Winter Park, FL Homes

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  /36

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft

  2478 Whitehall Cir, Winter Park, FL 32792

  Expect to be impressed with this updated 3BR home in one of Winter Park’s well-established neighborhoods. It starts with great curb appeal – meticulously manicuredfront lawn, decorative paver stones surrounding the entryway and a 3-car garage! Stepinside to space originally designed as formal living and dining rooms – versatile toarrange as you see fit. Walk back to the “WOW

  Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
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  /17

  $1,300 - $1,855 per month

  La Aloma

  1-3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  3040 Aloma Ave, Winter Park, FL 32792
• 

  

  /2

  $315,000 Sold Jun 30, 2025

  • 1,148 Sq Ft
  • $274/SF
  • 156 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  690 Osceola Ave Unit 209, Winter Park, FL 32789

  Welcome to 690 Osceola Avenue, a lakefront complex in the heart of Winter Park. This sleek, modern residence offers the perfect blend of contemporary design and convenient urban living, just minutes (less than a mile) from the charming shops, restaurants and cultural attractions of Winter Park's renowned Park Avenue. This two-bedroom, two-bath condominium has a private screened balcony with

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  690 Osceola Ave Unit 209, Winter Park, FL 32789
• 

  

  

  /18

  Est $442,817 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2805 Bright Bird Ln, Winter Park, FL 32792

  2805 Bright Bird Ln, Winter Park, FL 32792
• 

  

  

  /56

  $3,150,000

  • 6 Beds
  • 5 Baths
  • 4,767 Sq Ft

  575 Palmer Ave, Winter Park, FL 32789

  Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a

  Joe Devlin DEVLIN INVESTORS & ASSOCIATES

  575 Palmer Ave, Winter Park, FL 32789
• 

  

  /22

  $1,595 per month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792

  Winter Park, Updated 2/2 Condo! AVAILABLE JUNE 16th! Wow, this location is fantastic for the 2 bedroom, 2 bath, updated condo! This community of Lancelot at Winter Park, which is off of N. Goldenrod, has easy access to University Blvd. From University Blvd you can go into Seminole County or further into Orange County very easily! Your commute to downtown Orlando, UCF, Valencia, Full Sail, Rollins

  Hitesh Khatri CFRP REALTY LLC

  3651 N Goldenrod Rd Unit 103, Winter Park, FL 32792
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  /2

  $80,000 Sold Jun 30, 2025

  • 756 Sq Ft
  • $106/SF
  • 3 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  348 Scottsdale Square, Winter Park, FL 32792

  Don't miss this exceptional opportunity to invest in a 1-bedroom, 1-bathroom condo in the heart of Winter Park. Centrally located near Baldwin Park, Full Sail University, the University of Central Florida (UCF), Downtown Winter Park, and Orlando International Airport, this property offers unmatched convenience. Currently vacant, it presents a perfect chance for investors seeking a high-return

  Alan Barbosa DALTON WADE INC

  348 Scottsdale Square, Winter Park, FL 32792
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  /18

  Est $467,116 Not Listed For Sale

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

  2821 Bright Bird Ln, Winter Park, FL 32792

  2821 Bright Bird Ln, Winter Park, FL 32792
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  /27

  $339,500

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft

  3103 Ash Park Loop, Winter Park, FL 32792

  Welcome to Hyde Park, nestled off Howell Branch Road in Seminole County. First time offered. Wonderful two bedroom, two bath split plan, with two car garage and fireplace. The roof has been replaced as well as the A/C unit. Over 1,400 heated Sq. Ft. with fabulous large porch (no rear neighbors). This is ready to decorate to your liking! Bring a paint brush and replace flooring. Tons of

  Pam Hagood Ryan PREMIER SOTHEBY'S INTL. REALTY

  3103 Ash Park Loop, Winter Park, FL 32792
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  /34

  $1,250 - $1,800 per month

  Park Apartments

  1-3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  7528 Park Promenade Dr, Winter Park, FL 32792
• 

  /2

  $80,000 Sold Jun 30, 2025

  • 756 Sq Ft
  • $106/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  347 Scottsdale Square Unit 347, Winter Park, FL 32792

