Winter Park, FL Homes

• 

  

  

  /28

  $320,000 Open Sun 11AM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792

  FIRST-FLOOR LIVING WITH DIRECT WATER VIEWS AND AN UNBEATABLE LOCATION! Located in one of Winter Park’s most convenient and cared-for communities, The Gallery at Winter Park. This 2-bedroom, 2-bath condo showcases a beautifully updated kitchen and refreshed bathrooms. Contemporary luxury vinyl floors extend across the bedrooms and living areas for a clean, cohesive look. The primary suite is at

  Maria Elena Perez MEP REALTY INVESTMENTS LLC

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792
• 

  

  

  /16

  $2,330 per month

  • 3 Beds
  • 2 Baths
  • 1,633 Sq Ft
  • House for Rent

  5139 Ardmore Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2474.90. That covers your base rent, $2330.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5139 Ardmore Dr, Winter Park, FL 32792
• 

  

  /2

  $646,000 Sold Aug 12, 2025

  • 1,618 Sq Ft
  • $399/SF
  • 58 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1938

  2711 Parkland Dr, Winter Park, FL 32789

  Welcome to this delightful 1,600 sqft home in one of Winter Park's most coveted neighborhoods. This three-bedroom, two-bathroom home blends classic charm with modern updates. Roof replaced 2023,A/C replaced 2021, double pane windows installed 2020. The beautifully updated kitchen features newer appliances and opens to a cozy living area with a character-rich wood-burning fireplace. The versatile

  Greg Martinez CORCORAN PREMIER REALTY

  2711 Parkland Dr, Winter Park, FL 32789
• 

  

  

  /25

  Est $2,027,218 Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789
• 

  

  

  /25

  $195,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 232, Winter Park, FL 32789

  Just steps from the shore of Lake Killarney, welcome to Lake Killarney Living! This charming 1-bedroom, 1-bath end-unit condo offers lake access to the beautiful Winter Park Chain of Lakes along with partial lake views. Enjoy community amenities including a lakefront pool and clubhouse with stunning views, plus a private boat ramp to launch your boat and explore the water. The serene central

  Wendy Rodriguez COLDWELL BANKER RESIDENTIAL RE

  2500 Lee Rd Unit 232, Winter Park, FL 32789
• 

  

  /16

  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft
  • House for Rent

  430 Ololu Dr, Winter Park, FL 32789

  Interested in trying out the lake life in Winter Park? 430 Ololu is available FOR RENT beginning October 1st on Lake Killarney! This 2 bedroom, 1 bath home has a brand new metal roof, a newly renovated kitchen with new appliances, a newer washer and dryer, and a DREAM backyard with views of and private access to Lake Killarney. Bring your kayak, jet ski, boat, or even a seaplane and make your way

  Ellen Hencken MILLER GRANT AND COMPANY

  430 Ololu Dr, Winter Park, FL 32789
• 

  /2

  $185,000 Sold Aug 12, 2025

  • 1,018 Sq Ft
  • $182/SF
  • 331 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  3043 Antique Oaks Cir Unit 171, Winter Park, FL 32792

  Stop The Car!!! Here it is!!! A fantastic ground floor 2/2 condominium with pool view; in sought after Winter Park, Florida. This lovely home is conveniently located near fine dining, shopping, Baldwin Park, and amazing schools: Full Sail University, UCF, and Rollins College. Your future home offers an open floor plan with a kitchen looking out to the family room. Your fantastic kitchen is set up

  Mikhael Najm DALTON WADE INC

  3043 Antique Oaks Cir Unit 171, Winter Park, FL 32792
• 

  

  /25

  Est $382,573 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7494 Aloma Pines Ct, Winter Park, FL 32792

  7494 Aloma Pines Ct, Winter Park, FL 32792
• 

  

  /56

  $1,195,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft

  215 Salvador Square, Winter Park, FL 32789

  Welcome home to this lovely four-bedroom, three-and-a-half-bath pool home in the prestigious Sevilla neighborhood of Winter Park! Tucked off a charming brick-lined street just 1⁄4 mile from Park Avenue, this .40-acre property offers both privacy and convenience to your Winter Park lifestyle. Inside, you’ll find timeless details such as marble and parquet flooring, crown molding, plantation

  Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
• 

  

  /6

  $1,860 per month

  • 3 Beds
  • 2 Baths
  • 1,030 Sq Ft
  • House for Rent

  123 Oak Grove Rd, Winter Park, FL 32789

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2004.90. That covers your base rent, $1860.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  123 Oak Grove Rd, Winter Park, FL 32789
• 

