Homes in ZIP Code 32789

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  /11

  $916,050 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft

  Lot #21 Karolina Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a thoughtfully designed masterpiece, blending elegant country charm with the comfort and functionality today’s homeowners crave. One of three consecutive custom builds — each with its own

  Laura Hope COMPASS FLORIDA LLC

  Lot #21 Karolina Ave, Winter Park, FL 32789
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  /12

  $1,575 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  1565 Michigan Ave, Winter Park, FL 32789

  Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

  Troy Hensley BHHS FLORIDA REALTY

  1565 Michigan Ave, Winter Park, FL 32789
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  /49

  $1,650,000 Sold Mar 12, 2025

  1781 Goodrich Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,701 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $611/SF
  • 88 Days On Market

  Current Estimated Value $1,662,226

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  1781 Goodrich Ave, Winter Park, FL 32789
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  /88

  Est $1,910,791 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft

  1661 Hillcrest Ave, Winter Park, FL 32789

  1661 Hillcrest Ave, Winter Park, FL 32789
• 

  

  

  /25

  $475,000

  • 2 Beds
  • 2 Baths
  • 760 Sq Ft

  875 W Lyman Ave, Winter Park, FL 32789

  Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of only a handful of lots to have a view of

  Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

  875 W Lyman Ave, Winter Park, FL 32789
• 

  

  /58

  $4,850 per month

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Condo for Rent

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789

  Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you enter into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  104 S Interlachen Ave Unit 114, Winter Park, FL 32789
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  /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 $1,283,867

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
• 

  

  /39

  Est $871,351 Not Listed For Sale

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

  1770 Mondrian Cir, Winter Park, FL 32789

  1770 Mondrian Cir, Winter Park, FL 32789
• 

  

  /27

  $129,900

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E204, Winter Park, FL 32789

  Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

  Brandy Ray LOKATION

  1695 Lee Rd Unit E204, Winter Park, FL 32789
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  /42

  $3,295 per month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
• 

  /2

  $1,000,000 Sold Apr 04, 2025

  1001 Tuscany Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,458 Sq Ft
  • Built 1978

  Last Sold Summary

  • 22% Below List Price
  • $407/SF
  • 141 Days On Market

  Current Estimated Value $1,055,659

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
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  /44

  Est $1,063,648 Not Listed For Sale

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

  1768 Mondrian Cir, Winter Park, FL 32789

  1768 Mondrian Cir, Winter Park, FL 32789
• 

  

  /69

  $1,750,000

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

  446 Alberta Dr, Winter Park, FL 32789

  Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows residents to have walking access to Lake

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  446 Alberta Dr, Winter Park, FL 32789
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  /6

  $1,299 per month

  • 2 Beds
  • 1 Bath
  • 805 Sq Ft
  • Townhouse for Rent

  1436 Minnesota Ave, Winter Park, FL 32789

  Updated 2 bedroom and 1 bath apartment located in the heart of the industrial district of Winter Park 32789. Close to Advent Health (Rollins campus), I-4 , Orange Avenue, 17-92, Rollins College, Fairbanks, Mills 50, College Park and Downtown Winter Park. Please no pets.

  Ruth Harris COLDWELL BANKER RESIDENTIAL RE

  1436 Minnesota Ave, Winter Park, FL 32789
• 

  /2

  $1,002,000 Sold May 31, 2025

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $437/SF
  • 4 Days On Market

  Current Estimated Value $992,554

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  /25

  Est $2,016,711 Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789
• 

  

  /15

  $160,000 Pending

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

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Move-in Ready Renovated Condo – Prime Location!This beautifully renovated condo offers both style and convenience, situated right next to the community pool and playground. Enjoy modern upgrades throughout, along with the added assurance of a Home Warranty America coverage plan, valued up to $500, for extra peace of mind. Plus, you'll be just minutes from restaurants, shopping, major roads,

