Homes in ZIP Code 32789

• 

  

  

  /21

  Est $249,124

  Not Listed For Sale

  1500 Gay Rd Unit 25A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  1500 Gay Rd Unit 25A, Winter Park, FL 32789

  Last Sold Summary

  • 5 Days On Market
• 

  

  

  /20

  $275,000

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 6-12, Winter Park, FL 32789

  Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a

  Andrea Parra FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 6-12, Winter Park, FL 32789
• 

  

  /2

  $1,587,500

  Sold Jul 31, 2025

  279 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,472 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $457/SF
  • 318 Days On Market

  Current Estimated Value $1,628,947

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  279 Rippling Ln, Winter Park, FL 32789
• 

  

  

  /20

  Est $180,567

  Not Listed For Sale

  1500 Gay Rd Unit 6C, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft
  • Built 1972

  1500 Gay Rd Unit 6C, Winter Park, FL 32789

  Last Sold Summary

  • 8 Days On Market
• 

  

  

  /53

  $4,950,000

  New Construction $750K PRICE DROP Pending

  • 5 Beds
  • 6.5 Baths
  • 6,406 Sq Ft

  1660 Palmer Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1660 Palmer Ave, Winter Park, FL 32789
• 

  /2

  $13,000,000

  Sold Feb 24, 2026

  2203 Via Tuscany, Winter Park, FL 32789

  • 6 Beds
  • 9 Baths
  • 12,190 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Above List Price
  • $1,066/SF
  • 4 Days On Market

  Current Estimated Value $9,836,079

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2203 Via Tuscany, Winter Park, FL 32789
• 

  

  /73

  Est $2,352,135

  Not Listed For Sale

  125 S Interlachen Ave Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 3,244 Sq Ft
  • Built 2020

  125 S Interlachen Ave Unit 2, Winter Park, FL 32789

  Last Sold Summary

  • 120 Days On Market
• 

  

  /47

  $899,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,864 Sq Ft

  1960 E Winter Park Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this 1⁄4-acre lot presents the ideal opportunity to either build new, or remodel.Zoned for the

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1960 E Winter Park Rd, Winter Park, FL 32789
• 

  /2

  $2,155,000

  Sold Aug 23, 2025

  2915 Parkland Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft
  • Built 2025

  Last Sold Summary

  • $642/SF

  Current Estimated Value $1,701,177

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

  2915 Parkland Dr, Winter Park, FL 32789
• 

  

  /31

  Est $213,891

  Not Listed For Sale

  2500 Lee Rd Unit 207, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft
  • Built 1969

  2500 Lee Rd Unit 207, Winter Park, FL 32789

  Last Sold Summary

  • 36 Days On Market
• 

  

  /59

  $1,875,000

  Open Sat 1PM - 4PM $120K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,551 Sq Ft

  1813 Harland Park Dr, Winter Park, FL 32789

  Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents the perfect balance of functionality, comfort, and elevated indoor-outdoor living. This move-in ready home is sure to check all the boxes with 2 NEW HVAC units (2025), a downstairs Primary Suite, a convenient 1st floor private office/flex room, 2nd floor loft & bonus room, plus

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1813 Harland Park Dr, Winter Park, FL 32789
• 

  /2

  $1,607,160

  Sold Aug 01, 2025

  1541 Chestnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Above List Price
  • $566/SF
  • 2 Days On Market

  Current Estimated Value $1,611,657

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1541 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  Est $334,519

  Not Listed For Sale

  700 Melrose Ave Unit B4, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  700 Melrose Ave Unit B4, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market
• 

  

  /25

  $299,000

  $90K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
• 

  /2

  $690,000

  Sold Feb 20, 2026

  2904 Parkland Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1952

  Last Sold Summary

  • $456/SF
  • 0 Days On Market

  Current Estimated Value $685,791

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

  2904 Parkland Dr, Winter Park, FL 32789
• 

  

  /23

  Est $223,872

  Not Listed For Sale

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft
  • Built 1964

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  Last Sold Summary

  • 27 Days On Market
• 

  

  /46

  $899,000

  $51K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,884 Sq Ft

  1405 Miller Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Experience high-end luxury and effortless convenience in one of the most central locations in Winter Park. Built by Makeur Homes and thoughtfully updated by SMRS Design, this stunning Modern Mediterranean detached townhome showcases light-filled interiors and carefully curated custom finishes.Offering 3 bedrooms and 2.5 bathrooms across 1,884 square

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1405 Miller Ave, Winter Park, FL 32789
• 

  /2

  $560,000

  Sold May 08, 2026

  218 Orange Terrace Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft
  • Built 1955

  Last Sold Summary

  • 12% Below List Price
  • $346/SF
  • 30 Days On Market

  Current Estimated Value $588,815

  Last Listing Agent Arden Magee ANNE ROGERS REALTY GROUP INC

  218 Orange Terrace Dr, Winter Park, FL 32789
• 

  

  /22

  Est $214,612

  Not Listed For Sale

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft
  • Built 1964

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  Last Sold Summary

  • 4 Days On Market
• 

  

