Homes in ZIP Code 32789

• 

  

  

  /37

  $675,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,781 Sq Ft

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  You Found It!!! Beautiful Winter Park townhome that feels like a single-family residence. Situated on a private lane with no through-traffic. Ten-minute walk to Park Avenue and Rollins, five-minute walk to Lake Virginia. This exquisite end-unit is part of a sought-after 10-unit community. Three Bedrooms and two and a half Baths, volume ceilings, pristine travertine marble floors and an

  Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

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

  

  

  /16

  $2,875 per month

  • 4 Beds
  • 2 Baths
  • 1,970 Sq Ft
  • House for Rent

  2843 Riddle Dr, Winter Park, FL 32789

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  2843 Riddle Dr, Winter Park, FL 32789
• 

  

  /2

  $1,115,000 Sold Jul 10, 2025

  • 3,096 Sq Ft
  • $360/SF
  • 50 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1968

  309 Park Ct N, Winter Park, FL 32789

  Endless Potential in the Heart of Park North!Just steps from the charm and energy of Winter Park’s Park Avenue—where boutique cafes, fine dining, art galleries, museums, Central Park, and the Winter Park 9 Golf Course await—this rare Park North gem offers the ultimate opportunity to create your dream home.Nestled at the end of a peaceful cul-de-sac, this expansive .38-acre lot (16,534 SF)

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  309 Park Ct N, Winter Park, FL 32789
• 

  

  

  /24

  Est $350,623 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

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

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

  

  

  /54

  $479,000 Open Sat 11AM - 1PM

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

  130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789

  SUPERB LOCATION! Don’t miss out on this beautifully updated 2 bedroom 2.5 bath 2-story condo in Killarney Bay. Upon entering, you immediately notice the charm and character of this impeccably maintained condo. Recent updates include a fully renovated screened porch including floor, screen enclosure and roof, new sliding doors and windows, new refrigerator, new dishwasher, newly painted interior

  Lisa Gould KELLER WILLIAMS WINTER PARK

  130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
• 

  

  /19

  $3,100 per month

  • 3 Beds
  • 2.5 Baths
  • 1,645 Sq Ft
  • Townhouse for Rent

  1253 Indiana Ave, Winter Park, FL 32789

  Lovely townhouse in upscale Winter Park. All bedrooms upstairs. Great screened patio that connects to the garage. Walking distance to amazing restaurants and close to Downtown Winter Park and shopping.

  Lidya Gongage SPRING REALTY ORLANDO

  1253 Indiana Ave, Winter Park, FL 32789
• 

  /2

  $1,175,000 Sold Jul 08, 2025

  • 1,867 Sq Ft
  • $629/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1925

  835 Antonette Ave, Winter Park, FL 32789

  Charming 1925 Craftsman with Spanish-Style Guest Apartment in Winter Park's College Quarter.Nestled in the heart of the historic College Quarter, this beautifully preserved 1925 Craftsman home offers timeless character, modern livability, and a rare bonus: a separate Spanish/Moorish-style garage apartment with its own unique architectural flair.The main house features 3 bedrooms, 2

  Alexis Davis FANNIE HILLMAN & ASSOCIATES

  835 Antonette Ave, Winter Park, FL 32789
• 

  

  /30

  Est $655,742 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  1086 Azalea Ln Unit 1, Winter Park, FL 32789
• 

  

  /47

  $2,200,000

  • 5 Beds
  • 4.5 Baths
  • 3,174 Sq Ft

  1710 Oneco Ave, Winter Park, FL 32789

  Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5-bedroom, 4.5-bathroom home with bonus room that offers a perfect blend of comfort, and functionality. This exceptional residence features high-end designer finishes and exceptional craftsmanship throughout for modern

  Rhonda Chesmore KELLY PRICE & COMPANY LLC

  1710 Oneco Ave, Winter Park, FL 32789
• 

  /2

  $2,749 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  881 Julian St, Winter Park, FL 32789

  This home is currently undergoing exciting renovations and will be ready for you soon. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