  /2

  $630,000 Sold Aug 11, 2025

  • 2,264 Sq Ft
  • $278/SF
  • 1 Day On Market

  • 4 Beds
  • 3 Baths
  • Built 1958

  1792 Killarney Dr, Winter Park, FL 32789

  RENOVATED and MOVE-IN READY in WINTER PARK 32789 with DEEDED LAKE ACCESS! Located on a fully fenced 1⁄4-acre corner lot, this 4-bed, 3-bath charmer offers private access to Lake Killarney, a rare find. Step onto the welcoming front porch and into a home filled with character, upgrades, and natural light. The open layout flows effortlessly through spacious living areas and a beautifully updated

  Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789
• 

  

  /7

  Est $92,645 Not Listed For Sale

  • Studio
  • 1 Bath
  • 590 Sq Ft

  7309 Daniel Webster Dr Unit B, Winter Park, FL 32792

  7309 Daniel Webster Dr Unit B, Winter Park, FL 32792
• 

  

  /22

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet modern updates. Just minutes from Park Avenue and Winter Park Village, this 3-bedroom, 2-bath residence offers a lifestyle surrounded by boutique shopping, dining, and cultural experiences.Inside, rich wood flooring, natural light, and thoughtful touches create a warm and

  Brian Hyser THE AGENCY ORLANDO

  720 W Webster Ave, Winter Park, FL 32789
• 

  

  /20

  $1,500 per month

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

  2500 Lee Rd Unit 235, Winter Park, FL 32789

  Comfort and recreation in this charming 2-bedroom, 1-bathroom condo. Located in a sought-after lakefront community on Lake Killarney, you'll enjoy 851 sq. ft. of modern living with stainless steel appliances, wood laminate flooring, and a new, efficient AC. Enjoy the convenience of being less than a mile from I-4 while maintaining the tranquility of a quiet, safe neighborhood. Step outside and

  Laura Heredia NEW HEIGHTS REALTY GROUP

  2500 Lee Rd Unit 235, Winter Park, FL 32789
• 

  /2

  $245,900 Sold Aug 11, 2025

  • 1,132 Sq Ft
  • $217/SF
  • 2 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1986

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  Your Dream Home Awaits in Winter Park! 3 Beds 3.5 baths! Discover the perfect blend of comfort and convenience in the heart of Winter Park at Sandlewood Creek! This charming townhome-style condo offers a rare opportunity to own a piece of paradise with no neighbors above or below, ensuring a peaceful living environment. Plus, enjoy a very low HOA! Key Features: Financing Made Easy: FHA, VA, and

  Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
• 

  

  /36

  Est $1,418,180 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,950 Sq Ft

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  1405 Chapman Cir Unit OR, Winter Park, FL 32789
• 

  

  /52

  $700,000 Open Sun 1AM - 3PM

  • 4 Beds
  • 2 Baths
  • 2,372 Sq Ft

  1729 Golfside Dr, Winter Park, FL 32792

  Golfside living, beautifully reimagined. From the moment you step inside, your eyes are drawn to serene water and golf course views — a daily reminder of why this address is so special.This 4-bedroom, 2-bath retreat in Winter Park Pines marries timeless charm with thoughtful modern updates — from the warmth of a wood-burning fireplace to a dream kitchen dressed in quartz, honeycomb tile,

  Rebecca Bininger Junod KELLER WILLIAMS WINTER PARK

  1729 Golfside Dr, Winter Park, FL 32792
• 

  

  /20

  $1,795 per month

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Condo for Rent

  2667 Rook Cove Unit 2667 Rook Cove, Winter Park, FL 32792

  Property Id: 1997988Newly Remodeled Home in the Heart of Winter Park! - 2667 Rook Cove, Winter Park, FLWelcome to this stunning 2-bedroom, 1.5-bathroom home, nestled in a quiet cul-de-sac in the highly sought-after Winter Park area. Just remodeled, this unit features a brand-new kitchen with modern shaker-style cabinets, sparkling white granite countertops, and all-new stainless

  2667 Rook Cove Unit 2667 Rook Cove, Winter Park, FL 32792
• 

  /2

  $279,000 Sold Aug 11, 2025

  • 1,186 Sq Ft
  • $235/SF
  • 4 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1981

  Unlisted Address

  Step into refined living in this beautifully remodeled two-story condo, tucked within the charming Lazy Oaks community of Winter Park. Just over 1,200 sq ft, this 2-bedroom, 2.5-bath home offers tasteful updates, modern finishes, and effortless comfort—minutes from everything.The main floor features a spacious open layout with tiled flooring, combining kitchen, dining, and living areas.

