Winter Park, FL Homes

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  /45

  $475,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,835 Sq Ft

  326 Fitzhugh Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. MULTIPLE OFFERS. Calling for highest and best by Tuesday, 1/27/2026 at 9AM. Welcome home to a beautiful 4-bedroom, 3-bath split-plan residence, tucked away on a quiet dead-end street in unincorporated Winter Park. Offering 1,835 square feet of thoughtfully designed living space, this home offers timeless comfort. Enjoy true peace of mind with major

  Rebecca Bininger Junod KELLER WILLIAMS WINTER PARK

  326 Fitzhugh Rd, Winter Park, FL 32792
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  /17

  $1,600 per month

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

  3651 N Goldenrod Rd Unit F208, Winter Park, FL 32792

  Amazing 2 bedroom, 2 bathroom condo in Winter Park and move in ready. Amenities included: central air, central heat, dishwasher, pool, stainless steel appliances, updated kitchen, and washer/dryer combo. Utilities included: heat, air conditioning and water. Is pet friendly. An ideal location adds to this gem's overall appeal with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail,

  3651 N Goldenrod Rd Unit F208, Winter Park, FL 32792
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  /2

  $1,595,000 Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,572,177

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
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  /44

  Est $939,250 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  1403 Michigan Ave, Winter Park, FL 32789

  1403 Michigan Ave, Winter Park, FL 32789
• 

  

  

  /13

  $89,500 Pending

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  3060 George Mason Ave Unit 10, Winter Park, FL 32792

  Under contract-accepting backup offers. GREAT INVESTMENT OPPORTUNITY! Seller is motivated! Completely remodeled and move-in ready, this beautiful 1-bedroom, 1-bathroom condo in Winter Park offers the perfect blend of comfort, convenience, and value. Located just 11 minutes from Orlando International Airport and close to UCF, Full Sail University, shopping malls, restaurants, major highways, and

  John Silva JOHN SILVA REALTY & ASSOCIATES

  3060 George Mason Ave Unit 10, Winter Park, FL 32792
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  /75

  $3,700 per month

  • 5 Beds
  • 3 Baths
  • 2,132 Sq Ft
  • House for Rent

  730 W Swoope Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Charming Winter Park Corner Home for Rent - 730 W Swoope Ave Experience the best of Winter Park living in this beautifully renovated corner home! Located just three blocks from the iconic Park Avenue, this spacious 5-bedroom, 3 bathroom residence offers over 2,200 square feet of updated living space. The bright, open design and private rooms provide

  Andres Ospina Rivera LPT REALTY, LLC

  730 W Swoope Ave, Winter Park, FL 32789
• 

  /2

  $749,000 Sold Aug 13, 2025

  627 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,509 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $299/SF
  • 52 Days On Market

  Current Estimated Value $751,899

  Last Listing Agent Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  627 Darcey Dr, Winter Park, FL 32792
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  /43

  Est $980,146 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,310 Sq Ft

  1780 Mondrian Cir, Winter Park, FL 32789

  1780 Mondrian Cir, Winter Park, FL 32789
• 

  

  /27

  $265,000

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

  1500 Gay Rd Unit 21C, Winter Park, FL 32789

  ***Mortgage savings may be available to some buyers*** Enjoy Low Maintenance LAKEFRONT LIVING in this well appointed 2bedroom/2bathroom second floor condo on Lake Killarney. The Chateaux du Lac community offers an active, easily accessible lakefront lifestyle with a heated community pool, clubhouse, lakefront community deck, BBQ, community laundry, 2 on site saunas and a resident only boat ramp.

  John Callahan REDFIN CORPORATION

  1500 Gay Rd Unit 21C, Winter Park, FL 32789
• 

  

  /25

  $1,975 per month

  • 2 Beds
  • 2.5 Baths
  • 1,236 Sq Ft
  • Townhouse for Rent

  5169 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to Lazy Oaks condominium. This townhome features two levels with an open floor plan that consist of 2 bedrooms, 2.5 bathrooms, and a Florida Room. Also, it can be delivered furnished as well! Over 1200 sqft of living space awaits you with a upgraded laminate flooring, baseboards, lighting, and ceiling fans. A prime location that is nestled near Full Sail, UCF, Lynx bus stop, major

  Damon Mayers MAYERS REAL ESTATE LLC

  5169 Lazy Oaks Dr, Winter Park, FL 32792
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  /2

  $380,000 Sold May 02, 2025

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $266/SF
  • 42 Days On Market

