Winter Park, FL Homes for Sale

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  /34

  $260,000

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft

  151 N Orlando Ave Unit 101, Winter Park, FL 32789

  Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops,

  

  Elizabeth Fowler

  THE FLORIDA PROPERTY SHOP SALE

  (321) 463-4625

  151 N Orlando Ave Unit 101, Winter Park, FL 32789
• Explore Winter Park

• 

  

  

  /19

  $174,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  Well maintained 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The main living areas have wood laminate tile flooring and granite countertops in the kitchen. The bathrooms have been updated with sleek fixtures, modern design elements and newly painted. Nearby, you will find top rated schools and

  

  Monica Perlas

  COLDWELL BANKER REALTY

  (321) 449-2749

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
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  /50

  $449,900

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Seller is Motivated, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard features fresh SOD,

  

  Claudia Jenkins

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 450-7314

  2835 Bongart Rd, Winter Park, FL 32792
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  /39

  $675,000 Open Sun 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,752 Sq Ft

  1613 Oriole Ave, Orlando, FL 32803

  Just two blocks from East End Market and the Audubon Park K8 campus, this thoughtfully renewed four bedroom home sits in one of the area’s most loved walkable pockets. The renovation was approached with care, intention, and a focus on comfortable everyday living. The layout has been reworked to create an easy sense of flow, highlighted by a newly formed primary suite and a kitchen designed with

  

  Dave Zembala

  ZEMBALA GROUP

  (321) 513-1138

  1613 Oriole Ave, Orlando, FL 32803
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  /7

  $567,000

  • 5 Beds
  • 3 Baths
  • 2,615 Sq Ft

  7502 Waunaqua Dr, Winter Park, FL 32792

  Welcome home to Lake Waunatta Cove subdivision in Orange County. This attractive, beautifully decorated, very spacious 5 bedrooms, 3 full bathrooms, with a family room, and a very rare Basement. This roomy home is open and airy with vaulted ceilings, skylights, newer lighted ceiling fans in all bedrooms, living room, and family room, a wood burning fireplace in the living room, and a fantastic

  

  Carmen Vazquez

  REALTY TECH INC

  (689) 319-9633

  7502 Waunaqua Dr, Winter Park, FL 32792
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  /26

  $80,000

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  7341 Daniel Webster Dr Unit 2, Winter Park, FL 32792

  Affordable living in Winter Park. This 1-bedroom, 1-bath condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated, the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated Winter Park schools,

  

  Rob Aponte

  REAL BROKER, LLC

  (321) 321-8355

  7341 Daniel Webster Dr Unit 2, Winter Park, FL 32792
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  /22

  $79,900

  • 1 Bed
  • 1 Bath
  • 590 Sq Ft

  3075 Aaron Burr Ave Unit 6, Winter Park, FL 32792

  Affordable living in Winter Park. This 1-bedroom, 1-bath condo in The Colonies offers an excellent opportunity for investors or first-time buyers. Recently updated with new flooring, the unit is ready for a new owner. The location is a major draw, just minutes from Full Sail University, Valencia College, UCF, Park Avenue, Downtown Orlando, and Orlando International Airport. With highly rated

  

  Rob Aponte

  REAL BROKER, LLC

  (321) 463-6489

  3075 Aaron Burr Ave Unit 6, Winter Park, FL 32792
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  /8

  $260,000

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER RESIDENTIAL RE

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
• 

  

  /19

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

  7706 Country Place Unit A8, Winter Park, FL 32792
• 

  

  /15

  $139,900

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit B216, Winter Park, FL 32789

  Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. The end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a

  

  Martha Grasty

  RE/MAX ASSURED

  (321) 516-0992

  1695 Lee Rd Unit B216, Winter Park, FL 32789
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  /51

  $1,499,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  102 Bell Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

  102 Bell Place, Winter Park, FL 32792
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  /35

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  623 Saint Johns Ct Unit 623, Winter Park, FL 32792

