Homes in ZIP Code 32789

• 

  

  

  /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

  $1,095,000

  Sold Dec 01, 2025

  1450 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,942 Sq Ft
  • Built 2009

  Last Sold Summary

  • 16% Below List Price
  • $564/SF
  • 49 Days On Market

  Current Estimated Value $1,123,145

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
• 

  

  

  /3

  Est $2,238,215

  Not Listed For Sale

  150 Whipple Ave, Winter Park, FL 32789

  • 4 Beds
  • Built 2025

  150 Whipple Ave, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market
• 

  

  

  /26

  $629,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  685 Overspin Dr, Winter Park, FL 32789

  Super Location! Close to Urban Bike trail, Winter Park Village, Dubsdread Golf Course, Advent Health. This home was custom built with large white wood window casing, formal dining room with plenty of natural light, 10 foot ceilings, crown molding, 8 ft doors, upgraded tile, 3 sets of French Doors open to back and so much more. Gas fireplace in the family room with high-top bar seating in the

  Corey Van Dyke HOMEVEST REALTY

  685 Overspin Dr, Winter Park, FL 32789
• 

  

  /36

  $3,060 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,700 Sq Ft
  • Townhouse for Rent

  1415 Harmon Ave, Winter Park, FL 32789

  In the heart of Winter Park on a quiet cobbled street, this Mediterranean style 3-bedroom, 3-bathroom house is available to rent today. With beautiful Travertine floors throughout the downstairs of the home, granite countertop kitchen, marble countertop bathrooms, and limestone ornate pillars throughout the home, this home boasts character. Upstairs the home enjoys three bedrooms, two bathrooms,

  Moire McKibbin LA ROSA REALTY ORLANDO LLC

  1415 Harmon Ave, Winter Park, FL 32789
• 

  /2

  $220,000

  Sold Jan 30, 2026

  700 Melrose Ave Unit J23, Winter Park, FL 32789

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

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 107 Days On Market

  Current Estimated Value $217,744

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit J23, Winter Park, FL 32789
• 

  /2

  Est $806,080

  Not Listed For Sale

  1818 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2018

  1818 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 189 Days On Market
• 

  

  /55

  $475,000

  $75K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
• 

  

  /48

  $9,500 Per Month

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

  1760 Alabama Dr, Winter Park, FL 32789

  Behind a gated courtyard entrance in the Vias of Winter Park, just around the corner from Kraft Azalea Garden on the shores of Lake Maitland, this move-in ready residence offers privacy, thoughtful design and exceptional indoor-outdoor living. Surrounded by mature landscaping and accessed from both front and rear driveways, the property provides a rare sense of seclusion while remaining minutes

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1760 Alabama Dr, Winter Park, FL 32789
• 

  /2

  $805,000

  Sold Jul 01, 2025

  1795 Walker Ave, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 1,813 Sq Ft
  • Built 1958

  Last Sold Summary

  • 17% Below List Price
  • $444/SF
  • 143 Days On Market

  Current Estimated Value $808,096

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1795 Walker Ave, Winter Park, FL 32789
• 

  

  /9

  Est $437,084

  Not Listed For Sale

  822 Symonds Ave, Winter Park, FL 32789

  • 2 Beds
  • Built 1942

  822 Symonds Ave, Winter Park, FL 32789

  Last Sold Summary

  • 314 Days On Market
• 

  

  /81

  $3,799,000

  New Construction Pending

  • 5 Beds
  • 5 Baths
  • 4,451 Sq Ft

  150 Dana Way, Winter Park, FL 32789

  JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKETProudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  150 Dana Way, Winter Park, FL 32789
• 

  

  /25

  $5,490 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft
  • Condo for Rent

