28,401

Winter Park, FL Homes

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  • /36

    $509,000

    Pending
    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    641 W Lyman Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. LOCATION. LOCATION. LOCATION. Heres the thing; in Winter Park, that's not a cliché. It's everything. There are homes in Central Florida that require a car for everything. This is not one of them. 641 West Lyman Avenue doesn't sit near Hannibal Square. It sits on it. This corner lot property is literally at the edge of one of Winter Park's most beloved and

    Ted Moseley REAL BROKER, LLC

    641 W Lyman Ave, Winter Park, FL 32789
  • /12

    $2,950

    Total Monthly Price

    • 3 Beds
    • 3.5 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    223 Sandlewood Trail, Winter Park, FL 32789

    The townhouse has been renovated, including updates to the kitchen with modern countertops, cabinetry, and stainless steel appliances. The bathrooms are renovated with updated vanities, fixtures, and finishes. Includes community pool access and directly behind the property is a recreational area offering various amenities.

    223 Sandlewood Trail, Winter Park, FL 32789
  • /2

    $3,485,000

    Sold Oct 17, 2025

    2171 Forrest Rd, Winter Park, FL 32789

    • 5 Beds
    • 6 Baths
    • 4,565 Sq Ft
    • Built 2016

    Last Sold Summary

    • 9% Below List Price
    • $763/SF
    • 134 Days On Market

    Current Estimated Value $3,426,438

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

    2171 Forrest Rd, Winter Park, FL 32789
    • /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

  • /33

    $373,800

    $1K PRICE DROP Pending
    • 2 Beds
    • 1 Bath
    • 1,150 Sq Ft

    1307 Formosa Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living

    Tyler Gibson LPT REALTY, LLC

    1307 Formosa Ave, Winter Park, FL 32789
  • /12

    $1,300

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 713 Sq Ft
    • Condo for Rent

    1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789

    Centrally located 2/1 apartment. Near Shopping, gas, churches, golf, convenience store, park and much more. Across the street is Orlando. Hardwood floors. Over 100 restaurants within 1 mile. Easy on and off I-4. Good neighbors. No pets.

    1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789
  • /2

    $390,000

    Sold May 28, 2026

    1036 Manchester Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $248/SF
    • 22 Days On Market

    Current Estimated Value $398,120

    Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

    1036 Manchester Cir, Winter Park, FL 32792
    • /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

  • /84

    $2,188,888

    • 5 Beds
    • 4 Baths
    • 3,382 Sq Ft

    2032 Kimbrace Place, Winter Park, FL 32792

    A PRIVATE RESORT-STYLE SANCTUARY IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF | Saltwater Pool & Spa | Smart Home | Minutes to Park Avenue Welcome to a rare offering where luxury, tranquility, and architectural sophistication converge. Nestled within one of Winter Park's most desirable neighborhoods and just minutes from the boutiques, fine dining, and cultural attractions of

    Rob Sassos SIMPLICITY: A RE BROKERAGE CO

    2032 Kimbrace Place, Winter Park, FL 32792
  • /21

    $1,598 Per Month

    • 2 Beds
    • 2 Baths
    • 774 Sq Ft
    • Condo for Rent

    7338 Swallow Run Unit 7338, Winter Park, FL 32792

    Beautiful and affordable 2-bedroom, 2-bath condominium for rent in desirable East Winter Park! This renovated and move-in-ready unit features an open floor plan with modern plank-style tile flooring throughout the living areas, neutral colors, and plenty of natural light.The updated kitchen offers newer cabinets, countertops, appliances, and a stylish backsplash, creating a modern and

    Yuly Rodriguez DOUGLAS EDMUND REAL ESTATE LLC

    7338 Swallow Run Unit 7338, Winter Park, FL 32792
  • /2

    $335,000

    Sold Sep 23, 2025

    5144 N Orange Ave, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,274 Sq Ft
    • Built 1976

    Last Sold Summary

    • 16% Below List Price
    • $263/SF
    • 128 Days On Market

    Current Estimated Value $341,502

    Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

    5144 N Orange Ave, Winter Park, FL 32792
    • /2

      Est $1,177,754

      Not Listed For Sale

      1782 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,377 Sq Ft
      • Built 2023
      1782 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 2 Days On Market

