Winter Park, FL Homes

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  $1,999,999

  • 4,056 Sq Ft

  1903 S Lakemont Ave, Winter Park, FL 32792

  Location, location, location! This is an amazing opportunity to build/renovate on a premier lakefront lot in the charming and upscale Winter Park neighborhood of Orlando, Florida. Located on Lake Spier and across the street from the beautiful Baldwin Park, this exceptional-almost one acre property-includes six 1/1 units. This prime property is minutes from award winning restaurants, sidewalk

  Maria Tenner Platinum Properties Int'l Inc.

  1903 S Lakemont Ave, Winter Park, FL 32792
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  $1,595 per month

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Condo for Rent

  851 Miles Ave Unit 21, Winter Park, FL 32789

  Imagine living in this beautiful two-bedroom, one-bathroom condominium near downtown Winter Park at Aragon Condos. This intimate, two-building, two-story condominium community comprises just twenty-eight units focused around a central courtyard.This first-floor corner unit allows for privacy with only one adjoining neighbor.Features include:Granite kitchen countertops;

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  851 Miles Ave Unit 21, Winter Park, FL 32789
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  $602,500 Sold May 09, 2025

  777 S Denning Dr Unit B, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,762 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 37 Days On Market

  Current Estimated Value $601,937

  Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

  777 S Denning Dr Unit B, Winter Park, FL 32789
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  /16

  Est $1,025,582 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  2400 Roxbury Rd, Winter Park, FL 32789

  2400 Roxbury Rd, Winter Park, FL 32789
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  $4,750,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,850 Sq Ft

  1150 Via Salerno, Winter Park, FL 32789

  In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Designed and developed by Steve and Jodie Warrick Konold of Scout & Co., the 3,850 sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway and

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1150 Via Salerno, Winter Park, FL 32789
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  /11

  $1,700 per month

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft
  • Condo for Rent

  3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Great Furnished unit . First flour . Two bedrooms' and two bathroom in great quite safe community. 1 miles from SAM Wearhouse at Golden Road.It is new pint and include washer and dryer. Its clean and ready to move in.It is option to Buy also , Contact the owner for details

  Amin Abraham FLORIDA REALTY INVESTMENTS

  3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  $445,000 Sold Mar 20, 2025

  1663 Meadowgold Ct, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,851 Sq Ft
  • Built 1987

  Last Sold Summary

  • 11% Below List Price
  • $240/SF
  • 173 Days On Market

  Current Estimated Value $441,402

  Last Listing Agent Dallas Wittish ORLANDO REALTY & PROPERTY MGNT

  1663 Meadowgold Ct, Winter Park, FL 32792
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  /19

  Est $2,518,922 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft

  350 Beloit Ave, Winter Park, FL 32789

  350 Beloit Ave, Winter Park, FL 32789
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  $3,950,000

  • Land
  • 8.34 Acres
  • $473,621 per Acre

  2403 Euston Rd, Winter Park, FL 32789

  Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  2403 Euston Rd, Winter Park, FL 32789
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  /57

  $3,300 per month

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • House for Rent

  2128 Sycamore Dr, Winter Park, FL 32789

  MOVE-IN READY! Don’t miss this fantastic opportunity to rent a beautiful 3-bedroom, 2-bathroom home situated on a spacious .23-acre corner lot. This property has undergone a complete upgrade inside and out, making it perfect for those looking for a fresh start. Key Features: • Newer Septic Tank: Ensures peace of mind and efficiency. • 2016 Roof: A reliable roof that adds to the home’s longevity.

  Luis Perez Garcia EXP REALTY LLC

  2128 Sycamore Dr, Winter Park, FL 32789
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  $434,000 Sold Sep 12, 2025

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,556 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Above List Price
  • $279/SF
  • 55 Days On Market

  Current Estimated Value $440,038

  Last Listing Agent Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
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  /35

  Est $297,892 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  228 Balfour Dr Unit 17, Winter Park, FL 32792
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  $379,990 Pending

  • 4 Beds
  • 2 Baths
  • 1,530 Sq Ft

  1083 Eastbrook Blvd, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome Home to Eastbrook in Winter Park!This beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of comfort, charm, and modern updates — all nestled on an OVERSIZED CORNER LOT in the desirable Eastbrook community with NO HOA and NO CDD. Step inside to find 1,530 sq ft of thoughtfully designed living space, freshly painted in 2025 to

