Newest Homes for Sale in Winter Park, FL

• 

  

  

  /20

  $680,000

  $70K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,664 Sq Ft

  432 W Swoope Ave, Winter Park, FL 32789

  A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

  Thomas Bonner COLDWELL BANKER REALTY

  432 W Swoope Ave, Winter Park, FL 32789
• 

  

  

  /18

  $268,950

  $16K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  3220 Netherwood Dr, Winter Park, FL 32792

  BACK ON MARKET!! Buyer financing fell through! **Qualified buyers may be eligible for up to $40,000 in down payment assistance** Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future

  Nimrah Ashraf THE FIRM RE

  3220 Netherwood Dr, Winter Park, FL 32792
• 

  

  

  /20

  $299,999

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
• 

  

  

  /12

  $1,750,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  1840 Anzle Ave, Winter Park, FL 32789

  Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops,

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

  1840 Anzle Ave, Winter Park, FL 32789
• 

  

  

  /37

  $182,900

  $67K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  205 Lewfield Cir Unit 205, Winter Park, FL 32792

  Virtually Staged. NEW PRICE! Motivated seller! Move-in ready! Exceptional value in the heart of Winter Park!Welcome to this beautifully maintained 2-bedroom, 2-bath ground-floor condominium, where comfort, convenience, and an unbeatable location come together.The thoughtfully designed floor plan features an open-concept living and dining area, a screened patio overlooking peaceful

  Eimi Moreno Carrera LPT REALTY, LLC

  205 Lewfield Cir Unit 205, Winter Park, FL 32792
• 

  

  /19

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  2231 Nairn Dr, Winter Park, FL 32792

  Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

  David Auerbach PARK TOWN REAL ESTATE LLC

  2231 Nairn Dr, Winter Park, FL 32792
• 

  

  /12

  $499,000

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  230 Strathy Ln, Winter Park, FL 32792

  Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

  David Auerbach PARK TOWN REAL ESTATE LLC

  230 Strathy Ln, Winter Park, FL 32792
• 

  

  /65

  $1,399,000

  New Construction $151K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,164 Sq Ft

  1523 Miller Ave, Winter Park, FL 32789

  BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped

  Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

  1523 Miller Ave, Winter Park, FL 32789
• 

  

  /26

  $184,400

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 222, Winter Park, FL 32789

  Rent-to-own or lease option available with negotiable terms—Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil

  Christine Bouchard HOMESMART

  2500 Lee Rd Unit 222, Winter Park, FL 32789
• 

  

  /7

  $459,900

  $39K PRICE DROP

  • Land
  • 9,147 Sq Ft
  • $2,190,000 per Acre

  3601 Midiron Dr, Winter Park, FL 32789

  Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a

  Juliana Usquiano EMPIRE NETWORK REALTY

  3601 Midiron Dr, Winter Park, FL 32789
• 

  

  /7

  $899,000

  $100K PRICE DROP

  • Land
  • 8,276 Sq Ft
  • $4,731,579 per Acre

  731 Midget Dr, Winter Park, FL 32789

  Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and

  Juliana Usquiano EMPIRE NETWORK REALTY

  731 Midget Dr, Winter Park, FL 32789
• 

  

  /29

  $899,000

  $50K PRICE DROP

  • 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
• 

  

  /23

  $285,000

  $13K PRICE DROP

  • 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
• 

  

  /34

  $485,000

  $45K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,092 Sq Ft

  2217 Sussex Rd, Winter Park, FL 32792

  NEW FLOORS, POOL, NO HOA, 4-YEAR-OLD ROOF & NEWER A/C!** Move-in ready 4-bedroom + office home offering 2,092 SF in the desirable Winter Woods/Lake Howell area of Winter Park. This well-maintained home features **brand-new flooring**, an open floor plan, granite countertops, modern appliances, abundant cabinetry, and a wood-burning fireplace.Enjoy Florida living with an oversized enclosed

  Justin Hilton PREFERRED REAL ESTATE BROKERS

  2217 Sussex Rd, Winter Park, FL 32792
• 

  

  /59

  $2,195,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
• 

  

  /20

  $340,000

  $10K PRICE DROP

  • 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
• 

  

  /30

  $629,900

  $195K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,472 Sq Ft

  2612 Roxbury Rd, Winter Park, FL 32789

  RENT TO OWN OPTION AVAILABLE!!!Come view this NEXTGEN Home FULLY MODERNIZED 5-bedroom, 3-bathroom home offering flexibility, and comfort that Includes an Attached 2 Bed/1 Bath IN- LAW SUITE!! Step inside to an open and airy layout featuring Luxury plank flooring, fresh neutral paint, and large windows that fill the home with natural light. The upgraded kitchen is a true showstopper —

  Laura Mcadams EXP REALTY LLC

  2612 Roxbury Rd, Winter Park, FL 32789
• 

  

  /8

  $109,400

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft

  311 Scottsdale Square Unit 311, Winter Park, FL 32792

  This 1 bedroom, 1 bath condo at 311 Scottsdale Sq, Winter Park, FL 32792 is leased to a reliable long-term tenant paying $1,450 / month. Located on the first floor in the established Winter Park Woods community, this unit features an open-concept layout as soon as you walk in. The HOA includes water, access to two community pools, a playground, and tennis courts. Winter Park Woods is also zoned

  Omar Rodriguez EMPIRE NETWORK REALTY

  311 Scottsdale Square Unit 311, Winter Park, FL 32792
• 

  

  /14

  $179,900

  • 3 Beds
  • 2 Baths

  7340 Daniel Webster Dr, Winter Park, FL 32792

  This is a 3 bedroom and 2 bathroom condo. This condo has had everything replaced. Don't miss out on this opportunity. Call listing agent today for more information and to schedule a showing.

