Homes in ZIP Code 32789

• 

  

  

  /47

  $234,900

  $25K PRICE DROP Under Contract

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

  1500 Gay Rd Unit 17D, Winter Park, FL 32789

  Under contract-accepting backup offers. PRICE REDUCED TOTAL OF $25,000! AMAZING VALUE!!!Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 17D, Winter Park, FL 32789
• 

  

  

  /20

  $1,750 Per Month

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

  1720 Miller Ave, Winter Park, FL 32789

  Beautifully Updated 2 Bed / 1 Bath Duplex in Winter Park, FLStep into this freshly renovated 2-bedroom, 1-bath duplex offering a bright, modern living experience in one of Winter Park's most desirable neighborhoods. The home features new interior paint that gives every room a crisp, clean feel, paired with brand new flooring that adds warmth and style throughout the space. The living area is

  

  Bobby Keen

  KEEN REALTY GROUP, INC.

  1720 Miller Ave, Winter Park, FL 32789
• 

  

  /2

  $730,000

  Sold Sep 01, 2026

  950 S Kentucky Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,155 Sq Ft
  • Built 1941

  Last Sold Summary

  • 9% Below List Price
  • $339/SF
  • 8 Days On Market

  Current Estimated Value $639,225

  Last Listing Agent Gwendolen Flynn COLDWELL BANKER REALTY

  950 S Kentucky Ave, Winter Park, FL 32789
• 

  

  /2

  Est $805,550

  Not Listed For Sale

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Lois Rawson COLDWELL BANKER REALTY
• 

  

  

  /28

  $199,900

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 220, Winter Park, FL 32789

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 220, Winter Park, FL 32789
• 

  

  /4

  Starting at $4,995 Per Month

  • 3 Beds

  770 Annesley Place, Winter Park, FL 32789

  Oxford at Winterpark

  

  770 Annesley Place, Winter Park, FL 32789
• 

  /2

  $1,965,000

  Sold Jul 29, 2026

  2261 Mulbry Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,696 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $532/SF
  • 28 Days On Market

  Current Estimated Value $1,883,940

  Last Listing Agent Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  2261 Mulbry Dr, Winter Park, FL 32789
• 

  /2

  Est $613,840

  Not Listed For Sale

  535 N Interlachen Ave Unit 305, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,156 Sq Ft
  • Built 1972

  535 N Interlachen Ave Unit 305, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent A.V. Blalock COLDWELL BANKER REALTY
• 

  

  /22

  $245,000

  $17K PRICE DROP Under Contract

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

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  Under contract-accepting backup offers. DRASTIC PRICE REDUCTION!LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
• 

  

  /36

  $2,750 Per Month

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • House for Rent

  1627 Orange Ave, Winter Park, FL 32789

  Charming 3-bedroom, 2-bath bungalow located in the highly desirable, well-established Orwin Manor neighborhood in the City of Winter Park. Ideally situated between Downtown Orlando and Park Avenue, this home is just minutes from AdventHealth Hospital, Rollins College, and offers convenient access to I-4.The spacious retreat is located just across the hall from a beautifully renovated

  

  Peter Dang

  ALLIANCE RENTAL HOMES

  1627 Orange Ave, Winter Park, FL 32789
• 

  /2

  $955,000

  Sold Feb 24, 2026

  512 Clarendon Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $338/SF
  • 21 Days On Market

  Current Estimated Value $1,015,427

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
• 

  /2

  Est $2,037,770

  Not Listed For Sale

  141 Oakwood Way, Winter Park, FL 32789

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

  141 Oakwood Way, Winter Park, FL 32789

  Last Sold Summary

  • 170 Days On Market

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE
• 

  

  /81

  $3,600,000

  • 4 Beds
  • 5 Baths
  • 4,202 Sq Ft

  276 Detmar Dr, Winter Park, FL 32789

  Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light.The main level offers two bedrooms and three full bathrooms, including a

  

  Melanie Johnston

  CALL IT CLOSED INTL REALTY

  276 Detmar Dr, Winter Park, FL 32789
• 

  

  /28

  Starting at $1,627 Per Month

  • 1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  Elon Winter Park

  

  712 Nicolet Ave, Winter Park, FL 32789
• 

  /2

  $449,000

  Sold Aug 12, 2026

  2611 Lotafun Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,838 Sq Ft
  • Built 1962

  Last Sold Summary

  • $244/SF
  • 3 Days On Market

  Current Estimated Value $458,308

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  2611 Lotafun Ave, Winter Park, FL 32789
• 

  /2

  Est $835,289

  Not Listed For Sale

  1421 Sunset Dr, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,672 Sq Ft
  • Built 1977

  1421 Sunset Dr, Winter Park, FL 32789

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC
• 

  

  /67

  $575,000

  Open Sat 1PM - 4PM

  • 2 Beds
  • 2.5 Baths
  • 1,648 Sq Ft

  1259 Indiana Ave, Winter Park, FL 32789

  Virtually Staged. WINTER PARK, WITHIN REACH. A rare opportunity to step into one of Central Florida’s most coveted lifestyles. Bright, airy, remarkably spacious, this immaculate 2-bedroom townhome lives far larger than its approximately 1,600 sq.ft.suggests. Greet the day with a sunny disposition as morning light fills the oversized, east-facing primary bedroom. Step onto the private lanai with a

  

  Karan Wienker

  COLDWELL BANKER REALTY

  1259 Indiana Ave, Winter Park, FL 32789
• 

  

  /75

  Starting at $1,721 Per Month

  • 1 - 3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  Bainbridge Winter Park

  