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

  Steven Koleno BEYCOME OF FLORIDA LLC

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
• 

  /2

  $567,500

  Sold Dec 09, 2025

  1010 Aragon Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft
  • Built 1949

  Last Sold Summary

  • 1% Below List Price
  • $391/SF
  • 2 Days On Market

  Current Estimated Value $572,260

  Last Listing Agent Devin Loh COLDWELL BANKER REALTY

  1010 Aragon Ave, Winter Park, FL 32789
• 

  /2

  Est $2,284,725

  Not Listed For Sale

  1010 N Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,074 Sq Ft
  • Built 2017

  1010 N Pennsylvania Ave, Winter Park, FL 32789

  Last Sold Summary

  • 94 Days On Market
• 

  

  /58

  $1,899,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789

  Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789
• 

  

  /8

  $2,995 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  1137 S Pennsylvania Ave, Winter Park, FL 32789

  Location!!Walking distance to Rollins campus and to downtown Winter Park. Beautiful 3-bedroom 2-bathroom home. Recently renovated kitchen and freshly painted. Nearby schools include Audubon Park elementary, Glenridge Middle School, and Winter Park education center school. This house is in the perfect location, close to great restaurants and within walking distance to Winter Park farmer's

  Raquel Elliott COLDWELL BANKER REALTY

  1137 S Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  $2,078,500

  Sold Dec 11, 2025

  715 Via Bella, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 4,328 Sq Ft
  • Built 1976

  Last Sold Summary

  • 12% Below List Price
  • $480/SF
  • 70 Days On Market

  Current Estimated Value $2,150,831

  Last Listing Agent Adam Roark COMPASS FLORIDA LLC

  715 Via Bella, Winter Park, FL 32789
• 

  

  /50

  Est $2,015,526

  Not Listed For Sale

  270 E Lake Sue Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,151 Sq Ft
  • Built 2023

  270 E Lake Sue Ave, Winter Park, FL 32789

  Last Sold Summary
• 

  

  /53

  $1,299,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789

  On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789
• 

  /2

  $250,000

  Sold Mar 11, 2026

  2009 Cornell Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Below List Price
  • $328/SF
  • 95 Days On Market

  Current Estimated Value $267,851

  Last Listing Agent Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
• 

  

  /49

  Est $2,195,736

  Not Listed For Sale

  180 Whipple Ave, Winter Park, FL 32789

  • 4 Beds
  • Built 2025

  180 Whipple Ave, Winter Park, FL 32789

  Last Sold Summary

  • 353 Days On Market
• 

  

  /52

  $699,900

  Open Sat 11AM - 2PM $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,411 Sq Ft

  860 N Denning Dr, Winter Park, FL 32789

  **NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true

  LaDarrius Sanders OUTLET REALTY

  860 N Denning Dr, Winter Park, FL 32789
• 

  /2

  $375,000

  Sold Mar 06, 2026

  1007 Early Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 1956

  Last Sold Summary

  • 12% Below List Price
  • $218/SF
  • 101 Days On Market

  Current Estimated Value $382,604

  Last Listing Agent Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789
• 

  

  /17

  Not Listed For Sale

  700 Melrose Ave Unit K, Winter Park, FL 32789

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

  700 Melrose Ave Unit K, Winter Park, FL 32789

  Last Sold Summary

  • 188 Days On Market
• 

  

  /25

  $1,699,000

  $51K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 2,488 Sq Ft

  1110 Alabama Dr, Winter Park, FL 32789

  Come home to this stunning 3 Bed/3 Bath Winter Park residence, fully renovated down to the studs in 2020 and perfectly positioned on a premier corner lot at Alabama Drive and Palmer Avenue. Set among historic estate homes and the iconic tree-lined brick streets of the Chain of Lakes district, this home offers one of Winter Park’s most coveted addresses.Enjoy an unmatched lifestyle just moments

  Non-Member Mls Agent

  1110 Alabama Dr, Winter Park, FL 32789
• 

  /2

  $434,000

  Sold Sep 12, 2025

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,556 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Above List Price
  • $279/SF
  • 55 Days On Market