  /29

  $299,000

  $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,133 Sq Ft

  184 Sandlewood Trail Unit 2, Winter Park, FL 32789

  Tucked inside one of Winter Park's most sought-after zip codes, this FULLY RENOVATED two-story condo lives like a townhome — and feels like new construction. The main floor flows from a beautifully updated kitchen with new stainless appliances, contemporary finishes, and butcher block bar top into a bright open living space, with a convenient half bath for guests. Upstairs, both bedrooms are true

  Tom Noelke NOELKE REALTY

  184 Sandlewood Trail Unit 2, Winter Park, FL 32789
• 

  /2

  $610,000

  Sold Apr 13, 2026

  1860 Staunton Ave, Winter Park, FL 32789

  • Land
  • 13,503 Sq Ft
  • $1,967,742 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 9 Days On Market

  Current Estimated Value $636,278

  Last Listing Agent Leighton Hope COMPASS FLORIDA LLC

  1860 Staunton Ave, Winter Park, FL 32789
• 

  

  /18

  Est $172,251

  Not Listed For Sale

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  Last Sold Summary

  • 3 Days On Market
• 

  

  /34

  $1,449,900

  New Construction Open Sat 1PM - 3PM $180K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  NEW PRICE!!! Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, Winter Park, FL 32789
• 

  /2

  $750,000

  Sold Sep 25, 2025

  311 Cortland Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft
  • Built 1952

  Last Sold Summary

  • 6% Below List Price
  • $543/SF
  • 48 Days On Market

  Current Estimated Value $731,758

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  311 Cortland Ave, Winter Park, FL 32789
• 

  

  /30

  Est $766,717

  Not Listed For Sale

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  Last Sold Summary

  • 85 Days On Market
• 

  

  /22

  $298,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
• 

  /2

  $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 $249,588

  Last Listing Agent Alayna Phillips EXP REALTY LLC

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

  

  /29

  Est $1,041,726

  Not Listed For Sale

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789

  Last Sold Summary

  • 79 Days On Market
• 

  

  /8

  $358,000

  Pending

  • Land
  • 6,969 Sq Ft
  • $2,237,500 per Acre

  2002 Indiana Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Great buildable lot centrally located close to I-4 for easy access. Please consult the zoning and planning Dept. for info and guidelines for building. The lot has single family homes on both sides of it and faces a retention pond area across the street. Front half of the lot is cleared. Back half of the lot is wooded. Paved road frontage. Sign on the

  David Nicholson DAWN REALTY

  2002 Indiana Ave, Winter Park, FL 32789
• 

  /2

  $1,500,000

  Sold May 19, 2026

  246 Palmer Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 2,281 Sq Ft
  • Built 1948

  Last Sold Summary

  • $658/SF
  • 2 Days On Market

  Current Estimated Value $1,482,493

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  246 Palmer Ave, Winter Park, FL 32789
• 

  /2

  Est $643,260

  Not Listed For Sale

  100 S Interlachen Ave Unit 111, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 901 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 111, Winter Park, FL 32789

  Last Sold Summary

  • 53 Days On Market
• 

  

  /32

  $1,650,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 4 Baths
  • 2,467 Sq Ft

  1841 Lake Spier Dr, Winter Park, FL 32789

  Winter Park lakefront home! A rare opportunity to own a thoughtfully renovated mid century lakefront residence in Winter Park. This three bedroom four bath home offers stunning views, high ceilings and abundant natural light. The open layout flows effortlessly for everyday living and gatherings with friends and family. As you walk through the front door, you will be drawn to the large living area

  Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  1841 Lake Spier Dr, Winter Park, FL 32789
• 

  /2

  $1,600,000

  Sold Apr 22, 2026

  446 Alberta Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft
  • Built 1968

  Last Sold Summary

  • 12% Below List Price
  • $490/SF
  • 271 Days On Market

  Current Estimated Value $1,597,588

  Last Listing Agent Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  446 Alberta Dr, Winter Park, FL 32789
• 

  

  /19

  Est $178,954

  Not Listed For Sale

  700 Melrose Ave Unit E24, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft
  • Built 1964

  700 Melrose Ave Unit E24, Winter Park, FL 32789

  Last Sold Summary

  • 164 Days On Market
• 

  

  /6

  $3,650,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
• 

  /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 $534,410

  Last Listing Agent Ahmad Karain R MICHAELS REALTY LLC

  1409 Sunset Dr, Winter Park, FL 32789
• 

  /2

  Est $238,540

  Not Listed For Sale

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

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

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

  Last Sold Summary

  • 15 Days On Market
• 

  

  /38

  $1,429,000

  New Construction Open Sat 12AM - 3PM

  • 5 Beds
  • 4 Baths
  • 2,351 Sq Ft

  1473 Berkshire Ave, Winter Park, FL 32789

  LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 bedrooms, 4 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space. Situated on a charming, tree-lined street, the home combines timeless elegance with modern luxury. The open-concept floor plan features

  Gilson Rodrigues KARDOSH REALTY

  1473 Berkshire Ave, Winter Park, FL 32789
• 

  /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

  Current Estimated Value $4,739,331

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  641 Bonita Dr, Winter Park, FL 32789
• 

  /2

  Est $234,812

  Not Listed For Sale

  1500 Gay Rd Unit 10C, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  1500 Gay Rd Unit 10C, Winter Park, FL 32789

  Last Sold Summary

  • 75 Days On Market

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