Homes in ZIP Code 32789

• 

  

  

  /31

  $499,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  841 W Swoope Ave, Winter Park, FL 32789

  This Winter Park property offers exceptional potential in one of the most desirable and rapidly evolving areas of Central Florida. Zoned R-3, this parcel opens the door to redevelopment possibilities for builders, investors, or end users looking to create something special. Ideally located just minutes from Park Avenue and within walking distance to Winter Park Village, you’ll enjoy easy access

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 468-9259

  841 W Swoope Ave, Winter Park, FL 32789
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• 

  

  

  /35

  Starting at $1,750 Per Month

  • 2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  Hannibal Square

  (689) 207-6504

  

  433 W New England Ave, Winter Park, FL 32789
• 

  

  /2

  $890,000 Sold Jun 12, 2025

  1762 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $393/SF
  • 114 Days On Market

  Current Estimated Value $911,313

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1762 Mondrian Cir, Winter Park, FL 32789
• 

  

  /2

  Est $2,861,321 Not Listed For Sale

  1618 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 8 Baths
  • 4,807 Sq Ft
  • Built 2014

  1618 Holts Grove Cir, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $603/SF
  • 173 Days On Market

  • Last Sold Price $2,900,000
  • Feb 07, 2025

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY
• 

  

  

  /40

  $2,200,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,195 Sq Ft

  872 Granville Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. A rare offering in the highly sought-after Park Grove neighborhood, this expertly redesigned 4-bedroom residence blends elevated design with effortless everyday living. Originally renovated by award-winning interior designer John McClain and recognized with first-place honors in 2020, the home reflects a refined balance of style and functionality.??Ideally

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 485-7250

  872 Granville Dr, Winter Park, FL 32789
• 

  

  /27

  Starting at $1,469 Per Month

  • Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  Westmount at Winter Park

  (321) 248-5471

  

  1701 Lee Rd, Winter Park, FL 32789
• 

  /2

  $800,000 Sold Apr 30, 2026

  737 N Capen Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft
  • Built 2021

  Last Sold Summary

  • 13% Below List Price
  • $415/SF
  • 99 Days On Market

  Current Estimated Value $872,499

  Last Listing Agent Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
• 

  

  /43

  Est $1,770,852 Not Listed For Sale

  1809 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft
  • Built 2014

  1809 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 14% Above List Price
  • $423/SF
  • 8 Days On Market

  • Last Sold Price $1,550,000
  • May 12, 2023

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
• 

  

  /36

  $399,999

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  721 Dunbar St, Winter Park, FL 32789

  Welcome to 721 Dunbar St in Winter Park, a 2-bedroom, 2-bath home with a simple layout and plenty of potential. This property offers a comfortable starting point for everyday living and a great opportunity for buyers who want a home they can make their own over time. Inside, the home offers practical living spaces and a layout that works well for daily routines. The two-bedroom, two-bath setup

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 344-8781

  721 Dunbar St, Winter Park, FL 32789
• 

  

  /27

  Starting at $1,344 Per Month

  • 1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  Village Park Senior

  (689) 220-5720

  

  550 W Denning Dr, Winter Park, FL 32789
• 

  /2

  $1,575,000 Sold Aug 14, 2025

  1394 Grove Terrace, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,958 Sq Ft
  • Built 2002

  Last Sold Summary

  • $532/SF
  • 5 Days On Market

  Current Estimated Value $1,551,460

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1394 Grove Terrace, Winter Park, FL 32789
• 

  /2

  Est $1,838,118 Not Listed For Sale

  1411 Border Dr, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 4,638 Sq Ft
  • Built 2019

  1411 Border Dr, Winter Park, FL 32789

  Last Sold Summary

  • 9% Above List Price
  • $364/SF
  • 195 Days On Market

  • Last Sold Price $1,690,000
  • Sep 27, 2024

  Last Listing Agent Ana Scarlato CORCORAN PREMIER REALTY
• 

  

  /94

  $4,195,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,665 Sq Ft

  2020 Via Tuscany, Winter Park, FL 32789

  Under contract-accepting backup offers. PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept

  

  Mauro Costa

  VISTA CAY REALTY COMPANY

  (321) 978-0954

  2020 Via Tuscany, Winter Park, FL 32789
• 

  

  /8

  $1,650

  Total Monthly Price

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

  700 Melrose Ave, Winter Park, FL 32789

  Charming 1BR/BA condo in desirable Winter Park Gardens (+55 community). Recently renovated and located in the highly sought-after Winter Park Gardens community in Winter Park, FL. This bright and inviting second floor unit overlooks the pool and has an elevator nearby. Within walking distance of Park Avenue's Shops, restaurants and other activities. (no pets allowed )Adjacent to Winter

  (978) 984-3360

  700 Melrose Ave, Winter Park, FL 32789
• 

  /2

  $325,000 Sold Dec 30, 2025

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 6 Days On Market

  Current Estimated Value $329,134

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

  700 Melrose Ave Unit G, Winter Park, FL 32789

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

  700 Melrose Ave Unit G, Winter Park, FL 32789

  Last Sold Summary

  • $281/SF
  • 73 Days On Market

  • Last Sold Price $193,000
  • Jul 29, 2024

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY
• 

  

  /20

  $400,000

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  2482 Roxbury Rd, Winter Park, FL 32789

  Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready.But what truly sets this property apart is the location and land. With

  Gary Cohl COLDWELL BANKER REALTY

  2482 Roxbury Rd, Winter Park, FL 32789
• 

  

