Winter Park, FL Homes

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  /28

  $778,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,015 Sq Ft

  1317 Medinah Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. Fully updated 4 bed/2 bath Winter Park Pines home ready for a new owner! Tucked away at the end of a quiet cul-de-sac, this fully renovated home offers the perfect blend of modern luxury and serene surroundings. The brand new kitchen and bathrooms showcase quartz countertops, elegant gold fixtures, and custom details, complemented by new engineered wood

  Zach Mitchell SAND DOLLAR REALTY GROUP INC

  1317 Medinah Ct, Winter Park, FL 32792
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  /17

  $1,170 - $1,975 per month

  Sorrento

  Studio - 3 Beds

  2400 Howell Branch Rd, Winter Park, FL 32792

  2400 Howell Branch Rd, Winter Park, FL 32792
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  /2

  $550,000 Sold May 08, 2025

  2906 Rapidan Trail, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1965

  Last Sold Summary

  • $236/SF
  • 4 Days On Market

  Current Estimated Value $604,224

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2906 Rapidan Trail, Winter Park, FL 32789
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  /26

  Est $478,721 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  2469 Firstlight Way, Winter Park, FL 32792

  2469 Firstlight Way, Winter Park, FL 32792
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  /52

  $899,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  668 Overspin Dr, Winter Park, FL 32789

  Modern Elegance Meets Custom Craftsmanship in the Heart of Winter Park with easy access to major highways!Welcome to your dream home — a custom-built Winter Park masterpiece blending modern luxury with thoughtful design. With over 2,500 sq/ft of stunning living space, this 4-bedroom, 3-bathroom home was built to impress and designed to entertain.Step inside and be captivated by the

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  668 Overspin Dr, Winter Park, FL 32789
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  /19

  $1,690 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Townhouse for Rent

  211 Stefanik Rd, Winter Park, FL 32792

  Large 2-bedroom 2-bathroom home located on a quiet neighborhood tucked away right off Howell Branch Rd. This home offers a huge open layout with an updated kitchen and sliding doors that lead out into a private fenced in patio area. The huge master bedroom has a walk-in closet to match and a beautiful bathroom. This home has extra storage space and plenty of closet space. Washer and Dryer . The

  Vivian Lippi LIPPI REALTY LLC

  211 Stefanik Rd, Winter Park, FL 32792
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  /2

  $720,000 Sold Jan 20, 2026

  2955 Lolissa Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,538 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $204/SF
  • 47 Days On Market

  Last Listing Agent Catherine Williams COLDWELL BANKER RESIDENTIAL RE

  2955 Lolissa Ln, Winter Park, FL 32789
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  /47

  Est $1,082,774 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  1939 Woodcrest Dr, Winter Park, FL 32792

  1939 Woodcrest Dr, Winter Park, FL 32792
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  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez WF REALTY CORP.

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
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  /19

  $1,250 - $1,350 per month

  Eastbrook Apartments

  1 - 2 Beds

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792

  Nestled within the serene and picturesque neighborhood of Lake Howell, Eastbrook Apartments offers a peaceful lakeside living experience with all the conveniences of a big city. This charming community in the Winter Park area is ideal for those seeking a blend of tranquility and accessibility. With 29 exclusive units, Eastbrook provides an intimate living environment with spacious and

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792
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  /2

  $2,285,000 Sold Nov 19, 2025

  521 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,883 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $588/SF
  • 118 Days On Market

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
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  /2

  Est $376,740 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7604 Aloma Pines Ct, Winter Park, FL 32792

  7604 Aloma Pines Ct, Winter Park, FL 32792
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  /49

  $205,000

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7468 Canford Ct Unit 24, Winter Park, FL 32792

  This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under

  Javier Albelo Rivera EMPIRE NETWORK REALTY

  7468 Canford Ct Unit 24, Winter Park, FL 32792
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  /19

  $1,450 per month

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

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

  Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

  Praveen Setty RIGHTHOUSE REALTY LLC

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
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  /2

