Winter Park, FL Homes

• 

  

  

  /30

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  5418 Ardmore Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **WELCOME HOME** A generous .23 ACRE LOT, NO HOA, fresh UPDATES and SOLID CONSTRUCTION come together in this MOVE-IN READY 3-bedroom, 2-bath home in the desirable Wrenwood community of Winter Park! Thoughtfully maintained and upgraded, this property offers the timeless character and modern touches you have been searching for. ****Major improvements

  Jennifer Wemert WEMERT GROUP REALTY LLC

  5418 Ardmore Dr, Winter Park, FL 32792
• 

  

  

  /15

  $2,315 per month

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  1453 Hyde Park Dr, 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 $2459.90. That covers your base rent, $2315.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1453 Hyde Park Dr, Winter Park, FL 32792
• 

  

  /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 $891,360

  Last Listing Agent Dori Estrada LPT REALTY, LLC

  5325 Cypress Reserve Place, Winter Park, FL 32792
• 

  

  /2

  Est $196,425 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

  • 1% Below List Price
  • $163/SF
  • 80 Days On Market

  Last Sold Price $198,500

  Last Listing Agent John Muccigrosso RE/MAX
• 

  

  

  /26

  $499,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,864 Sq Ft

  275 N Ranger Blvd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to beautiful Winter Park! This spacious 4-bedroom, 3-bathroom home offers 1,864 square feet of living space and sits on a generous lot in an established neighborhood known for its mature trees, convenient location, and classic Florida charm. This home is solid, making it a fantastic opportunity for

  David Augello ON POINT REALTY LLC

  275 N Ranger Blvd, Winter Park, FL 32792
• 

  

  /50

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • House for Rent

  1835 Edwin Blvd, Winter Park, FL 32789

  Charming bungalow on a brick street in beautiful Winter Park, available March 1, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white cabinetry,

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1835 Edwin Blvd, Winter Park, FL 32789
• 

  /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 $181,175

  Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

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

  /2

  Est $1,283,088 Not Listed For Sale

  1830 Pineview Cir, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft
  • Built 2024

  1830 Pineview Cir, Winter Park, FL 32792

  Last Sold Summary

  • 14% Below List Price
  • $527/SF
  • 57 Days On Market

  Last Sold Price $1,499,000

  Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK
• 

  

  /17

  $185,000

  • 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
• 

  

  /15

  $2,440 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  3091 Crane Strand Dr, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  3091 Crane Strand Dr, 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 $1,967,770

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
• 

  /2

  Est $188,542 Not Listed For Sale

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1983

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

  Last Sold Summary

  • 17% Below List Price
  • $220/SF
  • 13 Days On Market

  Last Sold Price $227,000

  Last Listing Agent Ron Encarnacion RDE REALTY LLC
• 

  

  /68

  $850,000

  • 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
• 

  

  /27

  $3,995 per month

  • 3 Beds
  • 2.5 Baths
  • 2,317 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!! PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING! This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or the charming

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  438 W Swoope Ave, Winter Park, FL 32789
• 

  /2

  $170,000 Sold Jun 09, 2025

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $165/SF
  • 53 Days On Market

  Current Estimated Value $164,792

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792
• 

  /2

  Est $822,940 Not Listed For Sale

  1776 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2022

  1776 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • $376/SF
  • 88 Days On Market

  Last Sold Price $825,000

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
• 

  

  /50

  $2,298,000

  • 4 Beds
  • 2.5 Baths
  • 2,841 Sq Ft

  1760 Alabama Dr, Winter Park, FL 32789

  Welcome to 1760 Alabama Drive, a striking mid-century residence where architectural character, thoughtful modernization, and exceptional livability come together in one of Winter Park’s most desirable neighborhoods. Spanning 2,841 square feet, this distinctive home celebrates authentic mid-century design with clean lines, intentional geometry, and expansive walls of glass that bring the outdoors

  Brian Ruth DAILLAND REAL ESTATE

  1760 Alabama Dr, Winter Park, FL 32789
• 

  

  /20

  $1,745 per month

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Condo for Rent

  650 Trinidad Ct, Winter Park, FL 32792

  Welcome to the Full Sail/Winter Park 2/2 condo, a gem nestled in the heart of Winter Park, FL. This condo offers two spacious bedrooms and two full bathrooms, providing ample space for comfortable living. Master bedroom upstairs and 2nd bedroom downstairs. Ideal for roommates. The condo is part of a vibrant community that boasts a range of amenities designed to enhance your lifestyle. Enjoy a

  650 Trinidad Ct, Winter Park, FL 32792
• 

  /2

  $625,000 Sold May 09, 2025

  1401 Lone Feather Trail, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $353/SF
  • 75 Days On Market

  Current Estimated Value $618,043

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  1401 Lone Feather Trail, Winter Park, FL 32792
• 

  /2

  Not Listed For Sale

  663 Trinidad Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  663 Trinidad Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • $201/SF
  • 164 Days On Market

  Last Sold Price $224,900

  Last Listing Agent Ivan Tobon OUTLET REALTY
• 

  

  /32

  $775,000

  • 4 Beds
  • 3.5 Baths
  • 3,062 Sq Ft

  675 Overspin Dr, Winter Park, FL 32789

  Seller may consider buyer concessions if made in an offer ~ Beautiful upgrades, a versatile layout, and the best of Winter Park at your doorstep! With Dubsdread Golf Course just around the corner and Fairbanks Avenue minutes away, this 4-bedroom, 3.5-bath CUSTOM BUILT HOME puts you in the center of it all – NO HOA required! Major systems have been well maintained; including a NEW A/C UNIT with UV

