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

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  /33

  $248,900

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft

  193 Lewfield Cir, Winter Park, FL 32792

  Welcome to 193 Lewfield Cir, Winter Park, FL 32792, a spacious two-story end-unit townhome offering 2 bedrooms, 2.5 bathrooms, and 1,300 square feet of comfortable living space in the Stratford A Winter Park Condo community. This 2-bed townhouse in Winter Park features an open floorplan with a large living and dining area, updated wood-look flooring throughout the main living spaces and bedrooms,

  Efrain Reyes COLDWELL BANKER REALTY

  193 Lewfield Cir, Winter Park, FL 32792
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• 

  

  

  /18

  $135,000

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

  1695 Lee Rd Unit A116, Winter Park, FL 32789

  Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining.Each bedroom is equipped with a ceiling

  Bianca Pierre REAL BROKER, LLC

  1695 Lee Rd Unit A116, Winter Park, FL 32789
• 

  

  

  /17

  $174,900

  $24K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792

  Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!

  Christopher Franqui PROPERTY OUTLET INTERNATIONAL

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792
• 

  

  

  /22

  $154,900

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

  1695 Lee Rd Unit A101, Winter Park, FL 32789

  Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

  Daniel Zheng CINO INTERNATIONAL INC

  1695 Lee Rd Unit A101, Winter Park, FL 32789
• 

  

  

  /31

  $280,000

  • 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 into the

  Joyce Gary PAINE-ANDERSON PROPERTIES, INC

  5184 Lazy Oaks Dr, Winter Park, FL 32792
• 

  

  /28

  $108,000

  $7K 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
• 

  

  /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
• 

  

  /15

  $88,999

  $1K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft

  1695 Lee Rd Unit B108, Winter Park, FL 32789

  This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and everyday conveniences, it offers comfort, convenience, and excellent value.The kitchen comes fully equipped with a refrigerator, stove, dishwasher, and microwave, and the unit also includes a washer and dryer for added

  Brandy Ray LOKATION

  1695 Lee Rd Unit B108, Winter Park, FL 32789
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  /8

  $109,500

  • 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
• 

  

  /27

  $164,999

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 Saint Andrews Blvd Unit 704, Winter Park, FL 32792

  Excellent opportunity in the heart of Central Florida! Welcome to this charming 1-bedroom, 1-full-bath condominium located in the desirable Four Seasons Condominiums of Winter Park. Step inside to a spacious living area that flows seamlessly into the dining and kitchen spaces, creating a comfortable and functional layout perfect for everyday living or entertaining. The primary bedroom features a

  Veronica Figueroa EXP REALTY LLC

  200 Saint Andrews Blvd Unit 704, Winter Park, FL 32792
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  /37

  $289,900

  • 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

  NEW PRICE!!! 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

  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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  /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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  /21

  $230,000

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

  200 Saint Andrews Blvd Unit 2904, Winter Park, FL 32792

  WHAT A GEM! Tucked away in a private, sought after community and so conveniently located in breathtaking Winter Park. Here’s a beautifully maintained, upgraded and move-in ready home. With 2 large bedrooms and 1.5 bathrooms, this unit spans 1,219 square feet, providing an ideal space for cozy living. Enjoy the benefits of a peaceful and friendly community, with well-manicured grounds and a

  Sharon Mikol MAINFRAME REAL ESTATE

  200 Saint Andrews Blvd Unit 2904, 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
• 

  

  /41

  $285,000

  Coming Soon

  • 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 separate

  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

  $149,500

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  262 Lewfield Cir, Winter Park, FL 32792

  Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is everything

  Carl Buck Keller Williams Realty Fort Myers and the Islands

  262 Lewfield Cir, Winter Park, FL 32792
• 

  

  /3

  $179,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  Unlisted Address

  LOCATION! Welcome to this beautifully maintained 2-bedroom, 2-bathroom second -floor-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in august 2026. A fully renovated with new flooring, updated fixtures. The kitchen has also been, stone countertops, and a full suite of stainless steel appliances. Located near the University of Central

