Winter Park, FL Homes

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  /41

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,263 Sq Ft

  5331 Oak Ct, Winter Park, FL 32792

  Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

  Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

  5331 Oak Ct, Winter Park, FL 32792
• 

  

  

  /23

  $1,909 - $6,983 per month

  Juno Winter Park

  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,

  1305 Morgan Stanley Ave, 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
• 

  

  

  /36

  $535,000

  • 4 Beds
  • 2.5 Baths
  • 1,811 Sq Ft

  1819 Shadyhill Terrace, Winter Park, FL 32792

  Welcome to your own private retreat, perfectly situated at the end of a quiet cul-de-sac on one of the most scenic lots in the neighborhood. This beautiful home sits on a gorgeous, oversized lot with unobstructed pond views and is framed by mature trees, creating a natural canopy that offers both beauty and privacy. Whether you're sipping your morning coffee or winding down in the evening, the

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  1819 Shadyhill Terrace, Winter Park, FL 32792
• 

  

  /43

  $14,000 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

  $125,000 Sold Jul 14, 2025

  • 802 Sq Ft
  • $156/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1983

  7344 Swallow Run Unit 7344, Winter Park, FL 32792

  Step into this beautiful 2-bedroom, 2-bathroom condo, freshly painted and filled with natural light throughout. The open-concept floor plan is perfect for entertaining, while the split-bedroom layout ensures added privacy for residents or guests.The primary suite features a walk-in shower, ample storage, and a private en-suite bath. Enjoy serene views of lush green space and located in

  Merigan Barton DON HARKINS REALTY LLC

  7344 Swallow Run Unit 7344, Winter Park, FL 32792
• 

  

  /40

  Est $283,662 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792
• 

  

  /33

  $450,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  1471 Broad Wing Ln, Winter Park, FL 32792

  Step into comfort and style in this beautifully maintained townhome, built in 2020 and thoughtfully designed for modern living. The open-concept layout features granite countertops, sleek finishes, and an oversized, screened-in lanai that opens to a tranquil wooded backdrop—ideal for unwinding or entertaining. Upstairs, you'll find all the bedrooms, a spacious loft perfect for a home office or

  Kathryn West EXP REALTY LLC

  1471 Broad Wing Ln, Winter Park, FL 32792
• 

  

  /50

  $1,428 - $3,130 per month

  ARIUM Winter Park

  1-2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
• 

  /2

  $290,000 Sold Jul 14, 2025

  • 1,020 Sq Ft
  • $284/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1977

  2541 Leeward Way, Winter Park, FL 32792

  Discover One of Winter Park’s Best-Kept Secrets — Windward Square!Welcome to your beautifully renovated 2-bedroom, 2-bath townhome in the highly sought-after Windward Square community. This move-in ready home boasts a bright, open floor plan, with a modern kitchen that flows effortlessly into the spacious living area.The fully updated kitchen features brand-new stainless steel

  Jason Howell REAL BROKER, LLC

  2541 Leeward Way, Winter Park, FL 32792
• 

  

  /28

  Est $339,279 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  4870 Seminole Ave, Winter Park, FL 32792

  4870 Seminole Ave, Winter Park, FL 32792
• 

  

  /49

  $649,900 Open Sat 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1926 Natalen Rd, Winter Park, FL 32792

  *** MUST SEE WINTER PARK POOL HOME ***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing

  Peggy Bonnewitz EXP REALTY LLC

  1926 Natalen Rd, Winter Park, FL 32792
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  /11

  $2,300 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Townhouse for Rent

  5101 N Orange Ave Unit A, Winter Park, FL 32792

  A beautifully renovated 3 bedroom home with your own private, fully fenced yard in Winter Park. This location is conveniently located near shopping, dining, entertainment and more. Private parking area in front of the duplex.