  Jo Ann Ortiz ORANGE SLICE PROPERTIES

  1083 Eastbrook Blvd, Winter Park, FL 32792
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  $2,510 per month

  • 4 Beds
  • 2.5 Baths
  • 1,970 Sq Ft
  • House for Rent

  2843 Riddle Dr, Winter Park, FL 32789

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Daniel Reyes MAIN STREET RENEWAL LLC

  2843 Riddle Dr, Winter Park, FL 32789
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  /2

  $1,895,000 Sold Jan 22, 2025

  2612 Parkland Dr, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,282 Sq Ft
  • Built 2006

  Last Sold Summary

  • $577/SF
  • 9 Days On Market

  Current Estimated Value $1,896,821

  Last Listing Agent Brian Teach COLDWELL BANKER RESIDENTIAL RE

  2612 Parkland Dr, Winter Park, FL 32789
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  Est $1,173,786 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 4,307 Sq Ft

  1999 Soaring Oak Way, Winter Park, FL 32792

  1999 Soaring Oak Way, Winter Park, FL 32792
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  $439,000

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

  1900 Erudite Way, Winter Park, FL 32792

  Seller offering $10,000 credit to buyer at closing—may be applied toward buyer’s rate buy-down, closing costs, or prepaid expenses (subject to lender approval).Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features,

  Erica Diltz BALDWIN PARK REALTY LLC

  1900 Erudite Way, Winter Park, FL 32792
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  $3,350 per month

  • 6 Beds
  • 3 Baths
  • 2,722 Sq Ft
  • House for Rent

  1288 Michigan Ave, Winter Park, FL 32789

  5 bedrooms, 3 bathrooms super close to Winter Park Village and conveniently located close to all Winter Park activities. Lots of remodeling!! No garage, large treed backyard!

  Eric Weigand CQ ORLANDO REALTY INC

  1288 Michigan Ave, Winter Park, FL 32789
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  $505,000 Sold Aug 01, 2025

  715 Roughbeard Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1968

  Last Sold Summary

  • 12% Below List Price
  • $224/SF
  • 60 Days On Market

  Current Estimated Value $520,478

  Last Listing Agent Christine Gerardi NEXTHOME DIAMOND PROPERTIES

  715 Roughbeard Rd, Winter Park, FL 32792
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  Est $429,591 Not Listed For Sale

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

  2770 Bright Bird Ln, Winter Park, FL 32792

  2770 Bright Bird Ln, Winter Park, FL 32792
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  $136,000

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft

  7326 Swallow Run Unit 7326, Winter Park, FL 32792

  **** Ground floor 2 bed 2 bath condo in a nice quiet community *** move-in ready with granite tops, upgraded plumbing, on-demand water heater, vinyl plank flooring throughout. One of the best priced units available on MLS. Well maintained community and roof replaced within past two years. Owner is Listing Agent, Broker and Realtor so an efficient sale can be expected. All offers to be on FAR/BAR

  Kevin Mernan CREATIVE HOMES OF ORLANDO

  7326 Swallow Run Unit 7326, Winter Park, FL 32792
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  /15

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
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  $252,500 Sold Jul 17, 2025

  2309 Sun Valley Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,669 Sq Ft
  • Built 1985

  Last Sold Summary

  • 11% Below List Price
  • $151/SF
  • 65 Days On Market

  Current Estimated Value $259,070

  Last Listing Agent Kristin Vogt CENTURY 21 INTEGRA

  2309 Sun Valley Cir, Winter Park, FL 32792
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  Est $947,661 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft

  1913 S Lakemont Ave, Winter Park, FL 32792

  1913 S Lakemont Ave, Winter Park, FL 32792
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  /17

  $185,000

  • 3 Beds
  • 2 Baths
  • 1,117 Sq Ft

  7426 Wynnewood Square Unit 195, Winter Park, FL 32792

  Excellent opportunity to acquire a 3-bedroom, 2-bath first-floor end-unit condo offering approximately 1,117 sq ft in a well-established community. The unit features a functional layout and a highly desirable location near UCF, Full Sail University, Valencia College, and major shopping and dining. Priced to sell, this property is ideal for investors seeking a light-to-moderate rehab with strong

  Qing Lin SPRINGHILL PROPERTIES LLC

  7426 Wynnewood Square Unit 195, Winter Park, FL 32792
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  $2,450 per month

  • 4 Beds
  • 2.5 Baths
  • 1,701 Sq Ft
  • House for Rent

  2886 Carew Ave, Winter Park, FL 32789

  What a location! Available now for rent! Close to downtown Orlando! This charming home has 4 bedrooms, 2.5 baths, gorgeous wood flooring, family room with fireplace, one car garage, all appliances included! Primary bedroom has huge closet, private door to backyard and primary bath features dual sinks and shower. Landscaped backyard for privacy - partially fenced. Schedule your private tour today!

