72

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

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  • 2500 Lee Rd Unit 220, Winter Park, FL 32789
    2500 Lee Rd Unit 220, Winter Park, FL 32789
    2500 Lee Rd Unit 220, Winter Park, FL 32789
    /28

    $199,900

    • 2 Beds
    • 1 Bath
    • 851 Sq Ft

    2500 Lee Rd Unit 220, Winter Park, FL 32789

    **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    2500 Lee Rd Unit 220, Winter Park, FL 32789
  • 7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
    /36

    $199,000

    $31K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,578 Sq Ft

    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792

    Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park.Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining,

    Agent Photo

    Miranda Azer

    PARKVIEW REAL ESTATE

    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
  • 2475 Tahoe Cir, Winter Park, FL 32792
    2475 Tahoe Cir, Winter Park, FL 32792
    2475 Tahoe Cir, Winter Park, FL 32792
    /29

    $268,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,295 Sq Ft

    2475 Tahoe Cir, Winter Park, FL 32792

    Turnkey Living in the Heart of Winter Park!Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner.Inside, you'll find a thoughtfully

    Agent Photo

    Sarah Doyer

    COLDWELL BANKER REALTY

    2475 Tahoe Cir, Winter Park, FL 32792
  • 2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
    /22

    $180,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792

    PRICE IMPROVEMENT! TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. A NEW A/C SYSTEM INSTALLED IN 2026 adds extra peace of mind for the next owner. Step inside to find a bright and airy living and dining area with sliding

    Steven Pugh EXP REALTY LLC

    2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
  • 1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
    /5

    $138,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 776 Sq Ft

    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792

    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 items, along with pool

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
  • 1695 Lee Rd Unit D107, Winter Park, FL 32789
    1695 Lee Rd Unit D107, Winter Park, FL 32789
    /2

    $180,000

    • 1 Bed
    • 1 Bath
    • 638 Sq Ft

    1695 Lee Rd Unit D107, Winter Park, FL 32789

    Don't miss out the great opportunity to own a unit in the heart of Winter Park Area. A perfect primary or secondary residence or investment home. Waterfall Cove is a great community with spacious pool, playground and lots of lush landscaping. Easy access to Major Highways a minute from I-4, bike away from Downtown Winter Park, close to major theme parks, major shopping area, restaurant, movie

    Hoover Yap PRIMESTATE REALTY, INC.

    1695 Lee Rd Unit D107, Winter Park, FL 32789
  • 7476 Woodburn Ct Unit 38, Winter Park, FL 32792
    7476 Woodburn Ct Unit 38, Winter Park, FL 32792
    7476 Woodburn Ct Unit 38, Winter Park, FL 32792
    /28

    $170,000

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

    7476 Woodburn Ct Unit 38, Winter Park, FL 32792

    Terrific townhome in the Hidden Oaks community featuring an updated interior and its own private, fenced patio! Step inside to a bright and spacious living/dining area with beautiful wood laminate flooring and a convenient wet bar. The galley-style kitchen includes a breakfast area, along with a laundry closet equipped with a full-size washer and dryer. Upstairs, you'll find two spacious

    Habib Fahs COLDWELL BANKER REALTY

    7476 Woodburn Ct Unit 38, Winter Park, FL 32792
  • 7413 Belle River Ct Unit 3, Winter Park, FL 32792
    7413 Belle River Ct Unit 3, Winter Park, FL 32792
    7413 Belle River Ct Unit 3, Winter Park, FL 32792
    /11

    $214,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft

    7413 Belle River Ct Unit 3, Winter Park, FL 32792

    MOTIVATED SELLER...Welcome To This Beautifully 3 Bedroom, 2.5 Bathroom Condominium Located in the Desirable Hidden Oaks Community. Offering Updated Living Space, This Home Combines Comfort, Style, and an Unbeatable Location. Step Inside to a Spacious and Inviting Family Room Featuring Beautiful Laminate Flooring, Abundant Natural Light, and an Open, Welcoming Atmosphere. The Updated Kitchen Is