  Kerem Munoz- Franquiz LA ROSA REALTY CENTRAL FLORIDA

  1695 Lee Rd Unit E215, Winter Park, FL 32789
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  /52

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  1730 Oneco Ave, Winter Park, FL 32789

  Just completed full interior home renovation and ready to lease for first time on the Flowered Streets of Winter Park. This 3/2 offers an exceptional opportunity in Winter Park 32789 and features a 3/2 split floorplan, all new luxury vinyl wide plank flooring and new doors/door hardware throughout home. The sleek brand new kitchen features stainless appliances, Quartz countertops, and chic 1/2

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1730 Oneco Ave, Winter Park, FL 32789
• 

  /2

  $1,975,000 Sold Mar 27, 2025

  140 Dana Way, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 3,441 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $574/SF
  • 16 Days On Market

  Current Estimated Value $1,948,883

  Last Listing Agent Maria Blanchard OLDE TOWN BROKERS INC

  140 Dana Way, Winter Park, FL 32789
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  /36

  Est $1,439,935 Not Listed For Sale

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

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  1405 Chapman Cir Unit OR, Winter Park, FL 32789
• 

  

  /99

  $5,495,000

  • 5 Beds
  • 6.5 Baths
  • 7,278 Sq Ft

  2211 Azalea Place, Winter Park, FL 32789

  Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2211 Azalea Place, Winter Park, FL 32789
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  /37

  $3,400 per month

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Condo for Rent

  690 Osceola Ave Unit 203, Winter Park, FL 32789

  Experience upscale living in this stunning 2-bedroom, 2-bath luxury condo featuring gorgeous raw wood floors in this breathtaking lakefront complex situated on the shores of the Winter Park Chain of Lakes and walking distance to Park Avenue, shopping, museums, restaurants and parks. The open-concept layout offers a seamless flow between the living, dining, and kitchen areas—perfect for both

  Nancy Bhavsar ANNE ROGERS REALTY GROUP INC

  690 Osceola Ave Unit 203, Winter Park, FL 32789
• 

  /2

  $230,000 Sold Aug 29, 2025

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

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

  Last Sold Summary

  • 6% Below List Price
  • $224/SF
  • 205 Days On Market

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

  1500 Gay Rd Unit 7A, Winter Park, FL 32789
• 

  

  /55

  Est $1,071,972 Not Listed For Sale

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

  1772 Mondrian Cir, Winter Park, FL 32789

  1772 Mondrian Cir, Winter Park, FL 32789
• 

  

  /26

  $625,000

  • 3 Beds
  • 3 Baths
  • 1,890 Sq Ft

  1360 Formosa Ave, Winter Park, FL 32789

  Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the highly sought-after Winter Park market. This income-generating property features three fully rented one-bedroom, one-bathroom units, providing a strong and steady return on investment. With 100% occupancy, this property is already a cash-flowing asset, but its value-add potential makes it even more enticing

  Salvison Dickson TOP FLORIDA HOMES

  1360 Formosa Ave, Winter Park, FL 32789
• 

  

  /13

  $1,795 per month

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • House for Rent

  918 Gloriosa Ave, Winter Park, FL 32789

  **HOLIDAY SPECIAL, If you take occupancy by January 1st 2026 receive $800.00 off your first months rent** Discover the charm of Winter Park living in this beautiful 3-bedroom, 2-bath rental home! Nestled in a peaceful neighborhood, this property offers a bright and open floor plan perfect for both relaxing and entertaining. Enjoy a spacious kitchen with modern appliances, a comfortable living

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  918 Gloriosa Ave, Winter Park, FL 32789
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  /2

  $3,450,000 Sold Jul 25, 2025

  182 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 4,812 Sq Ft
  • Built 2025

  Last Sold Summary

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

  Current Estimated Value $3,405,789

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, 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
• 

  

  /62

  $5,300,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy glass, setting the tone for the artistry within. Inside, a European hotel–inspired