  881 Julian St, Winter Park, FL 32789
• 

  /2

  $1,825,000 Sold Jul 08, 2025

  • 3,830 Sq Ft
  • $477/SF
  • 10 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2007

  1665 Temple Dr, Winter Park, FL 32789

  A rare gem in the heart of the Vias – Nestled in one of Winter Park’s most sought-after neighborhoods, this beautifully designed home is the epitome of comfort, luxury, and convenience. Located just minutes from Park Avenue, top-rated schools, and the best dining and shopping in Central Florida, this property offers an unbeatable lifestyle in a truly prime location.Inside, the home

  Brandon Geers COMPASS FLORIDA LLC

  1665 Temple Dr, Winter Park, FL 32789
• 

  

  /8

  Est $702,158 Not Listed For Sale

  • 1 Bed

  470 W Comstock Ave, Winter Park, FL 32789

  470 W Comstock Ave, Winter Park, FL 32789
• 

  

  /56

  $3,150,000

  • 6 Beds
  • 5 Baths
  • 4,767 Sq Ft

  575 Palmer Ave, Winter Park, FL 32789

  Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a

  Joe Devlin DEVLIN INVESTORS & ASSOCIATES

  575 Palmer Ave, Winter Park, FL 32789
• 

  

  /25

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 1,130 Sq Ft
  • Townhouse for Rent

  152 Sandlewood Trail Unit 6, Winter Park, FL 32789

  Lovely, light and airy home with newer appliances, fresh paint throughout. This end unit townhome has a spacious kitchen with eat-in space, a large bay window that floods the room with natural light. The large living and dining room features a corner fireplace. It also has tile flooring and oversized sliders that open to a private back patio...the pool is a short walk across the yard. There is a

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  152 Sandlewood Trail Unit 6, Winter Park, FL 32789
• 

  /2

  $519,180 Sold Jul 08, 2025

  • 2,205 Sq Ft
  • $235/SF
  • 201 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  2518 Sweetwater Trail, Winter Park, FL 32789

  Welcome home! This beautiful 4-bed, 2-bath pool home boasts a spacious 2,205 square feet of living space with a fantastic floor plan in Winter Park. Along with a new roof and water heater this home is ready for years of memories to come. A cozy entry foyer greets you at the front door and provides access to the secondary bedrooms, formal dining room, and well-lit family room enhanced by its

  Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  2518 Sweetwater Trail, Winter Park, FL 32789
• 

  

  /41

  Est $1,549,722 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,287 Sq Ft

  1005 S Pennsylvania Ave, Winter Park, FL 32789

  1005 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /26

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment.Located on the first floor, this beautifully renovated 2-bed, 2-bath home features

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
• 

  

  /20

  $3,700 per month

  • 2 Beds
  • 1 Bath
  • 1,141 Sq Ft
  • Condo for Rent

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

  Welcome to this cozy and inviting 2-bedroom, 1-bathroom home, perfect for couples, small families, or solo travelers eager to explore Central Florida. Situated just 3 miles from Downtown Orlando, 12 miles from Universal Studios, and 8 miles from Disney, this home's location is unbeatable.This charming property features two spacious queen bedrooms, a full bathroom with a walk-in shower, and a

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
• 

  /2

  $965,000 Sold Jul 07, 2025

  • 2,245 Sq Ft
  • $430/SF
  • 11 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1760 Mondrian Cir, Winter Park, FL 32789

  Don’t miss out on the final new construction unit available - act fast! Discover unparalleled luxury at Mondrian Winter Park, where contemporary design meets the tranquil beauty of Lake Killarney. We are excited to share that this is the LAST corner unit of a highly coveted floor plan in our exclusive community of just 30 modern townhomes along the serene shoreline. Each residence features

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1760 Mondrian Cir, Winter Park, FL 32789
• 

  

  /89

  Est $1,346,624 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  3629 Midiron Dr, Winter Park, FL 32789

  3629 Midiron Dr, Winter Park, FL 32789
• 

  