    Ivan Tobon OUTLET REALTY

    7413 Belle River Ct Unit 3, Winter Park, FL 32792
  • 2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792
    2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792
    2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792
    /42

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,495 Sq Ft

    2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792

    Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland.This inviting home features a versatile upstairs loft overlooking the living and diningareas—perfect for a home office, fitness space, craft room, or additional guest accommodations.The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops,a glass

    Sheila Mathews COLDWELL BANKER REALTY

    2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792
  • 1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
    /11

    $138,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 776 Sq Ft

    1000 S Semoran Blvd Unit 408, Winter Park, FL 32792

    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 items, along with pool

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
  • 3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
    /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
  • 3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792
    3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792
    3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792
    /21

    $135,000

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

    3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792

    VALUE OPPORTUNITY IN WINTER PARK! Welcome to 3020 Antique Oaks Circle #129, a spacious 2-bedroom, 2-bath FIRST-FLOOR CONDO offering approximately 1,018 square feet in the conveniently located Parkview Village community in Winter Park, FL 32792. If you have been searching for an affordable Winter Park condo, investment property, renovation opportunity, first-floor condo or 2-bedroom condo in

    Cassie Lamoureux KELLER WILLIAMS CLASSIC

    3020 Antique Oaks Cir Unit 129, Winter Park, FL 32792
  • 3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
    3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
    3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
    /11

    $159,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

    Just Reduced $10k!! Priced to sell, already rented, perfect for investor buyer. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. Stainless Appliances, including Refrigerator, Microwave, Flat top Range/oven, Dishwasher, full size front load washer and Dryer in Laundry Closet. Community features a

    Hitesh Khatri CFRP REALTY LLC

    3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
  • 7450 Wynnewood Square Unit 189, Winter Park, FL 32792
    7450 Wynnewood Square Unit 189, Winter Park, FL 32792
    7450 Wynnewood Square Unit 189, Winter Park, FL 32792
    /45

    $170,000

    $15K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft

    7450 Wynnewood Square Unit 189, Winter Park, FL 32792

    ***Price Improvement*** This charming 2-bedroom, 2.5-bathroom townhome style condo offers the perfect blend of comfort and convenience. Enjoy the peace of mind that comes with a new AC (2025), a new roof (2021), newer water heater (2019) and new refrigerator and dishwasher ensuring your home is both energy-efficient and well-maintained. The entire first floor features ceramic tile, while the

    Kimberly King REAL ESTATE PROFESSIONALS SE

    7450 Wynnewood Square Unit 189, Winter Park, FL 32792
  • 5143 Lazy Oaks Dr, Winter Park, FL 32792
    5143 Lazy Oaks Dr, Winter Park, FL 32792
    5143 Lazy Oaks Dr, Winter Park, FL 32792
    /41

    $275,000

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    5143 Lazy Oaks Dr, Winter Park, FL 32792

    Virtually Staged. Quiet Living in the Desirable Lazy Oaks Community of Winter Park.Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA.This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed

    Mindy Machock KELLER WILLIAMS REALTY AT THE PARKS

    5143 Lazy Oaks Dr, Winter Park, FL 32792
  • 2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
    /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
  • 2500 Lee Rd Unit 143, Winter Park, FL 32789
    2500 Lee Rd Unit 143, Winter Park, FL 32789
    2500 Lee Rd Unit 143, Winter Park, FL 32789
    /18

    $130,000

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 143, Winter Park, FL 32789

    It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239

    Carol Wittman PALMANO GROUP RE BROKERAGE LLC

    2500 Lee Rd Unit 143, Winter Park, FL 32789
  • 3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792
    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792
    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792
    /20

    $172,000

    $3K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft

    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792

    Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new

    Jessie Lin SOGO REAL ESTATE SERVICES LLC

    3243 Forest Oaks Ct Unit 117, Winter Park, FL 32792
  • 2500 Lee Rd Unit 104, Winter Park, FL 32789
    2500 Lee Rd Unit 104, Winter Park, FL 32789
    2500 Lee Rd Unit 104, Winter Park, FL 32789
    /23

