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

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  /21

  $122,990

  $2K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  1000 S Semoran Blvd Unit 715, Winter Park, FL 32792

  Prime location meets exceptional value in the highly sought-after Winter Park area! This first-floor condo offers unbeatable convenience and strong investment potential in one of Central Florida’s most desirable communities. Ideally positioned just steps from the community pool and on-site laundry facilities, it provides easy, everyday access to key amenities. Whether you’re a first-time

  Lety Morales LPT REALTY, LLC

  1000 S Semoran Blvd Unit 715, Winter Park, FL 32792
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  /22

  $184,999

  $45K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792

  PRICE REDUCED, Seller motivated. Condo in Winter Park, FL Welcome to 2923 Antique Oaks Cir, Unit 39 — a beautifully updated 1,105 sq. ft. first-floor condo offering 2 bedrooms, 2 bathrooms, and modern upgrades throughout. Located in the highly sought-after Winter Park School District, this property combines comfort, style, and convenience. Property Highlights: Size & Layout: Spacious 1,105 square

  Michell Carrasquero GLOBALWIDE REALTY LLC

  2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792
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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

  $109,900

  • 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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  /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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  /42

  $194,900

  $5K PRICE DROP

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

  639 Saint Johns Ct Unit 639, Winter Park, FL 32792

  Freshly painted 2 Bedroom/2 Bath townhouse-style condo with no neighbors above or below, backing up to a peaceful pond & community amenities. The upstairs/downstairs split-bedroom floor plan offers privacy - ideal for roommates or families. The bright living area features soaring cathedral ceilings, a corner fireplace, and access to a partially covered patio, perfect for entertaining or BBQs.

  Adam Eisen PLATINUM REALTY GROUP FLORIDA INC

  639 Saint Johns Ct Unit 639, Winter Park, FL 32792
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  /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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  /49

  $175,000

  $55K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 208, Winter Park, FL 32789

  This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water, cable and internet are included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents

  Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 208, Winter Park, FL 32789
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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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  /18

  $180,000

  $10K 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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  /15

  $199,000

  $29K PRICE INCREASE

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

  7471 Canford Ct Unit 19, Winter Park, FL 32792

  This 2 bedroom, 1.5 bathroom condo features a townhome style layout with spacious living areas. Recent enhancements include the removal of dated laminate to reveal ceramic tile flooring throughout the main level, installation of stylish luxury vinyl plank on the upper level, new carpeting on the staircase and landing, and a full interior repaint. In addition, the sliding glass doors were

  Karen Salter IAD REAL ESTATE

  7471 Canford Ct Unit 19, Winter Park, FL 32792
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  /15

  $154,900

  $4K 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
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  /27

  $98,000

  $17K 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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  /52

  $224,999

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool &

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
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  /34

  $284,900

  $45K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you

  Mathew Kelly TURN-KEY MOVES REALTY

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789
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  /5

  $195,000

  • 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
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  /26

  $164,900

  • 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
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  /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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  /19

  $259,000

  $20K 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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  /43

  $290,000

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft

  700 Melrose Ave Unit H4, Winter Park, FL 32789

  Welcome to this charming ground-floor condo, nestled in the highly sought-after 55+ community of Winter Park Gardens. This TWO-bedroom, TWO-bathroom condo offers a perfect blend of comfort, and stunning picturesque views. The open layout seamlessly connects the kitchen to the living area, and into to the sunroom/Florida room. This space is perfect for enjoying the tranquil views, offering a

  Rob Rallo TAL BUSIDAN PA

  700 Melrose Ave Unit H4, Winter Park, FL 32789
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  /21

  $130,000

  • 2 Beds
  • 1 Bath

  1695 Lee Rd Unit B204, Winter Park, FL 32789

  2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New tile floor was installed and freshly painted. Long term tenant moved out recently and on the market for sale and for rent as well. Enjoy a highly walkable location close to Whole Foods, LA Fitness, Winter Park Village, shopping, dining, and more. Community amenities include a

  Mauricio Toro MTRE GROUPE LLC

  1695 Lee Rd Unit B204, Winter Park, FL 32789
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  /24

  $182,900

  $67K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  205 Lewfield Cir Unit 205, Winter Park, FL 32792

  MOTIVATED SELLER! Wonderful! Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a BBQ with family and friends at the community clubhouse or enjoy

  Eimi Moreno Carrera LPT REALTY, LLC

  205 Lewfield Cir Unit 205, Winter Park, FL 32792
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  /22

  $235,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  2712 Tortoise Cove, Winter Park, FL 32792

  Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restaurants. New roof installed 2025. Don't hesitate to come view!

  Lisa Wright CHARLES RUTENBERG REALTY ORLANDO

  2712 Tortoise Cove, Winter Park, FL 32792
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  /26

  $169,900

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  7336 Forest Hill Ct Unit 240, Winter Park, FL 32792

  Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained END unit is move in ready: two-story 2 Bedrooms 1.5 Bath townhome style condo with two designated parking spaces. Upon entering you are greeted with a large living and dining room space. Tiled floors, tons of light, neutral colors, wet bar area are a few of the amazing qualities of

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  7336 Forest Hill Ct Unit 240, Winter Park, FL 32792
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  /17

  $99,900

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft

  1000 S Semoran Blvd Unit 603, Winter Park, FL 32792

  Investor Special with Endless Potential in Winter Park! Opportunity knocks with this first-floor 2-bedroom, 2-bath condominium located in a great location in Winter Park. Whether you’re looking for your next renovation project, income-producing rental, or affordable entry into the Winter Park market, this property offers exceptional upside potential. Featuring a functional floor plan, spacious

  Cyndy Valence VALENCE REALTY GROUP

  1000 S Semoran Blvd Unit 603, Winter Park, FL 32792
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  /32

  $250,000

  Open Sat 1PM - 4PM $19K 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
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  /34

  $229,900

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

  Unlisted Address

  Welcome to this spacious and well-maintained two-story townhome nestled in the highly desirable Four Seasons community in the heart of Winter Park. Offering 2 bedrooms, 1.5 bathrooms, and 1,219 square feet of comfortable living space, this home features a functional floor plan designed for both everyday living and entertaining. The spacious kitchen offers abundant cabinetry, generous countertop

  Laila Ocampo COMPLETE REALTY STORE, LLC

  Unlisted Address
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  /32

  $179,900

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

  3381 Cedar Springs Place Unit 151, Winter Park, FL 32792

  Move right in and enjoy low-maintenance living in the desirable Hidden Oaks community of Winter Park. This meticulous maintained and nicely updated 2-bedroom, 2.5-bath townhome-style condo features two spacious primary suites, each with its own private en-suite bathroom, offering a flexible floor plan and exceptional functionality. The open and inviting layout includes an oversized great room,

  Alie Gattis MAINFRAME REAL ESTATE

  3381 Cedar Springs Place Unit 151, Winter Park, FL 32792
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  /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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  /16

  $157,900

  $1K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792

  Virtually Staged. Welcome to this inviting 2-bedroom, 2-bathroom condo located in the desirable Lancelot at Winter Park community, offering the perfect blend of comfort and convenience for investors, first-time buyers, or anyone seeking low-maintenance living. This well-appointed unit features an open and airy layout with abundant natural light, seamlessly connecting the living and dining areas

  Christina Munkberg COLDWELL BANKER REALTY

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792

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