Winter Park, FL Homes for Sale under $400,000

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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
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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

  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
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  /23

  $399,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft

  1092 Eastbrook Blvd, Winter Park, FL 32792

  Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled,

  Eva Firios JC FLORIDA REALTY LLC

  1092 Eastbrook Blvd, Winter Park, FL 32792
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  /25

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  2657 Exuma Way, Winter Park, FL 32792

  Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite

  Jerry Agan HAVEN PROPERTY GROUP LLC

  2657 Exuma Way, Winter Park, FL 32792
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  /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
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  /15

  $110,000

  $5K PRICE DROP

  • 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
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  /42

  $390,000

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  2512 Eastbrook Blvd, Winter Park, FL 32792

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting front porch, the perfect place to relax, enjoy conversations with friends, and greet neighbors passing by.Inside, the home features recently painted interiors and new laminate flooring in the bedrooms, creating a fresh and

  Joseph Firmin LPT REALTY, LLC

  2512 Eastbrook Blvd, Winter Park, FL 32792
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  /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
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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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  /20

  $267,000

  $12K PRICE DROP

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

  2317 Sun Valley Cir, Winter Park, FL 32792

  Seller financing at 4.9% APR is available for qualified buyers—an opportunity to start building equity from day one. Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence in the heart of Winter Park. The inviting living room features vaulted ceilings, while the fully equipped open-concept kitchen offers abundant cabinet space for everyday living and entertaining.

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  2317 Sun Valley Cir, 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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  /57

  $399,990

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft

  5503 Albert Dr, Winter Park, FL 32792

  No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof

  Fernando Perez de Armas AXEN REALTY, LLC

  5503 Albert Dr, Winter Park, FL 32792
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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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  /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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  /19

  $299,000

  Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,208 Sq Ft

  2168 Ridge Dr, Winter Park, FL 32792

  Virtually Staged. Prime Winter Park Opportunity – Original Terrazzo Floors, Solid Block Construction & Endless PotentialDiscover an exceptional opportunity to own a classic Winter Park home priced at just $299,000. Situated on a generous 0.20-acre lot, this 3-bedroom, 1-bath concrete block home offers 1,208 square feet of living space and the perfect foundation to create your dream home or

  Dragana Todorovic ENGEL & VOLKERS NEW SMYRNA

  2168 Ridge Dr, Winter Park, FL 32792
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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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  /20

  $365,000

  • 3 Beds
  • 2.5 Baths
  • 1,861 Sq Ft

  7506 Cranes Creek Ct Unit 30, Winter Park, FL 32792

  Beautiful, move in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home provides confort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4th room on the first floor, ideal for a home an office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and

  Sylvia Marchese TRANSCONTINENTAL REALTY GROUP,

  7506 Cranes Creek Ct Unit 30, Winter Park, FL 32792
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  /25

  $395,000

  • 2 Beds
  • 1 Bath
  • 945 Sq Ft

  1812 Janice Ave, Orlando, FL 32803

  This adorable property is located on a quiet dead end street just a block off the Corrine retail and restaurant area. It offers solid concrete block construction, an expanded driveway, beautiful hardwood floors in very good condition, stainless steel appliances in the kitchen, a beautifully renovated bathroom, a fully functional garage and a wonderful living space in the fenced backyard. With its

  Kris Santullo FLORIDA HOME TEAM REALTY LLC

  1812 Janice Ave, Orlando, FL 32803
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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
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  /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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  /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

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