  If you’re searching for a place that feels like home the moment you walk in—not just another condo—this one might be exactly what you’ve been looking for. Nearby to Full Sail University, UCF, restaurants, shopping, entertainment, and major road access, this property is in a prime location. Step through the covered front porch and into a bright, welcoming space with soaring vaulted ceilings, new

  David Dorman CENTURY 21 CARIOTI

  623 Saint Johns Ct Unit 623, Winter Park, FL 32792
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  /41

  $2,490,000

  • 5 Beds
  • 4 Baths
  • 3,948 Sq Ft

  1205 Mayfield Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 bedrooms and 4 bathrooms in the main home, plus a large separate pool home/In-Law Suite complete with

  Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
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  /27

  $320,000

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft

  615 Warrenton Rd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Don’t miss out on this beautifully maintained, 2 bed, 2 bath, single story townhome in the sought after Winter Park Pines with a LOW HOA! As you make your way towards the entrance you have 2 private, fenced-in courtyard areas for sitting out for a morning coffee, home gardening, or just getting out to enjoy the weather. As you enter the home you see

  Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
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  /33

  $650,000

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

  428 Selkirk Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Income-Producing Opportunity! Welcome to this versatile Winter Park POOL HOME! At present, this property is split into two separate living quarters with the main house offering 3 bedrooms & 2 bathrooms and the adjoining guest suite offering 1 bedroom & 1 bathroom. Each living quarter has its own kitchen, laundry, climate control & outdoor living

  Sheri Malin REDFIN CORPORATION

  428 Selkirk Dr, Winter Park, FL 32792
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  /44

  $3,399,999

  • 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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  /24

  $100,000

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Great location!! Discover the charm of this beautifully maintained condo at 126 Scottsdale Square, nestled in a serene and convenient Orlando community. This condo boasts 3 bedrooms and 2 bathrooms thoughtfully designed with a spacious layout perfect for comfortable living. From the bright and open living area to the modern kitchen with upgraded appliances. Every detail has been tailored for

  Thomas Hicks, Sr LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
• 

  

  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751
• 

  

  /29

  $949,000

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  560 Ololu Dr, Winter Park, FL 32789

  Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this

  Tiffany Yates COMPASS FLORIDA LLC

  560 Ololu Dr, Winter Park, FL 32789
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  /51

  $900,000

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

  350 N Phelps Ave, Winter Park, FL 32789

  Beautifully Updated Home in the Heart of Winter Park and Its Top-Rated Schools! Welcome to 350 North Phelps Avenue! This stunning move-in-ready home sits in the heart of Winter Park, offering four bedrooms, three full bathrooms, an open split floor plan, a bonus room with French doors, and a large fenced backyard perfect for a future pool. This home offers the perfect blend of modern elegance and

  Freddy DeCoster GOYAL & DECOSTER REALTY

  350 N Phelps Ave, Winter Park, FL 32789
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  /15

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7771 Country Place Unit 7, Winter Park, FL 32792

  Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate Flooring Flows

  Ivan Tobon OUTLET REALTY

  7771 Country Place Unit 7, Winter Park, FL 32792
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  /22

  $298,000 Open Sun 1:30PM - 3PM

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
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  /25

  $436,900

  • 3 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  2808 Bright Bird Ln, Winter Park, FL 32792

  Gorgeous 2-Story Townhome, newly built in 2024. Located in upscale Winter Park, Florida, close to fine dining, shopping and entertainment. Minutes from downtown Orlando and Orlando theme parks, this manicured gated community showcases beautiful landscaping and a sparkling pool surrounded by coveted modern architecture. The home contains the high-end Lux Fresh interior package, and owner has added

  Steven Koleno BEYCOME OF FLORIDA LLC

  2808 Bright Bird Ln, Winter Park, FL 32792
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  /36

  $329,000

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 6-3, Winter Park, FL 32789

  Discover your new downtown Winter Park ground-floor pied-à-terre. Two blocks from Park Avenue, the 1960s mid-century modern Whispering Waters Condominiums are a Winter Park landmark. Your remodeled end-unit studio features an updated open kitchen with plentiful wood cabinets, ceramic tile flooring throughout, new dual-pane windows, a stylish updated bathroom with a step-in shower, and wood

