Winter Park, FL Condos for Sale under $300,000

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  /32

  $184,900

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7468 Canford Ct Unit 24, Winter Park, FL 32792

  This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under

  Javier Albelo Rivera EMPIRE NETWORK REALTY

  7468 Canford Ct Unit 24, Winter Park, FL 32792
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• 

  

  

  /31

  $245,000

  • 2 Beds
  • 2 Baths
  • 913 Sq Ft

  1250 S Denning Dr Unit 233, Winter Park, FL 32789

  Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open

  Samuel Kingsford STOCKWORTH REALTY GROUP

  1250 S Denning Dr Unit 233, Winter Park, FL 32789
• 

  

  

  /24

  $254,000

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  2477 Tahoe Cir Unit 2477, Winter Park, FL 32792

  Virtually Staged. LIVE THE WINTER PARK LIFESTYLE!STYLE, SPACE & LOCATION—THIS ONE HAS IT ALL! Welcome to Cedarwood Village, where easy living meets one of Winter Park’s most desirable locations, just minutes from the charm, dining, shopping, and entertainment of Downtown Winter Park and Park Avenue.This beautifully maintained 2-bedroom, 2-bath residence with an enclosed bonus room

  Kyle Clark RE/MAX TOWN & COUNTRY REALTY

  2477 Tahoe Cir Unit 2477, Winter Park, FL 32792
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  /16

  $143,500

  $6K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  3019 Antique Oaks Cir Unit 127, Winter Park, FL 32792

  Beautifully renovated first-floor 1-bedroom, 1-bath condominium in the highly desirable Parkview Village community, conveniently located directly across from Full Sail University on Semoran Blvd. This move-in-ready home features a spacious open-concept layout, an oversized bedroom with a walk-in closet, a dedicated laundry closet with a washer and dryer, and a private screened-in patio

  Steven Koleno BEYCOME OF FLORIDA LLC

  3019 Antique Oaks Cir Unit 127, Winter Park, FL 32792
• 

  

  

  /31

  $275,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  5184 Lazy Oaks Dr, Winter Park, FL 32792

  Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space.The kitchen opens to a bright, inviting space with skylights that bring natural light

  Joyce Gary PAINE-ANDERSON PROPERTIES, INC

  5184 Lazy Oaks Dr, Winter Park, FL 32792
• 

  

  /18

  $165,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 109, Winter Park, FL 32792

  This is exactly what you are looking for! Adorable 2/2 close to Full Sail and UCF. Tons of shopping and restaurants and convenient to the 417 and the 408. Location makes this perfect for a primary residence or investment property. Split floor plan ideal for roommates. Walk to Full Sail. 15 minutes to downtown Orlando and approximately 30 minutes to most attractions. Exceptionally well taken care

  Valerie Wanzer REAL ESTATE PROFESSIONALS SE

  3651 N Goldenrod Rd Unit 109, Winter Park, FL 32792
• 

  

  /31

  $265,000

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 119, Winter Park, FL 32789

  Virtually Staged. Welcome to easy, low-maintenance living in the heart of Winter Park! This beautifully updated 2-bedroom, 2-full-bath, first-floor corner residence at Mead Garden Condominiums offers a fresh, move-in-ready interior paired with an exceptional location just minutes from some of Winter Park’s most desirable destinations.Recent updates include new luxury vinyl flooring

  Justin McCarthy FANNIE HILLMAN & ASSOCIATES

  1250 S Denning Dr Unit 119, Winter Park, FL 32789
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  /28

  $107,000

  $8K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit D211, Winter Park, FL 32789

  Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

  Brandy Ray LOKATION

  1695 Lee Rd Unit D211, Winter Park, FL 32789
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  /35

  $159,000

  $6K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  3027 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Step into this beautifully renovated two-story condo offering the perfect blend of modern style and everyday comfort. Featuring 2 spacious bedrooms and 2.5 updated bathrooms, this home has been thoughtfully upgraded from top to bottom. The first floor showcases elegant marble-look tile flooring, creating a sleek and durable living space ideal for both relaxing and entertaining. Upstairs, you’ll

  Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

  3027 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  /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
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  /37

  $279,900

  $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,236 Sq Ft

  5210 Lazy Oaks Dr, Winter Park, FL 32792

  Virtually Staged. DISCOVER THE SERENE BEAUTY OF THIS WINTER PARK TWO-STORY TOWNHOME! Located in the SOUGHT-AFTER Lazy Oaks community. Blending contemporary style with everyday convenience, GORGEOUS 2-BEDROOM, 2.5-BATHROOM, 1-CAR GARAGE HOME. From the moment you step inside, you’ll be greeted by an OPEN-CONCEPT LIVING AREA filled with NATURAL LIGHT, creating a warm and inviting atmosphere. Cook

  Karen Sweat IHOME REALTY FL LLC

  5210 Lazy Oaks Dr, 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
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  /42

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  2305 Sun Valley Cir, Winter Park, FL 32792

  Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas.