  Adriana Gonzalez PERFECT INVESTMENT REALTY

  Unlisted Address
• 

  

  /33

  Est $435,406 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2003 Canny Cove, Winter Park, FL 32792

  2003 Canny Cove, Winter Park, FL 32792
• 

  

  /25

  $349,900

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-a-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
• 

  

  /64

  $4,750 per month

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • House for Rent

  1368 Blue Stem Ln, Winter Park, FL 32792

  Available December 1st, 2025 - Distinctive, private, unique and full of character is what sets this estate apart from all other properties on the market. Welcome home to your freshly built and highly updated Anastasia plan in the fabulous newer Winter Park community of Hawk's Crest. Located only minutes from the iconic and historic Winter Park Avenue with plentiful shopping, amazing venues, epic

  Stephen Downes ECO LUXE REALTY

  1368 Blue Stem Ln, Winter Park, FL 32792
• 

  /2

  $357,000 Sold Aug 11, 2025

  • 1,628 Sq Ft
  • $219/SF
  • 30 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2003

  2548 Galliano Cir, Winter Park, FL 32792

  Charming Townhome with Modern Comforts! Step into comfort and convenience in this beautifully designed 3 bedroom 2 and 1/2 bath townhome. Perfectly suited for families, professionals or anyone seeking a stylish and low maintenance lifestyle. This END UNIT brings in a ton of natural light along with a thoughtful and spacious open floor plan. The main level features an open-concept living and

  Michelle Terry SYNCHRONICITY REAL ESTATE SOLUTIONS

  2548 Galliano Cir, Winter Park, FL 32792
• 

  

  /55

  Est $1,064,403 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1772 Mondrian Cir, Winter Park, FL 32789

  1772 Mondrian Cir, Winter Park, FL 32789
• 

  

  /24

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,222 Sq Ft

  1001 Early Ave, Winter Park, FL 32789

  Welcome to 1001 Early Ave—a beautifully updated 2-bedroom, 1-bath home that perfectly balances timeless character with contemporary style. Nestled on a spacious 7,405 sq ft lot, this 1,222 sq ft gem invites you in with parquet floors, decorator tile, and abundant natural light. The expanded kitchen is a showstopper, featuring stainless steel appliances, granite countertops, a wine cooler, and

  John Neusaenger COLDWELL BANKER REALTY

  1001 Early Ave, Winter Park, FL 32789
• 

  

  /15

  $2,120 per month

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft
  • House for Rent

  5191 Poinsetta Ave, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  5191 Poinsetta Ave, Winter Park, FL 32792
• 

  /2

  $610,000 Sold Aug 11, 2025

  • 1,232 Sq Ft
  • $495/SF
  • 67 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  843 W Swoope Ave, Winter Park, FL 32789

  Winter Park Beauty located just blocks from the renowned Park Avenue. You will be impressed upon entering the front door of this Recently and Fully Updated 3 Bedroom, 2 Bathroom home while noticing the Open Floor Plan highlighted by gorgeous Porcelain Wood Plank Tile throughout. The expansive windows and contemporary color scheme create a bright and airy atmosphere. The updated kitchen and

  Jean Chalifour COLDWELL BANKER RESIDENTIAL RE

  843 W Swoope Ave, Winter Park, FL 32789
• 

  

  /19

  Est $239,502 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792
• 

  

  /23

  $318,000

  • 2 Beds
  • 2 Baths
  • 1,457 Sq Ft

  2458 Grand Teton Cir, Winter Park, FL 32792

  Welcome to your dream home in Winter Park! This beautifully updated, spacious two-bedroom condo is nestled in the highly sought-after Cedarwood Village Condominium, a well-maintained community known for its charm and appeal. Meticulously cared for, this residence boasts modern elegance with gleaming quartz countertops and premium flooring throughout. The master suite is a true retreat, featuring

  Bryce Jones CHARLES RUTENBERG REALTY ORLANDO

  2458 Grand Teton Cir, Winter Park, FL 32792
• 

  

  /17

  $2,295 per month

  • 3 Beds
  • 2 Baths
  • 1,526 Sq Ft
  • House for Rent

  731 Bongart Rd, Winter Park, FL 32792

  This 3 bedroom, 2 bath pool home with 2 car garage includes: Living Room, Dining Room, Family Room, Carpet & Vinyl on a nice corner lot! Great Location! Pool service is included with monthly rent!. *Bonus Amenity Included* - All RE/MAX 200 Realty Property Management Division residents are enrolled in the Resident Benefits Package (RBP) for $49.95/month which includes liability insurance, credit