  Robert Castro RE/MAX - City Centre Realty

  7340 Daniel Webster Dr, Winter Park, FL 32792
• 

  

  /15

  $199,000

  $29K PRICE INCREASE

  • 2 Beds
  • 1.5 Baths
  • 1,393 Sq Ft

  7471 Canford Ct Unit 19, Winter Park, FL 32792

  One of the lowest-priced homes in Winter Park with nearly 1,400 square feet, a private carport, screened balcony, community pool, and easy access to UCF, Full Sail, Rollins, Valencia East, Orlando International Airport, and downtown Orlando! The monthly HOA covers many exterior maintenance items so you can enjoy low-maintenance living.This 2 bedroom, 1.5 bathroom condo features a townhome style

  Karen Salter IAD REAL ESTATE

  7471 Canford Ct Unit 19, Winter Park, FL 32792
• 

  

  /12

  $285,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,669 Sq Ft

  2336 Sun Valley Cir Unit BLDG 20, Winter Park, FL 32792

  Welcome to this spacious 2-bedroom, 2-bathroom condo with a versatile loft, ideally located in desirable Winter Park. Featuring one of the largest floor plans in the community, this home offers an abundance of living space and a flexible layout perfect for relaxing, entertaining, working from home, or creating a guest space.Recently painted and filled with natural light, the home features

  Elizabeth Beaudoin PR REAL ESTATE SERVICES

  2336 Sun Valley Cir Unit BLDG 20, Winter Park, FL 32792
• 

  

  /3

  $3,600,000

  New Construction $50K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
• 

  

  /39

  $3,075,000

  New Construction $420K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 3,863 Sq Ft

  1821 Englewood Rd, Winter Park, FL 32789

  This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1821 Englewood Rd, Winter Park, FL 32789
• 

  

  /33

  $150,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

  Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

  SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
• 

  

  /27

  $399,900

  $55K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,627 Sq Ft

  1849 Viburnum Ln, Winter Park, FL 32792

  This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor

  Lesly Hijar REAL BROKER, LLC

  1849 Viburnum Ln, Winter Park, FL 32792
• 

  

  /12

  $4,500,000

  $499K PRICE DROP

  • Land
  • 20,908 Sq Ft
  • $9,375,000 per Acre

  503 N Interlachen Ave, Winter Park, FL 32789

  RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,500,000! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed businesses.

  Kelly Price KELLY PRICE & COMPANY LLC

  503 N Interlachen Ave, Winter Park, FL 32789
• 

  

  /38

  $639,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,539 Sq Ft

  2758 Banchory Rd, Winter Park, FL 32792

  FULLY PAID SOLAR PANELS INCLUDED — NO SOLAR LOAN TO ASSUME! A rare added value for the next owner: enjoy the benefits of solar energy with the system included in the sale and no remaining solar panel balance. Welcome to 2758 Banchory Rd, a beautifully maintained 3-bedroom, 2-bath pool home in desirable Winter Park Pines. This charming ranch-style home offers a bright open layout, mature

  Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

  2758 Banchory Rd, Winter Park, FL 32792
• 

  

  /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
• 

  

  /26

  $182,500

  $27K PRICE DROP

  • 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

  $89,900

  $10K PRICE DROP

  • Studio
  • 1 Bath
  • 549 Sq Ft

  3071 George Mason Ave Unit 5, Winter Park, FL 32792

  Charming Studio Condo Near UCF & Full Sail – Ideal Investment or Cozy Retreat!Welcome to this well-maintained ground-floor studio condo, offering 549 square feet of comfortable living space in a prime location near UCF and Full Sail University. Perfect for a student, professional, or investor, this move-in-ready unit features tile flooring throughout, making it clean and easy to maintain.

  Katherine Bordelon CASTLE & COTTAGE REALTY LLC

  3071 George Mason Ave Unit 5, Winter Park, FL 32792
• 

  /2

  $205,000

  $5K PRICE DROP

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

  1695 Lee Rd Unit C202, Winter Park, FL 32789

  This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This

  Hoover Yap PRIMESTATE REALTY, INC.

  1695 Lee Rd Unit C202, Winter Park, FL 32789
• 

  

  /6

  $99,000

  • Studio
  • 1 Bath
  • 537 Sq Ft

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

  Lynda Cheros GOLDENCREST REALTY LLC

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
• 

  

  /25

  $284,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  2335 Inagua Way, Winter Park, FL 32792

  Rare opportunity in beautiful Winter Park - Move in ready 3 bed 2 bath townhome for under $300,000. Super low HOA at only $92/month. Spacious split plan with new roof, newer AC, new carpet in bedrooms, freshly painted, tile, inside laundry, atrium off living room and open floor plan. Patio with storage room and shed. Front entrance & parking area with beautiful pavers. Townhome is on

  Marion McGrath ABSOLUTE REALTY GROUP, LLC

  2335 Inagua Way, Winter Park, FL 32792
• 

  

  /26

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
• 

  

  /11

  $198,000

  $2K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez AROD PARTNERS REALTY

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
• 

  /2

  $2,450,000

  • 5 Beds
  • 5.5 Baths
  • 4,010 Sq Ft

  1771 Taylor Ave, Winter Park, FL 32789

  Custom Winter Park home completed in 2019 by FG Schaub Custom Home Builder. Contemporary Florida living awaits in this newly built home, boasting a spacious open floor plan spanning over 4,000 square feet with five bedrooms and five-and-a-half baths. Delight in the stunning gourmet kitchen, gas cooktop, oversized island and an extended walk-in pantry with cabinets. Distinctive features include

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1771 Taylor Ave, Winter Park, FL 32789

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