Winter Park, FL Homes

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  /74

  $860,000

  $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 3,950 Sq Ft

  1521 Heron Wood Place, Winter Park, FL 32792

  Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation.One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare

  Ronald Trotter RE/MAX INNOVATION

  1521 Heron Wood Place, Winter Park, FL 32792
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  /25

  $1,750 Per Month

  • 3 Beds
  • 2 Baths
  • 1,281 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 103, Winter Park, FL 32792

  Virtually Staged. Stylish Winter Park Condo Living – Spacious 3-Bedroom Home in a Prime Location! Welcome to 1000 S. Semoran Blvd #103, a beautifully maintained 3-bedroom, 2-bath residence offering comfort, convenience, and an unbeatable Winter Park location. Featuring a bright and open floor plan, this home provides the perfect space for relaxing, entertaining, and enjoying everyday living. The

  Jacob Hara TRANSCEND REALTY

  1000 S Semoran Blvd Unit 103, Winter Park, FL 32792
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  /2

  $260,000

  Sold Apr 03, 2026

  3580 Wilde Ave, Winter Park, FL 32792

  • Land
  • 35,283 Sq Ft
  • $320,988 per Acre

  Last Sold Summary

  • 340 Days On Market

  Current Estimated Value $261,624

  Last Listing Agent Gwendolen Flynn COLDWELL BANKER REALTY

  3580 Wilde Ave, Winter Park, FL 32792
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  /2

  Est $206,976

  Not Listed For Sale

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  Last Sold Summary

  • 108 Days On Market
• 

  

  

  /26

  $629,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  685 Overspin Dr, Winter Park, FL 32789

  Super Location! Close to Urban Bike trail, Winter Park Village, Dubsdread Golf Course, Advent Health. This home was custom built with large white wood window casing, formal dining room with plenty of natural light, 10 foot ceilings, crown molding, 8 ft doors, upgraded tile, 3 sets of French Doors open to back and so much more. Gas fireplace in the family room with high-top bar seating in the

  Corey Van Dyke HOMEVEST REALTY

  685 Overspin Dr, Winter Park, FL 32789
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  /26

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,158 Sq Ft
  • Winter Park 3 bedroom steps to shopping, dining.

  301 S Capen Ave, Winter Park, FL 32789

  Welcome to 301 S Capen, a 3-bedroom, 2-bath home located just minutes from Park Avenue.Inside, you'll find a bright and inviting kitchen featuring large bay windows and ample space for a breakfast table. The adjoining family room provides a comfortable gathering space and offers convenient access to the laundry room and attached one-car garage.Down the hall, you'll find three

  301 S Capen Ave, Winter Park, FL 32789
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  /2

  $417,100

  Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Current Estimated Value $427,343

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  /2

  Not Listed For Sale

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,079 Sq Ft
  • Built 1974

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  Last Sold Summary

  • 66 Days On Market
• 

  

  /27

  $515,000

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

  2008 Houndslake Dr Unit 1, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Spacious and full of potential, this 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community includes an attached flex room. Perfect for a nursery, mother in law suite, office, or man cave! In the heart of Winter Park, designed for both everyday living and entertaining, this home gives your family room to spread out and enjoy. Inside,

  Megan Hedrick Mark Spain Real Estate

  2008 Houndslake Dr Unit 1, Winter Park, FL 32792
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  /22

  $1,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft
  • Condo for Rent

  4796 Tangerine Ave Unit 4796, Winter Park, FL 32792

  Cute 2 bedroom, 2 bathroom, freshly painted condo in Winter Park. Amenities include a swimming pool, fitness center, clubhouse/conference room, well-maintained grounds, and ample parking. This property offers easy access to Full Sail University, University of Central Florida, Rollins College, Downtown Winter Park, Baldwin Park, and Downtown Orlando. Shopping, dining, entertainment, parks and

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  4796 Tangerine Ave Unit 4796, Winter Park, FL 32792
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  /2

  $435,800

  Sold Apr 27, 2026

  5418 Ardmore Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $279/SF
  • 5 Days On Market

  Current Estimated Value $441,958

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5418 Ardmore Dr, Winter Park, FL 32792
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  /2

  Est $457,590

  Not Listed For Sale

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  Unlisted Address

  Last Sold Summary
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  /55

  $475,000

  $75K PRICE DROP

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

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
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  /11

  $1,385 Per Month

  • 2 Beds
  • 2 Baths
  • 1,045 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

  LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

  1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
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  /2

  $1,200,000

  Sold Mar 20, 2026

  950 Aragon Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 2020

  Last Sold Summary

  • $463/SF
  • 5 Days On Market

  Current Estimated Value $1,183,121

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  950 Aragon Ave, Winter Park, FL 32789
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  /2

  Est $441,053

  Not Listed For Sale

  2838 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2838 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 8 Days On Market
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  /81

  $3,799,000

  New Construction Pending

  • 5 Beds
  • 5 Baths
  • 4,451 Sq Ft

  150 Dana Way, Winter Park, FL 32789

  JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKETProudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  150 Dana Way, Winter Park, FL 32789
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  /24

  $8,295 Per Month

  • 4 Beds
  • 5.5 Baths
  • 3,295 Sq Ft
  • House for Rent

  2234 Howard Dr, Winter Park, FL 32789

  Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility.Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal

  Raquel Elliott COLDWELL BANKER REALTY

  2234 Howard Dr, Winter Park, FL 32789
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  /2

  $1,206,400

  Sold Oct 15, 2025

  4048 Gilder Rose Place, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,321 Sq Ft
  • Built 1992

  Last Sold Summary

  • $363/SF
  • 101 Days On Market

  Current Estimated Value $1,190,451

  Last Listing Agent Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
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  /35

  Est $214,156

  Not Listed For Sale

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Built 1981

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • 27 Days On Market
• 

  

  /29

  $504,900

  $15K PRICE DROP

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

  2715 Prince John Rd, Winter Park, FL 32792

  GREAT HOME & GREAT VALUE — home needs some TLC and if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE

  Donna Peebles VIA PROPERTIES LLC

  2715 Prince John Rd, Winter Park, FL 32792
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  /11

  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 850 Sq Ft
  • 2 bed 2 bath in winterpark!