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  311 E Morse Blvd Unit 6-3, Winter Park, FL 32789
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  /15

  $1,107,750

  • 2 Beds
  • 2 Baths
  • 1,329 Sq Ft

  240 E Lake Sue Ave, Winter Park, FL 32789

  Discover the perfect blend of convenience and tranquility with this delightful single-family home located in the sought-after Winter Park community. Situated on East Lake Sue Avenue, this property sits on a beautifully maintained lot featuring mature trees and lush landscaping that provides plenty of shade and privacy. Enjoy the ultimate Winter Park lifestyle with close proximity to Park Avenue’s

  Tika Van Den Hurk Compass Florida, LLC

  240 E Lake Sue Ave, Winter Park, FL 32789
• 

  

  /17

  $235,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  151 N Orlando Ave Unit 226, Winter Park, FL 32789

  Take advantage of this newly updated 2 Bedrooms and 1 Bathroom condo with attractive low interest rate seller financing for first two years! Conveniently located in Winter Park/Orlando next to all of shops and restaurants. With private lake access to launch and dock your watercraft within the community for boating and fishing. Walk to Trader Joes next door and Winter Park Village to enjoy great

  Mike Wang LOKATION

  151 N Orlando Ave Unit 226, Winter Park, FL 32789
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  /58

  $1,750,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 4.5 Baths
  • 3,164 Sq Ft

  1630 Chestnut Ave, Winter Park, FL 32789

  Discover a fresh take on modern living in one of Winter Park's most admired neighborhoods - the "Tree Streets." This custom three-story LunDev home marries modern minimalism with subtle Dutch Colonial influences, creating a distinctive and inviting retreat. The carefully curated neutral palette sets a relaxed tone throughout, blending timeless design elements with contemporary

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1630 Chestnut Ave, Winter Park, FL 32789
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  /67

  $439,000

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

  1900 Erudite Way, Winter Park, FL 32792

  Seller offering $10,000 credit to buyer at closing—may be applied toward buyer’s rate buy-down, closing costs, or prepaid expenses (subject to lender approval).Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features,

  Erica Diltz BALDWIN PARK REALTY LLC

  1900 Erudite Way, Winter Park, FL 32792
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  /41

  $1,190,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft

  1150 Kenwood Ave, Winter Park, FL 32789

  Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welcoming living room, versatile bonus/flex space, dining room with built-ins, a well-appointed kitchen,

  JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
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  /48

  $460,000

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft

  2420 Firstlight Way, Winter Park, FL 32792

  Welcome to this beautifully designed, move-in-ready townhome— the largest end-unit in one of Winter Park’s most sought-after gated communities! This spacious townhome is conveniently located in the gated community of Hawks Crest, offering 2,312 sq ft of low-maintenance living. With 3 bedrooms, 2.5 bathrooms, a 2-car garage, filled with natural light thanks to abundant windows and soaring

  Kristan Hayden ATRIUM REALTY, LLC

  2420 Firstlight Way, Winter Park, FL 32792
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  /54

  $950,000

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  668 Overspin Dr, Winter Park, FL 32789

  Modern Elegance Meets Custom Craftsmanship in the Heart of Winter ParkWelcome to your dream home — a custom-built Winter Park masterpiece blending modern luxury with thoughtful design. With over 2,500 sq/ft of stunning living space, this 4-bedroom, 3-bathroom home was built to impress and designed to entertain.Step inside and be captivated by the seamless open layout, drenched in natural

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  668 Overspin Dr, Winter Park, FL 32789
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  /53

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  1447 Broad Wing Ln, Winter Park, FL 32792

  **Take advantage of a seller paid promotion towards closing costs or rate buy down.** This 3-bedroom, 2.5-bath townhome combines style, functionality, and low-maintenance living and is ready for you to move right in. It features a paver driveway and walkway framed by lush landscaping. As you step inside the home, you will find a versatile flex space, which is perfect as a home office, or