  Don't miss this exceptional opportunity to invest in a 1-bedroom, 1-bathroom condo in the heart of Winter Park. Centrally located near Baldwin Park, Full Sail University, the University of Central Florida (UCF), Downtown Winter Park, and Orlando International Airport, this property offers unmatched convenience. Currently vacant, it presents a perfect chance for investors seeking a high-return

  Alan Barbosa DALTON WADE INC

  347 Scottsdale Square Unit 347, Winter Park, FL 32792
• 

  

  /18

  Est $471,135 Not Listed For Sale

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

  2796 Bright Bird Ln, Winter Park, FL 32792

  2796 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /26

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

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

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment.Located on the first floor, this beautifully renovated 2-bed, 2-bath home features

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
• 

  

  /21

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Townhouse for Rent

  3019 Casselwood St, Winter Park, FL 32792

  ATTENTION GOOD RENTERS!! COME TO SHOW THIS WONDERFUL OPORTUNITY FOR RENT THIS WONDERFUL TOWNHOUSE IN A REALLY GOOD LOCATION IN WINTER PARK AREA NEAR TO SEMORAN. THIS TOWNHOUSE HAS 2 BED AND 2 BATH WITH A NICE DISTRIBUTION INSIDE. IT HAS AS WELL, A BACK YARD WHERE YOU CAN ENJOY WITH FAMILY AND FRIENDS. IT HAS AS WELL TWO PARKING CAR IN FRONT OF THE TOWNHOUSE. VERY CONVINIENT LOCATION!!! NEAR TO

  Maria G Camacho ORLANDO KEY REALTY LLC

  3019 Casselwood St, Winter Park, FL 32792
• 

  /2

  $80,000 Sold Jun 30, 2025

  • 756 Sq Ft
  • $106/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  327 Scottsdale Square, Winter Park, FL 32792

  Prime Investment Opportunity in Winter ParkDiscover a high-return investment with this centrally located 1-bedroom, 1-bathroom condo. Positioned near Baldwin Park, Full Sail University, the University of Central Florida (UCF), Downtown Winter Park, and Orlando International Airport, this property offers unparalleled convenience. A lease is already in place, ensuring immediate income

  Alan Barbosa DALTON WADE INC

  327 Scottsdale Square, Winter Park, FL 32792
• 

  

  /88

  Est $1,910,502 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
• 

  

  /21

  $630,000

  • 4 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  7988 Pleasant Pine Cir, Winter Park, FL 32792

  Stylish, Updated & Move-In Ready in Gated Winter Park Community!Welcome to this impeccably maintained 4-bedroom, 2.5-bath home offering nearly 2,300 square feet of thoughtfully designed living space in the desirable Enclave at Aloma. From the charming covered front porch to the spacious screened lanai, every detail of this home has been crafted with comfort, style, and functionality in

  David Teller ABSOLUTE REALTY GROUP, LLC

  7988 Pleasant Pine Cir, Winter Park, FL 32792
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  /35

  $1,032 - $1,543 per month

  Carlton Arms of Winter Park

  Studio-3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  /2

  $228,000 Sold Jun 27, 2025

  • 736 Sq Ft
  • $310/SF
  • 16 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1948

  1979 Staunton Ave, Winter Park, FL 32789

  This cozy 1-bedroom, 1-bath bungalow is your ticket into one of Winter Park’s most desirable neighborhoods—just steps from beautiful Lake Killarney and surrounded by some of the city’s best dining, shopping, and entertainment. Whether you’re looking for a charming personal retreat, a smart investment, or a renovation project with serious upside, this property delivers with its unbeatable location

  Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  /2

  Est $479,765 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft

  2719 Bright Bird Ln, Winter Park, FL 32792

  2719 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /38

  $595,000

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  2708 Lion Heart Rd, Winter Park, FL 32792

  Here is a fantastic home in Winter Park Pines, a well established and sought after community and location in Winter Park! This property is located on a corner lot and has a private pool as well as a two-car garage. This a great way to obtain home ownership at an affordable price. The construction is a Block/Brick built home making it a solid home unlike one you could buy new today. The Roof and

  Corey Cannon BHHS FLORIDA REALTY

  2708 Lion Heart Rd, Winter Park, FL 32792
• 

  