  Ryan Barnett MARKET CONNECT REALTY LLC

  2305 Sun Valley Cir, Winter Park, FL 32792
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  /24

  $134,900

  • 2 Beds
  • 2 Baths
  • 756 Sq Ft

  7302 Swallow Run Unit 7302, Winter Park, FL 32792

  Welcome to 7302 Swallow Run! This beautiful, move-in ready 2-bedroom, 2-bathroom condo offers the highly sought-after first-floor location and a prime setting directly across from both community pools. Nestled within the desirable Whisperwood community in Winter Park, this single-story condo features a wonderful split-bedroom floor plan and an open living concept with plenty of space to relax and

  Katherine Nguyen THE NAVY HOUSE

  7302 Swallow Run Unit 7302, Winter Park, FL 32792
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  /21

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  2918 Antique Oaks Cir Unit 25, Winter Park, FL 32792

  2 Bedroom 2 bath condo 1 block south of University Blvd great location for UCF or Full Sail University this quiet neighborhood has tree lined streets and a community pool. Great investment opportunity for parents looking to house their and rent out after they graduate.

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  2918 Antique Oaks Cir Unit 25, Winter Park, FL 32792
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  /13

  $138,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 796 Sq Ft

  1000 S Semoran Blvd Unit 306, Winter Park, FL 32792

  Virtually Staged. Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 306, Winter Park, FL 32792
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  /24

  $175,000

  $15K PRICE DROP

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

  7327 Forest Hill Ct Unit 223, Winter Park, FL 32792

  Looking for the perfect starter home or great little rental. This townhhouse-style condo with 2 master suites. With granite countertop on kitchen. Open floor plan, inside laundry closet off the dinette. Tile flooring downstairs and carpet up, additional exterior storage room and fenced in patio. garbage. Hidden Oaks community features community pool & fenced playground area. Zoned for Winter Park

  Leda Vaz M L VAZ REALTY INC

  7327 Forest Hill Ct Unit 223, Winter Park, FL 32792
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  /41

  $285,000

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft

  283 Sandlewood Trail Unit 3, Winter Park, FL 32789

  Virtually Staged. MOVE IN READY in Winter Park with nearly $30,000 in recent upgrades and improvements! This beautifully updated 2 bedroom, 2.5 bathroom condo in Sandlewood Creek offers a bright, open layout, conservation views and a quiet community setting in an incredibly convenient location.The main level features a spacious open living and dining area with plenty of room to create

  Crystal Adams RE/MAX INNOVATION

  283 Sandlewood Trail Unit 3, Winter Park, FL 32789
• 

  

  /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
• 

  

  /15

  $105,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 796 Sq Ft

  1000 S Semoran Blvd Unit 302, Winter Park, FL 32792

  Virtually Staged. 2018 AC, ROOF REPLACED BY HOA WITHIN THE LAST 3 YEARS ***Welcome to this exceptionally well-maintained 1-bedroom, 1-bathroom condominium ideally located in Winter Park! Lovingly cared for by its longtime owner, this home offers a wonderful combination of comfort, functionality, and convenience. *WASHER AND DRYER LOCATED IN UNIT* Inside, you'll find a spacious, thoughtfully

  Amaal Barakat KELLER WILLIAMS ADVANTAGE III

  1000 S Semoran Blvd Unit 302, Winter Park, FL 32792
• 

  

  /30

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  5108 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light.The spacious living room features a beautiful brick fireplace and sliding glass door

  Steven Koleno BEYCOME OF FLORIDA LLC

  5108 Lazy Oaks Dr, Winter Park, FL 32792
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  /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
• 

  

  /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
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  /47

  $189,900

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  222 Lewfield Cir, Winter Park, FL 32792

