28,402

Winter Park, FL Homes

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  • /39

    $489,900

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,746 Sq Ft

    5340 N Lake Burkett Ln, Winter Park, FL 32792

    Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation

    Tanya McDonnell RE/MAX TOWN & COUNTRY REALTY

    5340 N Lake Burkett Ln, Winter Park, FL 32792
  • /17

    $1,300 Per Month

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

    1695 Lee Rd Unit D213, Winter Park, FL 32789

    Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

    Rachel DeCamp RLL Real Estate Group

    1695 Lee Rd Unit D213, Winter Park, FL 32789
  • /2

    $298,000

    Sold Aug 15, 2025

    2206 Bonanza Ave, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,776 Sq Ft
    • Built 1971

    Last Sold Summary

    • 15% Below List Price
    • $168/SF
    • 9 Days On Market

    Current Estimated Value $423,998

    Last Listing Agent Hannah Evans FLORIDA REALTY INVESTMENTS

    2206 Bonanza Ave, Winter Park, FL 32792
    • /2

      Est $293,365

      Not Listed For Sale

      5879 Marble Ct, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,041 Sq Ft
      • Built 1988
      5879 Marble Ct, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /36

    $377,880

    • 3 Beds
    • 2 Baths
    • 1,128 Sq Ft

    2973 Sanbina St, Winter Park, FL 32789

    Welcome to an incredible opportunity to own a home in one of Central Florida’s most desirable zip codes — Winter Park 32789 — for under $400,000! Surrounded by million-dollar neighborhoods, this 3-bedroom, 2-bath home offers outstanding value, endless potential, and a prime location close to shopping, dining, parks, and everything Winter Park has to offer.Located in a highly sought-after

    Nicholas Musashe SUN PROPERTIES, INC.

    2973 Sanbina St, Winter Park, FL 32789
  • /11

    $2,050 Per Month

    • 3 Beds
    • 2 Baths
    • 1,317 Sq Ft
    • Winter Park 3 Bedroom 2 Bath Renovated!

    5171 N Orange Ave, Winter Park, FL 32792

    You don't want to miss out on this Winter Park Beauty! This lovely, RENOVATED, 3/2 block home, is situated on a large, fenced in lot and has been recently renovated ! The house has a nice open floor plan, with a great room and family room. The great room even has a wood burning fireplace. Renovations include...laminate wood floors throughout, interior paint, almost new kitchen appliances,

    5171 N Orange Ave, Winter Park, FL 32792
  • /2

    $279,000

    Sold Aug 11, 2025

    Unlisted Address

    • 2 Beds
    • 2.5 Baths
    • 1,186 Sq Ft
    • Built 1981

    Last Sold Summary

    • $235/SF
    • 4 Days On Market

    Current Estimated Value $282,025

    Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

    Unlisted Address
    • /2

      Est $638,787

      Not Listed For Sale

      1401 Lone Feather Trail, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,770 Sq Ft
      • Built 2022
      1401 Lone Feather Trail, Winter Park, FL 32792

      Last Sold Summary

      • 75 Days On Market

  • /26

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,283 Sq Ft

    780 Baffie Ave, Winter Park, FL 32789

    Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

    Melissa Woodman FANNIE HILLMAN & ASSOCIATES

    780 Baffie Ave, Winter Park, FL 32789
  • /12

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,441 Sq Ft
    • House for Rent

    1540 Oneco Ave, Winter Park, FL 32789

    Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with

    Tara Mason WATSON REALTY CORP

    1540 Oneco Ave, Winter Park, FL 32789
  • /24

    $649,000

    Sold Oct 17, 2025

    2304 Depauw Ave, Orlando, FL 32804

    • 3 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $389/SF
    • 199 Days On Market

    Current Estimated Value $658,000

    David Weekley Homes Central Living - Downtown

    2304 Depauw Ave, Orlando, FL 32804
    • /2

      Est $308,278

      Not Listed For Sale

      2762 Hilda Cove, Winter Park, FL 32792

      • 3 Beds
      • 2 Baths
      • 1,493 Sq Ft
      • Built 1981
      2762 Hilda Cove, Winter Park, FL 32792

      Last Sold Summary

      • 119 Days On Market

  • /46

    $825,000

    • 4 Beds
    • 3.5 Baths
    • 2,589 Sq Ft

    1369 Blue Stem Ln, Winter Park, FL 32792

    Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer

    He Gao U S GLORY REALTY

    1369 Blue Stem Ln, Winter Park, FL 32792
  • /28

    $2,275 Per Month

    • 3 Beds
    • 2 Baths
    • 1,381 Sq Ft
    • Townhouse for Rent

    7800 Fernbrook Way, Winter Park, FL 32792

    Townhome in Winter Park, a refreshed 3-bedroom, 2-bath residence featuring new interior paint and laminated wood flooring throughout. Ceiling fans help maintain comfort in each living area, and a dedicated office/bonus room provides flexible space for work or hobbies. A washer and dryer are included for added convenience. Thoughtfully updated and move-in ready, this townhome offers a tasteful,

