Winter Park, FL Homes

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  /26

  $439,900 Pending

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Opportunities like this are rare. Perfectly suited for multi-generational living, mother-in-law suite potential, or rental income, this versatile POOL home sits on an oversized lot with no HOA in one of Central Florida’s most desirable locations — Winter Park.The flexible floor plan allows for comfortable

  Irina Paul FUTURE HOME REALTY INC

  2835 Bongart Rd, Winter Park, FL 32792
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  /50

  $1,680 - $3,372 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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  /2

  $690,000 Sold Aug 14, 2025

  2433 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Above List Price
  • $375/SF
  • 2 Days On Market

  Current Estimated Value $637,887

  Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2433 Whitehall Cir, Winter Park, FL 32792
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  /2

  Est $351,908 Not Listed For Sale

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

  5229 N Woodcrest Dr, Winter Park, FL 32792

  5229 N Woodcrest Dr, Winter Park, FL 32792
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  /54

  $439,900

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers

  Brian Bauer SOUTHERN LAND & HOMES

  1367 Tierra Cir, Winter Park, FL 32792
• 

  

  /13

  $1,475 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Townhouse for Rent

  1300 Indiana Ave Unit A, Winter Park, FL 32789

  Available SOON! *Tenant just vacated. Some interior work pending.* Cozy and quaint 1/2 duplex unit! 1 Bed/1 Bath located in Winter Park!!! This unit has been lovingly renovated with new kitchen cabinets, appliances, granite counters, new fans, lights, sink, and so much more!! Stackable washer/dryer included for your convenience. Hard wood floors in the living room and dining room, with tile in

  Vicky Ramos ALL COUNTY CFL PROPERTY MGMT

  1300 Indiana Ave Unit A, Winter Park, FL 32789
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  /2

  $555,000 Sold Apr 25, 2025

  633 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $547,413

  Last Listing Agent Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  633 London Rd, Winter Park, FL 32792
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  /2

  Est $304,837 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2327 Antilles Dr, Winter Park, FL 32792

  2327 Antilles Dr, Winter Park, FL 32792
• 

  

  /35

  $200,000 Pending

  • 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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  /36

  $904 - $2,041 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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  /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 $244,330

  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 $2,612,281 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,648 Sq Ft

  1215 Via Salerno, Winter Park, FL 32789

  1215 Via Salerno, Winter Park, FL 32789
• 

  

  /40

  $899,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,554 Sq Ft

  2609 Summerfield Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. Luxury living meets the fairways in this exceptional 5/2, 2554 sqft. retreat, perfectly positioned across from the Winter Park Pines Golf Course and its vibrant clubhouse for dining and drinks. Professionally designed from top to bottom, this sun-filled home blends timeless elegance with modern peace of mind—every detail thoughtfully upgraded, every space

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  2609 Summerfield Rd, Winter Park, FL 32792
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  /23

  $1,495 per month

  • 2 Beds
  • 1 Bath
  • 3,822 Sq Ft
  • Condo for Rent

  1380 Indiana Ave Unit 3, Winter Park, FL 32789

  Winter Park at your door step! This is a second floor 2 bedroom unit, in secured building. Large open backyard with rear balcony and patio space and plenty of parking. Unit has full kitchen, and washer/dryer in unit! Two full bedrooms both with walk-in closets and a full bath. Living room is large open/bright. Only a few blocks walk to Orlando Ave with all its shopping, Publix and restaurants.

  Scott Butts KIMBRIDGE REALTY, LLC

  1380 Indiana Ave Unit 3, Winter Park, FL 32789
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  /2

  $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 $403,206

  Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
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  /2

  Est $542,217 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,040 Sq Ft

  1981 Japonica Rd, Winter Park, FL 32792

  1981 Japonica Rd, 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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  /2

  $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 $1,343,077

  Last Listing Agent Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
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  /2

  Est $1,007,055 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,304 Sq Ft

  241 W Lake Sue Ave, Winter Park, FL 32789

  241 W Lake Sue Ave, Winter Park, FL 32789
• 

  

  /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
• 

  

  /19

  $1,750 per month

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

  3355 River View Way Unit 42, Winter Park, FL 32792

  Beautifully remodeled 2-bedroom, 1.5-bath condo located in the desirable Hidden Oaks community of Winter Park. This move-in-ready home features porcelain tile and vinyl flooring throughout, updated granite countertops in the bathrooms, and a spacious, functional layout. Enjoy modern finishes, ample living space, and a convenient location close to shopping, dining, parks, and major roadways. A

  Antonella Martino EPIQUE REALTY, INC.