  Current Estimated Value $388,807

  Last Listing Agent Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
• 

  

  /18

  Est $414,548 Not Listed For Sale

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

  2809 Bright Bird Ln, Winter Park, FL 32792

  2809 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /26

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft

  2020 Cocos Ct, Winter Park, FL 32792

  Fully Renovated Home in Winter Park!Beautifully 3-bedroom, 2-bathroom POOL home located in the desirable Eastbrook community of Winter Park. Situated on an oversized .30-acre corner lot in a quiet cul-de-sac with no HOA.This property offers 1,715 sq. ft. of living space, a 1-car garage, and a spacious fenced backyard—the perfect combination of comfort, style, and location. Updates include

  Julimar Barreiro Pastrana SERHANT

  2020 Cocos Ct, Winter Park, FL 32792
• 

  

  /11

  $3,800 per month

  • 4 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • House for Rent

  1690 Dale Ave, Winter Park, FL 32789

  Located in one of the best areas of Winter Park, this home offers top- rated schools, welcoming neighborhood, and unbeatable convenience. just a mile from Park Avenue, you will enjoy easy access to shops, restaurants, and all the charm Winter Park is known for.With plenty to do nearby and a family - friendly environment, this is the perfect place to raise a family and enjoy the Winter Park

  Farzaneh Alijani ZAMIN INC

  1690 Dale Ave, Winter Park, FL 32789
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  /2

  $1,095,000 Sold Dec 01, 2025

  1450 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,942 Sq Ft
  • Built 2009

  Last Sold Summary

  • 16% Below List Price
  • $564/SF
  • 49 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
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  /18

  Est $411,202 Not Listed For Sale

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

  2805 Bright Bird Ln, Winter Park, FL 32792

  2805 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /61

  $619,500

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  1451 Cavendish Rd, Winter Park, FL 32789

  Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and prominent corner lot, this move-in-ready home perfectly balances charm, safety, and convenience just minutes from Park Avenue, Downtown Orlando, and the Mills District. Enjoy extensive upgrades including new AC, attic

  Spencer Flory LoKation

  1451 Cavendish Rd, Winter Park, FL 32789
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  /36

  $4,895 per month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst Ave, Winter Park, FL 32789
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  /2

  $260,000 Sold Feb 27, 2025

  5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1982

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 1 Day On Market

  Current Estimated Value $259,201

  Last Listing Agent Natalia Moege PARK 26 REALTY LLC

  5132 Lazy Oaks Dr Unit 5132, Winter Park, FL 32792
• 

  

  /18

  Est $425,560 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2821 Bright Bird Ln, Winter Park, FL 32792

  2821 Bright Bird Ln, Winter Park, FL 32792
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  /38

  $539,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,885 Sq Ft

  2665 Tierra Cir, Winter Park, FL 32792

  Welcome to 2665 Tierra Circle, a captivating Mediterranean-inspired residence nestled in the desirable Casa Aloma neighborhood of Winter Park. This thoughtfully maintained 4-bedroom, 2-bath home spans 1,885 square feet and has been lovingly cared for by a single owner for the past 23 years, evident in every detail throughout. Step inside to discover a flowing floor plan featuring distinct living,

  Kelly Price KELLY PRICE & COMPANY LLC

  2665 Tierra Cir, Winter Park, FL 32792
• 

  

  /39

  $7,900 per month

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • House for Rent

  300 Killarney Dr, Winter Park, FL 32789

  Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

  Kelly Price KELLY PRICE & COMPANY LLC

  300 Killarney Dr, Winter Park, FL 32789
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  /2

  $220,000 Sold Jan 30, 2026

  700 Melrose Ave Unit J23, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 772 Sq Ft
  • Built 1964

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 107 Days On Market

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit J23, Winter Park, FL 32789
• 

  

  /18

  Est $434,522 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2796 Bright Bird Ln, Winter Park, FL 32792

  2796 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /34

  $320,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  2401 Antilles Dr, Winter Park, FL 32792

  Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. This is a wonderful space and great to prep for a dinner party! Open floor concept with dining room and family

  George Freelove KELLER WILLIAMS REALTY AT THE PARKS

  2401 Antilles Dr, Winter Park, FL 32792
• 

  

  /49

  $6,995 per month

  • 4 Beds
  • 5 Baths
  • 3,478 Sq Ft
  • House for Rent

  1350 Lyndale Blvd, Winter Park, FL 32789

  Gorgeous, Custom & recently renovated! This home features 4 bedrooms, 3 full baths & 2 half baths. Spacious, light & bright with 10’ ceilings, Brazilian cherry floors, and a gourmet kitchen. The kitchen is a chef's dream and perfect for entertaining. It boasts natural wood cabinets, large center island, dual fuel six-burner range, wine fridge and a built-in refrigerator. It overlooks a casual