  /50

  $1,349,500 Open Sat 1PM - 4PM

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

  1371 Lyndale Blvd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city limits of Winter Park, you're immediately welcomed by a bright, open living and dining area anchored by a stunning wet bar, complete with sink, cabinetry, ice maker, and floating shelves. All completed with light modern porcelain tile flooring. To your right, the kitchen

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
• 

  

  /30

  $6,200 per month

  • 4 Beds
  • 4 Baths
  • 3,654 Sq Ft
  • House for Rent

  960 Georgia Ave, Winter Park, FL 32789

  Quintessential Winter Park Stunner. This well appointed home is situated on a half acre corner lot just two blocks away from Winter Park's shopping and dining district, Park Avenue. Surrounded by majestic oak trees you find this classic 4 bedroom, 4 bath home with 3600sq ft of living space. An abundance of natural light welcomes you in the homes central hub, the Family Room. Anchored by one of

  Alison Ashby CORCORAN PREMIER REALTY

  960 Georgia Ave, Winter Park, FL 32789
• 

  /2

  $2,100,000 Sold Jul 07, 2025

  • 3,182 Sq Ft
  • $660/SF
  • 36 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1926

  104 Cortland Ave, Winter Park, FL 32789

  Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  104 Cortland Ave, Winter Park, FL 32789
• 

  

  /44

  Est $894,417 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  1403 Michigan Ave, Winter Park, FL 32789

  1403 Michigan Ave, Winter Park, FL 32789
• 

  

  /44

  $1,100,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 2,826 Sq Ft

  512 Clarendon Ave, Winter Park, FL 32789

  Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for Audubon K-8! This spacious 2,826 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood like tile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen

  Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
• 

  

  /7

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • House for Rent

  1399 Miller Ave, Winter Park, FL 32789

  Property Id: 1795045Charming 1926 bungalow. 2 bedroom/1 bathroom house in prime location of Winter Park. Wood floors throughout the home, cast iron bathtub, hexagon tile in bathroom. Short drive to I-4, Park Ave, Rollins College, shopping, restaurants, downtown Orlando, hospitals, and more. Extra large front porch, fireplace, full kitchen, and washer and dryer.Renter responsible

  1399 Miller Ave, Winter Park, FL 32789
• 

  /2

  $1,050,000 Sold Jul 07, 2025

  • 3,377 Sq Ft
  • $311/SF
  • 9 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1964

  2923 Cove Trail, Winter Park, FL 32789

  A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market for the FIRST TIME. 2923 Cove Trail is nestled between the best of Winter Park & Maitland. Masterly created by the renowned Charlie Clayton it blends unmatched craftsmanship with modern design & flexibility craved by you, today’s discerning buyer. REIMAGINED in 2011 this

  Robin Delaney KELLER WILLIAMS ADVANTAGE III

  2923 Cove Trail, Winter Park, FL 32789
• 

  

  /43

  Est $1,112,898 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,310 Sq Ft

  1780 Mondrian Cir, Winter Park, FL 32789

  1780 Mondrian Cir, Winter Park, FL 32789
• 

  

  /40

  $399,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement & Motivated Seller! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789
• 

  

  /28

  $3,850 per month

  • 2 Beds
  • 1.5 Baths
  • 897 Sq Ft
  • Condo for Rent

  640 N Park Ave Unit 3, Winter Park, FL 32789

  Iconic, Art-Deco Park Aire Condominiums in Winter Park. This first floor property has been fully renovated with elegant, high-end finishes. Beautiful, wood floors throughout. Light & airy - this condo is surrounded by windows and light cascades through the large picture window that looks out over the surrounding scenery & landmarks, including Casa Feliz, St. Margaret Mary and the Winter Park

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  640 N Park Ave Unit 3, Winter Park, FL 32789
• 

  /2

  $705,000 Sold Jul 03, 2025

  • 2,245 Sq Ft
  • $314/SF
  • 13 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  1840 Laurel Rd, Winter Park, FL 32789

