28,231

Winter Park, FL Homes

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  • /11

    $159,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

    Just Reduced $10k!! Priced to sell, already rented, perfect for investor buyer. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. Stainless Appliances, including Refrigerator, Microwave, Flat top Range/oven, Dishwasher, full size front load washer and Dryer in Laundry Closet. Community features a

    Hitesh Khatri CFRP REALTY LLC

    3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
  • /30

    $2,300

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft
    • Condo for Rent

    151 N Orlando Ave Unit 262, Winter Park, FL 32789

    Modern furnished waterfront 1bdrm/1bath condo rental, move-in ready. Fully renovated, equipped kitchen with smooth stone countertops, stainless steel-appliances (Fridge/Stove/Dishwasher), a sleek under-mount sink, and minimalist cabinetry. In unit full-size stacked washer & dryer, walk-in closet. Remote control blinds throughout, including blackout one in the bedroom.Fresh, modern interior

    151 N Orlando Ave Unit 262, Winter Park, FL 32789
  • /2

    $530,000

    Sold Aug 31, 2026

    2552 Brookshire Ave, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,314 Sq Ft
    • Built 1959

    Last Sold Summary

    • $403/SF
    • 3 Days On Market

    Current Estimated Value $528,189

    Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

    2552 Brookshire Ave, Winter Park, FL 32792
    • /2

      Est $702,624

      Not Listed For Sale

      2602 Winter Park Rd, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,966 Sq Ft
      • Built 1975
      2602 Winter Park Rd, Winter Park, FL 32789

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Brandon Thompson KELLER WILLIAMS ADVANTAGE III

  • /53

    $1,725,000

    • 4 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    1840 Bryan Ave, Winter Park, FL 32789

    Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community. Offering nearly 3,800 sq. ft. of sophisticated yet comfortable living space, this 4-bedroom, 3.5-bath residence combines timeless architectural details—including soaring vaulted ceilings, crown molding, and dark hardwood

    Jennifer Draper REAL BROKER, LLC

    1840 Bryan Ave, Winter Park, FL 32789
  • /42

    $2,950 Per Month

    • 4 Beds
    • 3 Baths
    • 2,151 Sq Ft
    • House for Rent

    7033 Easter St, Winter Park, FL 32792

    This active, single-family rental listing at 7033 Easter St, Winter Park, FL 32792. This spacious residence features a 4-bedroom, 3-bathroom split floor plan spanning 2,151 heated square feet, situated on an expansive, fenced 0.76-acre lot down a quiet, unpaved lane. The exterior highlights include a private, screen-enclosed swimming pool (with chemical and pool maintenance fully covered by the

    Tab Bish LLC REAL BROKER, LLC

    7033 Easter St, Winter Park, FL 32792
  • /2

    $1,905,000

    Sold Apr 10, 2026

    501 Henkel Cir, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,746 Sq Ft
    • Built 2009

    Last Sold Summary

    • 4% Above List Price
    • $509/SF
    • 4 Days On Market

    Current Estimated Value $1,956,262

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    501 Henkel Cir, Winter Park, FL 32789
    • /22

      Est $5,790,046

      Not Listed For Sale

      300 S Interlachen Ave Unit 601, Winter Park, FL 32789

      • 4 Beds
      • 4.5 Baths
      • 5,430 Sq Ft
      • Built 2005
      300 S Interlachen Ave Unit 601, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

      Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  • /67

    $4,900,000

    Pending
    • 5 Beds
    • 5.5 Baths
    • 4,961 Sq Ft

    1180 Via Lugano, Winter Park, FL 32789

    A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue,

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    1180 Via Lugano, Winter Park, FL 32789
  • /15

    $1,350 Per Month

    • 1 Bed
    • 1 Bath
    • 763 Sq Ft
    • House for Rent

    4874 Tangerine Ave, Winter Park, FL 32792

    Discover comfort and convenience in this charming 1-bedroom, 1-bathroom condo. The unit comes equipped with a stove and refrigerator, perfect for your culinary needs. Enjoy the cozy ambiance provided by carpeted floors and the elegant touch of wood cabinets. This property is part of a well-maintained community featuring a refreshing pool, ideal for relaxing and unwinding. Don’t miss out on this