  Gaelle Cenord FOWLKES REALTY CO

  1447 Broad Wing Ln, Winter Park, FL 32792
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  /47

  $925,000

  • 4 Beds
  • 3.5 Baths
  • 2,173 Sq Ft

  208 Brewer Ave, Winter Park, FL 32789

  Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic architectural details and a welcoming front porch that set the tone for what’s inside. All major items have been taken care of as well allowing you to just move on in, HVAC 2021, ROOF

  Cassandra King COMPASS FLORIDA LLC

  208 Brewer Ave, Winter Park, FL 32789
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  /26

  $198,500

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

  Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two generously sized master suites, each with its own

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
• 

  

  /19

  $194,900

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792

  JUST REDUCED! Motivated Seller! *ALL ROOM FURNITURE IN LISTING PHOTOS CAN BE INCLUDED AS AN OPTION* Fully Renovated 1-Bedroom First-Floor Condo – Stylish & Convenient Living. Move-in ready! Gorgeous new flooring throughout, sophisticated modern lighting, freshly painted walls with contemporary baseboards and trim, impeccably styled. Welcome to 4768 Tangerine Ave #4768, a beautifully renovated

  Christopher Franqui PROPERTY OUTLET INTERNATIONAL

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792
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  /72

  $1,095,000

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  2607 Lafayette Ave, Winter Park, FL 32789

  Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining.Step inside to discover an open-concept layout that seamlessly connects the kitchen,

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2607 Lafayette Ave, Winter Park, FL 32789
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  /33

  $200,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  225 Lewfield Cir, Winter Park, FL 32792
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  /38

  $975,000

  • 3 Beds
  • 2 Baths
  • 1,887 Sq Ft

  913 Moss Ln, Winter Park, FL 32789

  ***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL – A 2023 Masterpiece Awaits! Step into luxury living at 913 Moss Lane, a breathtakingly renovated 3-bedroom, 2-bath haven in the heart of Winter Park, boasting 1,887 square feet of modern elegance and timeless Florida charm.

  Peter Rodriguez VECTOR REALTY

  913 Moss Ln, Winter Park, FL 32789
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  /33

  $229,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 204, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Back on Market. Buyer financing fell through. Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen

  Eddie Cooper MAINFRAME REAL ESTATE

  151 N Orlando Ave Unit 204, Winter Park, FL 32789
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  /68

  $950,000

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  250 Cortland Ave, Winter Park, FL 32789

  Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

  Alexandra Nordine EXP REALTY LLC

  250 Cortland Ave, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 8

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Learn more about living in Winter Park

Frequently Asked Questions

What is the average home price in Winter Park, FL?

Homes for sale in Winter Park, FL have an average home price of $970,483.

How many homes have sold over the last 12 months in Winter Park, FL?

1,046 homes have sold in Winter Park, FL over the last 12 months.

What are the most popular zip codes in Winter Park, FL?

The most popular zip codes in Winter Park, FL include 32789, 32751, 32792, 32803 and 32814.

How much do you need to make to afford a house in Winter Park?

The median home price in Winter Park is $539,900. If you put a 20% down payment of $108,000 and had a 30-year fixed mortgage with an interest rate of 6.19%, your estimated principal and interest payment would be $2,640 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $113K a year to afford the median home price in Winter Park. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Winter Park, FL?

Winter Park, FL has highly rated public and private schools. Some of the best schools in Winter Park based on Niche Grades are Trinity Preparatory School, Audubon Park School and Baldwin Park Elementary. Browse all the schools in Winter Park, FL to learn more.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 63 days on the market compared to the national average of 53 days. The median sale price for homes in Winter Park, FL over the last 12 months is $494,000, up 5% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$494,000

Median Single Family Sale Price

$610,000

Median Townhouse Sale Price

$460,000

Median 2 Bedroom Sale Price

$227,100

Median 1 Bedroom Sale Price

$152,000

Average Price Per Sq Ft

$371

Number of Homes for Sale

277

Last 12 months Home Sales

1,046

Months of Supply

3.20

Median List Price

$539,900

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

5%