    $242,400

    $18K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    2500 Lee Rd Unit 104, Winter Park, FL 32789

    Back on market due to buyer circumstances unrelated to property condition. Inspection completed successfully.Price improvement! Move-in ready in Winter Park 32789. This beautifully renovated first-floor 2-bedroom, 2-bath condo features an open layout, custom soft-close cabinetry, high-end quartzite countertops, sleek matching appliances, and stylishly updated bathrooms, including a

    Stephen Hachey FLAT FEE MLS REALTY

    2500 Lee Rd Unit 104, Winter Park, FL 32789
  • 3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
    3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
    3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
    /26

    $179,990

    $30K 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
  • 2463 Grand Teton Cir, Winter Park, FL 32792
    2463 Grand Teton Cir, Winter Park, FL 32792
    2463 Grand Teton Cir, Winter Park, FL 32792
    /19

    $249,000

    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    2463 Grand Teton Cir, Winter Park, FL 32792

    Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point.While the home could

    Jessica Polanco MAINFRAME REAL ESTATE

    2463 Grand Teton Cir, Winter Park, FL 32792
  • 1250 S Denning Dr Unit 127, Winter Park, FL 32789
    1250 S Denning Dr Unit 127, Winter Park, FL 32789
    1250 S Denning Dr Unit 127, Winter Park, FL 32789
    /28

    $245,000

    • 2 Beds
    • 2 Baths
    • 908 Sq Ft

    1250 S Denning Dr Unit 127, Winter Park, FL 32789

    Virtually Staged. Updated two-bedroom, two-bath residence offering 908 square feet and a first-floor, pool-facing location in Mead Garden Condominium. The move-in-ready interior features luxury vinyl plank flooring throughout the living areas and bedrooms, tile flooring in the baths and defined living and dining spaces. The kitchen is appointed with white transitional cabinetry, granite

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    1250 S Denning Dr Unit 127, Winter Park, FL 32789
  • 1500 Gay Rd Unit 3C, Winter Park, FL 32789
    1500 Gay Rd Unit 3C, Winter Park, FL 32789
    1500 Gay Rd Unit 3C, Winter Park, FL 32789
    /26

    $235,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 3C, Winter Park, FL 32789

    NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring

    Heather Frazee FANNIE HILLMAN & ASSOCIATES

    1500 Gay Rd Unit 3C, Winter Park, FL 32789
  • 1695 Lee Rd Unit C206, Winter Park, FL 32789
    1695 Lee Rd Unit C206, Winter Park, FL 32789
    1695 Lee Rd Unit C206, Winter Park, FL 32789
    /24

    $140,000

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft

    1695 Lee Rd Unit C206, Winter Park, FL 32789

    Welcome to this bright and beautifully updated second-floor condo located in one of Winter Park's most desirable communities! This 2-bedroom, 1-bathroom residence offers the perfect blend of comfort, modern upgrades, and an unbeatable location. Updated Kitchen: Features dark wood cabinetry, light quartz counter tops, black and stainless-steel appliances, a modern commercial-style faucet, and an

    Ingrid Garcia Rodriguez INVESTMENT REALTY

    1695 Lee Rd Unit C206, Winter Park, FL 32789
  • 3060 George Mason Ave Unit 12, Winter Park, FL 32792
    3060 George Mason Ave Unit 12, Winter Park, FL 32792
    3060 George Mason Ave Unit 12, Winter Park, FL 32792
    /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
  • 1500 Gay Rd Unit 4D, Winter Park, FL 32789
    1500 Gay Rd Unit 4D, Winter Park, FL 32789
    1500 Gay Rd Unit 4D, Winter Park, FL 32789
    /15

    $164,500

    Open Sun 1PM - 4PM $11K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 732 Sq Ft

    1500 Gay Rd Unit 4D, Winter Park, FL 32789

    ANOTHER PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping!One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional

    Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 4D, Winter Park, FL 32789
  • 2450 Grand Teton Cir Unit 2450, Winter Park, FL 32792
    2450 Grand Teton Cir Unit 2450, Winter Park, FL 32792
    2450 Grand Teton Cir Unit 2450, Winter Park, FL 32792
    /37

    $250,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    2450 Grand Teton Cir Unit 2450, Winter Park, FL 32792

    Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park.This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow

    John Campese CHARLES RUTENBERG REALTY ORLANDO

    2450 Grand Teton Cir Unit 2450, Winter Park, FL 32792
  • 1000 S Semoran Blvd Unit 305, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 305, Winter Park, FL 32792
    1000 S Semoran Blvd Unit 305, Winter Park, FL 32792
    /22

    $115,000

    $14K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 735 Sq Ft

    1000 S Semoran Blvd Unit 305, Winter Park, FL 32792

    Freshly Updated 1-Bedroom Condo – Perfect for Homeowners or Investors! Whether you're looking for your first home, downsizing, or adding to your investment portfolio, this move-in-ready 1-bedroom, 1-bath condominium is an excellent opportunity. Featuring brand-new luxury vinyl plank flooring and a freshly painted interior, this home offers a clean, modern feel throughout. The open-concept floor

    Melissa Vance MAINFRAME REAL ESTATE

    1000 S Semoran Blvd Unit 305, Winter Park, FL 32792
  • 151 N Orlando Ave Unit 142, Winter Park, FL 32789
    151 N Orlando Ave Unit 142, Winter Park, FL 32789
    151 N Orlando Ave Unit 142, Winter Park, FL 32789
    /30

    $199,900

    • 1 Bed
    • 1 Bath
    • 582 Sq Ft

    151 N Orlando Ave Unit 142, Winter Park, FL 32789

    **Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** Welcome home to this beautifully updated, turn-key 1-bedroom, 1-bathroom first-floor condominium located in the highly desirable Lake Killarney Condominiums community. Offering the perfect blend of modern interior updates, stress-free maintenance, and an unbeatable location, this unit is an absolute gem for first-time

    Chris Creegan CREEGAN GROUP

    151 N Orlando Ave Unit 142, Winter Park, FL 32789
  • 151 N Orlando Ave Unit 115, Winter Park, FL 32789
    151 N Orlando Ave Unit 115, Winter Park, FL 32789
    151 N Orlando Ave Unit 115, 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
  • 7454 Wynnewood Square Unit 188, Winter Park, FL 32792
    7454 Wynnewood Square Unit 188, Winter Park, FL 32792
    7454 Wynnewood Square Unit 188, Winter Park, FL 32792
    /29

    $229,000

    • 3 Beds
    • 2.5 Baths
    • 1,151 Sq Ft

    7454 Wynnewood Square Unit 188, Winter Park, FL 32792

    Updated Winter Park Townhome!! If you are looking for LOCATION this is the property for you. This well maintained unit is move in ready: two-story 3 Bedrooms 2.5 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 this

    Manoj Patel APPLE REALTY

    7454 Wynnewood Square Unit 188, Winter Park, FL 32792
  • 151 N Orlando Ave Unit 118, Winter Park, FL 32789
    151 N Orlando Ave Unit 118, Winter Park, FL 32789
    151 N Orlando Ave Unit 118, Winter Park, FL 32789
    /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
  • 2336 Sun Valley Cir Unit BLDG 20, Winter Park, FL 32792
    2336 Sun Valley Cir Unit BLDG 20, Winter Park, FL 32792
    2336 Sun Valley Cir Unit BLDG 20, 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
  • 2500 Lee Rd Unit 222, Winter Park, FL 32789
    2500 Lee Rd Unit 222, Winter Park, FL 32789
    2500 Lee Rd Unit 222, 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
  • 2383 Sun Valley Cir Unit 2383, Winter Park, FL 32792
    2383 Sun Valley Cir Unit 2383, Winter Park, FL 32792
    2383 Sun Valley Cir Unit 2383, Winter Park, FL 32792
    /33