  /18

  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • House for Rent

  1902 Azalea Ave, Winter Park, FL 32792

  Welcome to 1902 Azalea Street, a beautifully maintained 3-bedroom, 2-bathroom home in the heart of Winter Park. This delightful property blends classic Florida charm with modern updates, offering a bright and inviting interior. Nestled on a quiet, tree-lined street, the home is perfect for relaxing or entertaining. Just minutes from Park Avenue, Rollins College, and top-rated schools, you’ll

  Alison Ashby CORCORAN PREMIER REALTY

  1902 Azalea Ave, Winter Park, FL 32792
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  /2

  $421,000 Sold Jun 27, 2025

  • 1,619 Sq Ft
  • $260/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  2817 Fitzooth Dr, Winter Park, FL 32792

  Spectacular pool home in the Winter Park Pines on a corner lot with a side entry 2 car garage. Roof replaced in 2018. This 3 bedroom 2 bath home is a blank canvas just waiting to be customized to your particular taste. Pool has gunite with diamond brite finish. The particular location of this home could be perfect for raising a family and pets. Breakfast bar in kitchen. Sliding glass doors in

  Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  2817 Fitzooth Dr, Winter Park, FL 32792
• 

  

  /18

  Est $469,506 Not Listed For Sale

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

  2790 Bright Bird Ln, Winter Park, FL 32792

  2790 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /37

  $500,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,906 Sq Ft

  7602 Lodge Pole Trail, Winter Park, FL 32792

  Nestled in desirable Arrowhead Cove, this meticulously maintained 3-bedroom, 2.5-bath home represents the pinnacle of Winter Park living. With 1,906 square feet of thoughtfully designed space, this move-in-ready residence blends character, comfort, and convenience in Central Florida's most coveted school district. BONUS FEATURE: PRIVATE WELL IRRIGATION SYSTEM – Enjoy beautifully maintained

  Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

  7602 Lodge Pole Trail, Winter Park, FL 32792
• 

  

  /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
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  /2

  $250,000 Sold Jun 27, 2025

  • 1,114 Sq Ft
  • $224/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1990

  1827 Blaine Terrace, Winter Park, FL 32792

  Welcome to this charming 3-bedroom, 2-bath home nestled in the desirable Villas of Casselberry community. This zero-lot-line property offers low-maintenance living with the privacy of a single-family home. Featuring a functional layout and a 1-car garage, rear patio and outside storage. This starter home is perfect for first-time buyers, or as an investment.Enjoy easy access to top

  Kerry Jeffcoat-Squeteri COMPASS FLORIDA LLC

  1827 Blaine Terrace, Winter Park, FL 32792
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  /39

  Est $853,832 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
• 

  

  /17

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  2206 Bonanza Ave, Winter Park, FL 32792

  This Winter Park BLOCK home offers 4 bedrooms, 2 full bathrooms and all with no HOA. This home features a SPLIT FLOOR PLAN and NEW ROOF (2022). The oversized enclosed porch is perfect for entertaining or relaxing after a long day of work. Front screened in patio to enjoy as well. Storage will not be an issue, as there is a 2 CAR GARAGE You're also located in a very established community that's

  Hannah Thompson FLORIDA REALTY INVESTMENTS

  2206 Bonanza Ave, Winter Park, FL 32792
• 

  

  /20

  $3,200 per month

  • 4 Beds
  • 2.5 Baths
  • 2,442 Sq Ft
  • House for Rent

  650 S Lakemont Ave, Winter Park, FL 32792

  Welcome to 650 S Lakemont Avenue WINTER PARK! COME SEE THIS SPECTACULAR WINTER PARK HOME COMPLETELY UPDATED INCLUDING A STUNNING KITCHEN! This home has SOLAR PANELS IN PLACE WHICH HAVE ALLOWED OWNERS LAST COUPLE OF UTILITIES BILLS TO BE AROUND $60 PER MONTH FOR WATER, SEWER, ELECTRIC AND TRASH COMBINED! This four bedroom two and a half bath home has been meticulously updated and cared for! This

  Lori Gilmore LORI GILMORE REAL ESTATE LLC

  650 S Lakemont Ave, Winter Park, FL 32792
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  /2

  $750,000 Sold Jun 27, 2025

  • 2,196 Sq Ft
  • $342/SF
  • 22 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2020

