Homes in ZIP Code 32789

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  /51

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  860 N Denning Dr, Winter Park, FL 32789

  FULLY FURNISHED | NEW CONSTRUCTION–QUALITY | WALKABLE WINTER PARK | FULL SMART HOME This is not a renovation—this is a complete architectural transformation. Taken down to the studs and roofline, expanded, and rebuilt with intention, this custom luxury residence is ideally located just steps from Winter Park Village and minutes from iconic Park Avenue, offering a truly walkable, car-optional

  LaDarrius Sanders OUTLET REALTY

  860 N Denning Dr, Winter Park, FL 32789
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  /42

  $3,295 per month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
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  /2

  $350,000 Sold Feb 12, 2025

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789

  • 1 Bed
  • 1.5 Baths
  • 726 Sq Ft
  • Built 1972

  Last Sold Summary

  • 11% Below List Price
  • $482/SF
  • 82 Days On Market

  Current Estimated Value $365,401

  Last Listing Agent Jennifer Cornette HOLT REAL ESTATE LLC

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789
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  /2

  Est $407,401 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,214 Sq Ft

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

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /75

  $3,180,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,129 Sq Ft

  151 Oakwood Way, Winter Park, FL 32789

  Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

  Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
• 

  

  /18

  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1148 Park Green Place, Winter Park, FL 32789

  Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

  Linda Baez DON ASHER & ASSOCIATES, INC.

  1148 Park Green Place, Winter Park, FL 32789
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  /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 $3,029,401

  Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
• 

  /2

  Est $561,233 Not Listed For Sale

  • 18 Beds
  • 18 Baths
  • 1,852 Sq Ft

  875 Miles Ave Unit 4, Winter Park, FL 32789

  875 Miles Ave Unit 4, Winter Park, FL 32789
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  /100

  $6,600,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,636 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 09/26/2025!! SELLER FINANCING AVAILABLE WITH VERY ATTRACTIVE TERMSIntroducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest

  Prescilla Vazquez COMPASS FLORIDA LLC

  2661 Vía Tuscany, Winter Park, FL 32789
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  /33

  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • House for Rent

  1622 Arbor Park Dr, Winter Park, FL 32789

  Offering a $500 move-in incentive if moved in by the end of February! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  1622 Arbor Park Dr, Winter Park, FL 32789
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  /2

  $799,000 Sold Apr 30, 2025

  2320 Janice Ave, Winter Park, FL 32789

  • Land
  • 0.28 Acre
  • $2,853,571 per Acre

  Last Sold Summary

  • 2 Days On Market

  Current Estimated Value $807,333

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2320 Janice Ave, Winter Park, FL 32789
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  /89

  Est $1,322,073 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
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  /30

  $698,000

  • 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!!A FULLY MODERNIZED 5-bedroom, 3-bathroom home offering Modern style, flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury vinyl plank flooring, fresh neutral paint, and large windows that fill the home with natural

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
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  /90

  $15,500 per month

  • 8 Beds
  • 6 Baths
  • 7,000 Sq Ft
  • House for Rent

  1860 Via Contessa, Winter Park, FL 32789

  Step into your dream home in Winter Park! This stunning 7,000 SF residence, nestled on a peaceful street in the coveted Viasneighborhood,offers ample space across three levels, making it an ideal choice for those who crave both room to spread out and a welcomingatmosphere.Gorgeous hardwood floors flow throughout the main living areas, enhancing the home's inviting, warm ambiance. The

  Sylvester Harding SIERRA REALTY GROUP LLC

  1860 Via Contessa, Winter Park, FL 32789
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  /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

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  /2

  Est $377,046 Not Listed For Sale

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

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

  230 Killarney Bay Ct Unit 3, Winter Park, FL 32789
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  /26

  $625,000

  • 3 Beds
  • 1.5 Baths
  • 1,485 Sq Ft

  1500 Berkshire Ave, Winter Park, FL 32789

  Welcome to this beautifully renovated historic home in the heart of Orwin Manor, one of Winter Park’s most treasured neighborhoods. Thoughtfully updated while preserving its timeless character, this 3 bedroom 1 and a half bath home blends classic architectural charm with today’s modern conveniences. Major system improvements include updated plumbing and electrical, a new roof in 2025, new HVAC in

