Homes in ZIP Code 32789

• 

  

  

  /30

  $630,000

  $195K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  2612 Roxbury Rd, Winter Park, FL 32789

  SELLER MOTIVATED!! Potential of an extra one percent for closing costs, just ask your agent!!Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
• 

  

  

  /65

  $5,500 Per Month

  • 4 Beds
  • 3 Baths
  • 2,511 Sq Ft
  • Hidden Winter Park Oasis

  610 Gaines Way, Winter Park, FL 32789

  Tucked away at the quiet end of a private cul-de-sac in Winter Park’s premier 32789 zip code, this exceptional property blends classic elegance with a bright, modern lifestyle. From the gleaming wood floors that flow throughout the entire home to the thoughtful architectural details, this residence is designed for those who appreciate both privacy and top-tier entertaining.The Interior

  610 Gaines Way, Winter Park, FL 32789
• 

  

  /2

  $3,020,000

  Sold Oct 02, 2025

  1820 Englewood Rd, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,263 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $708/SF
  • 70 Days On Market

  Current Estimated Value $3,037,611

  Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
• 

  

  

  /39

  Est $819,938

  Not Listed For Sale

  1770 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2023

  1770 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 18 Days On Market
• 

  

  

  /36

  $3,095,000

  Pending

  • 3 Beds
  • 5 Baths
  • 4,425 Sq Ft

  1724 Pine Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Beautifully renovated and thoughtfully designed, this exceptional residence is nestled in the heart of Winter Park’s sought-after Tree Streets neighborhood. Privately behind entry gates, the home welcomes you with a picturesque front courtyard highlighted by a tranquil water feature, setting the tone for the sophisticated living experience that awaits.

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1724 Pine Ave, Winter Park, FL 32789
• 

  

  /29

  $5,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,940 Sq Ft
  • Townhouse for Rent

  784 S Pennsylvania Ave, Winter Park, FL 32789

  Discover modern living in this beautifully designed townhome located in the heart of Winter Park. This residence has a spacious layout with contemporary finishes, high ceilings, modern light fixtures and shades, and abundant natural light. Enjoy the convenience of a well-appointed kitchen, an inviting living area, and a private patio for relaxing, and private access to the community pool! The

  Steven Koleno BEYCOME OF FLORIDA LLC

  784 S Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  $389,900

  Sold Mar 18, 2026

  700 Melrose Ave Unit M4, Winter Park, FL 32789

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

  Last Sold Summary

  • 1% Below List Price
  • $363/SF
  • 7 Days On Market

  Current Estimated Value $381,081

  Last Listing Agent Mary Harmening ROAM FLORIDA REALTY LLC

  700 Melrose Ave Unit M4, Winter Park, FL 32789
• 

  

  /25

  Est $2,025,887

  Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789

  Last Sold Summary

  • 33 Days On Market
• 

  

  /35

  $649,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,101 Sq Ft

  1037 N Virginia Ave, Winter Park, FL 32789

  THE best kept secret in WP! Newly renovated charming bungalow located directly on famed 4th Fairway on WP9 – Winter Park Golf Course! Quiet, private & secluded setting with gorgeous views on dead end street. Walk or bike to Park Avenue, dining and shopping, Rollins College and Winter Park Village. New roof and water heater 2023, refinished hardwood floors, new kitchen with stainless appliances,

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1037 N Virginia Ave, Winter Park, FL 32789
• 

  

  /15

  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft
  • Winter Park 3/2 Rental

  521 Ohio St, Winter Park, FL 32789

  WINTER PARK! 3 bedroom/2 bathroom single family home blocks from I-4. Newer luxury vinyl floors installed throughout home. Stainless steel refrigerator and range, new SS dishwasher, separate dining room, family room, living room, and 2 bonus rooms for offices or storage. 2-car carport with private drive. Big yard (1/3 acre lot) corner lot, rear patio. Inside laundry room with washer / dryer

  521 Ohio St, Winter Park, FL 32789
• 

  /2

  $417,100

  Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Current Estimated Value $427,343

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
• 

  /2

  Est $1,040,055

  Not Listed For Sale

  311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 2,096 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

  Last Sold Summary

  • 102 Days On Market
• 

  

