74

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

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  • 2475 Tahoe Cir, Winter Park, FL 32792
    2475 Tahoe Cir, Winter Park, FL 32792
    2475 Tahoe Cir, Winter Park, FL 32792
    /29

    $278,000

    • 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
  • 1695 Lee Rd Unit E103, Winter Park, FL 32789
    1695 Lee Rd Unit E103, Winter Park, FL 32789
    1695 Lee Rd Unit E103, Winter Park, FL 32789
    /24

    $129,900

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 881 Sq Ft

    1695 Lee Rd Unit E103, Winter Park, FL 32789

    Virtually Staged. Virtually Staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the condo, you're greeted by a bright and spacious living area,

    Agent Photo

    Jason Price

    RE/MAX SELECT GROUP

    1695 Lee Rd Unit E103, Winter Park, FL 32789
  • 1500 Gay Rd Unit 17D, Winter Park, FL 32789
    1500 Gay Rd Unit 17D, Winter Park, FL 32789
    1500 Gay Rd Unit 17D, Winter Park, FL 32789
    /47

    $239,500

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 17D, Winter Park, FL 32789

    ANOTHER PRICE ADJUSTMENT! AMAZING VALUE!!!Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 17D, Winter Park, FL 32789
  • 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
  • 1500 Gay Rd Unit 20D, Winter Park, FL 32789
    1500 Gay Rd Unit 20D, Winter Park, FL 32789
    1500 Gay Rd Unit 20D, Winter Park, FL 32789
    /22

    $258,000

    $4K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 20D, Winter Park, FL 32789

    LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 20D, 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

    $210,000

    $20K 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, Covered

    Agent Photo

    Miranda Azer

    PARKVIEW REAL ESTATE

    7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
  • 2433 Grand Teton Cir Unit 112433, Winter Park, FL 32792
    2433 Grand Teton Cir Unit 112433, Winter Park, FL 32792
    2433 Grand Teton Cir Unit 112433, Winter Park, FL 32792
    /31

    $259,000

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

    2433 Grand Teton Cir Unit 112433, Winter Park, FL 32792

    Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The

    Agent Photo

    Alexis Jacobsen

    EXP REALTY LLC

    2433 Grand Teton Cir Unit 112433, 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

    $169,900

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 732 Sq Ft

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

    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 Built-in

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 4D, Winter Park, FL 32789
  • 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. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax

    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
  • 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

    $229,900

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

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

    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 Sure to Impress with

    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 dining areas—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 tile

    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
  • 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
    /41

    $185,000

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

    7450 Wynnewood Square Unit 189, Winter Park, FL 32792

    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 upstairs boasts beautiful

    Kimberly King GLOBAL PROPERTIES SALES & MGMT

    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 floor

    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
  • 252 Scottsdale Square Unit 252, Winter Park, FL 32792
    252 Scottsdale Square Unit 252, Winter Park, FL 32792
    252 Scottsdale Square Unit 252, Winter Park, FL 32792
    /3

    $85,000

    • 2 Beds
    • 1.5 Baths
    • 1,085 Sq Ft

    252 Scottsdale Square Unit 252, Winter Park, FL 32792

    Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

    Lisa Wright CHARLES RUTENBERG REALTY ORLANDO

    252 Scottsdale Square Unit 252, Winter Park, FL 32792
  • 291 Lewfield Cir Unit 291, Winter Park, FL 32792
    291 Lewfield Cir Unit 291, Winter Park, FL 32792
    291 Lewfield Cir Unit 291, Winter Park, FL 32792
    /32

    $144,000

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    291 Lewfield Cir Unit 291, Winter Park, FL 32792

    One of the best patio views in this community. Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system,

    Barbara Coy WATSON REALTY CORP

    291 Lewfield Cir Unit 291, Winter Park, FL 32792
  • 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
  • 262 Lewfield Cir Unit 262, Winter Park, FL 32792
    262 Lewfield Cir Unit 262, Winter Park, FL 32792
    262 Lewfield Cir Unit 262, Winter Park, FL 32792
    /36

    $149,500

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

    262 Lewfield Cir Unit 262, 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 fixtures 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

    Drew Bishop KW FLORIDA LIVING

    262 Lewfield Cir Unit 262, 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

    $249,900

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

    2500 Lee Rd Unit 104, Winter Park, FL 32789

    At under $250,000, this renovated 2-bedroom, 2-bath condominium is truly move-in ready. The heart of the home is the custom kitchen (2025), which features soft-close cabinetry with a built-in refrigerator surround, matching energy-efficient appliances, quartzite countertops, white granite sink, and antique brass hardware. Additional updates include vinyl flooring throughout, renovated primary

    Stephen Hachey REALTY OF RIVERVIEW LLC

    2500 Lee Rd Unit 104, Winter Park, FL 32789
  • 3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
    3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
    3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
    /26

    $139,500

    $36K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 749 Sq Ft

    3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

    PRICE IMPROVEMENT!! What better value! Accepting offers. Clean, Crisp and Fresh! Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a