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1350 Lyndale Blvd, Winter Park, FL 32789
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  /2

  $538,500 Sold May 16, 2025

  2855 Cady Way, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft
  • Built 1964

  Last Sold Summary

  • 9% Below List Price
  • $310/SF
  • 76 Days On Market

  Current Estimated Value $532,187

  Last Listing Agent Joe Cremonese GLOBAL PROPERTIES SALES & MGMT

  2855 Cady Way, Winter Park, FL 32792
• 

  

  /88

  Est $1,928,597 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft

  1661 Hillcrest Ave, Winter Park, FL 32789

  1661 Hillcrest Ave, Winter Park, FL 32789
• 

  

  /24

  $179,900 Pending

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1905, Winter Park, FL 32792

  Under contract-accepting backup offers. A Wonderful Opportunity Awaits!! Discover the ease of low-maintenance living in this well-maintained GROUND-FLOOR unit in the always-popular Four Seasons community. Currently leased for $1,800/month to an excellent tenant who would love to stay (month-to-month with 60-day notice), this condo offers built-in stability for investors or a smooth transition for

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  200 Saint Andrews Blvd Unit 1905, Winter Park, FL 32792
• 

  

  /12

  $1,525 per month

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

  1565 Michigan Ave, Winter Park, FL 32789

  Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

  Troy Hensley BHHS FLORIDA REALTY

  1565 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $284,000 Sold May 23, 2025

  2539 Antilles Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $249/SF
  • 50 Days On Market

  Current Estimated Value $280,034

  Last Listing Agent Allie George CORCORAN PREMIER REALTY

  2539 Antilles Dr, Winter Park, FL 32792
• 

  /2

  Est $426,509 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  2719 Bright Bird Ln, Winter Park, FL 32792

  2719 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /21

  $129,900

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  3053 George Mason Ave Unit 8, Winter Park, FL 32792

  Updated 2-bedroom, 2-bath condo featuring modern finishes throughout! This condo features laminate floors, sleek granite countertops, and stainless steel appliances in the kitchen. A rare find with an in-unit washer and dryer for added convenience. Step out onto the brand new deck, upgraded with durable composite decking—perfect for relaxing or entertaining. Ideally located just minutes from Full

  Daniel Graves GRAVES REALTY

  3053 George Mason Ave Unit 8, Winter Park, FL 32792
• 

  

  /42

  $3,295 per month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
• 

  /2

  $290,000 Sold Sep 22, 2025

  7102 Easter St, Winter Park, FL 32792

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 67 Days On Market

  Current Estimated Value $287,506

  Last Listing Agent Mayken Giraldo THE C SMITH REAL ESTATE GROUP LLC

  7102 Easter St, Winter Park, FL 32792
• 

  

  /18

  Est $426,907 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2790 Bright Bird Ln, Winter Park, FL 32792

  2790 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /31

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,556 Sq Ft

  1951 Staunton Ave, Winter Park, FL 32789

  Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently

  Veronica Figueroa EXP REALTY LLC

  1951 Staunton Ave, Winter Park, FL 32789
• 

  

  /30

  $2,275 per month

  • 3 Beds
  • 2 Baths
  • 1,266 Sq Ft
  • Townhouse for Rent

  3055 Autumn Ct, Winter Park, FL 32792

  Welcome to this charming and modern village-style home ideally located near Winter Park, top-rated schools, major roads, shopping, and restaurants. This residence features an open-concept floor plan with stainless steel appliances, laminate flooring in the main living areas, and cozy carpet in the bedrooms. The fenced backyard provides the perfect space for outdoor enjoyment and privacy. Modern

  Elias Kilci AGENT TRUST REALTY CORPORATION

  3055 Autumn Ct, Winter Park, FL 32792
• 

  /2

  $805,000 Sold Jul 01, 2025

  1795 Walker Ave, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 1958

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 143 Days On Market

  Current Estimated Value $784,301

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1795 Walker Ave, Winter Park, FL 32789
• 

  

  /39

  Est $863,539 Not Listed For Sale

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

  1770 Mondrian Cir, Winter Park, FL 32789

  1770 Mondrian Cir, Winter Park, FL 32789

Showing Results 521 - 560, Page 14 of 18