  Current Estimated Value $465,911

  Last Listing Agent Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
• 

  /2

  Est $1,314,967

  Not Listed For Sale

  242 W Lyman Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,199 Sq Ft
  • Built 2014

  242 W Lyman Ave, Winter Park, FL 32789

  Last Sold Summary

  • 12 Days On Market
• 

  

  /26

  $250,000

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

  1500 Gay Rd Unit 3C, Winter Park, FL 32789

  WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and

  Heather Frazee FANNIE HILLMAN & ASSOCIATES

  1500 Gay Rd Unit 3C, Winter Park, FL 32789
• 

  /2

  $850,000

  Sold Mar 25, 2026

  465 N Phelps Ave, Winter Park, FL 32789

  • Land
  • 11,761 Sq Ft
  • $3,148,148 per Acre

  Last Sold Summary

  • 7 Days On Market

  Current Estimated Value $834,246

  Last Listing Agent Hircanys Vicioso FIDICITY REALTY INC

  465 N Phelps Ave, Winter Park, FL 32789
• 

  /2

  Est $1,084,331

  Not Listed For Sale

  625 N Interlachen Ave Unit A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,718 Sq Ft
  • Built 1981

  625 N Interlachen Ave Unit A, Winter Park, FL 32789

  Last Sold Summary

  • 196 Days On Market
• 

  

  /58

  $999,000

  $201K PRICE DROP

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

  241 W Lake Sue Ave, Winter Park, FL 32789

  Price reduced for a quick sale, creating a fantastic opportunity for the right buyer. Don’t let this one slip away. Welcome to 241 W. Lake Sue Avenue, a rare offering in Virginia Heights, one of Winter Park’s most coveted and established neighborhoods. Set along a charming oak-canopied brick street and surrounded by multimillion-dollar estates, this beautifully updated pool home sits on an

  Ken Dalton COLDWELL BANKER REALTY

  241 W Lake Sue Ave, Winter Park, FL 32789
• 

  /2

  $1,110,000

  Sold Aug 26, 2025

  233 Hampden Place, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 2,813 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $395/SF
  • 7 Days On Market

  Current Estimated Value $1,211,574

  Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
• 

  /2

  Est $792,106

  Not Listed For Sale

  1820 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,252 Sq Ft
  • Built 2018

  1820 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 81 Days On Market
• 

  

  /61

  $2,394,500

  New Construction Pending

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft

  2412 Chantilly Ave, Winter Park, FL 32789

  Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 5 bedroom, 6.5 bath home offers over 4,500 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom glass front door into the foyer leading to your main living area featuring a fireplace and sliding glass walls for indoor-outdoor living. This

  Tab Bish LLC REAL BROKER, LLC

  2412 Chantilly Ave, Winter Park, FL 32789
• 

  /2

  $3,200,000

  Sold Nov 04, 2025

  1900 W Fawsett Rd, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $696/SF
  • 6 Days On Market

  Current Estimated Value $3,167,326

  Last Listing Agent Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  1900 W Fawsett Rd, Winter Park, FL 32789
• 

  

  /77

  Est $1,159,456

  Not Listed For Sale

  690 Osceola Ave Unit 504, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,079 Sq Ft
  • Built 1969

  690 Osceola Ave Unit 504, Winter Park, FL 32789

  Last Sold Summary

  • 74 Days On Market
• 

  

  /38

  $879,000

  • 3 Beds
  • 3.5 Baths
  • 2,030 Sq Ft

  1265 Arlington Place, Winter Park, FL 32789

  Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood

  Erika Beerbower FANNIE HILLMAN & ASSOCIATES

  1265 Arlington Place, Winter Park, FL 32789
• 

  /2

  $630,000

  Sold Aug 11, 2025

  1792 Killarney Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,264 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Below List Price
  • $278/SF
  • 1 Day On Market

  Current Estimated Value $664,443

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789

Showing Results 201 - 240, Page 6 of 18