  1400 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /2

  $2,295,000

  Sold Dec 16, 2025

  1661 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,570 Sq Ft
  • Built 2025

  Last Sold Summary

  • 12% Below List Price
  • $643/SF
  • 26 Days On Market

  Current Estimated Value $2,153,705

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $1,346,034

  Not Listed For Sale

  1049 Tuscany Place, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,471 Sq Ft
  • Built 1979

  1049 Tuscany Place, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC
• 

  

  /31

  $369,900

  $10K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  440 Cambridge Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  440 Cambridge Blvd, Winter Park, FL 32789
• 

  

  /50

  Starting at $2,111 Per Month

  • 1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  Paseo at Winter Park Village

  

  940 W Canton Ave, Winter Park, FL 32789
• 

  /2

  $2,700,000

  Sold Oct 30, 2025

  1020 Mayfield Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $1,014/SF
  • 149 Days On Market

  Current Estimated Value $2,794,128

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
• 

  /2

  Est $364,492

  Not Listed For Sale

  657 Overspin Dr, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,349 Sq Ft
  • Built 1955

  657 Overspin Dr, Winter Park, FL 32789

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY
• 

  

  /15

  $164,500

  $11K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 4D, Winter Park, FL 32789

  ANOTHER PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping!One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 4D, Winter Park, FL 32789
• 

  

  /50

  Starting at $1,695 Per Month

  • Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  Seven41 Winter Park

  

  741 Clay St, Winter Park, FL 32789
• 

  /2

  $4,250,000

  Sold Jun 01, 2026

  1336 College Point, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 3,181 Sq Ft
  • Built 1926

  Last Sold Summary

  • 8% Below List Price
  • $1,336/SF
  • 109 Days On Market

  Current Estimated Value $4,208,723

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

  1336 College Point, Winter Park, FL 32789
• 

  /2

  Est $1,718,259

  Not Listed For Sale

  2402.5 Temple Dr, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,248 Sq Ft
  • Built 2015

  2402.5 Temple Dr, Winter Park, FL 32789

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Steve Schiffer OLDE TOWN BROKERS INC
• 

  

  /65

  $950,000

  $200K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Virtually Staged. JULY 2026 NEW CONCRETE CIRCULAR DRIVE AND NEW CONCRETE SIDEWALKS! PRICE IMPROVEMENT! NO HOA! SEPTIC INSPECTED AND CERTIFIED. Experience refined living in this renovated custom designed home on a corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  1800 Magnolia Ave, Winter Park, FL 32789
• 

  

  /50

  Starting at $1,662 Per Month

  • Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  Juno Winter Park

  

  1305 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /2

  $1,590,000

  Sold Mar 06, 2026

  1166 Oaks Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $556/SF
  • 153 Days On Market

  Current Estimated Value $1,610,305

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
• 

  

  /42

  Est $1,681,358

  Not Listed For Sale

  1805 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft
  • Built 2014

  1805 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  /24

  $629,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,249 Sq Ft

  2825 Mulford Ave, Winter Park, FL 32789

  Enjoy the best of Winter Park living from this charming 2-bedroom, 2-bath home just minutes from Park Avenue, Baldwin Park, Mills 50, Downtown Orlando, local parks, shopping, and dining. The home offers a versatile layout with a bonus room that can be used as an office, den, playroom, or additional living space, plus a second bedroom with a built-in Murphy bed for added flexibility. Outside, the

  

  Yusuf Gencay

  RE/MAX Town & Country Realty

  2825 Mulford Ave, Winter Park, FL 32789
• 

  

  /35

  Starting at $1,475 Per Month

  • Studio - 3 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

  

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

  /2

  $2,050,000

  Sold Apr 30, 2026

  1205 Mayfield Ave, Winter Park, FL 32789

  • Land
  • 23,958 Sq Ft
  • $3,727,273 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 89 Days On Market

  Current Estimated Value $2,145,964

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
• 

  /2

  Est $272,000

  Not Listed For Sale

  2446 Lotafun Ave, Winter Park, FL 32789

  2446 Lotafun Ave, Winter Park, FL 32789

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent David Francetic COLDWELL BANKER REALTY
• 

  

  /13

  $450,000

  • Land
  • 4,791 Sq Ft
  • $4,090,909 per Acre

  786 W Canton Ave, Winter Park, FL 32789

  HIGH & DRY | PRIME WINTER PARK LOCATION | BUILD YOUR DREAM HOME Rarely does an opportunity like this become available in the heart of Winter Park! This high-and-dry homesite is ideally situated in a highly desirable area surrounded by beautiful new construction homes, including a newer community of impressive million-dollar residences directly across the street. Located in coveted Old Winter

  

  Laurie Cain

  CHARLES RUTENBERG REALTY ORLANDO

  786 W Canton Ave, Winter Park, FL 32789
• 

  

  /27

  Starting at $1,457

  Total Monthly Price

  • Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  There's 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

  Westmount at Winter Park

  

  1701 Lee Rd, Winter Park, FL 32789
• 

  /2

  $261,000

  Sold May 13, 2026

  1500 Gay Rd Unit 8D, Winter Park, FL 32789

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

  Last Sold Summary

  • 2% Below List Price
  • $254/SF
  • 19 Days On Market

  Current Estimated Value $259,669

  Last Listing Agent Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

  1500 Gay Rd Unit 8D, Winter Park, FL 32789
• 

  /2

  Est $2,775,195

  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

  • 173 Days On Market

  Last Listing Agent Shirley Jones COLDWELL BANKER REALTY

Showing Results 1 - 40, Page 1 of 18