  Unlock the potential of this charming 3-bedroom, 2-bathroom home—ideal for renovation or building your custom dream residence. Nestled among a mix of beautifully preserved historic homes and stunning new construction, this property is located in one of Central Florida’s most sought-after neighborhoods.The home features classic terracotta tile flooring, two cozy wood-burning fireplaces—one

  Julie Glass KEYSEEKERS REAL ESTATE

  1840 Laurel Rd, Winter Park, FL 32789
• 

  

  /88

  Est $1,910,502 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
• 

  

  /43

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 3,363 Sq Ft

  800 Hamilton Place Ct, Winter Park, FL 32789

  Custom-built and beautifully maintained, this large 3-bedroom home with loft is located in prime Old Winter Park on a quiet cul-de-sac. The interior boasts 20'+ high ceilings, creating a grand and airy atmosphere throughout the main living spaces. High-end finishes include Viking stainless steel appliances, dolomite marble tile flooring, and a thoughtfully designed, functional layout ideal for

  Julian Torres, Jr EPIC REAL ESTATE ADVISORS LLC

  800 Hamilton Place Ct, Winter Park, FL 32789
• 

  

  /12

  $2,349 per month

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

  324 Lake Fair Ln, Winter Park, FL 32789

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2493.90. That covers your base rent, $2349.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  324 Lake Fair Ln, Winter Park, FL 32789
• 

  /2

  $750,000 Sold Jul 03, 2025

  • 960 Sq Ft
  • $781/SF
  • 263 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1941

  731 Midget Dr, Winter Park, FL 32789

  SPECTACULAR WINTER PARK OPPORTUNITY! This oversized corner lot in Fairbanks Park overlooking Lake Midget and Lake Midget Park is a rare opportunity to build your dream home in Winter Park. The 2-bedroom/1-bath home, original owners since 1941, is available for renovation or new construction. Serene views of Lake Midget from the front porch, that can’t be beat. New restaurant and retail space is

  Laura Heidrich COLDWELL BANKER RESIDENTIAL RE

  731 Midget Dr, Winter Park, FL 32789
• 

  

  /39

  Est $853,832 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
• 

  

  /32

  $410,000

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

  240 Killarney Bay Ct Unit 4, Winter Park, FL 32789

  Welcome to Killarney Bay—Winter Park’s best-kept secret for tranquil lakeside living, and just steps from the city’s finest shopping and dining!This beautifully updated and spacious 2-bedroom, 2.5-bath townhome-style condo offers a rare blend of modern upgrades and classic charm. Enjoy vaulted ceilings, a wood-burning fireplace, and rich wood-like flooring throughout. The open-concept kitchen

  Blaike Gill KELLER WILLIAMS WINTER PARK

  240 Killarney Bay Ct Unit 4, Winter Park, FL 32789
• 

  

  /23

  $1,895 per month

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

  851 Miles Ave Unit 9, Winter Park, FL 32789

  Imagine living in this completely renovated two-bedroom, one-bathroom second-floor condominium unit near downtown Winter Park at Aragon Condos. This intimate, two-building, two-story condominium community comprises just twenty-eight units focused around a central courtyard.Features include: • Recently remodeled kitchen including all cabinetry, countertops, marble tile backsplash,

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  851 Miles Ave Unit 9, Winter Park, FL 32789
• 

  /2

  $2,440,000 Sold Jul 01, 2025

  • 3,770 Sq Ft
  • $647/SF
  • 41 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2016

  1700 Palm Ave, Winter Park, FL 32789

  One lucky Buyer's gain is this Seller's bittersweet goodbye. A job relocation has these homeowners leaving behind a home they absolutely love, and now, you can make 1700 Palm Ave. yours! Modern sophistication and everyday functionality come together seamlessly in this exceptional Winter Park residence.With 3,770 square feet of thoughtfully designed living space, this 4-bedroom, 4.1-bath home

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1700 Palm Ave, Winter Park, FL 32789
• 

  

  /44

  Est $1,015,662 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

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