    4874 Tangerine Ave, Winter Park, FL 32792
  • /2

    $489,000

    Sold Jun 17, 2026

    5236 Albert Dr, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,843 Sq Ft
    • Built 1979

    Last Sold Summary

    • $265/SF
    • 3 Days On Market

    Current Estimated Value $488,813

    Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

    5236 Albert Dr, Winter Park, FL 32792
    • /2

      Est $2,778,937

      Not Listed For Sale

      1737 Lookout Landing Cir, Winter Park, FL 32789

      • 5 Beds
      • 5.5 Baths
      • 5,066 Sq Ft
      • Built 2013
      1737 Lookout Landing Cir, Winter Park, FL 32789

      Last Sold Summary

      • 232 Days On Market

      Last Listing Agent Amy Wilson KELLER WILLIAMS REALTY AT THE PARKS

  • /83

    $1,800,000

    $389K PRICE DROP
    • 5 Beds
    • 4 Baths
    • 3,382 Sq Ft

    2032 Kimbrace Place, Winter Park, FL 32792

    A PRIVATE BALINESE RESORT IN THE HEART OF WINTER PARK5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park AvenueWelcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled in one of Winter Park's most desirable neighborhoods, just minutes from the boutiques, fine dining, and cultural attractions of Park Avenue, this custom

    Rob Sassos SIMPLICITY: A RE BROKERAGE CO

    2032 Kimbrace Place, Winter Park, FL 32792
  • /14

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 802 Sq Ft
    • Townhouse for Rent

    1618 Indiana Ave Unit 1616, Winter Park, FL 32789

    Freshly reimagined and ready for its next resident, this newly remodeled duplex in the heart of Winter Park pairs modern updates with an unbeatable central location. Offering two bedrooms, one bathroom, and 805 square feet of thoughtfully arranged living space, this half of a charming duplex feels both smart and welcoming from the moment you step inside. This duplex has been recently updated from

    Brock Stocksett HOMEVEST REALTY

    1618 Indiana Ave Unit 1616, Winter Park, FL 32789
  • /2

    $399,900

    Sold Oct 08, 2025

    7553 Laurel Springs Dr, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft
    • Built 1973

    Last Sold Summary

    • $338/SF
    • 20 Days On Market

    Current Estimated Value $404,058

    Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

    7553 Laurel Springs Dr, Winter Park, FL 32792
    • /42

      Est $745,661

      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

      Last Listing Agent Scott Garstka CHARLES RUTENBERG REALTY ORLANDO

  • /37

    $599,000

    $96K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,669 Sq Ft

    1707 Harmon Ave, Winter Park, FL 32789

    A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborhood of Orwin Manor in Winter Park. Rich in character and thoughtfully updated throughout, this exceptional residence seamlessly combines the elegance of its original architecture with the comfort and sophistication of modern

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    1707 Harmon Ave, Winter Park, FL 32789
  • /16

    $1,250 Per Month

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • House for Rent

    2500 Lee Rd, Winter Park, FL 32789

    Serene scenes surround the Lakeside Manor, absolutely beautiful through all the seasons. Waterfront Complex on Lake Killarney. Found on the ground floor, the unit opens up to the living room and dining room. Tile is laid all throughout the property, easy to clean and maintain! The bedroom and bathroom are toward the back of the unit. The bedroom features two closets! The community amenities

    2500 Lee Rd, Winter Park, FL 32789
  • /2

    $420,000

    Sold Jan 15, 2026

    1847 Azalea Ave, Winter Park, FL 32789

    • 4 Beds
    • 2.5 Baths
    • 1,477 Sq Ft
    • Built 1961

    Last Sold Summary

    • $284/SF
    • 1 Day On Market

    Current Estimated Value $440,159

    Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

    1847 Azalea Ave, Winter Park, FL 32789
    • /2

      Est $377,227

      Not Listed For Sale

      311 E Morse Blvd Unit 6-7, Winter Park, FL 32789

      • 1 Bed
      • 1 Bath
      • 884 Sq Ft
      • Built 1960
      311 E Morse Blvd Unit 6-7, Winter Park, FL 32789

