Homes in ZIP Code 32789

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  $259,000 Sold Aug 29, 2025

  1250 S Denning Dr Unit 111, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  Last Sold Summary

  • $285/SF
  • 76 Days On Market

  Current Estimated Value $256,565

  Last Listing Agent Alayna Phillips EXP REALTY LLC

  1250 S Denning Dr Unit 111, Winter Park, FL 32789
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  /2

  Est $1,939,411 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,361 Sq Ft

  331 E Reading Way, Winter Park, FL 32789

  331 E Reading Way, Winter Park, FL 32789
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  /26

  $199,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 222, Winter Park, FL 32789

  Welcome to your next chapter of lakeside living! This charming one-bedroom, one-bathroom condo offers a perfect blend of tranquility and convenience in the heart of Winter Park. Step inside to discover a thoughtfully designed space where comfort meets style. The open-concept living area welcomes you with beautiful engineered wood floors, creating a seamless flow between the living room and

  Christine Bouchard HOMESMART

  2500 Lee Rd Unit 222, Winter Park, FL 32789
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  /2

  $435,000 Sold Jun 06, 2025

  693 Minnesota Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Built 2000

  Last Sold Summary

  • $419/SF

  Current Estimated Value $434,497

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

  693 Minnesota Ave, Winter Park, FL 32789
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  /27

  Est $1,050,411 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,043 Sq Ft

  2529 Modac Trail, Winter Park, FL 32789

  2529 Modac Trail, Winter Park, FL 32789
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  /32

  $420,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  740 Baffie Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this fully remodeled, move in ready home perfectly situated on a spacious corner lot in Winter Park, just blocks from the Dubsdread Golf Course and close to the shops, restaurants, and charm of College Park and downtown Winter Park. Every inch of this 3 bedroom, 2 bath home has been thoughtfully updated to blend modern comfort with timeless

  Chris Creegan CREEGAN GROUP

  740 Baffie Ave, Winter Park, FL 32789
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  /2

  $530,000 Sold Oct 02, 2025

  1409 Sunset Dr, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,107 Sq Ft
  • Built 1930

  Last Sold Summary

  • 2% Above List Price
  • $479/SF
  • 4 Days On Market

  Current Estimated Value $525,110

  Last Listing Agent Ahmad Karain R MICHAELS REALTY LLC

  1409 Sunset Dr, Winter Park, FL 32789
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  /23

  Est $1,315,466 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft

  1600 Alabama Dr Unit 201, Winter Park, FL 32789

  1600 Alabama Dr Unit 201, Winter Park, FL 32789
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  /41

  $725,000 Pending

  • Land
  • 0.34 Acre
  • $2,132,353 per Acre

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789

  Under contract-accepting backup offers. Here it is! Almost impossible to find 2 adjacent 75x100 R-3 lots for a total of 75x200 or 15,000 sq/ft in top Winter Park location! Located at northwest corner of proposed Winter Park Commons project. The vacant lot to be simultaneously purchased with adjacent parcel (TAX ID 06-22-30-1168-02-022) fronting Webster with BONUS 4/2 Bungalow. Walk to WP Village,

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789
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  /2

  $4,800,000 Sold Jan 02, 2026

  641 Bonita Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 6,699 Sq Ft
  • Built 1948

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 0 Days On Market

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  641 Bonita Dr, Winter Park, FL 32789
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  /29

  Est $978,112 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 993 Sq Ft

  1602 Alabama Dr Unit 107, Winter Park, FL 32789

  1602 Alabama Dr Unit 107, Winter Park, FL 32789
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  /38

  $650,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  1399 Aloma Ave, Winter Park, FL 32789

  ***Price Adjustment *** Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter Park, moments from Rollins College, Park Avenue, and Winter Park Hospital. Just a short walk provides coveted access to the Winter Park Chain of Lakes, bring your paddle board or canoe. Step inside

  Cheryl Bennett FLORIDA HOMES REALTY & MORTGAGE

  1399 Aloma Ave, Winter Park, FL 32789
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  /2

  $1,100,000 Sold Mar 28, 2025

  567 Osceola Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,651 Sq Ft
  • Built 1912

  Last Sold Summary

  • 12% Below List Price
  • $415/SF
  • 42 Days On Market

  Current Estimated Value $1,116,234

  Last Listing Agent Susannah Dance COLDWELL BANKER RESIDENTIAL RE

  567 Osceola Ave, Winter Park, FL 32789
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  /2

  Est $208,255 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 26, Winter Park, FL 32789