  /24

  $259,999

  Open Sun 1PM - 3PM

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 104, Winter Park, FL 32789

  Beautifully renovated and move-in ready 2-bedroom, 2-bath condominium offers thoughtful upgrades and a seamless open layout in one of Winter Park's most desirable lakefront communities. The heart of the home is the fully renovated kitchen (2025), featuring custom, soft close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, a white

  Stephen Hachey REALTY OF RIVERVIEW LLC

  2500 Lee Rd Unit 104, Winter Park, FL 32789
• 

  

  /24

  $8,295 Per Month

  • 4 Beds
  • 5.5 Baths
  • 3,295 Sq Ft
  • House for Rent

  2234 Howard Dr, Winter Park, FL 32789

  Welcome to an extraordinary two-story, 4-bedroom, 5.5-bath executive estate nestled in one of Winter Park's most sought-after neighborhoods. Designed with timeless elegance and modern convenience, this expansive home effortlessly blends luxury, comfort, and versatility.Inside, vaulted ceilings create a grand sense of space, while multiple living areas offer flexibility for both formal

  Raquel Elliott COLDWELL BANKER REALTY

  2234 Howard Dr, Winter Park, FL 32789
• 

  /2

  $1,200,000

  Sold Mar 20, 2026

  950 Aragon Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 2020

  Last Sold Summary

  • $463/SF
  • 5 Days On Market

  Current Estimated Value $1,183,121

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  950 Aragon Ave, Winter Park, FL 32789
• 

  

  /36

  Est $1,403,530

  Not Listed For Sale

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  • 3 Beds
  • 4 Baths
  • 2,950 Sq Ft
  • Built 2007

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market
• 

  

  /39

  $1,395,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,821 Sq Ft

  321 Sylvan Blvd, Winter Park, FL 32789

  Set on a rare double lot in one of Winter Park's most coveted locations, this charming 1940 Craftsman-style residence presents an extraordinary opportunity to enjoy one of Central Florida's most celebrated lifestyles while envisioning the future. Just moments from the Winter Park Chain of Lakes, the boutiques and acclaimed dining of Park Avenue, and the timeless beauty of Rollins College, the

  Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

  321 Sylvan Blvd, Winter Park, FL 32789
• 

  

  /27

  $1,455 Per Month

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft
  • Condo for Rent

  2500 Lee Rd Unit 103, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This spacious 2-bedroom, 2-bath condo offers comfortable living in one of the most convenient locations in the Orlando/Winter Park area. The unit features a bright and open living space and generously sized bedrooms.Residents of Lakeside Manor enjoy access to community amenities including private Lake Killarney access, a community

  2500 Lee Rd Unit 103, Winter Park, FL 32789
• 

  /2

  $625,090

  Sold Jun 03, 2026

  2713 Eastern Pkwy, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $479/SF
  • 12 Days On Market

  Current Estimated Value $679,803

  Last Listing Agent Helen Thompson RE/MAX SELECT GROUP

  2713 Eastern Pkwy, Winter Park, FL 32789
• 

  

  /55

  Est $1,143,009

  Not Listed For Sale

  1772 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2023

  1772 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 83 Days On Market
• 

  

  /82

  $135,000

  $25K PRICE DROP

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

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Located in the heart of Winter Park, this charming condo stands ready to welcome you home. This three-bedroom, two-bathroom sanctuary offers a blend of comfort and modern elegance, perfect for those who cherish both relaxation and entertaining. As you step inside, the spacious living and dining areas greet you with an abundance of natural light, creating a warm and inviting atmosphere. Imagine

  Jenaia Fowlkes FOWLKES REALTY CO

  1695 Lee Rd Unit E215, Winter Park, FL 32789
• 

  

  /17

  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
• 

  /2

  $637,500

  Sold Jan 16, 2026

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,951 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 149 Days On Market

  Current Estimated Value $644,110

  Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

  595 Huntington Ave Unit 4, Winter Park, FL 32789
• 

  

  /16

  Est $1,013,361

  Not Listed For Sale

  2400 Roxbury Rd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft
  • Built 2023

  2400 Roxbury Rd, Winter Park, FL 32789

  Last Sold Summary

  • 55 Days On Market
• 

  

  /25

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  1881 Lake Spier Dr, Winter Park, FL 32789

  Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier.Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy,

