Homes in ZIP Code 32789

• 

  

  

  /77

  $2,900,000 Open Sun 10AM - 3PM

  • 4 Beds
  • 7 Baths
  • 5,416 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was crafted with care.The heart of

  Terry Yonker BUCKEYE REALTY LLC

  1401 Green Cove Rd, Winter Park, FL 32789
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Get Started
• 

  

  

  /42

  $1,482 - $2,124 per month

  Westmount at Winter Park

  Studio-3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Westmount at Winter Park has everything you desire and more in prestigious Winter Park. Enjoy access to I-4, shopping and the best restaurants around!

  1701 Lee Rd, Winter Park, FL 32789
• 

  

  /2

  $916,000 Sold Jul 17, 2025

  • 1,981 Sq Ft
  • $462/SF
  • 8 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1960

  609 Langholm Dr, Winter Park, FL 32789

  Nestled in the heart of Winter Park in one of the area’s most sought-after neighborhoods, this professionally designed and fully renovated 3-bedroom, 2.5-bathroom home offers luxurious living with timeless modern style.Step inside to an open-concept layout featuring a gourmet kitchen outfitted with custom cabinetry, stunning quartz countertops, GE Cafe appliances, a Thermador drawer-style

  Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
• 

  

  

  /60

  Est $1,675,376 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft

  1318 Chapman Cir, Winter Park, FL 32789

  1318 Chapman Cir, Winter Park, FL 32789
• 

  

  

  /66

  $1,249,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,993 Sq Ft

  2525 Venetian Way, Winter Park, FL 32789

  Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake AccessThis meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace.The sleek, chef-inspired

  Kimberly Slinger KELLY PRICE & COMPANY LLC

  2525 Venetian Way, Winter Park, FL 32789
• 

  

  /37

  $3,400 per month

  • 3 Beds
  • 2.5 Baths
  • 1,798 Sq Ft
  • Townhouse for Rent

  1273 Michigan Ave, Winter Park, FL 32789

  **Luxury Townhomes for Lease in the Heart of Winter Park!**Experience upscale living in this stunning townhome community crafted by award-winning Osprey Custom Home Builders. These **3-bedroom, 2.5-bath Florida Green Certified Homes** offer an open-concept layout with high-end designer finishes throughout.The first floor features spacious living and dining areas and a gourmet kitchen

  Miranda Azer PARKVIEW REAL ESTATE

  1273 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $1,335,000 Sold Jul 15, 2025

  • 3,046 Sq Ft
  • $438/SF
  • 75 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2025

  1077 Minnesota Ave, Winter Park, FL 32789

  Under Construction. New Construction in the Heart of Winter Park by Nautilus Homes - Introducing an exceptional opportunity to own a brand-new luxury residence by award-winning builder Nautilus Homes, ideally situated between Orlando Avenue and Orange Avenue—just moments from Winter Park’s renowned shops, dining, and cultural attractions.This thoughtfully designed 4-bedroom, 4-bath estate

  Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
• 

  

  /14

  Est $595,255 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789
• 

  

  /37

  $950,000

  • 3 Beds
  • 3.5 Baths
  • 2,116 Sq Ft

  1251 Arlington Place, Winter Park, FL 32789

  STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

  Brad Barnett ANNE ROGERS REALTY GROUP INC

  1251 Arlington Place, Winter Park, FL 32789
• 

  

  /50

  $1,765 - $3,399 per month

  Seven41 Winter Park

  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.

  741 Clay St, Winter Park, FL 32789
• 

  /2

  $1,400,000 Sold Jul 15, 2025

  • 2,637 Sq Ft
  • $531/SF
  • 91 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1960

  1750 Winchester Dr, Winter Park, FL 32789

  Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timberlane Shores. The heart of this home is a chef's dream kitchen, featuring a professional WOLF range, custom two-tone cabinetry in rich wood and sophisticated navy blue, and premium stone countertops that extend to a generous entertainment island. Gleaming terrazzo floors flow

  Michael Ford FANNIE HILLMAN & ASSOCIATES

  1750 Winchester Dr, Winter Park, FL 32789
• 

  

  /24

  Est $876,877 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
• 

  

  /48

  $2,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft

  1560 Woodland Ave, Winter Park, FL 32789

  You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool and relaxing spa. A separate suite with its own entrance is available for use by the mother-in-law

  Manny Alvarez LOKATION

  1560 Woodland Ave, Winter Park, FL 32789
• 

  