  Gloria Florez LA ROSA REALTY PREMIER LLC

  Unlisted Address
• 

  

  /15

  $115,000

  • 1 Bed
  • 1 Bath
  • 796 Sq Ft

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

  Virtually Staged. ***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 designed layout featuring a generous living area, an

  Amaal Barakat KELLER WILLIAMS ADVANTAGE III

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

  

  /27

  $89,000

  $26K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft

  1695 Lee Rd Unit B210, Winter Park, FL 32789

  This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

  giuseppina moriconi GM SUNSHINE REALTY LLC

  1695 Lee Rd Unit B210, Winter Park, FL 32789
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  /6

  $185,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4756 Tangerine Ave Unit 4756, Winter Park, FL 32792

  Discover the potential of this 2-bedroom, 2-bath end-unit condominium located in the desirable Wrenwood Condominium community in Winter Park, Florida. Offering 1,058 square feet of living space, this home presents an excellent opportunity for buyers seeking affordability, convenience, and the chance to add their own personal style. Inside, you'll find ceramic tile flooring throughout, knockdown

  Ada Sanchez HOME BUYER HELPER REAL ESTATE LLC

  4756 Tangerine Ave Unit 4756, 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
• 

  

  /29

  $148,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  3014 Antique Oaks Cir Unit 120, Winter Park, FL 32792

  Great location! Light and bright, MOVE -IN READY! 1 bedroom, 1 bathroom on the 2nd floor in Parkview Village Condo community. Spacious living area with vaulted ceiling that allows natural light throughout the day. Tile flooring throughout, laundry closet with washer and dryer! Screened patio with relaxing views of green space. The community is centrally located near Full Sail University, UCF,

  Linda Jaramillo DON ASHER & ASSOCIATES, INC.

  3014 Antique Oaks Cir Unit 120, Winter Park, FL 32792
• 

  

  /26

  $149,000

  $16K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 232, Winter Park, FL 32789

  LAKEFRONT living just steps from the shore of 239-acre, spring-fed Lake Killarney! Welcome to Lakeside Manor and this charming second-floor end-unit condo offering partial lake views, private lake access, and an ideal blend of comfort and convenience.This 1-bedroom, 1-bath unit features a bright and inviting layout with luxury vinyl plank flooring throughout the main living areas,

  Wendy Rodriguez COLDWELL BANKER REALTY

  2500 Lee Rd Unit 232, 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
• 

  

  /20

  $267,000

  $12K PRICE DROP

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

  2317 Sun Valley Cir, Winter Park, FL 32792

  Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant,

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  2317 Sun Valley Cir, Winter Park, FL 32792
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  /32

  $245,000

  Open Sun 1PM - 5PM $24K PRICE DROP

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

  2383 Sun Valley Cir, Winter Park, FL 32792

  Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance

  Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

  2383 Sun Valley Cir, Winter Park, FL 32792
• 

  

  /20

  $249,900

  • 2 Beds
  • 2.5 Baths
  • 1,611 Sq Ft

  7487 Canford Ct Unit 5, Winter Park, FL 32792

  OWNER FINANCE may be available with down payment. Unique 4 Bedroom 3 bath unit. Perfect for investors looking to rent to college attendees at UCF and surrounding or for larger families needing 4th bedroom. Lots of upgrades including 2 new bathrooms, new laundry room, new flooring and lots of new paint. Brand new AC system installed in 2025 and hot water heater in 2022. Granite counters, stainless

  Christopher Jordan KINGS REALTY & PROPERTY MGMT.

  7487 Canford Ct 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
• 

  

  /17

  $164,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

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

  Perfect for Investor or Owner Occupied. Why pay rent when you can own. This beautifully maintained 2-bedroom, 2-bathroom first-floor unit boasts an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. Includes a full suite of Whirlpool stainless steel appliances, including Refrigerator, Microwave, Flat top Range/oven, Dishwasher. Additionally a

  Hitesh Khatri CFRP REALTY LLC

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

  

  /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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