  One or more photos was virtually staged. This 2 Bedroom, 2 Bath, 953 SF Winter Park condo in the amazing Stratford community offers a comfortable, functional floor plan complemented by fresh interior paint, updated flooring, and a 2026 HVAC system. The spacious living area features a ceiling fan and sliding glass doors that bring in natural light and open to a covered balcony, creating an easy

  Joshua Neudigate MARKET CONNECT REALTY LLC

  222 Lewfield Cir, Winter Park, FL 32792
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  /25

  $269,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 242, Winter Park, FL 32789

  Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll

  Alex Scures COLONIALTOWN REALTY

  151 N Orlando Ave Unit 242, Winter Park, FL 32789
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  /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
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  /13

  $100,000

  • 1 Bed
  • 1 Bath
  • 785 Sq Ft

  173 Scottsdale Square, Winter Park, FL 32792

  INVESTMENT OPPORTUNITY! Add this well-maintained condo to your investment portfolio or make it your next income-producing property. Featuring a functional layout, neutral finishes, easy-care flooring, stainless-steel appliances, and plenty of natural light, this unit offers an attractive and low-maintenance option for investors. The comfortable living area flows to the outdoor space through

  Paola Jimenez AXEN REALTY, LLC

  173 Scottsdale Square, Winter Park, FL 32792
• 

  

  /20

  $150,000

  • 2 Beds
  • 2 Baths
  • 1,063 Sq Ft

  7453 Daniel Webster Dr Unit 5, Winter Park, FL 32792

  Welcome to this beautifully updated 2-bedroom, 2-bathroom condo in Winter Park. The home features a newer HVAC system installed in 2021, repiped plumbing completed in 2021, and a new electrical panel installed in 2021. One bedroom provides direct access to the patio, offering convenient outdoor space. The property is conveniently located near UCF, shopping, dining, major roadways, Downtown

  Laila Dkhissi LA ROSA REALTY PREMIER LLC

  7453 Daniel Webster Dr Unit 5, Winter Park, FL 32792
• 

  

  /21

  $140,000

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792

  Townhouse opportunity—ideal for either personal residence or investment—featuring 2 bedrooms and 2.5 bathrooms. Conveniently located near supermarkets, shops, universities, and public transportation. At closing, all outstanding HOA special assessments will be paid off. The Townhome is rent $1,600. The unit is located in Winter Park Area HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

  Daiana Garcia Medrano NAIM REAL ESTATE LLC

  3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792
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  /34

  $159,000

  $6K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,108 Sq Ft

  7300 Daniel Webster Dr Unit 7, Winter Park, FL 32792

  Welcome home to this stunningly updated two-story condo that perfectly combines modern elegance with everyday comfort. Featuring 2 spacious bedrooms and 2.5 baths, this home has been thoughtfully updated with high-end designer finishes throughout. The first floor showcases stunning new tile flooring in a striking neutral pattern, creating a modern and inviting living space, while the second floor

  Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

  7300 Daniel Webster Dr Unit 7, Winter Park, FL 32792
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  /63

  $249,000

  $10K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 1,328 Sq Ft

  1713 Gulfview Dr Unit 435B, Maitland, FL 32751

  Welcome home to this beautifully updated two-story condo nestled in one of Maitland's most established communities, where lush mature landscaping, winding sidewalks, a community pool, lake access and a private dock create a peaceful setting just minutes from some of Central Florida's favorite restaurants, shopping and entertainment. Enjoy easy access to Enzian Theater, Winter Park Village, Trader

  Becki Douglas MAINFRAME REAL ESTATE

  1713 Gulfview Dr Unit 435B, Maitland, FL 32751
• 

  

  /14

  $239,000

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft

  1711 Grove St Unit 519, Maitland, FL 32751

  Virtually Staged. Rare updated 2/2 | | Top-Rated SchoolsWelcome to peaceful Park Lake Villas! This fully updated single-story condo has spacious living, major energy-efficient upgrades, and an unbeatable location zoned for Dommerich Elementary, Maitland Middle, and Edgewater High.Key Features Brand New A/C (2025) & Updated R-38 Insulation Low-E Thermal Pane Windows & Slider Door replaced

  Steven Koleno BEYCOME OF FLORIDA LLC

  1711 Grove St Unit 519, Maitland, FL 32751

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