  Mo Jabr RE/MAX 200 REALTY

  731 Bongart Rd, Winter Park, FL 32792
• 

  /2

  $200,000 Sold Aug 08, 2025

  • 1,281 Sq Ft
  • $156/SF
  • 4 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1973

  4786 Tangerine Ave Unit 4786, Winter Park, FL 32792

  Welcome to this beautifully upgraded 2-bedroom, 2-bathroom condo—an unbeatable value in sought-after Winter Park! Step inside to find ceramic tile flooring throughout, stylish lighting, and an open-concept living/dining area perfect for relaxing or entertaining. Enjoy the Florida lifestyle on your private screened-in porch overlooking a serene green space—with an extra storage closet for added

  John Muccigrosso RE/MAX 200 REALTY

  4786 Tangerine Ave Unit 4786, Winter Park, FL 32792
• 

  

  /43

  Est $780,586 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7984 Pleasant Pine Cir, Winter Park, FL 32792

  7984 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /3

  $1,700,000

  • Land
  • 0.3 Acre
  • $5,666,667 per Acre

  1181 Via Capri, Winter Park, FL 32789

  Arguably one of the top streets in Winter Park, this Via Capri lot is level, lovely, and large.Phil Kean has designed a lovely home for the property, but for those that might be looking for something somewhat different PKDG would be happy to design and build a home to your specifications, or simply sell the property as is.

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  1181 Via Capri, Winter Park, FL 32789
• 

  

  /17

  $2,630 per month

  • 3 Beds
  • 2.5 Baths
  • 2,378 Sq Ft
  • House for Rent

  1427 Broad Wing Ln, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2689.90. That covers your base rent, $2630.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Smart

  1427 Broad Wing Ln, Winter Park, FL 32792
• 

  /2

  $255,000 Sold Aug 08, 2025

  • 1,080 Sq Ft
  • $236/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  3005 Casselwood St, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Freshly updated and ready for easy living, this concrete-block villa delivers three bedrooms, including a versatile flex room, plus two full baths across a smart 1,080-square-foot, single-story layout. The curb appeal pops thanks to 2023 exterior paint, a brand-new roof (2023), and a privacy fence (2023) that frames the fully fenced backyard. Step

  Jason Ricks COLDWELL BANKER REALTY

  3005 Casselwood St, Winter Park, FL 32792
• 

  

  /40

  Est $805,326 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,706 Sq Ft

  2035 Soaring Oak Way, Winter Park, FL 32792

  2035 Soaring Oak Way, Winter Park, FL 32792
• 

  

  /19

  $389,000

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

  3117 Shady Pine Ave, Winter Park, FL 32792

  Impeccably maintained and extensively updated, this 3-bedroom, 2-bath home is located in a quiet, established Winter Park neighborhood with no HOA. Recent improvements include brand-new luxury vinyl plank flooring throughout (August 2025), fresh interior paint, a fully remodeled guest bathroom (2024), updated kitchen accessories, and a paver driveway added in 2021. Major systems have been

  Alistair Baxter EXP REALTY LLC

  3117 Shady Pine Ave, Winter Park, FL 32792
• 

  

  /29

  $2,550 per month

  • 4 Beds
  • 2.5 Baths
  • 1,701 Sq Ft
  • House for Rent

  2886 Carew Ave, Winter Park, FL 32789

  What a location! Available now for rent! Close to downtown Orlando! This charming home has 4 bedrooms, 2.5 baths, gorgeous wood flooring, family room with fireplace, one car garage, all appliances included! Fenced back yard! Schedule your private tour today!

  Chris Watts THE TEAM REAL ESTATE GROUP INC

  2886 Carew Ave, Winter Park, FL 32789
• 

  /2

  $430,000 Sold Aug 08, 2025

  • 2,130 Sq Ft
  • $202/SF
  • 7 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1974

  1006 Bradford Dr, Winter Park, FL 32792

  Winter Park delight. Discover the potential of this wonderful, spacious Seminole County residence nestled in a well-established neighborhood. Amazing split floor plan with tons of potential. Picture creating your ideal kitchen, updating the bathrooms to your taste and opening up the living spaces to create a more contemporary flow. Gorgeous backyard oasis pool with pavers and waterfall. Fresh

  Paul Giannotti TERZA REAL ESTATE

  1006 Bradford Dr, Winter Park, FL 32792
• 

  

  /25

  Est $249,000 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft

  5408 Peaco Place, Winter Park, FL 32792

  5408 Peaco Place, Winter Park, FL 32792

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