  3355 River View Way Unit 42, Winter Park, FL 32792
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  /2

  $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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  /2

  Est $4,314,337 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 5,633 Sq Ft

  1231 Via Salerno, Winter Park, FL 32789

  1231 Via Salerno, Winter Park, FL 32789
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  /66

  $1,495,000

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft

  3711 Vinsetta Ct, Winter Park, FL 32792

  Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  3711 Vinsetta Ct, 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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  /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 $626,620

  Last Listing Agent Chris Creegan CREEGAN GROUP

  3006 Northwood Blvd, Winter Park, FL 32789
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  /2

  Est $414,199 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,525 Sq Ft

  1190 Village Forest Place, Winter Park, FL 32792

  1190 Village Forest Place, Winter Park, FL 32792
• 

  

  /23

  $255,000

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, Winter Park, FL 32792
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  /2

  $2,500 per month

  • Property for Rent

  Unlisted Address

  Rare Winter Park Lakefront Boathouse - $2,500/MonthExperience the quintessential Central Florida lifestyle in this exceptional boathouse rental on the renowned Winter Park Chain of Lakes. This direct lakefront property offers unparalleled access to year-round water activities, from kayaking and paddleboarding to boating and fishing right from your doorstep. Positioned just off the scenic

  Kelly Price KELLY PRICE & COMPANY LLC

  Unlisted Address
• 

  /2

  $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 $903,996

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1762 Mondrian Cir, Winter Park, FL 32789
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  /2

  Est $328,178 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,162 Sq Ft

  2886 Roxbury Rd, Winter Park, FL 32789

  2886 Roxbury Rd, Winter Park, FL 32789
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  /44

  $1,590,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft

  1166 Oaks Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. HUGE PRICE IMPROVEMENT-MOTIVATED SELLER-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout its expansive 2,860 square feet of

  Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  /50

  $1,467 - $3,912 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
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  /2

  $440,000 Sold Jan 29, 2026

  1621 Puritan Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Below List Price
  • $249/SF
  • 342 Days On Market

  Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
• 

  /2

  Est $84,478 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 756 Sq Ft

  328 Scottsdale Square Unit N328, Winter Park, FL 32792

  328 Scottsdale Square Unit N328, Winter Park, FL 32792
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  /37

  $824,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft

  737 N Capen Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this stunning Mid-century style 3 bedroom, 2 bath, 1930 sq ft home with a 2 car garage, where sleek modern design meets functionality. Step into the open-concept living space and be captivated by the abundance of natural light streaming through the large windows, creating a warm and inviting atmosphere. The centerpiece of this home is the gourmet

  Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
• 

  

  /19

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • House for Rent

  1925 S Lakemont Ave, Winter Park, FL 32792

  Enjoy lakefront living in this charming waterfront Studio B apartment with beautiful views of Baldwin Lake, offering a desirable Winter Park address and the highly sought-after Baldwin Park lifestyle. Located directly across from the Lake Baldwin Trail, you’ll love being near scenic surroundings and stunning sunsets over the water. This studio includes a private bathroom and a brand new

  Elena Sanchez BALDWIN PARK REALTY LLC

  1925 S Lakemont Ave, Winter Park, FL 32792
• 

  /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 $395,233

  Last Listing Agent Ray Al-Malt EXP REALTY LLC

  627 Carvell Dr, Winter Park, FL 32792
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  /2

  Est $1,649,304 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,287 Sq Ft

  1321 Lakeview Dr, Winter Park, FL 32789

  1321 Lakeview Dr, Winter Park, FL 32789

Showing Results 81 - 120, Page 3 of 18