  7328 Swallow Run, Winter Park, FL 32792

  2 bed 2 bath in winterpark!

  7328 Swallow Run, Winter Park, FL 32792
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  /2

  $630,000

  Sold Apr 16, 2026

  649 Berwick Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,943 Sq Ft
  • Built 1966

  Last Sold Summary

  • 3% Above List Price
  • $324/SF
  • 3 Days On Market

  Current Estimated Value $621,087

  Last Listing Agent Caroline Fiore MAINFRAME REAL ESTATE

  649 Berwick Dr, Winter Park, FL 32792
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  /2

  Est $388,153

  Not Listed For Sale

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1986

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Last Sold Summary

  • 53 Days On Market
• 

  

  /58

  $1,899,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789

  Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789
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  /17

  $2,000 Per Month

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

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
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  /2

  $625,090

  Sold Jun 03, 2026

  2713 Eastern Pkwy, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $479/SF
  • 12 Days On Market

  Current Estimated Value $679,803

  Last Listing Agent Helen Thompson RE/MAX SELECT GROUP

  2713 Eastern Pkwy, Winter Park, FL 32789
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  /24

  Est $335,846

  Not Listed For Sale

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft
  • Built 1980

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  Last Sold Summary

  • 6 Days On Market
• 

  

  /53

  $1,299,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789

  On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789
• 

  

  /11

  $1,495 Per Month

  • 2 Beds
  • 2 Baths
  • 1,104 Sq Ft
  • Condo for Rent

  3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792

  Great location! Spacious SECOND FLOOR 2 bedroom + 2 full bath condo featuring an open living room/dining room combo and large kitchen. Conveniently located across from the pool. Stackable washer/dryer in unit. NEW CARPET in bedrooms! Parking permit required. Two pet max permitted. Available now! NOTE: Petscreening required on all applications, whether tenant has a pet or not. . $30 per pet to

  3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792
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  /2

  $637,500

  Sold Jan 16, 2026

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,951 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 149 Days On Market

  Current Estimated Value $644,110

  Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

  595 Huntington Ave Unit 4, Winter Park, FL 32789
• 

  

  /18

  Est $440,325

  Not Listed For Sale

  2786 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2786 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 7 Days On Market
• 

  

  /35

  $180,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4798 Tangerine Ave, Winter Park, FL 32792

  Welcome to this charming and well-maintained condominium located in the desirable Winter Park area, offering the perfect blend of comfort, convenience, and low-maintenance living. This inviting residence features a spacious and functional layout filled with natural light, creating a warm and welcoming atmosphere ideal for everyday living or entertaining. Enjoy an open living and dining area that

  Vincenza Di Cesare De Vieira LPT REALTY, LLC

  4798 Tangerine Ave, Winter Park, FL 32792
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  /33

  $1,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Apartment for Rent

  652 Saint Johns Ct Unit 652, Winter Park, FL 32792

  Don't miss this opportunity! Beautiful apartment located in Winter Park, one of the most convenient and desirable areas in the Orlando region. Conveniently located near Full Sail University, Rollins College, shopping centers, restaurants, entertainment, and major highways. Enjoy the comfort of a well-maintained community featuring a swimming pool and common areas for relaxation. This apartment

  David Carballo HOME PRIME REALTY LLC

  652 Saint Johns Ct Unit 652, Winter Park, FL 32792
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  /2

  $1,250,000

  Sold Dec 29, 2025

  359 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1979

  Last Sold Summary

  • $522/SF
  • 0 Days On Market

  Current Estimated Value $1,255,064

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  359 Beloit Ave, Winter Park, FL 32789
• 

  

  /29

  Not Listed For Sale

  7482 Canford Ct Unit 7482, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,393 Sq Ft
  • Built 1974

  7482 Canford Ct Unit 7482, Winter Park, FL 32792

  Last Sold Summary

  • 9 Days On Market
• 

  

  /11

  $317,500

  $30K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  121 Stefanik Rd, Winter Park, FL 32792

  A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. Third bedroom has its own separate entrance as well. Large foyer and living room. Kitchen has beautiful 40 inch cabinets and granite counter tops. Septic system was just replaced in September. Close to everything.

  Moe Mossa SAVVY AVENUE, LLC

  121 Stefanik Rd, Winter Park, FL 32792
• 

  

  /46

  $2,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Beautiful Remodeled/Renovated 3/2/2 with Large Screen Porch

  5360 N Lake Burkett Ln, Winter Park, FL 32792

  Nice renovations include Modern Kitchen & Baths with Large walk-in shower in Primary Bathroom. Open Floor Plan. All New cabinets, Quartz Counters, Indirect lighting in Living Room. New Stainless Steel Appliances. All New Vinyl Plank flooring. Spacious bedrooms. Large Screen Porch. Fenced Back Yard. Large garage with new stainless steel utility sink. Storage Shed in backyard. Community Pool.

  5360 N Lake Burkett Ln, Winter Park, FL 32792
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  /2

  $775,000

  Sold May 22, 2026

  521 Fairfax Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $367/SF
  • 2 Days On Market

  Current Estimated Value $780,768

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  521 Fairfax Ave, Winter Park, FL 32789
• 

  

  /11

  Est $451,509

  Not Listed For Sale

  2711 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2023

  2711 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

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