    7800 Fernbrook Way, Winter Park, FL 32792
  • /2

    $500,000

    Sold May 27, 2026

    720 W Webster Ave, Winter Park, FL 32789

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft
    • Built 1950

    Last Sold Summary

    • 9% Below List Price
    • $369/SF
    • 54 Days On Market

    Current Estimated Value $515,477

    Last Listing Agent Vincent Cordaro SERHANT

    720 W Webster Ave, Winter Park, FL 32789
    • /2

      Est $749,740

      Not Listed For Sale

      1166 Wildmeadow Run, Winter Park, FL 32792

      • 4 Beds
      • 3.5 Baths
      • 2,589 Sq Ft
      • Built 2021
      1166 Wildmeadow Run, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

  • /26

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    1995 Canny Cove, Winter Park, FL 32792

    Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe

    Rosemary Siegler KELLER WILLIAMS ELITE PARTNERS III REALTY

    1995 Canny Cove, Winter Park, FL 32792
  • /16

    $1,400 Per Month

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

    1695 Lee Rd Unit C110, Winter Park, FL 32789

    Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit C110, Winter Park, FL 32789
  • /2

    $230,000

    Sold Aug 29, 2025

    1500 Gay Rd Unit 7A, Winter Park, FL 32789

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

    Last Sold Summary

    • 6% Below List Price
    • $224/SF
    • 205 Days On Market

    Current Estimated Value $232,398

    Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

    1500 Gay Rd Unit 7A, Winter Park, FL 32789
    • /2

      Est $775,084

      Not Listed For Sale

      2255 Marsh Sedge Ln, Winter Park, FL 32792

      • 4 Beds
      • 3 Baths
      • 2,192 Sq Ft
      • Built 2020
      2255 Marsh Sedge Ln, Winter Park, FL 32792

      Last Sold Summary

      • 0 Days On Market

  • /26

    $390,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,471 Sq Ft

    7505 Laurel Springs Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Must see! This adorable three-bedroom, two-bath home is in a great location close to shopping, restaurants and freeways. A 2023 roof and no HOA! The home features gorgeous travertine flooring and a huge laundry room with extra storage. This exceptionally cared for home has character, charm and warmth. The fenced backyard and patio offer peaceful privacy.

    Paula Dale PREMIER SOTHEBYS INT'L REALTY

    7505 Laurel Springs Dr, Winter Park, FL 32792
  • /14

    $1,995 Per Month

    • 3 Beds
    • 1 Bath
    • 1,038 Sq Ft
    • House for Rent

    830 Carver St, Winter Park, FL 32789

    Fabulous Winter Park home with upgraded kitchen. Super adorable 3 bedroom 1 bath home in Winter Park with all tile flooring, screened patio, bonus room and close to Winter Park Village, Park Ave., Rollins College. Fenced yard and plenty of parking. Home available for move-in now. Please call to schedule an appointment to view this wonderful home. All applicants whether you have a pet or not will

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

    $3,450,000

    Sold Jul 25, 2025

    182 N Phelps Ave, Winter Park, FL 32789

    • 4 Beds
    • 5 Baths
    • 4,812 Sq Ft
    • Built 2025

    Last Sold Summary

    • 4% Below List Price
    • $717/SF
    • 61 Days On Market

    Current Estimated Value $2,938,183

    Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

    182 N Phelps Ave, Winter Park, FL 32789
    • /2

      Est $438,328

      Not Listed For Sale

      1935 Canny Cove, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2023
      1935 Canny Cove, Winter Park, FL 32792

      Last Sold Summary

      • 60 Days On Market

  • /41

    $650,000

    Open Sat 12PM - 2PM $49K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    1009 Lake Bell Dr, Winter Park, FL 32789

    Rarely does a property offer this combination of waterfront living, privacy, and walkable convenience in the heart of Winter Park. Situated on nearly half an acre at the end of a quiet dead-end street, this unique property features approximately 133 feet of waterfront frontage with direct access to private Lake Bell. The existing 3-bedroom, 2-bath home is comfortable and move-in ready, offering