  Rafael Zenke Pinhao NOVA REAL ESTATE SERVICES INC

  1881 Lake Spier Dr, Winter Park, FL 32789
• 

  

  /14

  $1,595 Per Month

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

  1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789

  2 Bedrooms, 1 Bathroom located on the first floor. Galley kitchen (with a dishwasher, microwave, range, refrigerator, and a washer/dryer combo), walk-in closet in the primary bedroom, and an open living/dining room combo filled with natural light. A private patio, playground, and park. It includes 1 assigned parking space.This property offers an option of a security deposit-free lease

  1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789
• 

  /2

  $1,250,000

  Sold Dec 29, 2025

  359 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1979

  Last Sold Summary

  • $522/SF
  • 0 Days On Market

  Current Estimated Value $1,255,064

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  359 Beloit Ave, Winter Park, FL 32789
• 

  

  /19

  Est $2,500,402

  Not Listed For Sale

  350 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft
  • Built 2018

  350 Beloit Ave, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market
• 

  

  /47

  $2,800,000

  Open Sat 1PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 3,286 Sq Ft

  660 W Morse Blvd, Winter Park, FL 32789

  Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking

  Jennifer Sloan COMPASS FLORIDA LLC

  660 W Morse Blvd, Winter Park, FL 32789
• 

  

  /24

  $2,200 Per Month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
• 

  /2

  $775,000

  Sold May 22, 2026

  521 Fairfax Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $367/SF
  • 2 Days On Market

  Current Estimated Value $780,768

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  521 Fairfax Ave, Winter Park, FL 32789
• 

  

  /46

  Est $952,014

  Not Listed For Sale

  1913 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft
  • Built 2023

  1913 S Lakemont Ave, Winter Park, FL 32792

  Last Sold Summary

  • 119 Days On Market
• 

  

  /46

  $1,725,000

  $175K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  1840 Bryan Ave, Winter Park, FL 32789

  This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1840 Bryan Ave, Winter Park, FL 32789
• 

  

  /19

  $1,175 Per Month

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

  1695 Lee Rd, Winter Park, FL 32789

  Don't miss out on this cozy 1-bedroom, 1-bathroom condo at Waterfall Cove. The unit has been newly painted throughout and features kitchen appliances, upgraded blinds, ceiling fans, and a full-size washer and dryer. You can also enjoy your morning coffee on the private patio. The community offers excellent amenities, including a pool, playground, and picnic area. Waterfall Cove is ideally located

  1695 Lee Rd, Winter Park, FL 32789
• 

  /2

  $1,199,000

  Sold Jun 09, 2026

  1807 Magnolia Ave, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 2,618 Sq Ft
  • Built 2026

  Last Sold Summary

  • $458/SF
  • 9 Days On Market

  Current Estimated Value $1,143,370

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1807 Magnolia Ave, Winter Park, FL 32789
• 

  /2

  Est $5,549,607

  Not Listed For Sale

  654 W Morse Blvd, Winter Park, FL 32789

  • 5 Beds
  • 7.5 Baths
  • 8,752 Sq Ft
  • Built 2022

  654 W Morse Blvd, Winter Park, FL 32789

  Last Sold Summary

  • 120 Days On Market
• 

  

  /27

  $114,000

  $16K PRICE DROP

  • 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
• 

  

  /13

  $2,050 Per Month

  • 2 Beds
  • 1 Bath
  • 1,125 Sq Ft
  • House for Rent

  503 Kilshore Ln, Winter Park, FL 32789

  LOCATION! LOCATION! LOCATION! Home well positioned on large 0.28 acre lot in 32789. Gorgeous two bedroom home right in the heart of Winter Park , that just had a new roof put on.. At just a ten minute drive from Orlando, this home is in a very convenient location for anyone who wants to be in and out of the city whenever they'd like. Beautiful interior, with original wood flooring throughout.

  Vincent Paige, PA COLDWELL BANKER REALTY

  503 Kilshore Ln, Winter Park, FL 32789
• 

  /2

  $1,595,000

  Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,613,895

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
• 

  /2

  Est $530,004

  Not Listed For Sale

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft
  • Built 1987

  1051 Aragon Ave Unit 1051, Winter Park, FL 32789

  Last Sold Summary

  • 104 Days On Market

Showing Results 161 - 200, Page 5 of 18