  Jennifer Wemert WEMERT GROUP REALTY LLC

  675 Overspin Dr, Winter Park, FL 32789
• 

  

  /32

  $1,545 per month

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792

  2-bedroom, 1.5-bathroom, two-story condo in Four Seasons Condos of Winter Park. This well maintained condo includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with

  Amy Spano WILSON MANAGEMENT GROUP

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792
• 

  /2

  $912,500 Sold Jan 14, 2026

  210 Laurel Park Ct, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,838 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $322/SF
  • 25 Days On Market

  Current Estimated Value $918,318

  Last Listing Agent Alireza Partovi EXP REALTY LLC

  210 Laurel Park Ct, Winter Park, FL 32792
• 

  /2

  Est $1,099,283 Not Listed For Sale

  2726 Lake Howell Ln, Winter Park, FL 32792

  • 3 Beds
  • Built 1960

  2726 Lake Howell Ln, Winter Park, FL 32792

  Last Sold Summary

  • 19% Below List Price
  • $870/SF
  • 49 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Julie Sidorevskaya JULIES REALTY, LLC
• 

  

  /53

  $2,265,000 Open Tue 12PM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  NEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
• 

  

  /20

  $2,610 per month

  • 4 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • House for Rent

  1790 Viburnum Ln, 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 $2874.90. That covers your base rent, $2610.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1790 Viburnum Ln, Winter Park, FL 32792
• 

  /2

  $324,000 Sold Jun 17, 2025

  1920 Magnolia Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1986

  Last Sold Summary

  • $242/SF

  Current Estimated Value $332,504

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

  1920 Magnolia Ave, Winter Park, FL 32792
• 

  /2

  Est $306,806 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

  • 1% Below List Price
  • $298/SF
  • 6 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Deanna Armel ARMEL REAL ESTATE INC
• 

  

  /29

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  2779 Sanbina St, Winter Park, FL 32789

  Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a

  Caroline Fiore MAINFRAME REAL ESTATE

  2779 Sanbina St, Winter Park, FL 32789
• 

  

  /17

  $3,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  1302 Michigan Ave, Winter Park, FL 32789

  This is a unique opportunity to live in this glamorous, impeccably maintained 3 bedrooms, 2.5 baths in the heart of Winter Park (Unfurnished). This beautiful home features formal living and dining rooms that open to the impressive gourmet kitchen fitted with wood cabinetry, stainless steel appliances, granite countertops, a breakfast bar, there is also room for a breakfast nook. Through the

  Mo Jabr RE/MAX 200 REALTY

  1302 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $485,000 Sold Aug 18, 2025

  1921 Japonica Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 1971

  Last Sold Summary

  • $223/SF
  • 11 Days On Market

  Current Estimated Value $485,686

  Last Listing Agent Jose Gabriel Rodriguez COLDWELL BANKER REALTY

  1921 Japonica Rd, Winter Park, FL 32792
• 

  /2

  Est $743,559 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

  • $288/SF
  • 6 Days On Market

  Last Sold Price $745,000

  Last Listing Agent Liz Jones ORANGE SLICE PROPERTIES
• 

  

  /32

  $675,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,240 Sq Ft

  630 Saint Dunstan Way, Winter Park, FL 32792

  Under contract-accepting backup offers. Experience the best of Winter Park living at 630 Saint Dunstan Way, where modern comfort meets everyday functionality. Located just one block from the Cady Way Biking and Walking Trail, this beautifully renovated home showcases a stunning kitchen with a statement island, beverage center, and custom coffee station—perfect for both daily living and

  Melissa Johnson EXP REALTY LLC

  630 Saint Dunstan Way, Winter Park, FL 32792
• 

  

  /83

  $3,120 per month

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

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

  The advertised rate of $3,120/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 20, 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

  $335,000 Sold Oct 31, 2025

  3525 Baxter Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Above List Price
  • $215/SF
  • 5 Days On Market

  Current Estimated Value $324,590

  Last Listing Agent Ashley Fisak COLDWELL BANKER REALTY

  3525 Baxter Dr, Winter Park, FL 32792
• 

  /2

  Est $436,369 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

  • 3% Below List Price
  • $236/SF
  • 60 Days On Market

  Last Sold Price $450,000

  Last Listing Agent Nick Lally COMPASS FLORIDA LLC
• 

  

  /31

  $389,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft

  7213 Silver Place, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bath home tucked away on a quiet cul-de-sac in the Oakcrest community of Winter Park. Offering 1,252 square feet of comfortable living space, this single-story ranch sits on a generously sized 0.22-acre lot that provides plenty of room to enjoy outdoor living, entertain guests, or create your own backyard retreat.

  Michael Rogers INNOVATIVE REALTY, LLC

  7213 Silver Place, Winter Park, FL 32792
• 

  

  /6

  $1,300 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  3212 Netherwood Dr, Winter Park, FL 32792

  This 400sqft QUICK MOVE in-law suite, with kitchen, bedroom and bathroom, along with living room space. Water and electricity are included with your rent. Laundry on-site. Suitable for 2-person occupancy.

  Sara Cruz FLORIDA HOMES REALTY & MORTGAGE

  3212 Netherwood Dr, Winter Park, FL 32792
• 

  

  /45

  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,154,852

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
• 

  /2

  Est $767,817 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

  • 13% Above List Price
  • $416/SF
  • 45 Days On Market

  Last Sold Price $678,000

  Last Listing Agent Rafael Casallas, Pa EMPIRE NETWORK REALTY

Showing Results 361 - 400, Page 10 of 18