  Chris Watts THE TEAM REAL ESTATE GROUP INC

  2886 Carew Ave, Winter Park, FL 32789
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  $458,000 Sold Feb 25, 2025

  3455 Athena Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,161 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $212/SF
  • 135 Days On Market

  Current Estimated Value $462,398

  Last Listing Agent Stephanie Kovats KELLER WILLIAMS ADVANTAGE REALTY

  3455 Athena Dr, Winter Park, FL 32792
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  Not Listed For Sale

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

  0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792
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  /15

  $239,900

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

  7771 Country Place Unit 7, Winter Park, FL 32792

  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 Flooring Flows

  Ivan Tobon OUTLET REALTY

  7771 Country Place Unit 7, Winter Park, FL 32792
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  /15

  $1,740 per month

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Condo for Rent

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

  Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
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  $660,000 Sold Apr 14, 2025

  1037 Fairway Dr, Winter Park, FL 32792

  • 3 Beds
  • 3 Baths
  • 2,145 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $308/SF
  • 29 Days On Market

  Current Estimated Value $656,043

  Last Listing Agent Skip Juma LEGACY REALTY & BROKERS LLC

  1037 Fairway Dr, Winter Park, FL 32792
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  Est $431,396 Not Listed For Sale

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

  2737 Bright Bird Ln, Winter Park, FL 32792

  2737 Bright Bird Ln, Winter Park, FL 32792
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  $709,000

  • 5 Beds
  • 3.5 Baths
  • 3,152 Sq Ft

  5275 Pine Lily Cir, Winter Park, FL 32792

  Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that

  Kathy Williams COMPASS FLORIDA LLC

  5275 Pine Lily Cir, Winter Park, FL 32792
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  $2,100 per month

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave, Winter Park, FL 32789

  Charming 3-Bedroom Home for Rent in Winter Park This beautiful 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. Featuring spacious living areas and modern appliances, it offers a comfortable and convenient living environment. Located in a quiet, family-friendly neighborhood, it provides easy access to local shops, restaurants, and

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave, Winter Park, FL 32789
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  $3,550,000 Sold Mar 24, 2025

  443 Lakewood Dr, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 2,803 Sq Ft
  • Built 1954

  Last Sold Summary

  • 1% Above List Price
  • $1,267/SF
  • 0 Days On Market

  Current Estimated Value $3,401,343

  Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES

  443 Lakewood Dr, Winter Park, FL 32789
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  /21

  Est $437,360 Not Listed For Sale

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

  2861 Clever Ln, Winter Park, FL 32792

  2861 Clever Ln, Winter Park, FL 32792
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  $3,600,000

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  In one of Winter Park’s desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 automation offers a blend of luxury and function. Designed with sleek lines and open-concept living, the home showcases Italian engineered wood flooring throughout, creating an elegant yet inviting atmosphere. Expansive windows flood the interiors with natural light, seamlessly

  Nathalie Bates PREMIER SOTHEBY'S INTL. REALTY

  1742 Temple Dr, Winter Park, FL 32789
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  $3,750 per month

  • 3 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • House for Rent

  1681 Walnut Ave, Winter Park, FL 32789

  Fully furnished with dishes and all ! Tastefully decorated !Can be rented unfurnished if needed .Also month to a year lease is ok !Two separate living quarters en suite with private entrance and small fridge and microwave /dining /living area ( or master )Fully renovated this adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods.Fully

  Natalie Citarelli CITARELLI REALTY GROUP LLC

  1681 Walnut Ave, Winter Park, FL 32789
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  $468,000 Sold Aug 28, 2025

  541 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,899 Sq Ft
  • Built 1965

  Last Sold Summary

  • $246/SF
  • 8 Days On Market

  Current Estimated Value $476,047

  Last Listing Agent Christopher Bauman REVEL REALTY LLC

  541 London Rd, Winter Park, FL 32792
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  Est $327,802 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,442 Sq Ft

  3197 Crown Jewel Ct, Winter Park, FL 32792

  3197 Crown Jewel Ct, Winter Park, FL 32792

Showing Results 561 - 600, Page 15 of 18