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  /16

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • House for Rent

  2111 Biscayne Dr, Winter Park, FL 32789

  Remodeled Winter Park 3 Bedroom Home For RentPriced Low, Call Now! This Property Has Been Professionally Refurbished And Features A 1-car Garage, Screened-in Patio, Fenced-in Yard, And Large Private Backyard. Enjoy Granite Countertops, An Upgraded Kitchen, Fresh Paint, And Beautiful Wood Plank Tile Flooring Throughout. Blinds Are Included. Located Just 10 Minutes To Downtown Orlando And 30

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  2111 Biscayne Dr, Winter Park, FL 32789
• 

  /2

  $1,950,000 Sold Sep 16, 2025

  141 Oakwood Way, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft
  • Built 2015

  Last Sold Summary

  • 14% Below List Price
  • $499/SF
  • 170 Days On Market

  Current Estimated Value $1,933,544

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
• 

  

  /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
• 

  

  /20

  $275,000

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

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

  One or more photo(s) has been virtually staged. Fully renovated two-bedroom, two-bath residence in the sought-after Mead Garden Condominium community. Spanning 908 square feet, this second-floor home offers a move-in-ready interior with a contemporary open-concept layout and elevated finishes throughout. The kitchen features quartz countertops, soft-close cabinetry, stainless steel appliances, a

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1250 S Denning Dr Unit 213, Winter Park, FL 32789
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  /68

  $8,900 per month

  • 4 Beds
  • 5 Baths
  • 3,611 Sq Ft
  • House for Rent

  1442 Palm Ave, Winter Park, FL 32789

  Discover this exquisite property featuring a main house, complemented by a separate guest apartment equipped with one bedroom, one bathroom, a full living room, and a kitchen. The main house boasts an inviting open floor plan adorned with tall ceilings and beautiful hardwood floors throughout. On the upper level, relax in the luxurious master suite, accompanied by two additional bedrooms and

  Bianca Botelho RE/MAX ASSURED

  1442 Palm Ave, Winter Park, FL 32789
• 

  /2

  $1,125,000 Sold Jan 08, 2025

  805 Hamilton Place Ct, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 2,810 Sq Ft
  • Built 2007

  Last Sold Summary

  • 2% Above List Price
  • $400/SF
  • 4 Days On Market

  Current Estimated Value $1,157,824

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  805 Hamilton Place Ct, Winter Park, FL 32789
• 

  

  /46

  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
• 

  

  /61

  $619,500

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft

  1451 Cavendish Rd, Winter Park, FL 32789

  Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and prominent corner lot, this move-in-ready home perfectly balances charm, safety, and convenience just minutes from Park Avenue, Downtown Orlando, and the Mills District. Enjoy extensive upgrades including new AC, attic

  Spencer Flory LoKation

  1451 Cavendish Rd, Winter Park, FL 32789
• 

  

  /38

  $5,400 per month

  • 4 Beds
  • 3 Baths
  • 2,841 Sq Ft
  • House for Rent

  1701 Palmer Ave, Winter Park, FL 32789

  Winter Park– Prime 32789 Location!Live in style in this spacious 4-bedroom, 3-bath home with a private pool, just steps from Phelps Park and minutes from Park Avenue dining, shopping, and Rollins College.Enjoy bright open living spaces, a large kitchen with wood cabinetry and wine fridge, and French doors leading to a courtyard and pool area — perfect for entertaining or relaxing.

  Rhonda Fisher TRUST EQUITY GROUP LLC

  1701 Palmer Ave, Winter Park, FL 32789
• 

  /2

  $850,000 Sold Dec 27, 2024

  1621 Lasbury Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,267 Sq Ft
  • Built 1986

  Last Sold Summary

  • 22% Below List Price
  • $375/SF
  • 211 Days On Market

  Current Estimated Value $913,476

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1621 Lasbury Ave, Winter Park, FL 32789
• 

  

  /18

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft

  1411 Miller Ave, Winter Park, FL 32789

  1411 Miller Ave, Winter Park, FL 32789

Showing Results 161 - 200, Page 5 of 18