Winter Park, FL Homes

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  $200,000

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

  623 Saint Johns Ct Unit 623, Winter Park, FL 32792

  If you’re searching for a place that feels like home the moment you walk in—not just another condo—this one might be exactly what you’ve been looking for. Nearby to Full Sail University, UCF, restaurants, shopping, entertainment, and major road access, this property is in a prime location. Step through the covered front porch and into a bright, welcoming space with soaring vaulted ceilings, new

  David Dorman CENTURY 21 CARIOTI

  623 Saint Johns Ct Unit 623, Winter Park, FL 32792
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  $1,235 - $2,026 per month

  Cranes Landing Apartments

  1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

  3440 N Goldenrod Rd, Winter Park, FL 32792
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  $500,000 Sold Feb 06, 2025

  2842 Eastern Pkwy, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,048 Sq Ft
  • Built 1953

  Last Sold Summary

  • $477/SF
  • 0 Days On Market

  Current Estimated Value $510,438

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  2842 Eastern Pkwy, Winter Park, FL 32789
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  /2

  Est $471,963 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1402 Bessmor Rd, Winter Park, FL 32789

  1402 Bessmor Rd, Winter Park, FL 32789
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  $649,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1926 Natalen Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. *** MUST SEE WINTER PARK POOL HOME ***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted

  Peggy Bonnewitz EXP REALTY LLC

  1926 Natalen Rd, Winter Park, FL 32792
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  /24

  $2,775 per month

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft
  • Townhouse for Rent

  2460 Firstlight Way, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2460 Firstlight Way, Winter Park, FL 32792
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  /2

  $245,000 Sold Jun 26, 2025

  2471 Tahoe Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $189/SF
  • 84 Days On Market

  Current Estimated Value $243,413

  Last Listing Agent Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

  2471 Tahoe Cir, Winter Park, FL 32792
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  /2

  Est $394,249 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft

  1360 Westdale Ave, Winter Park, FL 32792

  1360 Westdale Ave, Winter Park, FL 32792
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  $3,399,999

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
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  $1,680 - $3,440 per month

  Seven41 Winter Park

  Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  741 Clay St, Winter Park, FL 32789
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  $400,000 Sold Jul 16, 2025

  3443 Arnel Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 15 Days On Market

  Current Estimated Value $400,724

  Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
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  Est $1,566,537 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft

  1805 Harland Park Dr, Winter Park, FL 32789

  1805 Harland Park Dr, Winter Park, FL 32789
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  /35

  $390,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,821 Sq Ft

  2829 Aloma Ave, Winter Park, FL 32792

  Rare Opportunity in Highly Sought-After Winter Park! APPRAISED FOR 500K THIS YEAR.....Don’t miss your chance to own this fantastic ...LISTED WELL BELOW APPRAISED VALUE ! Known for its top-rated schools and unbeatable location as well , this home exudes timeless charm with elegant terrazzo floors throughout. Newer Roof ( 2021) and Newer A/C ( 2019) Too!Step inside to a spacious

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  2829 Aloma Ave, Winter Park, FL 32792
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  /16

  $2,665 per month

  • 5 Beds
  • 3 Baths
  • 2,047 Sq Ft
  • House for Rent

  3117 Raiders Run, Winter Park, FL 32792

  TWO MASTER SUITESThis spacious 5 bedroom 3 bathroom features a split floor plan with double master bedrooms, and a large bonus room with a private entrance. Updated kitchen, new flooring, screened back porch and fenced yard. Fantastic location with easy access to major highways and close to the Winter Park shopping and dining district. Zoned for Lakemont Elementary, Maitland Middle and Winter

  Chantel Gutierrez-Davis RISE 24 REAL ESTATE LLC

  3117 Raiders Run, Winter Park, FL 32792
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  $1,335,000 Sold Jul 15, 2025

  1077 Minnesota Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,046 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $438/SF
  • 75 Days On Market

  Current Estimated Value $1,299,936

  Last Listing Agent Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
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  /26

  Est $478,665 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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  $2,350,000

  • 5 Beds
  • 4 Baths
  • 3,948 Sq Ft

  1205 Mayfield Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 bedrooms and 4 bathrooms in the main home, plus a large separate pool home/In-Law Suite complete with

  Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
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  /40

  $991 - $2,295 per month

  The Taylor at Winter Park

  Studio - 3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  2000 Village Ln, Winter Park, FL 32792
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  $510,000 Sold Mar 25, 2025

  5101 N Orange Ave, Winter Park, FL 32792

  • 6 Beds
  • 2 Baths
  • 1,922 Sq Ft
  • Built 1956

  Last Sold Summary

  • 27% Below List Price
  • $265/SF
  • 198 Days On Market

  Last Listing Agent Sonia Reyes INVESTOR'S HOME REALTY

  5101 N Orange Ave, Winter Park, FL 32792
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  Est $1,175,089 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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  /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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  /23