    $234,900

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

    2383 Sun Valley Cir Unit 2383, Winter Park, FL 32792

    Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood

    Carmen Aridas RE/MAX PRIME PROPERTIES

    2383 Sun Valley Cir Unit 2383, Winter Park, FL 32792
  • 602 Trinidad Ct Unit 602, Winter Park, FL 32792
    602 Trinidad Ct Unit 602, Winter Park, FL 32792
    602 Trinidad Ct Unit 602, Winter Park, FL 32792
    /31

    $227,000

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

    602 Trinidad Ct Unit 602, Winter Park, FL 32792

    Virtually Staged. Beautiful Winter Park Condo with Vaulted Ceilings & Private Fenced Patio!Come home to this beautiful and spacious condo featuring vaulted ceilings, abundant natural light, and an open split floor plan designed for comfortable Florida living.The home features 18" tile flooring, neutral paint, ceiling fans, recessed lighting, blinds, a dry bar, and decorative

    Clara Herrera CLARA HERRERA REALTY

    602 Trinidad Ct Unit 602, Winter Park, FL 32792
  • 623 Grenadine Ct, Winter Park, FL 32792
    623 Grenadine Ct, Winter Park, FL 32792
    623 Grenadine Ct, Winter Park, FL 32792
    /36

    $194,900

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft

    623 Grenadine Ct, Winter Park, FL 32792

    PRICE ADJUSTMENT! Welcome to this Desirable Winter Park Villas Condo FIRST FLOOR 2 BEDROOM, 2 FULL BATH, 1037 square feet, featuring NEW AIR CONDITIONING SYSTEM and BRAND NEW CARPET freshly installed! EXCELLENT LOCATION walking or bike riding distance to FULL SAIL UNIVERSITY and easy access to UCF! Ideally located in rear of community with ample open parking. Your spacious Kitchen features ample

    Carolyn Kickhofel COLDWELL BANKER REALTY

    623 Grenadine Ct, Winter Park, FL 32792
  • 193 Lewfield Cir, Winter Park, FL 32792
    193 Lewfield Cir, Winter Park, FL 32792
    193 Lewfield Cir, Winter Park, FL 32792
    /41

    $248,900

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

    193 Lewfield Cir, Winter Park, FL 32792

    Virtually Staged. 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

    Efrain Reyes COLDWELL BANKER REALTY

    193 Lewfield Cir, Winter Park, FL 32792
  • 1695 Lee Rd Unit A101, Winter Park, FL 32789
    1695 Lee Rd Unit A101, Winter Park, FL 32789
    1695 Lee Rd Unit A101, Winter Park, FL 32789
    /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
  • 285 Lewfield Cir Unit 285, Winter Park, FL 32792
    285 Lewfield Cir Unit 285, Winter Park, FL 32792
    285 Lewfield Cir Unit 285, Winter Park, FL 32792
    /25

    $147,000

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    285 Lewfield Cir Unit 285, Winter Park, FL 32792

    Virtually Staged. LOCATION, CONVENIENCE, AND EASY LIVING IN WINTER PARK! This move-in-ready first-floor, 1-bedroom, 1-bath condo features an open living and dining area, wood flooring throughout the main living areas, tile flooring in the primary bedroom, a private screened-in balcony, a fully equipped kitchen, and a stackable washer and dryer. Conveniently located near UCF, Rollins College,

    Millie Soto COLDWELL BANKER REALTY

    285 Lewfield Cir Unit 285, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 2

Florida Orange County

Condos in Winter Park, FL under $300,000

Condo Prices in Winter Park, FL

The median price for condos in Winter Park is $199,900, and there are 72 condo listings available for sale.

Condo Price Trends

Median Condo Price
$199,900
Median 1-Bedroom Condo Price
$150,000
Median 2-Bedroom Condo Price
$208,500
Median 3-Bedroom Condo Price
$330,000
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