  • /76

    $2,249,000

    New Construction Open Sat 12PM - 4PM $146K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 3,130 Sq Ft

    2361 Mulbry Dr, Winter Park, FL 32789

    Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement home located within one of Winter Park's most desirable pockets and zoned for Audubon Park K-8. From the moment of arrival, the home's striking blend of natural stone, warm white oak, rich textures, and beautifully composed architectural lines creates an unforgettable first

    Ahmad Hassan COMPASS FLORIDA LLC

    2361 Mulbry Dr, Winter Park, FL 32789
  • /12

    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,096 Sq Ft
    • House for Rent

    851 Carver St, Winter Park, FL 32789

    Welcome home to this beautiful 3-bedroom, 2-bathroom residence located in the highly desirable Winter Park area. This inviting home offers a spacious and functional floor plan with comfortable living areas, a well-appointed kitchen, and generously sized bedrooms designed for everyday living.Enjoy the convenience of being close to shopping, dining, entertainment, major roadways, and

    851 Carver St, Winter Park, FL 32789
  • /2

    $397,000

    Sold Jul 01, 2025

    1109 Denton Rd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,236 Sq Ft
    • Built 1963

    Last Sold Summary

    • 3% Below List Price
    • $321/SF
    • 83 Days On Market

    Current Estimated Value $399,730

    Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    1109 Denton Rd, Winter Park, FL 32792
    • /2

      Est $455,874

      Not Listed For Sale

      1596 Little Wren Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,964 Sq Ft
      • Built 2020
      1596 Little Wren Ln, Winter Park, FL 32792

      Last Sold Summary

      • 40 Days On Market

  • /23

    $417,500

    Pending
    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft

    1016 Manchester Cir, Winter Park, FL 32792

    Under contract-accepting backup offers. Virtually Staged. Welcome to this move-in-ready Winter Park home, where major updates have already been completed and everyday convenience is right around the corner. Enjoy peace of mind with a new roof (2020), A/C (2021), water heater (2021), updated plumbing (2021), and an updated electrical panel. Inside, the flexible floor plan offers a living room,

    Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

    1016 Manchester Cir, Winter Park, FL 32792
  • /23

    $3,200 Per Month

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

    640 N Park Ave Unit 5, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Welcome to Park Aire, a small iconic condo community located on Park Avenue by the WP9 golf course. 1st floor unit with oversized window views of the golf course and Casa Feliz. This one bedroom unit has an updated kitchen and bath. Amenities include a covered parking space, swimming pool, social room, a guest room for rent, open air patios on the

    Andy Holland PREMIER SOTHEBY'S INTL. REALTY

    640 N Park Ave Unit 5, Winter Park, FL 32789
  • /2

    $145,000

    Sold Aug 13, 2025

    7352 Swallow Run, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 802 Sq Ft
    • Built 1983

    Last Sold Summary

    • 39% Below List Price
    • $181/SF
    • 68 Days On Market

    Current Estimated Value $148,937

    Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

    7352 Swallow Run, Winter Park, FL 32792
    • /2

      Est $743,936

      Not Listed For Sale

      1804 Mondrian Cir, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 2,016 Sq Ft
      • Built 2018
      1804 Mondrian Cir, Winter Park, FL 32789

      Last Sold Summary

      • 68 Days On Market

  • /37

    $649,000

    $46K 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
  • /6

    $1,950 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    520 Holt Ave, Winter Park, FL 32789

    Property Id: 578482One-bedroom / one-bathroom cottage style apartment located within a five-minute walk to Rollins College, Park Avenue, and Hannibal Square. Newly-renovated interior includes condominium grade appliances, upgraded bathroom, and in-unit washer dryer. Unit includes off-street parking and private entry porch. Available for lease beginning of June 2026. Rent includes