  Shannon Cruz Acosta CITARELLI REALTY GROUP LLC

  5101 N Orange Ave Unit A, Winter Park, FL 32792
• 

  /2

  $365,000 Sold Jul 14, 2025

  • 1,368 Sq Ft
  • $267/SF
  • 22 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1987

  1748 Harvest Cove, Winter Park, FL 32792

  Tucked away in a quiet Winter Park cul-de-sac, this 3-bedroom, 2-bathroom home sits in one of the area’s most convenient spots with low taxes, low HOA, and access to top-rated schools.The layout flows well, with updated bathrooms, an enclosed porch for extra living space, and a backyard that’s great for entertaining. There’s even a partial pond view that adds a little extra charm. Whether

  Matt Anderson EXP REALTY LLC

  1748 Harvest Cove, Winter Park, FL 32792
• 

  

  /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
• 

  

  /54

  $3,544,999 Open Sat 11AM - 1PM

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /12

  $1,289 - $4,416 per month

  Liv at Winter Park Apartment Homes

  Studio-3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  /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
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  /32

  Est $229,842 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft

  200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792
• 

  

  /80

  $1,210,000

  • 4 Beds
  • 3.5 Baths
  • 3,321 Sq Ft

  4048 Gilder Rose Place, Winter Park, FL 32792

  Welcome to 4048 Gilder Rose Pl, an impressive four-bedroom, three and a half bathroom residence spanning over 3,300 square feet, located in Winter Park at Bear Gully Pointe, a gated community featuring a spring fed 137 acre lake. This beautifully updated home perfectly balances modern style with practical living, offering an inviting retreat for those seeking both comfort, sophistication and

  Abby Greenberg COMPASS FLORIDA LLC

  4048 Gilder Rose Place, Winter Park, FL 32792
• 

  

  /13

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • House for Rent

  689 Overspin Dr, Winter Park, FL 32789

  Welcome to 689 Overspin Rd – a beautifully maintained 2-bedroom, 2-bathroom home in the heart of Winter Park! This inviting residence features stunning hardwood floors throughout, creating a warm and stylish ambiance from the moment you walk in. Enjoy cooking and entertaining in the large open kitchen, complete with stainless steel appliances, ample counter space, and plenty of storage. Cozy up

  Megan Teal MAINFRAME REAL ESTATE

  689 Overspin Dr, 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
• 

  

  /66

  $1,249,000

  • 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
• 

  

  /50

  $1,477 - $1,998 per month

  Calibre Bend Apartments

  1-2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  3924 Calibre Bend Ln, Winter Park, FL 32792
• 

  /2

  $705,000 Sold Jul 14, 2025

  • 2,385 Sq Ft
  • $296/SF
  • 57 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1139 Fairway Dr, Winter Park, FL 32792

  NEW LOWER PRICE 6/3/25, OWNER WANTS OFFERS. NO HOA. Fabulous RENOVATED home in the heart of Winter Park, where timeless charm meets tranquil Winter Park Pines golf course living. Nestled on a lush, manicured lot right on the 9th fairway, this expansive REMODELLED OPEN AND AIRY SPLIT-plan residence offers a SPLIT PLAN WITH 4 generously sized bedrooms, 2 full baths, and FABULOUS FLEX SPACE that

  Gale Milgrim KELLER WILLIAMS WINTER PARK

  1139 Fairway Dr, Winter Park, FL 32792
• 

  

  /20

  Est $267,652 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  5498 Peaco Place, Winter Park, FL 32792

  5498 Peaco Place, Winter Park, FL 32792
• 

  

  /37

  $950,000 Open Sun 12PM - 2PM

  • 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
• 

  

  /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

  $1,942,000 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
• 

  

  /85

  $1,590,000

  • 5 Beds
  • 4.5 Baths
  • 5,329 Sq Ft

  8041 Lake Waunatta Dr, Winter Park, FL 32792

  Modern Lakefront Dream home NOW AVAILABLE! Nestled in the peaceful Lake Waunatta Woods neighborhood, this stunning renovated lakefront estate seamlessly blends modern style with effortless luxury. With over 5,300 square feet, five spacious bedrooms, and breathtaking panoramic views of Lake Waunatta from nearly every room, this one-of-a-kind property offers the ultimate waterfront lifestyle.

  Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

  8041 Lake Waunatta Dr, Winter Park, FL 32792
• 

  

  /36

  $1,216 - $3,210 per month

  Summerlin at Winter Park Apartments

  1-3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
• 

  /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
• 

  

  /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
• 

  

  /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

  $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
• 

  

  /37

  Est $831,225 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,044 Sq Ft

  1361 Heavenly Cove, Winter Park, FL 32792

  1361 Heavenly Cove, Winter Park, FL 32792

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