      Last Sold Summary

      • 103 Days On Market

      Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  • /34

    $624,444

    $165K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,228 Sq Ft

    2418 Euston Rd, Winter Park, FL 32789

    Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the highly sought-after Winter Park 32789 zip code, just moments from scenic Lake Killarney. Situated on an oversized 0.27-acre lot with no HOA, this exceptional property offers endless possibilities, including ample space to add a pool, guest house/ADU, or create the custom outdoor living space of your

    Richard Bavec TOLARIS REALTY GROUP LLC

    2418 Euston Rd, Winter Park, FL 32789
  • /5

    $1,295 Per Month

    • 1 Bed
    • 1 Bath
    • 620 Sq Ft
    • Townhouse for Rent

    1600 Indiana Ave, Winter Park, FL 32789

    This 1 bedroom, 1 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 tile throughout the main living area, dining room, utility room with washer/dryer hookups, and a

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

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

    $199,900

    Sold Nov 03, 2025

    2500 Lee Rd Unit 134, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Below List Price
    • $310/SF
    • 130 Days On Market

    Current Estimated Value $185,870

    Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

    2500 Lee Rd Unit 134, Winter Park, FL 32789
    • /30

      Est $1,355,145

      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

      Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  • /27

    $1,574,900

    New Construction
    • 5 Beds
    • 4.5 Baths
    • 3,252 Sq Ft

    1526 Miller Ave, Winter Park, FL 32789

    New Construction! New photos coming soon! First photo is a rendering of the new home and the following photos are interiors of a similar model by the builder. Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the

    Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    1526 Miller Ave, Winter Park, FL 32789
  • /54

    $6,350 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,379 Sq Ft
    • House for Rent

    1403 Michigan Ave, Winter Park, FL 32789

    !PRICE DROP! Graceful, distinctive, and effortlessly inviting, 1403 Michigan Avenue captures the essence of modern Winter Park elegance.A distinctive Winter Park residence offering 4 bedrooms and 3.5 bathrooms, where timeless charm meets a fully elevated modern lifestyle. Beyond its inviting design and prime location, this home has been thoughtfully enhanced with features that

    1403 Michigan Ave, Winter Park, FL 32789
  • /2

    $340,000

    Sold Feb 26, 2026

    7580 Aloma Pines Ct, Winter Park, FL 32792

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • Built 2016

    Last Sold Summary

    • 7% Below List Price
    • $182/SF
    • 94 Days On Market

    Current Estimated Value $349,920

    Last Listing Agent Simon Colak USCO CAPITAL GROUP

    7580 Aloma Pines Ct, Winter Park, FL 32792
    • /2

      Est $1,070,510

      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

      Last Listing Agent Emily Bearden COMPASS FLORIDA LLC

  • /20

    $399,999

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    1840 Aster Dr, Winter Park, FL 32792

    Virtually Staged. WOW WINTER PARK! PRICED $50,000 BELOW CURRENT MARKET VALUE. A well maintained 3 bedroom 2 bath home located in a highly sought after Winter Park, Garden Lake Estates. Nestled in Seminole County, an A rated school zone! The home also sits on a large lot with plenty of room for outdoor living, No rear neighbors for added privacy, gardening or future expansion. The property offers

    Brendon Spalding KONA REALTY SERVICES LLC

    1840 Aster Dr, Winter Park, FL 32792
  • /34

    $3,895 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,553 Sq Ft
    • House for Rent

    2348 Kestrel Perch Place, Winter Park, FL 32792

    A beautiful tile roof single-family house is available in Hawks Crest, the only gated community in Winter Park! UV sanitizing lights are installed in all bathrooms. A water filter system is installed in the kitchen sink. This 4-bed 3.5-bathroom plus an office and second-floor loft is ready to move in. When you enter the home, an open-concept floor plan leads you to the family room and the