  $2,200 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Apartment for Rent

  2918 Antique Oaks Cir Unit 31, Winter Park, FL 32792

  Property Description (For Lease – Fully Furnished) This beautifully updated, fully furnished two-bedroom, two-bathroom ground-floor condominium is available for lease in the highly desirable Parkview Village Community. Designed for comfort and convenience, this move-in-ready home offers a modern living experience in the heart of Winter Park. The open-concept floor plan features premium luxury

  Yahui Li FLORIDA REALTY INVESTMENTS

  2918 Antique Oaks Cir Unit 31, Winter Park, FL 32792
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  /2

  $580,000 Sold Apr 21, 2025

  3006 Northwood Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $339/SF
  • 1 Day On Market

  Current Estimated Value $652,346

  Last Listing Agent Chris Creegan CREEGAN GROUP

  3006 Northwood Blvd, Winter Park, FL 32789
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  /2

  Est $398,849 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

  $1,215,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living areas, kitchens, and

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
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  /50

  $1,499 - $2,018 per month

  Calibre Bend Apartments

  1 - 2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  3924 Calibre Bend Ln, Winter Park, FL 32792
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  $890,000 Sold Jun 12, 2025

  1762 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $393/SF
  • 114 Days On Market

  Current Estimated Value $897,262

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1762 Mondrian Cir, Winter Park, FL 32789
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  Est $488,466 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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  $1,225,000

  • 3 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  501 W Canton Ave, Winter Park, FL 32789

  Introducing a rare opportunity to own a brand-new, luxury modern townhome just steps from Park Avenue in the heart of Winter Park. This stunning two-story, all-block construction residence offers the perfect blend of design, quality, and location—within walking distance to Hannibal Square, Rollins College, upscale dining, boutique shopping, and more. Inside, soaring 13-foot ceilings, custom wood

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  501 W Canton Ave, Winter Park, FL 32789
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  /24

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  Unlisted Address

  Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

  Yarmmys Vargas ZEN LIVING HOMES LLC

  Unlisted Address
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  /2

  $420,000 Sold May 06, 2025

  627 Carvell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $312/SF
  • 152 Days On Market

  Current Estimated Value $397,767

  Last Listing Agent Ray Al-Malt EXP REALTY LLC

  627 Carvell Dr, Winter Park, FL 32792
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  /2

  Est $259,498 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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  /23

  $310,000

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  2458 Grand Teton Cir, Winter Park, FL 32792

  Welcome to your dream home in Winter Park! This beautifully updated, spacious two-bedroom condo is nestled in the highly sought-after Cedarwood Village Condominium, a well-maintained community known for its charm and appeal. Meticulously cared for, this residence boasts modern elegance with gleaming quartz countertops and premium flooring throughout. The master suite is a true retreat, featuring

  Bryce Jones CHARLES RUTENBERG REALTY ORLANDO

  2458 Grand Teton Cir, Winter Park, FL 32792
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  /50

  $1,150 - $2,848 per month

  Sovereignty at Winter Park Apartments

  1 - 2 Beds

  7745 Brandywood Cir, Winter Park, FL 32792

  We offer 1 and 2 bedroom apartment homes with fully equipped kitchens, garden tubs, vaulted ceilings, ornamental chair rails, and so much more. Our community has a designer clubhouse, state-of-the-art fitness center, a sparkling pool, planned social activities, a high-speed internet business center, and 24 hour emergency maintenance. Winter Park location convenient to Full Sail, UCF, Valencia,

  7745 Brandywood Cir, Winter Park, FL 32792
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  $223,000 Sold Oct 30, 2025

  1378 Chilean Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1960

  Last Sold Summary

  • $168/SF

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

  1378 Chilean Ln, Winter Park, FL 32792
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  Est $1,746,382 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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  /25

  $315,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft

  1920 Carrigan Ave, Winter Park, FL 32792

  Welcome home to 1920 Carrigan Avenue! Located in the highly desirable Winter Park section of Seminole County, this beautifully updated 3-bedroom, 2-bathroom home sits on an oversized 0.22-acre lot with mature trees and no HOA. Inside, you’ll find a modern and inviting space featuring remodeled bathrooms, an updated kitchen with stainless steel appliances, stylish laminate flooring, and fresh

  Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
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  /27

  $2,690 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  1973 Canny Cove, Winter Park, FL 32792

  -HOLIDAY SPECIAL - 1 MONTH FREE if you apply before December 31st! -Spacious townhome in Winter Park with 1 GB Fiber Internet + TV included. Washer & Dryer in-unit. -Gated community with pool and cabana in a quaint neighborhood. -Minutes to all of Orlando's top dining, shopping and attractions. This deal won't last, schedule your showing today!

  Krys Guillaume CENTURY 21 CARIOTI

  1973 Canny Cove, Winter Park, FL 32792
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  /2

  $1,575,000 Sold Aug 14, 2025

  1394 Grove Terrace, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,958 Sq Ft
  • Built 2002

  Last Sold Summary

  • $532/SF
  • 5 Days On Market

  Current Estimated Value $1,558,272

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
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  Est $1,836,587 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

Showing Results 81 - 120, Page 3 of 18