  Lianna D'Angelo SOTERA LIVING

  1500 Berkshire Ave, Winter Park, FL 32789
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  /25

  $8,500 per month

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • House for Rent

  1530 Via Tuscany, Winter Park, FL 32789

  Newly Remodeled Pool home located on premier street in Winter Park. This 4 bedroom home has just been totally updated with very tasteful upgrades. Notable items include: new paint in and out, new flooring in foyer, kitchen, baths. All baths remodeled, new light fixtures, new pavers on rear patio and pool, new landscaping package. The kitchen features new stone counters and backsplash. Also there

  Dan Haber CORCORAN PREMIER REALTY

  1530 Via Tuscany, Winter Park, FL 32789
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  /2

  $1,640,000 Sold Mar 06, 2025

  508 W Swoope Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,133 Sq Ft
  • Built 2021

  Last Sold Summary

  • 17% Below List Price
  • $397/SF
  • 258 Days On Market

  Last Listing Agent Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

  508 W Swoope Ave, Winter Park, FL 32789
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  /44

  Est $939,250 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
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  /25

  $425,000 Pending

  • 2 Beds
  • 2 Baths
  • 760 Sq Ft

  875 W Lyman Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of

  Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

  875 W Lyman Ave, Winter Park, FL 32789
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  /15

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Apartment for Rent

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

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
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  /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

  Last Listing Agent Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

  595 Huntington Ave Unit 4, Winter Park, FL 32789
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  /43

  Est $980,146 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
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  /52

  $5,250,000

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft

  1221 Richmond Rd, Winter Park, FL 32789

  Now offered with a significant price improvement, this award-winning custom residence presents a rare opportunity in Winter Park’s sought-after Virginia Heights neighborhood, prized for its proximity to Park Avenue, placement within an A-rated school district, and deeded access to the Winter Park Chain of Lakes. Created by an award-winning builder as a personal family residence, this home

  Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

  1221 Richmond Rd, Winter Park, FL 32789
• 

  

  /15

  $2,000 per month

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave, Winter Park, FL 32789

  Charming 3-Bedroom Home for Rent in Winter Park This charming 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. The main home offers a functional and comfortable layout, ideal for everyday living. The property also includes a separate efficiency unit and a rear unit, both currently rented and featuring independent entrances, providing

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave, Winter Park, FL 32789
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  /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

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  359 Beloit Ave, Winter Park, FL 32789
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  /88

  Est $1,928,597 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
• 

  

  /86

  $3,895,000 Pending

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft

  637 N Park Ave, Winter Park, FL 32789

  A refined, custom brownstone with an exclusive Park Avenue address, offering an unparalleled Winter Park lifestyle enhanced by the finest designer selections throughout. The timeless brick elevation and expansive windows evoke the charm of a favorite city street while preserving the tranquility of this sought-after setting. This three-story townhouse offers 4,237 square feet of thoughtfully

  Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

  637 N Park Ave, Winter Park, FL 32789
• 

  

  /23

  $1,500 per month

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

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
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  /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 $1,572,177

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
• 

  

  /39

  Est $863,539 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
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  /67

  $12,900,000 Pending

  • 6 Beds
  • 9 Baths
  • 12,190 Sq Ft

  2203 Via Tuscany, Winter Park, FL 32789

  Under contract-accepting backup offers. Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2203 Via Tuscany, Winter Park, FL 32789
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  /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

  $380,000 Sold May 02, 2025

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

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $266/SF
  • 42 Days On Market

  Current Estimated Value $388,807

  Last Listing Agent Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /44

  Est $1,061,720 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
• 

  

  /11

  $630,000

  • Land
  • 0.31 Acre
  • $2,032,258 per Acre

  1860 Staunton Ave, Winter Park, FL 32789

  Large double lot in the highly desirable Killarney Shores neighborhood of Winter Park. The property has already received county approval to revert to the original platting, subdivide into two 50' x 135' lots. Located just one block from Lake Killarney. This prime location is minutes from Park Avenue, College Park, and I-4, providing both convenience and long-term value. A rare opportunity to

  Leighton Hope COMPASS FLORIDA LLC

  1860 Staunton Ave, 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

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1450 Chestnut Ave, Winter Park, FL 32789
• 

  

  /25

  Est $2,027,917 Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789
• 

  

  /27

  $127,400

  • 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

Showing Results 201 - 240, Page 6 of 18