  851 Miles Ave Unit 26, Winter Park, FL 32789
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  /29

  $644,900

  • 2 Beds
  • 1.5 Baths
  • 1,149 Sq Ft

  1137 Oaks Blvd, Winter Park, FL 32789

  Charming Mid-Century Winter Park bungalow with tremendous potential * Not ready to build a new home but would like to have that option someday? This property provides the unique opportunity of being move-in ready while being undervalued for the neighborhood * The majority of the homes on the street are brand new or recently built, consequently, there is great value in being one of the few

  David Gallup RE/MAX 200 REALTY

  1137 Oaks Blvd, Winter Park, FL 32789
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  /2

  $760,000 Sold Jun 09, 2025

  2838 Wright Ave, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft
  • Built 1952

  Last Sold Summary

  • 5% Below List Price
  • $674/SF
  • 2 Days On Market

  Current Estimated Value $743,488

  Last Listing Agent Jordan Suglio BALDWIN PARK REALTY LLC

  2838 Wright Ave, Winter Park, FL 32789
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  /16

  Est $221,460 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 28, Winter Park, FL 32789

  851 Miles Ave Unit 28, Winter Park, FL 32789
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  /45

  $1,146,000

  • 3 Beds
  • 2.5 Baths
  • 2,342 Sq Ft

  503 W Canton Ave, Winter Park, FL 32789

  Walk to Park Avenue! Model Home, tons of upgrades. Enjoy luxury living and premium sought after location at Vilasa Homes in Winter Park, FL 32789. Park Avenue lifestyle, arts and culture, a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. Modern finishes for this 2-story townhome personally

  Jennifer Sloan COMPASS FLORIDA LLC

  503 W Canton Ave, Winter Park, FL 32789
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  $341,000 Sold Aug 08, 2025

  2827 Euston Rd, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1956

  Last Sold Summary

  • 20% Below List Price
  • $217/SF
  • 205 Days On Market

  Current Estimated Value $345,038

  Last Listing Agent Evelyn Tejada REGENCY REAL ESTATE LLC

  2827 Euston Rd, Winter Park, FL 32789
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  /2

  Est $200,797 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 4, Winter Park, FL 32789

  851 Miles Ave Unit 4, Winter Park, FL 32789
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  /23

  $169,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 237, Winter Park, FL 32789

  Welcome to lakeside living! This cozy one-bedroom, one-bathroom condo offers a blend of amenities and convenience. This perfectly located condominium has low HOA FEES and has no assessment fees! Enjoy your days fishing, boating, or hanging out by the pool overlooking gorgeous Lake Killarney, a 240 acre spring-fed lake! Cherish living on the shores of Lake Killarney, complete with coveted dock

  Lydia Cassaro LPT REALTY LLC (DB)

  2500 Lee Rd Unit 237, Winter Park, FL 32789
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  /2

  $2,288,215 Sold Dec 19, 2025

  1602 Alabama Dr Unit 404, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,709 Sq Ft
  • Built 1981

  Last Sold Summary

  • 8% Below List Price
  • $845/SF
  • 179 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1602 Alabama Dr Unit 404, Winter Park, FL 32789
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  /18

  Est $219,005 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 25, Winter Park, FL 32789

  851 Miles Ave Unit 25, Winter Park, FL 32789
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  /57

  $3,599,000 Open Sun 2AM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,676 Sq Ft

  948 Poinciana Ln, Winter Park, FL 32789

  Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted LocationDiscover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lane. This meticulously reimagined estate represents the pinnacle of refined living in one of Winter Park's most prestigious neighborhoods, offering an effortless blend of classic architecture and

  Kelly Price KELLY PRICE & COMPANY LLC

  948 Poinciana Ln, Winter Park, FL 32789
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  /2

  $699,000 Sold Jul 31, 2025

  1891 Bryan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft
  • Built 1989

  Last Sold Summary

  • $431/SF
  • 14 Days On Market

  Current Estimated Value $702,258

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1891 Bryan Ave, Winter Park, FL 32789
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  /25