  $110,000 Sold Mar 14, 2025

  291 Lewfield Cir Unit 291, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft
  • Built 1973

  Last Sold Summary

  • $162/SF
  • 7 Days On Market

  Current Estimated Value $124,384

  Last Listing Agent Christopher Courtney DENIZ REALTY PARTNERS LLC

  291 Lewfield Cir Unit 291, Winter Park, FL 32792
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  /2

  Est $489,518 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  1761 Indiana Ave Unit F, Winter Park, FL 32789
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  /37

  $779,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,778 Sq Ft

  5233 Lake Howell Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to 5233 Lake Howell Road, a thoughtfully updated residence offering modern finishes, extensive upgrades, and a private backyard retreat designed for both everyday living and effortless entertaining.Inside, white porcelain tile flooring and recessed lighting create a bright, cohesive atmosphere throughout the main living spaces. Expansive

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  5233 Lake Howell Rd, Winter Park, FL 32792
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  /24

  $1,330 - $1,610 per month

  Park East - Park Knowles Apartments

  Studio - 2 Beds

  311 N Knowles Ave, Winter Park, FL 32789

  Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

  311 N Knowles Ave, Winter Park, FL 32789
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  /2

  $430,000 Sold Jul 25, 2025

  2003 Bentwood Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,675 Sq Ft
  • Built 1981

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 16 Days On Market

  Current Estimated Value $430,723

  Last Listing Agent Heather Kolin PALMANO GROUP RE BROKERAGE LLC

  2003 Bentwood Dr, Winter Park, FL 32792
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  /2

  Est $260,764 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,565 Sq Ft

  7148 Swallow Run Unit E1, Winter Park, FL 32792

  7148 Swallow Run Unit E1, Winter Park, FL 32792
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  /15

  $229,900

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7771 Country Place Unit 7, Winter Park, FL 32792

  Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate

  Ivan Tobon OUTLET REALTY

  7771 Country Place Unit 7, Winter Park, FL 32792
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  /18

  $2,799 per month

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • House for Rent

  7345 Grand Ave, Winter Park, FL 32792

  Welcome to Winter Park living at its finest. This beautifully updated 3-bedroom, 2-bath pool home is perfectly positioned in one of the area’s most desirable and safe neighborhoods, zoned for top-rated schools and just minutes from all major shopping, dining, and everyday conveniences. With a truly central location, everything you need is right at your fingertips.Inside, the home offers a

  Sina Albekord CORCORAN PREMIER REALTY

  7345 Grand Ave, Winter Park, FL 32792
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  /2

  $450,000 Sold Aug 28, 2025

  2151 Conifer Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $249/SF
  • 32 Days On Market

  Current Estimated Value $448,400

  Last Listing Agent Denise Korrey KORR REALTY CORP

  2151 Conifer Ave, Winter Park, FL 32792
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  /2

  Est $276,770 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft

  222 Balfour Dr Unit 14, Winter Park, FL 32792

  222 Balfour Dr Unit 14, Winter Park, FL 32792
• 

  

  /23

  $230,000

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 104, Winter Park, FL 32789

  This ground-floor condo offers a practical layout with comfortable living spaces and easy accessibility. The unit provides a blank canvas for buyers looking to personalize their home or investment.Enjoy the convenience of being just minutes from Park Avenue, Rollins College, dining, shopping making commuting and everyday errands effortless. The community offers a low-maintenance lifestyle,

  John Harbuck SERHANT

  1250 S Denning Dr Unit 104, Winter Park, FL 32789
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  /16

  $1,549 - $1,799 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  Move in special:$1,000 off!*Restricted units only*App and Admin special for only $175!Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore,

  4704 Lucier Ct, Winter Park, FL 32792
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  /2

  $290,000 Sold Nov 24, 2025

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $289/SF
  • 54 Days On Market

  Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792
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  /43

  Est $1,762,315 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  1809 Harland Park Dr, Winter Park, FL 32789

  1809 Harland Park Dr, Winter Park, FL 32789
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  /60

  $789,000

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft

  2222 Marsh Sedge Ln, Winter Park, FL 32792

  Welcome to your dream Home! This stunning and elegant single-story home, built by Meritage Homes in the gated community of Hawk's Crest in Winter Park, includes numerous upgrades. This is the Pomelo model, equipped with an upgraded kitchen package that includes built-in double ovens and a stainless steel range hood. Beautiful quartz countertops feature an oversized kitchen island with excellent

  Carmen Molina LA ROSA REALTY LLC

  2222 Marsh Sedge Ln, Winter Park, FL 32792
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  /20

  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Townhouse for Rent

  685 Grenadine Ct Unit 685, Winter Park, FL 32792

  Spacious, updated 3-bedroom, 2-bath 1,350 SqFt corner two-story townhome located in the highly desirable Winter Park Villas. This residence features high-end finishes and numerous upgrades, including tile and wood flooring throughout the living areas, vaulted ceilings, and a modern open kitchen with granite countertops. Additional highlights include a cozy wood-burning fireplace, screened back

  Debbie Bahamon Synergy International Realty, Inc.

  685 Grenadine Ct Unit 685, Winter Park, FL 32792
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  /2

  $330,000 Sold May 09, 2025

  992 Carnation Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $330/SF
  • 57 Days On Market

  Current Estimated Value $335,364

  Last Listing Agent Bianca Botelho RE/MAX ASSURED

  992 Carnation Dr, Winter Park, FL 32792
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  /2

  Est $1,836,874 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 4,638 Sq Ft

  1411 Border Dr, Winter Park, FL 32789

  1411 Border Dr, Winter Park, FL 32789
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  /68

  $948,000

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  250 Cortland Ave, Winter Park, FL 32789

  Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

  Alexandra Nordine EXP REALTY LLC

  250 Cortland Ave, Winter Park, FL 32789
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  /14

  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

  7528 Park Promenade Dr, Winter Park, FL 32792
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  /2

  $580,000 Sold May 16, 2025

  1392 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2008

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 123 Days On Market

  Current Estimated Value $552,286

  Last Listing Agent Cody Hancock COLDWELL BANKER RESIDENTIAL RE

  1392 Indiana Ave, Winter Park, FL 32789
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  /44

  Est $847,279 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  436 W Swoope Ave, Winter Park, FL 32789

  436 W Swoope Ave, Winter Park, FL 32789
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  /26

  $249,900 Pending

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

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792

  Under contract-accepting backup offers. THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESSELED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES

  Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

  3254 Oak Lake Place Unit 137, Winter Park, FL 32792
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  /28

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 116, Winter Park, FL 32792

  Call to schedule a showing. Ready to move - in! You will love to have NEW PAINTING AND NEW MODERN STYLE TILE. Energy Efficient A/C unit installed 2023. Opportunity to rent 2 bedrooms and 2 bathroom at Golfside Villas located on the 2nd. Floor. Corner unit. Rent includes grounds maintenance, water and sewer. Upgrades done in 2021: laminate Flooring and bathroom sink/ cabinets. Kitchen and master

  Zaira Mejia SPACES & STYLES GROUP

  1000 S Semoran Blvd Unit 116, Winter Park, FL 32792
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  /2

  $426,000 Sold Jul 03, 2025

  2028 Sussex Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1973

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 39 Days On Market

  Current Estimated Value $426,569

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  2028 Sussex Rd, Winter Park, FL 32792
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  /33

  Est $625,616 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,265 Sq Ft

  5319 Pine Lily Cir, Winter Park, FL 32792

  5319 Pine Lily Cir, Winter Park, FL 32792

Showing Results 161 - 200, Page 5 of 18