
    • 1,160 Sq Ft
    • Built 1986

    Last Sold Summary

    • 7% Below List Price
    • $280/SF
    • 6 Days On Market

    Current Estimated Value $321,938

    Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

    520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
    • /2

      Est $1,300,304

      Not Listed For Sale

      1500 Mizell Ave, Winter Park, FL 32789

      • 4 Beds
      • 3 Baths
      • 2,303 Sq Ft
      • Built 1957
      1500 Mizell Ave, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  • /27

    $389,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2017 Canny Cove, Winter Park, FL 32792

    BUYER INCENTIVE! Nearly-New 2023 Pulte Townhome • 3BD/2.5BA + Garage • Quartz Counters • Rate Buydown AvailableImagine owning a beautifully maintained, nearly-new Pulte townhome in the heart of Winter Park. Built in 2023 and still covered by the transferable Pulte 10-year structural warranty, this home offers modern design, energy efficiency, and peace of mind. The seller is offering a rate

    Janny Goulder KELLER WILLIAMS WINTER PARK

    2017 Canny Cove, Winter Park, FL 32792
  • /20

    Starting at $1,358 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

    $517,000

    Sold Nov 07, 2025

    1628 Lawndale Cir, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 1,716 Sq Ft
    • Built 1984

    Last Sold Summary

    • 6% Below List Price
    • $301/SF
    • 6 Days On Market

    Current Estimated Value $517,519

    Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

    1628 Lawndale Cir, Winter Park, FL 32792
    • /2

      Est $955,612

      Not Listed For Sale

      1764 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,265 Sq Ft
      • Built 2024
      1764 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  • /21

    $562,000

    $88K PRICE DROP Pending
    • 4 Beds
    • 3 Baths
    • 1,778 Sq Ft

    5233 Lake Howell Rd, Winter Park, FL 32792

    Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your

    Miranda Cady CADENCE LIFESTYLE REAL ESTATE

    5233 Lake Howell Rd, Winter Park, FL 32792
  • /20

    $2,395 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 $2539.90. That covers your base rent, $2395.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

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

    $779,000

    Sold Aug 31, 2026

    1826 Banchory Rd, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 2,391 Sq Ft
    • Built 1962

    Last Sold Summary

    • $326/SF
    • 0 Days On Market

    Current Estimated Value $864,499

    Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY

    1826 Banchory Rd, Winter Park, FL 32789
    • /42

      Est $1,630,476

      Not Listed For Sale

      1805 Harland Park Dr, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 3,052 Sq Ft
      • Built 2014
      1805 Harland Park Dr, Winter Park, FL 32789

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

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