  /17

  $2,999 per month

  • 3 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • House for Rent

  101 S Lakemont Ave, Winter Park, FL 32792

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom single-family home, perfectly positioned just minutes away from shopping, dining, and all the charm of Winter Park. This home combines modern luxury with everyday convenience. As you step inside, you're greeted by the elegance of Calacatta Quartz countertops, sleek waterproof flooring, and top-of-the-line appliances that set the tone for

  Robert Isaac Rodriguez RE/MAX DOWNTOWN

  101 S Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $1,050,000 Sold Jul 14, 2025

  • 2,374 Sq Ft
  • $442/SF
  • 23 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2017

  795 W Canton Ave, Winter Park, FL 32789

  Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and Winter Park Village, this stunning modern Craftsman by David Weekley Homes perfectly blends luxury, comfort, and convenience.The thoughtfully designed floor plan features a downstairs primary suite, rich hardwood flooring, and sliding barn doors opening to a versatile

  Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

  795 W Canton Ave, Winter Park, FL 32789
• 

  

  /22

  Est $5,806,670 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789
• 

  

  /59

  $1,575,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  690 Osceola Ave Unit 604, Winter Park, FL 32789

  Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

  Larry Slung COLDWELL BANKER RESIDENTIAL RE

  690 Osceola Ave Unit 604, Winter Park, FL 32789
• 

  

  /39

  $1,625 - $1,895 per month

  The Lofts of Winter Park Village

  1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  520 N Orlando Ave, Winter Park, FL 32789
• 

  /2

  $2,435,000 Sold Jul 14, 2025

  • 3,852 Sq Ft
  • $632/SF
  • 31 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2019

  1795 Greenwich Ave, Winter Park, FL 32789

  Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful functionality, and resort-style amenities. Designed by Origins Residential Design and meticulously constructed by Native Homes, this 5-bedroom, 5.5-bathroom showplace is located in one of Winter Park’s most sought-after neighborhoods—just minutes from Park Avenue, Baldwin Park,

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  1795 Greenwich Ave, Winter Park, FL 32789
• 

  

  /42

  Est $686,002 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789
• 

  

  /28

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue! Discover the perfect blend of luxury, comfort, and convenience with this immaculate, move-in-ready condo, in the heart of Winter Park. Recently transformed with meticulous attention to detail, this lock-and-leave gem boasts an elegant, high-end renovation that exudes

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
• 

  

  /32

  $3,200 per month

  • 3 Beds
  • 2 Baths
  • 1,732 Sq Ft
  • House for Rent

  1816 Mizell Ave, Winter Park, FL 32789

  Welcome to this charming 3-bedroom, 2-bath home in the heart of Winter Park, complete with a 1-car garage and unbeatable location. Just minutes from Park Avenue, Winter Park Hospital, top-rated shopping, and dining, convenience is at your doorstep. Start your mornings with peaceful strolls through the beautiful Windsong neighborhood and take in the serene views of Lake Mizell. Whether you're

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  1816 Mizell Ave, Winter Park, FL 32789
• 

  /2

  $1,942,000 Sold Jul 14, 2025

  • 3,907 Sq Ft
  • $497/SF
  • 50 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1961

  1394 Stewart St, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Five-bedroom, 3900+ sq ft pool home with 3 car garage on a large corner lot in the sought -after Park Grove neighborhood near Lake Maitland and Park Avenue. Great Room consists of a Family Room area with a wood-burning fireplace and tray ceilings and a Sun Room area with bay windows and french doors overlooking the pool deck. Kitchen

  Richard Vaughn REALTY ONE GROUP INSPIRATION

  1394 Stewart St, Winter Park, FL 32789
• 

  

  /30

  Est $746,963 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789
• 

  

  /31

  $1,490,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,838 Sq Ft

  2408 Lafayette Ave, Winter Park, FL 32789

  This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
• 

  

  /35

  $1,500 - $2,750 per month

  Hannibal Square

  Studio-2 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,

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

  /2

  $5,400,000 Sold Jul 14, 2025

  • 4,725 Sq Ft
  • $1143/SF
  • 152 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2008

  541 Virginia Dr, Winter Park, FL 32789

  *Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home.Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers

  Keith Moore HOMEVEST REALTY

  541 Virginia Dr, Winter Park, FL 32789
• 

  

  /63

  Est $3,617,953 Not Listed For Sale

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

  637 N Park Ave, Winter Park, FL 32789

  637 N Park Ave, Winter Park, FL 32789
• 

  

  /25

  $349,000 Pending

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

  657 Overspin Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing

  Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789
• 

  