  /12

  Starting at $3,350 Per Month

  • 2 Beds

  1894 Demetree Dr, Winter Park, FL 32789

  Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter ParkWelcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals.This thoughtfully

  Waterbridge Subdivision

  (844) 871-1098

  1894 Demetree Dr, Winter Park, FL 32789
• 

  /2

  $720,000 Sold Jan 20, 2026

  2955 Lolissa Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,538 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $204/SF
  • 47 Days On Market

  Current Estimated Value $742,021

  Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

  2955 Lolissa Ln, Winter Park, FL 32789
• 

  

  /60

  Est $1,629,069 Not Listed For Sale

  1318 Chapman Cir, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft
  • Built 2014

  1318 Chapman Cir, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $519/SF
  • 162 Days On Market

  • Last Sold Price $1,612,000
  • Feb 23, 2024

  Last Listing Agent Lance Kotowski Properties By Lanko, Inc
• 

  

  /66

  $2,295,000

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
• 

  

  /3

  $2,300 Per Month

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Condo for Rent

  2827 Riddle Dr, Winter Park, FL 32789

  Welcome to your new oasis in the charming city of Winter Park, FL! This beautiful property is perfect for those seeking comfort and convenience in a vibrant community. With nearby restaurants offering a delightful culinary experience, you'll always have something new to explore.This property features spacious accommodations designed for your relaxation. Enjoy a comfortable living

  (321) 381-3659

  2827 Riddle Dr, Winter Park, FL 32789
• 

  /2

  $2,285,000 Sold Nov 19, 2025

  521 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,883 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $588/SF
  • 118 Days On Market

  Current Estimated Value $2,223,005

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
• 

  

  /14

  Est $556,063 Not Listed For Sale

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft
  • Built 2006

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $303/SF
  • 0 Days On Market

  • Last Sold Price $550,000
  • May 03, 2024

  Last Listing Agent nicoletta buonaccordo ALTIS REALTY
• 

  

  /48

  $1,275,000

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  1651 Westchester Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome

  Shawn Layton SERHANT

  1651 Westchester Ave, Winter Park, FL 32789
• 

  

  /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

  (321) 304-2205

  520 Holt Ave, Winter Park, FL 32789
• 

  /2

  $580,000 Sold May 16, 2025

  1392 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2008

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 123 Days On Market

  Current Estimated Value $556,574

  Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

  1392 Indiana Ave, Winter Park, FL 32789
• 

  

  /24

  Est $787,373 Not Listed For Sale

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Built 2004

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • $401/SF
  • 280 Days On Market

  • Last Sold Price $785,000
  • Jun 16, 2023

  Last Listing Agent Tyler Reik KELLER WILLIAMS WINTER PARK
• 

  

  /44

  $670,000 Pending

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

  2713 Eastern Pkwy, Winter Park, FL 32789

  Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart of Winter Park—lovingly cared for by the same owner for over 30 years. This home reflects true pride of ownership with thoughtful updates and improvements that provide both comfort and peace of mind. Enjoy entertaining in the spacious eat in kitchen with full Stainless appliance package. Outdoor living

  Helen Thompson RE/MAX SELECT GROUP

  2713 Eastern Pkwy, Winter Park, FL 32789
• 

  

  /20

  $2,726

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789

  The advertised rate of $2,726/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 26, 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

  (321) 483-3204

  662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789
• 

  /2

  $4,772,500 Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,664,184

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

  765 Via Lugano, Winter Park, FL 32789
• 

  

  /22

  Est $5,401,250 Not Listed For Sale

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft
  • Built 2005

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $1,104/SF
  • 0 Days On Market

  • Last Sold Price $5,995,000
  • Dec 20, 2023

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

  

  /51

  $2,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  541 W Canton Ave, Winter Park, FL 32789

  Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

  Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  541 W Canton Ave, Winter Park, FL 32789
• 

  

  /20

  $2,700

  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 $2,700/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 22, 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

  (321) 265-3710

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

  /2

  $3,100,000 Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,939,252

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
• 

  /2

  Est $2,743,939 Not Listed For Sale

  1737 Lookout Landing Cir, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 5,066 Sq Ft
  • Built 2013

  1737 Lookout Landing Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $533/SF
  • 232 Days On Market

  • Last Sold Price $2,699,999
  • Oct 15, 2024

  Last Listing Agent Amy Wilson KELLER WILLIAMS REALTY AT THE PARKS
• 

  

  /54

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
• 

  

  /10

  $3,300 Per Month

  • 3 Beds
  • 1 Bath
  • 820 Sq Ft
  • House for Rent

  853 W Lyman Ave, Winter Park, FL 32789

  Property Id: 1403118Our home is convenient for your extended friends and family, remote workers, traveling nurses, Rollins College parents and alum, snowbirds, conference attendees, or exploring travelers who prefer to stay in our home away from home.Three bedrooms (one queen and two double beds) accommodate three couples, Living room has large sectional and flat screen TV (bring

  (386) 267-8041

  853 W Lyman Ave, 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 $2,654,470

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

  1445 Holts Grove Cir, Winter Park, FL 32789
• 

  

  /42

  Est $726,214 Not Listed For Sale

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  Last Sold Summary

  • 4% Above List Price
  • $445/SF
  • 75 Days On Market

  • Last Sold Price $700,000
  • Jul 02, 2024

  Last Listing Agent Scott Garstka CHARLES RUTENBERG REALTY ORLANDO

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