    Cassandra Kelly Flores COLDWELL BANKER REALTY

    3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
  • 1695 Lee Rd Unit E204, Winter Park, FL 32789
    1695 Lee Rd Unit E204, Winter Park, FL 32789
    1695 Lee Rd Unit E204, Winter Park, FL 32789
    /27

    $108,000

    $22K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 881 Sq Ft

    1695 Lee Rd Unit E204, 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 E204, 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

    $244,900

    $5K 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
  • 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
  • 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

    $255,000

    • 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
  • 303 Scottsdale Square, Winter Park, FL 32792
    303 Scottsdale Square, Winter Park, FL 32792
    303 Scottsdale Square, Winter Park, FL 32792
    /3

    $80,000

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft

    303 Scottsdale Square, Winter Park, FL 32792

    Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to seethis one before it is gone!

    Lisa Wright CHARLES RUTENBERG REALTY ORLANDO

    303 Scottsdale Square, 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
  • 311 E Morse Blvd Unit 6-12, Winter Park, FL 32789
    311 E Morse Blvd Unit 6-12, Winter Park, FL 32789
    311 E Morse Blvd Unit 6-12, Winter Park, FL 32789
    /20

    $275,000

    • 1 Bed
    • 1 Bath
    • 570 Sq Ft

    311 E Morse Blvd Unit 6-12, Winter Park, FL 32789

    Welcome to easy living in the heart of Winter Park. Located just two blocks from Park Avenue, this studio condo puts you right in the center of it all—award-winning restaurants, boutique shopping, coffee shops, museums, and the iconic Winter Park boat tour are all just steps away. Situated on the third floor of Building 6 with convenient elevator access, this light-filled unit offers a

    Andrea Parra FANNIE HILLMAN & ASSOCIATES

    311 E Morse Blvd Unit 6-12, Winter Park, FL 32789
  • 1250 S Denning Dr Unit 109, Winter Park, FL 32789
    1250 S Denning Dr Unit 109, Winter Park, FL 32789
    1250 S Denning Dr Unit 109, Winter Park, FL 32789
    /27

    $190,000

    • 1 Bed
    • 1 Bath
    • 658 Sq Ft

    1250 S Denning Dr Unit 109, Winter Park, FL 32789

    Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright, clean interior with tasteful finishes and a functional layout designed for comfortable, low-maintenance living. A spacious screened porch overlooks a serene courtyard, creating the perfect spot to enjoy your morning coffee or

    Randy Wilson FAIRBANKS REALTY

    1250 S Denning Dr Unit 109, Winter Park, FL 32789
  • 311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
    311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
    311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
    /25

    $279,000

    $110K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 570 Sq Ft

    311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

    Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

    Mary Colton FANNIE HILLMAN & ASSOCIATES

    311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
  • 263 Scottsdale Square Unit 263, Winter Park, FL 32792
    263 Scottsdale Square Unit 263, Winter Park, FL 32792
    263 Scottsdale Square Unit 263, Winter Park, FL 32792
    /3

    $80,000

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft

    263 Scottsdale Square Unit 263, Winter Park, FL 32792

    Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

    Lisa Wright CHARLES RUTENBERG REALTY ORLANDO

    263 Scottsdale Square Unit 263, Winter Park, FL 32792
  • 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
    /22

    $290,000

    $8K 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
  • 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

    This is one of the largest floor plans in the community. Two bedrooms, two bathrooms, with a loft that can be used as a third bedroom, home office, or gym. Welcome to the well-established and well-maintained community of Cedarwood Village, located in highly desirable Winter Park! The TREE-LINED STREETS lead you to this two-story, BLOCK-CONSTRUCTED condominium offering 1,669 square feet of

    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

    $184,900

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

    2500 Lee Rd Unit 222, Winter Park, FL 32789

    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 lakefront gazebo. Perfectly located just minutes from the

    Christine Bouchard HOMESMART

    2500 Lee Rd Unit 222, Winter Park, FL 32789
  • 2503 Tahoe Cir, Winter Park, FL 32792
    2503 Tahoe Cir, Winter Park, FL 32792
    2503 Tahoe Cir, Winter Park, FL 32792
    /20

    $225,000

    $25K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,173 Sq Ft

    2503 Tahoe Cir, Winter Park, FL 32792

    This charming one story condo is located in the desirable Cedarwood Village. This unique home boasts an open layout that is different from many others in the community. The home showcases engineered hardwood floors, skylights and wonderful natural light. The kitchen provides ample cabinet space, granite counters, built-in wine rack and beautiful custom tile work. The kitchen overlooks the dining

    Beth Logullo KELLER WILLIAMS WINTER PARK

    2503 Tahoe Cir, 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 $196,191, and there are 74 condo listings available for sale.

Condo Price Trends

Median Condo Price
$196,191
Median 1-Bedroom Condo Price
$157,500
Median 2-Bedroom Condo Price
$205,000
Median 3-Bedroom Condo Price
$275,000
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