    520 Holt Ave, Winter Park, FL 32789
  • /2

    $228,000

    Sold Jun 27, 2025

    1979 Staunton Ave, Winter Park, FL 32789

    • 1 Bed
    • 1 Bath
    • 736 Sq Ft
    • Built 1948

    Last Sold Summary

    • 24% Below List Price
    • $310/SF
    • 16 Days On Market

    Current Estimated Value $242,411

    Last Listing Agent Michael Kara CORBELO LLC

    1979 Staunton Ave, Winter Park, FL 32789
    • /2

      Est $505,764

      Not Listed For Sale

      1303 Merrydale Way, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 2,312 Sq Ft
      • Built 2021
      1303 Merrydale Way, Winter Park, FL 32792

      Last Sold Summary

      • 14 Days On Market

  • /34

    $671,111

    $118K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,048 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 dreams.

    Richard Bavec TOLARIS REALTY GROUP LLC

    2418 Euston Rd, Winter Park, FL 32789
  • /15

    $2,495 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,787 Sq Ft
    • Townhouse for Rent

    7628 Aloma Pines Ct, Winter Park, FL 32792

    This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    7628 Aloma Pines Ct, 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 $1,924,828

    Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    501 Henkel Cir, Winter Park, FL 32789
    • /2

      Est $398,416

      Not Listed For Sale

      740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 1,536 Sq Ft
      • Built 1986
      740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

      Last Sold Summary

      • 171 Days On Market

  • /20

    $439,900

    Open Sun 1PM - 4PM $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    1840 Aster Dr, Winter Park, FL 32792

    Step into this well maintained 3 bedroom 2 bath home located in a highly sought after Winter Park, Garden Lake Estates. Nestled in Seminole County, 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. This property offers endless potential. Featuring a newer roof, this home offers added

    Brendon Spalding KONA REALTY SERVICES LLC

    1840 Aster Dr, Winter Park, FL 32792
  • /83

    $2,873

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 990 Sq Ft
    • Condo for Rent

    2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789

    The advertised rate of $2,873/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 21, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789
  • /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 $492,861

    Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

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

      Est $221,349

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,165 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

      Last Sold Summary

      • 134 Days On Market

  • /17

    $170,000

    $25K PRICE DROP Pending
    • 1 Bed
    • 1 Bath
    • 732 Sq Ft

    1500 Gay Rd Unit 5, Winter Park, FL 32789

    Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features

    Jacob Hara TRANSCEND REALTY

    1500 Gay Rd Unit 5, Winter Park, FL 32789
  • /16

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • Condo for Rent

    1603 Alabama Dr, Winter Park, FL 32789

    FOR THE QUICKEST RESPONSE AND ASSISTANCE WITH ANY INQUIRIES, PLEASE CONTACT OUR OFFICE DIRECTLY BY PHONE. Application required prior to scheduling a showing. Available September 7th .Pet-friendly property. The Alabama, an iconic, historic Winter Park landmark on the shores of Lake Maitland. This meticulously fully renovated property perfectly blends timeless Mediterranean architecture with

    Maria Ottinger Maria Ottinger R.E Broker

    1603 Alabama Dr, 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 $401,287

    Last Listing Agent Yamila Lopez EMPIRE NETWORK REALTY

    7553 Laurel Springs Dr, Winter Park, FL 32792
    • /2

      Est $206,791

      Not Listed For Sale

      200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 1,219 Sq Ft
      • Built 1970
      200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

      Last Sold Summary

      • 80 Days On Market

  • /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
  • /16

    $1,399 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 $421,722

    Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

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

      Not Listed For Sale

      1630 Haven Dr, Orlando, FL 32803

      • 3 Beds
      • 2.5 Baths
      • 1,668 Sq Ft
      • Built 2024
      1630 Haven Dr, Orlando, FL 32803

      Last Sold Summary

      • 53 Days On Market

Showing Results 241 - 280, Page 7 of 18

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