  /18

  $3,600 per month

  • 4 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • House for Rent

  1846 Barker Dr, Winter Park, FL 32789

  Welcome to 1846 Barker Dr- a charming and well maintained single family home located in one of Winter Park's most desirable neighborhoods. This inviting 4- bedrooms, -2 bath residence offers a perfect blend of comfort and convenience, just minutes from top-rated schools, beautiful parks, shopping, dining and all amenities of the sought-after Winter Park-Baldwin Park lifestyle. Enjoy a bright and

  Cliff Glansen FLATFEE.COM

  1846 Barker Dr, Winter Park, FL 32789
• 

  /2

  $385,000 Sold Jul 12, 2025

  • 1,000 Sq Ft
  • $385/SF
  • 355 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  151 N Orlando Ave Unit 131, Winter Park, FL 32789

  FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability).

  Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 131, Winter Park, FL 32789
• 

  

  /30

  Est $1,440,169 Not Listed For Sale

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

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789
• 

  

  /61

  $487,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft

  1545 Indiana Ave Unit B, Winter Park, FL 32789

  Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and

  Ron Murray MAGIC REALTY LLC

  1545 Indiana Ave Unit B, Winter Park, FL 32789
• 

  

  /15

  $2,950 per month

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • House for Rent

  779 W Lyman Ave, Winter Park, FL 32789

  Charming 3BR/2BA Home in the Heart of Winter Park – Walk to Park Ave & Hannibal Square!Rent: $2,950/monthAvailable: 8/1/2025Location: Winter Park, FL 32789Discover this cozy and well-maintained 3-bedroom, 2-bathroom home nestled in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue and Hannibal Square, you'll enjoy premier shopping,

  779 W Lyman Ave, Winter Park, FL 32789
• 

  /2

  $420,000 Sold Jul 11, 2025

  • 1,140 Sq Ft
  • $368/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  2809 Sanbina St, Winter Park, FL 32789

  Beautifully Updated 3 Bedroom, 2 Bath Pool Home in Desirable Winter Park! Welcome to your dream home! This spacious one story gem features 3 bedrooms, 2 full baths, and a private POOL, perfect for enjoying Florida living year round. Step inside to find brand NEW LUXURY VINYL PLANK flooring and FRESH INTERIOR PAINT throughout, giving the home a modern and move-in ready feel. The open layout offers

  Harry Kazarian STRONG FOUNDATION REALTY LLC

  2809 Sanbina St, Winter Park, FL 32789
• 

  

  /38

  Est $3,271,487 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  140 E Morse Blvd Unit G, Winter Park, FL 32789
• 

  

  /50

  $790,000

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft

  438 W Swoope Ave, Winter Park, FL 32789

  Located within the private enclave of 400 West—an exclusive 9-residence community just steps from Park Avenue—this contemporary townhome offers a rare blend of quality construction, refined interiors & exceptional walkability. From the moment you step inside—whether through the private garage or along the garden-style front path—you’re met with a bright open-concept main floor that blends

  Padgett McCormick KELLY PRICE & COMPANY LLC

  438 W Swoope Ave, Winter Park, FL 32789
• 

  

  /43

  $9,995 per month

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • House for Rent

  2020 Venetian Way, Winter Park, FL 32789

  This RARE LAKEFRONT retreat is located on a quiet, tree-lined street in the highly sought-after Vias of Winter Park. Custom-built and elevated on a prime lot with 90 feet of frontage on Lake Maitland, this one-of-a-kind mid-century home offers sweeping views of Lake Maitland and the Isle of Sicily. It combines timeless design, complete privacy, and a premier location just minutes from Park Avenue

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  2020 Venetian Way, Winter Park, FL 32789
• 

  /2

  $675,000 Sold Jul 10, 2025

  • 1,275 Sq Ft
  • $529/SF
  • 1 Day On Market

  • 2 Beds
  • 2 Baths
  • Built 1960

  1511 Chestnut Ave, Winter Park, FL 32789

  Attention builders and investors! Here’s your chance to own a prime property in the coveted Tree Streets of Winter Park, one of Central Florida’s most desirable neighborhoods. Whether you’re looking for immediate rental income or planning to build your dream home in the future, this opportunity is not to be missed!Tucked away just minutes from Phelps Park, the Winter Park YMCA, Lake

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
• 

  

  /30

  Est $1,597,911 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

  311 E Morse Blvd Unit 1-1, Winter Park, FL 32789

Showing Results 41 - 80, Page 2 of 18