25

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

Section Image Section Image
  • /41

    $245,000

    • 2 Beds
    • 2 Baths
    • 956 Sq Ft

    2500 Lee Rd Unit 229, Winter Park, FL 32789

    DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (321) 252-5096

    2500 Lee Rd Unit 229, Winter Park, FL 32789
  • /21

    $261,500

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1500 Gay Rd Unit 24B, Winter Park, FL 32789

    ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

    Janice Erickson

    REALCOM REAL ESTATE SERVICES INC

    (321) 450-8960

    1500 Gay Rd Unit 24B, Winter Park, FL 32789
  • /22

    $262,000

    • 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

    (689) 399-5336

    1500 Gay Rd Unit 20D, Winter Park, FL 32789
  • /33

    $220,000

    • 2 Beds
    • 2 Baths
    • 953 Sq Ft

    225 Lewfield Cir, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 237-3113

    225 Lewfield Cir, Winter Park, FL 32792
  • /19

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft

    7706 Country Place Unit A8, Winter Park, FL 32792

    Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

    Agent Photo

    Carmen Vazquez

    REALTY TECH INC

    (321) 339-0107

    7706 Country Place Unit A8, 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

    Agent Photo

    Manoj Patel

    APPLE REALTY

    (321) 497-0912

    7454 Wynnewood Square Unit 188, Winter Park, FL 32792
  • /26

    $285,000

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

    2401 Sun Valley Cir, Winter Park, FL 32792

    Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and

    Jamie Vanosdol EXP REALTY LLC

    2401 Sun Valley Cir, Winter Park, FL 32792
  • /32

    $269,000

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

    2383 Sun Valley Cir, Winter Park, FL 32792

    You'll fall in love with this charming one-story Winter Park condo located in Cedarwood Village. You can tell how meticulous the owners are as soon as you walk in. This beautiful home has an updated kitchen with granite countertops. Bathrooms and the wet bar in the dining room have also been updated with the same cabinets and granite as the kitchen. There is an eat-in kitchen area with slider

    Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

    2383 Sun Valley Cir, Winter Park, FL 32792
  • /17

    $241,900

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft

    7794 Country Place Unit 2, Winter Park, FL 32792

    Winter Park Clean, updated condo in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features more contemporary open floor plans and high ceilings. Enjoy the One story living. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - private!!** This unit is second

    Tom Bercini CHARLES RUTENBERG REALTY ORLANDO

    7794 Country Place Unit 2, Winter Park, FL 32792
  • /18

    $279,000

    • 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
  • /38

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    5143 Lazy Oaks Dr, Winter Park, FL 32792

    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 plan with an

    Mindy Machock KELLER WILLIAMS REALTY AT THE PARKS

    5143 Lazy Oaks Dr, Winter Park, FL 32792
  • /29

    $225,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 1.5 Baths
    • 1,266 Sq Ft

    200 Saint Andrews Blvd Unit 2901, Winter Park, FL 32792

    Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood

    Amy Turner KELLER WILLIAMS WINTER PARK

    200 Saint Andrews Blvd Unit 2901, Winter Park, FL 32792
  • /25

    $209,900

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

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

    Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated home located in the highly desirable area of Winter Park. Combining comfort, style, and convenience, this property offers a thoughtfully designed open floor plan that creates a seamless flow between the main living spaces, making it ideal for both everyday living and entertaining. The home features two

    Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
  • /36

    $274,900

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    2384 Sun Valley Cir, Winter Park, FL 32792

    Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit condo located within the quaint community of Cedarwood Village with a desirable Winter Park address! This light and bright home features vaulted ceilings in the living room, creating an open and airy feel. The kitchen offers an eat-in space, stainless steel appliances, a convenient pass through to the

    Anna Lohr URBANISTA BROKERS

    2384 Sun Valley Cir, Winter Park, FL 32792
  • /22

    $249,800

    • 3 Beds
    • 2.5 Baths
    • 1,565 Sq Ft

    7117 Swallow Run Unit G-1, Winter Park, FL 32792

    Welcome home! You've found it, a spacious end unit townhome style condo with private 1 car garage with extra storage space. Open floorplan first floor, when you walk in the front door you walk into a huge living room/dining room combination room with views out the back of your private screened patio overlooking a pond. The kitchen features lots of counter space, breakfast bar on the kitchen

    Greg Traub COMPLETE FLORIDA REALTY LLC

    7117 Swallow Run Unit G-1, Winter Park, FL 32792
  • /34

    $299,900

    • 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
  • /25

    $235,000

    • 2 Beds
    • 2 Baths
    • 927 Sq Ft

    205 Lewfield Cir Unit 205, Winter Park, FL 32792

    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 barbeque with family and friends at the community clubhouse or enjoy shopping at the

    Eimi Moreno Carrera LPT REALTY, LLC

    205 Lewfield Cir Unit 205, Winter Park, FL 32792
  • /24

    $209,999

    • 2 Beds
    • 1 Bath
    • 808 Sq Ft

    851 Miles Ave Unit 13, Winter Park, FL 32789

    Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready.As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to

    Eric Campbell LPT REALTY, LLC

    851 Miles Ave Unit 13, Winter Park, FL 32789
  • /15

    $219,900

    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft

    7771 Country Place Unit 7, Winter Park, FL 32792

    Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate

    Ivan Tobon OUTLET REALTY

    7771 Country Place Unit 7, Winter Park, FL 32792
  • /22

    $298,000

    • 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
  • /12

    $295,000

    • 2 Beds
    • 2 Baths
    • 1,669 Sq Ft

    2336 Sun Valley Cir Unit BLDG 20, Winter Park, FL 32792

    PRICED TO SELL!!! This is the largest floorplan in the community. Two bedrooms, two bathrooms, and a loft that you can use as a third bedroom, home office, or gym. Welcome to the established and well-maintained community of Cedarwood Village, located in highly desirable Winter Park! TREE-LINED STREETS lead you to this two-story, 2-bedroom, 2-bath BLOCK-CONSTRUCTED condominium offering 1,669

    Elizabeth Beaudoin PR REAL ESTATE SERVICES

    2336 Sun Valley Cir Unit BLDG 20, Winter Park, FL 32792
  • /23

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft

    7707 Country Place Unit 4, Winter Park, FL 32792

    Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

    Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

    7707 Country Place Unit 4, Winter Park, FL 32792
  • /39

    $234,999

    • 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 enjoy 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
  • /20

    $205,000

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

    3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

    This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

    Manny Celi YOUNG REAL ESTATE

    3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
  • /2

    $210,000

    • 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

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$605,000
Median Townhouse Sale Price
$455,000
Median 2 Bedroom Sale Price
$199,000
Median 1 Bedroom Sale Price
$153,000
Average Price Per Sq Ft
$366
Number of Homes for Sale
305
Last 12 months Home Sales
1,009
Months of Supply
3.60
Median List Price
$529,900
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
1%
How to Buy a Home How to Finance a Home How to Sell a Home