  1151 Wildmeadow Run, Winter Park, FL 32792

  Beautifully appointed on a premier homesite within the gated enclave of Hawk’s Crest, this contemporary masterpiece combines grandeur and elegance for your enjoyment of living. From the moment you step through the front door, soaring ceilings and a gracious foyer welcome you into a world of refined living. The luxurious, all-white kitchen is outfitted with top-of-the-line Cafe appliances and

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  1151 Wildmeadow Run, Winter Park, FL 32792
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  /44

  Est $1,015,662 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
• 

  

  /22

  $249,900

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7744 Country Place Unit C4, Winter Park, FL 32792

  Location, Location, Location! This highly sought-after two-bedroom, two-bath condo in Winter Park won’t last long! Ideally situated close to the University of Central Florida, it's a perfect investment opportunity for parents offering lower monthly payments compared to the high costs of on-campus housing.Upgrades made in 2020 include a new roof, air conditioning system, and enhanced attic

  Travis Sorci DALTON WADE INC

  7744 Country Place Unit C4, Winter Park, FL 32792
• 

  

  /20

  $3,850 per month

  • 2 Beds
  • 1 Bath
  • 1,141 Sq Ft
  • Condo for Rent

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

  Welcome to this cozy and inviting 2-bedroom, 1-bathroom home, perfect for couples, small families, or solo travelers eager to explore Central Florida. Situated just 3 miles from Downtown Orlando, 12 miles from Universal Studios, and 8 miles from Disney, this home's location is unbeatable.This charming property features two spacious queen bedrooms, a full bathroom with a walk-in shower, and a

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
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  /2

  $672,000 Sold Jun 27, 2025

  • 1,350 Sq Ft
  • $498/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  300 Carolina Ave Unit 304, Winter Park, FL 32789

  Welcome to Park West — an exclusive, gated enclave ideally situated just moments from the vibrant heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bathroom residence with a versatile den offers an exceptional combination of elegance, comfort, and convenience. The den, currently utilized as a private home office, can easily serve as a third bedroom to accommodate your

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  300 Carolina Ave Unit 304, Winter Park, FL 32789
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  /32

  Not Listed For Sale

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792
• 

  

  /75

  $1,295,000 Open Sun 1PM - 3PM

  • 6 Beds
  • 4 Baths
  • 4,161 Sq Ft

  1422 Via Sangro Place, Winter Park, FL 32792

  Welcome to your WATERFRONT dream home in the prestigious Lakeside Estates, a private gated community situated on Garden Lake. Highly desirable cul-de-sac location and short stroll to the playground. The Kerrville model home is designed for stylish, easy living and offers an open floor plan with high-end finishes throughout. Impress your family and friends with the inviting foyer, 20+ ceilings,

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  1422 Via Sangro Place, Winter Park, FL 32792
• 

  

  /11

  $2,730 per month

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • House for Rent

  460 Cambridge Blvd Unit A, Winter Park, FL 32789

  Fully renovated 3-bedroom, 2-bath home in the heart of Winter Park—available for immediate move-in! This charming unit features an updated kitchen with stainless steel appliances, durable vinyl plank flooring throughout, and a full-sized washer and dryer for added convenience. Enjoy private parking and an oversized fenced backyard, perfect for entertaining or relaxing outdoors. Located near

  Amy Fouraker 4 ACRE REALTY LLC

  460 Cambridge Blvd Unit A, Winter Park, FL 32789
• 

  /2

  $3,100,000 Sold Jun 27, 2025

  • 4,260 Sq Ft
  • $728/SF
  • 45 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 2025

  731 Williams Dr, Winter Park, FL 32789

  Introducing a stunning brand-new custom home by Butler Ridge Development, located in the highly desirable Park Grove neighborhood—strolling distance to Winter Park’s famed Park Avenue. This home offers timeless elegance, modern luxury, and walkable access to top-tier dining, shopping, and culture. From the inviting circular drive and professionally designed landscaping by Joe Knight, including a

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
• 

  

  /18

  Est $452,367 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2778 Bright Bird Ln, Winter Park, FL 32792

  2778 Bright Bird Ln, Winter Park, FL 32792

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