Homes in ZIP Code 32789

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  /76

  $6,495,000

  New Construction $705K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
• 

  

  

  /16

  $1,399 Per Month

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

  2500 Lee Rd, Winter Park, FL 32789

  Serene scenes surround the Lakeside Manor, absolutely beautiful through all the seasons. Waterfront Complex on Lake Killarney. Found on the ground floor, the unit opens up to the living room and dining room. Tile is laid all throughout the property, easy to clean and maintain! The bedroom and bathroom are toward the back of the unit. The bedroom features two closets! The community amenities

  2500 Lee Rd, Winter Park, FL 32789
• 

  

  /2

  $2,700,000

  Sold Oct 02, 2025

  1445 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,489 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $601/SF
  • 2 Days On Market

  Current Estimated Value $2,704,546

  Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

  1445 Holts Grove Cir, Winter Park, FL 32789
• 

  

  /2

  Est $1,038,083

  Not Listed For Sale

  1975 Biscayne Dr, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,270 Sq Ft
  • Built 2020

  1975 Biscayne Dr, Winter Park, FL 32789

  Last Sold Summary

  • 68 Days On Market
• 

  

  

  /29

  $1,850,000

  $75K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 2,653 Sq Ft

  721 Pansy Ave, Winter Park, FL 32789

  Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  721 Pansy Ave, Winter Park, FL 32789
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  /16

  $2,400 Per Month

  • 2 Beds
  • 2 Baths
  • Condo for Rent

  1603 Alabama Dr, Winter Park, FL 32789

  FOR THE QUICKEST RESPONSE AND ASSISTANCE WITH ANY INQUIRIES, PLEASE CONTACT OUR OFFICE DIRECTLY BY PHONE. Application required prior to scheduling a showing. Available September 7th .Pet-friendly property. The Alabama, an iconic, historic Winter Park landmark on the shores of Lake Maitland. This meticulously fully renovated property perfectly blends timeless Mediterranean architecture with

  Maria Ottinger Maria Ottinger R.E Broker

  1603 Alabama Dr, Winter Park, FL 32789
• 

  /2

  $916,000

  Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $911,312

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
• 

  /2

  Est $1,761,051

  Not Listed For Sale

  643 Balmoral Rd, Winter Park, FL 32789

  643 Balmoral Rd, Winter Park, FL 32789

  Last Sold Summary

  • 17 Days On Market
• 

  

  /6

  $2,235,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,150 Sq Ft

  926 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

  Laura Earl CORCORAN PREMIER REALTY

  926 Enclave Place, Winter Park, FL 32792
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  /12

  $2,250 Per Month

  • 3 Beds
  • 2 Baths
  • 1,096 Sq Ft
  • House for Rent

  851 Carver St, Winter Park, FL 32789

  Welcome home to this beautiful 3-bedroom, 2-bathroom residence located in the highly desirable Winter Park area. This inviting home offers a spacious and functional floor plan with comfortable living areas, a well-appointed kitchen, and generously sized bedrooms designed for everyday living.Enjoy the convenience of being close to shopping, dining, entertainment, major roadways, and

  851 Carver St, Winter Park, FL 32789
• 

  /2

  $3,485,000

  Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,426,438

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

  2171 Forrest Rd, Winter Park, FL 32789
• 

  /2

  Est $304,301

  Not Listed For Sale

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  Last Sold Summary

  • 3 Days On Market
• 

  

  /8

  $849,000

  $49K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  1780 Bryan Ave, Winter Park, FL 32789

  Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value.The lot’s generous dimensions

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1780 Bryan Ave, Winter Park, FL 32789
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  /12

  $6,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Apartment for Rent

  301 W Comstock Ave, Winter Park, FL 32789

  Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

  Sydney Brownlee THE SYDGAN CORP

  301 W Comstock Ave, Winter Park, FL 32789
• 

  /2

  $228,000

  Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $242,411

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
• 

  /2

  Est $1,177,754

  Not Listed For Sale

  1782 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft
  • Built 2023

  1782 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market
• 

  

  /48

  $4,200,000

  • Land
  • 14,810 Sq Ft
  • $12,352,941 per Acre

  1298 Beachview Ave, Winter Park, FL 32789

  This is a rare Lake Killarney portfolio offering of four parcels in Winter Park. An exceptional opportunity to acquire a four-parcel assemblage in one of Winter Park’s most coveted locations, just moments from the shores of Lake Killarney. This offering includes 1321 Fairview Ave. and 230 and 240 Killarney Drive, all with potential for private dock access, and a desirable live/work parcel on 1298

  Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

  1298 Beachview Ave, Winter Park, FL 32789
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  /6

  $1,950 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  520 Holt Ave, Winter Park, FL 32789

  Property Id: 578482One-bedroom / one-bathroom cottage style apartment located within a five-minute walk to Rollins College, Park Avenue, and Hannibal Square. Newly-renovated interior includes condominium grade appliances, upgraded bathroom, and in-unit washer dryer. Unit includes off-street parking and private entry porch. Available for lease beginning of June 2026. Rent includes

  520 Holt Ave, Winter Park, FL 32789
• 

  /2

  $1,905,000

  Sold Apr 10, 2026

  501 Henkel Cir, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,746 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Above List Price
  • $509/SF
  • 4 Days On Market

  Current Estimated Value $1,924,828

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  501 Henkel Cir, Winter Park, FL 32789
• 

  /2

  Est $743,936

  Not Listed For Sale

  1804 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  1804 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 68 Days On Market
• 

  /2

  $999,000

  $51K PRICE DROP

  • Land
  • 11,325 Sq Ft
  • $3,842,308 per Acre

  1836 Grinnell Terrace, Winter Park, FL 32789

  Opportunity to build your dream home in gorgeous Winter Park. This large lot includes a 3 bedroom 2 bath updated home. With a lot comprising 140 x 78 (11,305 square feet) there is plenty of room for a pool. Live in the house while you make your future plans!

  Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

  1836 Grinnell Terrace, Winter Park, FL 32789
• 

  

  /17

  $1,300 Per Month

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

  1695 Lee Rd Unit D213, Winter Park, FL 32789

  Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

  Rachel DeCamp RLL Real Estate Group

  1695 Lee Rd Unit D213, Winter Park, FL 32789
• 

  /2

  $420,000

  Sold Jan 15, 2026

  1847 Azalea Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft
  • Built 1961

  Last Sold Summary

  • $284/SF
  • 1 Day On Market

  Current Estimated Value $421,722

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
• 

  /2

  Est $398,416

  Not Listed For Sale

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

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

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

  Last Sold Summary

  • 171 Days On Market
• 

  

  /36

  $509,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,120 Sq Ft

  641 W Lyman Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. LOCATION. LOCATION. LOCATION. Heres the thing; in Winter Park, that's not a cliché. It's everything. There are homes in Central Florida that require a car for everything. This is not one of them. 641 West Lyman Avenue doesn't sit near Hannibal Square. It sits on it. This corner lot property is literally at the edge of one of Winter Park's most beloved and

  Ted Moseley REAL BROKER, LLC

  641 W Lyman Ave, Winter Park, FL 32789
• 

  

  /83

  $2,873

  Total Monthly Price

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

  2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789

  The advertised rate of $2,873/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 21, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789
• 

  /2

  $199,900

  Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Current Estimated Value $192,989

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

  1630 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 2024

  1630 Haven Dr, Orlando, FL 32803

  Last Sold Summary

  • 53 Days On Market
• 

  

  /33

  $373,800

  $1K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 1,150 Sq Ft

  1307 Formosa Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Charming 2-bed home in Winter Park located in the Golfview subdivision offering approximately 1,150 square feet of living space on a 6,414 square foot lot. Built in 1946, this single family residence features a functional layout with a blend of original character and updated interior finishes. The home includes original pine flooring in the main living

  Tyler Gibson LPT REALTY, LLC

  1307 Formosa Ave, Winter Park, FL 32789
• 

  

  /12

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,441 Sq Ft
  • House for Rent

  1540 Oneco Ave, Winter Park, FL 32789

  Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location just minutes from Park Avenue, Rollins College, shopping, dining, and entertainment. Inside, you'll find a spacious floor plan featuring a formal living room, dining room, and family room, providing plenty of space for both relaxing and entertaining. The kitchen is equipped with

  Tara Mason WATSON REALTY CORP

  1540 Oneco Ave, Winter Park, FL 32789
• 

  /2

  $266,000

  Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

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

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Current Estimated Value $258,285

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

  255 Sandlewood Trail, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Built 1984

  255 Sandlewood Trail, Winter Park, FL 32789

  Last Sold Summary

  • 24 Days On Market
• 

  

  /76

  $2,249,000

  New Construction Open Sat 12PM - 4PM $146K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,130 Sq Ft

  2361 Mulbry Dr, Winter Park, FL 32789

  Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement home located within one of Winter Park's most desirable pockets and zoned for Audubon Park K-8. From the moment of arrival, the home's striking blend of natural stone, warm white oak, rich textures, and beautifully composed architectural lines creates an unforgettable first

  Ahmad Hassan COMPASS FLORIDA LLC

  2361 Mulbry Dr, Winter Park, FL 32789
• 

  

  /22

  $1,450 Per Month

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

  151 N Orlando Ave, Winter Park, FL 32789

  Discover comfortable living in this charming 1-bedroom, 1-bathroom residential condo at 151 N Orlando Ave, Winter Park, FL. Spanning 600 sq ft, this unit features modern hardwood flooring, large closets, and a private patio perfect for relaxing or entertaining. The kitchen is equipped with a range and refrigerator, complemented by air conditioning for year-round comfort. Water and trash services

  151 N Orlando Ave, Winter Park, FL 32789
• 

  /2

  $245,900

  Sold Aug 11, 2025

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,132 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $217/SF
  • 2 Days On Market

  Current Estimated Value $251,521

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

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

  /2

  Est $864,520

  Not Listed For Sale

  1919 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft
  • Built 2024

  1919 S Lakemont Ave, Winter Park, FL 32792

  Last Sold Summary

  • 282 Days On Market
• 

  

  /37

  $649,000

  $46K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,669 Sq Ft

  1707 Harmon Ave, Winter Park, FL 32789

  A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled in the highly sought-after and peaceful neighborhood of Orwin Manor in Winter Park. Rich in character and thoughtfully updated throughout, this exceptional residence seamlessly combines the elegance of its original architecture with the comfort and sophistication of modern

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  1707 Harmon Ave, Winter Park, FL 32789
• 

  

  /16

  $1,400 Per Month

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
• 

  /2

  $1,300,000

  Sold Sep 22, 2025

  1371 Lyndale Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $479/SF
  • 8 Days On Market

  Current Estimated Value $1,287,836

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
• 

  /2

  Est $824,236

  Not Listed For Sale

  1776 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2022

  1776 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 88 Days On Market

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