    Padgett McCormick KELLY PRICE & COMPANY LLC

    1009 Lake Bell Dr, Winter Park, FL 32789
  • /21

    $2,900 Per Month

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • House for Rent

    540 W Comstock Ave, Winter Park, FL 32789

    Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior

    Fredrick Jacobs KELLER WILLIAMS GAINESVILLE REALTY PARTNERS

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

    $905,000

    Sold Mar 11, 2026

    5325 Cypress Reserve Place, Winter Park, FL 32792

    • 5 Beds
    • 3.5 Baths
    • 3,598 Sq Ft
    • Built 1998

    Last Sold Summary

    • 5% Below List Price
    • $252/SF
    • 322 Days On Market

    Current Estimated Value $891,828

    Last Listing Agent Dori Estrada AXEN REALTY, LLC

    5325 Cypress Reserve Place, Winter Park, FL 32792
    • /2

      Est $774,092

      Not Listed For Sale

      1421 Wooddale Ave, Winter Park, FL 32789

      • 3 Beds
      • 2 Baths
      • 1,628 Sq Ft
      • Built 1950
      1421 Wooddale Ave, Winter Park, FL 32789

      Last Sold Summary

      • 45 Days On Market

  • /32

    $144,000

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    291 Lewfield Cir Unit 291, Winter Park, FL 32792

    One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system,

    Barbara Coy WATSON REALTY CORP

    291 Lewfield Cir Unit 291, Winter Park, FL 32792
  • /15

    $1,795 Per Month

    • 3 Beds
    • 2 Baths
    • 1,332 Sq Ft
    • House for Rent

    5523 Cretan Way, Winter Park, FL 32792

    3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and

    5523 Cretan Way, Winter Park, FL 32792
  • /2

    $180,000

    Sold Jan 06, 2026

    2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Below List Price
    • $177/SF
    • 8 Days On Market

    Current Estimated Value $183,770

    Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

    2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
    • /2

      Est $305,591

      Not Listed For Sale

      5804 Shale Ct, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,055 Sq Ft
      • Built 1985
      5804 Shale Ct, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

  • /20

    $172,000

    $3K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft

    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792

    Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new

    Jessie Lin SOGO REAL ESTATE SERVICES LLC

    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792
  • /21

    $2,650 Per Month

    • 4 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • House for Rent

    887 Eastbrook Blvd Unit 2, Winter Park, FL 32792

    Come see this 4 bedroom 2 bath in the beautiful Winter Park neighborhood of Eastbrook. This home is completely move in ready with granite counter-tops and stainless steel appliances in the kitchen and new microwave. Large open kitchen/living room. Spacious bedrooms with lots of closets and storage space. Updated modern light fixtures and fans adorn the rooms throughout the home. Home is tiled and

    Courtney Davis ABSOLUTE REALTY GROUP, LLC

    887 Eastbrook Blvd Unit 2, Winter Park, FL 32792
  • /2

    $1,950,000

    Sold Sep 16, 2025

    141 Oakwood Way, Winter Park, FL 32789

    • 5 Beds
    • 4 Baths
    • 3,909 Sq Ft
    • Built 2015

    Last Sold Summary

    • 14% Below List Price
    • $499/SF
    • 170 Days On Market

    Current Estimated Value $1,979,738

    Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

    141 Oakwood Way, Winter Park, FL 32789
    • /2

      Not Listed For Sale

      677 Grenadine Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,037 Sq Ft
      • Built 1981
      677 Grenadine Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 103 Days On Market

  • /30

    $630,000

    $195K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,472 Sq Ft

    2612 Roxbury Rd, Winter Park, FL 32789

    SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!!Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with

    Laura Mcadams EXP REALTY LLC

    2612 Roxbury Rd, Winter Park, FL 32789
  • /14

    $1,620 Per Month

    • 2 Beds
    • 1 Bath
    • 865 Sq Ft
    • House for Rent

    1941 Lanier Ct, Winter Park, FL 32792

    AVAILABLE NOW! Please call or text to schedule a showing. This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all Downtown Winter Park has to offer, 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 an open main

    1941 Lanier Ct, Winter Park, FL 32792
  • /2

    $160,000

    Sold Jun 05, 2026

    2500 Lee Rd Unit 122, Winter Park, FL 32789

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

    Last Sold Summary

    • 11% Below List Price
    • $248/SF
    • 60 Days On Market

    Current Estimated Value $176,362

    Last Listing Agent Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

    2500 Lee Rd Unit 122, Winter Park, FL 32789
    • /2

      Est $267,165

      Not Listed For Sale

      7164 Swallow Run Unit GE, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,470 Sq Ft
      • Built 2012
      7164 Swallow Run Unit GE, Winter Park, FL 32792

      Last Sold Summary

      • 13 Days On Market

Showing Results 321 - 360, Page 9 of 18

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