  Est $510,412 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,606 Sq Ft

  1545 Indiana Ave Unit A, Winter Park, FL 32789

  1545 Indiana Ave Unit A, Winter Park, FL 32789
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  /2

  $650,000

  • 6 Beds
  • 3 Baths
  • 3,145 Sq Ft

  2600 Euston Rd, Winter Park, FL 32789

  STUNNING 6-BEDROOM HOME FOR SALE: 2600 Euston Rd, Winter Park, FL 32789 Imagine yourself in this gorgeous 6-bedroom, 3-bath home, perfectly situated in a desirable Winter Park neighborhood!With 3,145 sqft of living space, this property offers endless possibilities for large families, multi-generational living, or those who love to entertain. Spacious Layout: 6 bedrooms, 3 bathrooms, and

  Adriano Grullon Lara YOUNG REAL ESTATE

  2600 Euston Rd, Winter Park, FL 32789
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  /2

  $2,250,000 Sold Jun 25, 2025

  301 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,694 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $609/SF
  • 98 Days On Market

  Current Estimated Value $2,231,353

  Last Listing Agent Cynthia Fernandez XCLUSIVE HOMES LLC

  301 Rippling Ln, Winter Park, FL 32789
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  /19

  Est $216,982 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 27, Winter Park, FL 32789

  851 Miles Ave Unit 27, Winter Park, FL 32789
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  /51

  $599,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 3 Baths
  • 1,920 Sq Ft

  423 Ololu Dr, Winter Park, FL 32789

  Welcome to this distinctive 3-bedroom, 3-bath, two-story residence in Winter Park, offering a rare and versatile layout ideal for multi-generational living, college roommates or those seeking flexible space. Thoughtfully designed with two separate living areas, this home provides privacy, functionality, and room to grow—all just minutes from major highways and the charm of downtown Winter Park.

  Jill Healey KELLER WILLIAMS WINTER PARK

  423 Ololu Dr, Winter Park, FL 32789
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  $260,000 Sold Jan 30, 2026

  1250 S Denning Dr Unit 213, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  Last Sold Summary

  • 5% Below List Price
  • $286/SF
  • 114 Days On Market

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1250 S Denning Dr Unit 213, Winter Park, FL 32789
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  /2

  Est $197,389 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 3, Winter Park, FL 32789

  851 Miles Ave Unit 3, Winter Park, FL 32789
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  /29

  $659,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft

  2805 Northwood Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. This lovely updated mid-century modern home is waiting for you to make it your own! The home is located on a large corner lot, boasts three bedrooms two baths, has hand scraped wood laminate floors throughout, with an open spacious living area separated by a small step down that can accommodate your family room or den, the master bedroom en-suite features a

  Daniel Francoforte LIVE OAK EQUITIES

  2805 Northwood Blvd, Winter Park, FL 32789
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  /2

  $1,000,000 Sold Nov 03, 2025

  215 Salvador Square, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $390/SF
  • 44 Days On Market

  Current Estimated Value $1,048,121

  Last Listing Agent Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
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  /32

  Est $187,907 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 111, Winter Park, FL 32789

  2500 Lee Rd Unit 111, Winter Park, FL 32789
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  /17

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  PRICE REDUCTION!\Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this 2 Bedroom 2 Bath Beautifully Renovated Unit. New Kitchen Cabinets and Quartz Counters, Stainless Steel Appliances, Raised Ceiling with Lighting,

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
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  /2

  $675,000 Sold Nov 28, 2025

  2190 Temple Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $468/SF
  • 108 Days On Market

  Last Listing Agent Sharon Mikol MAINFRAME REAL ESTATE

  2190 Temple Dr, Winter Park, FL 32789
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  /16

  Est $259,260 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 203, Winter Park, FL 32789

  1250 S Denning Dr Unit 203, Winter Park, FL 32789
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  /18

  $249,900 Pending

  • 2 Beds
  • 1 Bath
  • 818 Sq Ft

  1996 Indiana Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Investor Special – Fixer Upper Opportunity in Winter Park / College Park Area. Rare opportunity to acquire a true fixer-upper in the desirable Winter Park area of College Park. This 2 bedroom, 1 bathroom property needs a full renovation and is being sold as a shell—perfect for investors or builders looking for their next project. Situated on an oversized

  Mike Rance RE/MAX 200 REALTY

  1996 Indiana Ave, Winter Park, FL 32789
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  $380,000 Sold Sep 26, 2025

  690 Osceola Ave Unit 209, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $331/SF
  • 34 Days On Market

  Current Estimated Value $382,813

  Last Listing Agent Mike Wang LOKATION

  690 Osceola Ave Unit 209, Winter Park, FL 32789

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