    Yan Zuo EAST PEARL REALTY

    2348 Kestrel Perch Place, Winter Park, FL 32792
  • /2

    $250,000

    Sold Apr 10, 2026

    1823 Maywood Rd, Winter Park, FL 32792

    • 3 Beds
    • 1.5 Baths
    • 1,232 Sq Ft
    • Built 1956

    Last Sold Summary

    • $203/SF
    • 1 Day On Market

    Current Estimated Value $244,436

    Last Listing Agent Abby Nelson RE/MAX 200 REALTY

    1823 Maywood Rd, Winter Park, FL 32792
    • /2

      Est $139,285

      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

      Last Listing Agent Christopher Courtney PREFERRED REAL ESTATE BROKERS

  • /36

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft

    2349 Shadowland Loop, Winter Park, FL 32792

    Welcome to the Enclave at Hawks Crest, where this modern 3-bedroom, 2.5-bath townhome gives you 1,755 square feet of space without a long list of things to maintain. A paver driveway, two-car garage, and clean exterior make a great first impression, and inside, high ceilings and plenty of natural light keep the main level feeling open and bright. The kitchen sits right in the middle of it all

    Lindsey Hudson REAL BROKER, LLC

    2349 Shadowland Loop, Winter Park, FL 32792
  • /25

    $1,895 Per Month

    • 2 Beds
    • 2 Baths
    • 1,098 Sq Ft
    • Townhouse for Rent

    162 Moyses Rd, Winter Park, FL 32792

    Property Id: 2563758 Be the first to live in this beautifully renovated home that has been completely remodeled from top to bottom! Everything is brand new, giving you the feel of moving into a new home with modern finishes throughout. This home features 2 spacious bedrooms and 1 full bathroom upstairs, creating a private and comfortable living space. The first floor offers an open

    162 Moyses Rd, Winter Park, FL 32792
  • /2

    $266,000

    Sold Nov 19, 2025

    1500 Gay Rd Unit 9B, Winter Park, FL 32789

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

    Last Sold Summary

    • 1% Below List Price
    • $259/SF
    • 5 Days On Market

    Current Estimated Value $255,091

    Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 9B, Winter Park, FL 32789
    • /39

      Est $218,373

      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

      Last Listing Agent Alex Galitsky TOP ORLANDO REALTY

  • /68

    $820,000

    $30K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,242 Sq Ft

    1927 Eland Ave, Winter Park, FL 32789

    *Ask about a lender provided credit up to $12,500 on this home!*1927 Eland Avenue is a rare single family home for sale in Winter Park FL 32789, located on a quiet dead end street with no rear neighbors. This Winter Park home features a main residence plus a detached in law suite ADU built in 2022, offering exceptional flexibility for multi generational living, guest accommodations, or rental

    Ryan Leitter CHARLES RUTENBERG REALTY ORLANDO

    1927 Eland Ave, Winter Park, FL 32789
  • /17

    $6,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Apartment for Rent

    301 W Comstock Ave, Winter Park, FL 32789

    Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

    Sydney Brownlee THE SYDGAN CORP

    301 W Comstock Ave, Winter Park, FL 32789
  • /2

    $470,000

    Sold Jan 15, 2026

    3319 Ellwood Ct, Winter Park, FL 32792

    • 5 Beds
    • 3 Baths
    • 1,546 Sq Ft
    • Built 1968

    Last Sold Summary

    • 2% Above List Price
    • $304/SF
    • 78 Days On Market

    Current Estimated Value $471,829

    Last Listing Agent Elena Sanchez BALDWIN PARK REALTY LLC

    3319 Ellwood Ct, Winter Park, FL 32792
    • /2

      Est $88,667

      Not Listed For Sale

      7309 Daniel Webster Dr Unit D, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 590 Sq Ft
      • Built 1974
      7309 Daniel Webster Dr Unit D, Winter Park, FL 32792

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Benjamin W Berry EXP REALTY LLC

Showing Results 241 - 280, Page 7 of 18

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