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Homes for Sale in Winter Park, FL with 3-Bedrooms & a Private Pool

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  • /58

    $479,900 Open Sun 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,770 Sq Ft

    3463 Arnel Dr, Winter Park, FL 32792

    Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, along with a two-car garage and extended driveway for additional parking. Located in the established Eastbrook community with no HOA. Key updates include a roof replaced in 2018, solar panels installed in 2020 (fully paid off), water heater replaced

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (689) 356-6537

    3463 Arnel Dr, Winter Park, FL 32792
  • /22

    $464,900

    • 3 Beds
    • 2 Baths
    • 1,715 Sq Ft

    2020 Cocos Ct, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac with no HOA. The home offers a bright

    Julimar Barreiro Pastrana SERHANT

    2020 Cocos Ct, Winter Park, FL 32792
  • /54

    $424,900

    • 3 Beds
    • 2 Baths
    • 2,083 Sq Ft

    1367 Tierra Cir, Winter Park, FL 32792

    Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers

    Brian Bauer SOUTHERN LAND & HOMES

    1367 Tierra Cir, Winter Park, FL 32792
  • /44

    $975,000

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

    1507 Golfside Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    1507 Golfside Dr, Winter Park, FL 32792
  • /53

    $1,750,000

    • 3 Beds
    • 3 Baths
    • 2,488 Sq Ft

    1110 Alabama Dr, Winter Park, FL 32789

    Masterclass in Modern Luxury on Alabama Drive 3 Beds | 3 Baths | Premier Corner Lot | Winter Park, FL Nestled on a premier corner lot at the intersection of Alabama Drive and Palmer Avenue, this fully renovated 3-bedroom, 3-bathroom residence stands as a masterclass in modern luxury. Located in one of Winter Park’s most highly sought-after areas, the property is beautifully framed by the iconic

    Omar Albaba COLDWELL BANKER REALTY

    1110 Alabama Dr, Winter Park, FL 32789
  • /38

    $1,795,000

    • 3 Beds
    • 3.5 Baths
    • 2,399 Sq Ft

    621 Huntington Ave, Winter Park, FL 32789

    Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come together seamlessly. This 3-bedroom, 3.5-bath pool home offers approximately 2,400 square feet of impeccably curated living space, designed for those who appreciate both style and substance. Expertly designed by Morrone Interiors,

    Noelle LeBlanc OLDE TOWN BROKERS INC

    621 Huntington Ave, Winter Park, FL 32789
  • /69

    $2,200,000 Open Sat 1PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 2,433 Sq Ft

    318 Vitoria Ave, Winter Park, FL 32789

    Elegant 1922 Mission Revival home, located in popular College Quarter is a registered historic place in Winter Park, FL. Lifestyle is neighborly/relaxed/pet friendly/enhanced by proximity to Lake Virginia/lakeshore sidewalks/Rollins College campus/downtown Winter Park/Central Park/museums/shops/restaurants/cultural events, most walking distance. College Quarter residents enjoy exclusive use of

    Wendy Brandon KELLER WILLIAMS WINTER PARK

    318 Vitoria Ave, Winter Park, FL 32789
  • /43

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,413 Sq Ft

    512 N Lakemont Ave, Winter Park, FL 32792

    Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

    David Plasencia COLDWELL BANKER REALTY

    512 N Lakemont Ave, Winter Park, FL 32792
  • /38

    $779,000

    • 3 Beds
    • 2 Baths
    • 2,325 Sq Ft

    2919 Bower Rd, Winter Park, FL 32792

    Beautifully updated 3BR/2BA pool home in the highly sought-after Winter Pines community of Winter Park! This move-in ready home offers a bright, open layout with multiple living spaces, perfect for both everyday living and entertaining.The upgraded kitchen features stainless steel appliances, granite countertops, breakfast bar, custom cabinetry, and a farmhouse-style undermount sink, all

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    2919 Bower Rd, Winter Park, FL 32792
  • /28

    $600,000

    • 3 Beds
    • 2 Baths
    • 1,618 Sq Ft

    218 Orange Terrace Dr, Winter Park, FL 32789

    Come see this charming pool home on a desirable corner lot near Lake Killarney in Winter Park. This beautifully maintained mid-century residence features 3 bedrooms and 2 baths with warm wood floors and timeless character throughout. The private, fully fenced backyard is turfed for low maintenance and perfect for relaxing and entertaining. Major updates provide peace of mind, including new

    Arden Magee ANNE ROGERS REALTY GROUP INC

    218 Orange Terrace Dr, Winter Park, FL 32789
  • /44

    $649,900

    • 3 Beds
    • 2 Baths
    • 1,469 Sq Ft

    1926 Natalen Rd, Winter Park, FL 32792

    ***MUST SEE WINTER PARK POOL HOME***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block poolhome nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features anopen layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing kitchen

    Joseph Cosgrove JAMIESON PROPERTIES, INC.

    1926 Natalen Rd, Winter Park, FL 32792
  • /47

    $629,500

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    2708 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning

    Navid Rokh EQUITYPRO LLC

    2708 Lion Heart Rd, Winter Park, FL 32792
  • /18

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft

    4872 N Orange Ave, Winter Park, FL 32792

    3 bedroom 3 bathroom pool home. Enjoy the large backyard. Schedule your showing today!

    Thai Nguyen ALFA REAL ESTATE LLC

    4872 N Orange Ave, Winter Park, FL 32792
  • /31

    $495,000

    • 3 Beds
    • 2 Baths
    • 2,028 Sq Ft

    3207 Lowndes Dr, Winter Park, FL 32792

    Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll

    Courtney Pelfrey MILLER GRANT AND COMPANY

    3207 Lowndes Dr, Winter Park, FL 32792
  • /25

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,624 Sq Ft

    1280 Gladiolas Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting

    Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

    1280 Gladiolas Dr, Winter Park, FL 32792
  • /35

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,827 Sq Ft

    676 Dunblane Dr, Winter Park, FL 32792

    This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as

    Emma Kaplan BALDWIN PARK REALTY LLC

    676 Dunblane Dr, Winter Park, FL 32792
  • /32

    $675,000

    • 3 Beds
    • 2 Baths
    • 2,193 Sq Ft

    1427 Lake Florence Way, Winter Park, FL 32792

    Welcome to this beautifully maintained, Stunning Better-Than-New 6-Year-Old Custom Home in Gated Lake FlorencePreserve, one-owner custom home that truly has it all. From the moment you enter, you’ll appreciate the exceptional quality and craftsmanship, including upgraded 8' interior doors, 10-foot ceilings, crown molding, and elegant tray ceilings throughout—even in the primary suite. One of

    Doug Addeo COMMUNITY REALTY ASSOCIATES

    1427 Lake Florence Way, Winter Park, FL 32792
  • /37

    $598,000

    • 3 Beds
    • 2.5 Baths
    • 1,539 Sq Ft

    2758 Banchory Rd, Winter Park, FL 32792

    Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street, this

    Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

    2758 Banchory Rd, Winter Park, FL 32792
  • /38

    $3,800,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 3,413 Sq Ft

    1120 Palmer Ave, Winter Park, FL 32789

    Miami Beach/Coral Gables meets Winter Park high-end luxury for today's upscale lifestyle. Phil Kean completely re-imagined this 3400 sq ft one story home from top to bottom leaving virtually nothing untouched! If you are looking for one level, indoor-outdoor living, all of the most up-to-date Bells and Whistles, in a #10 location,on a private oversized lot with circular driveway, minutes to

    Brad Grosberg PHIL KEAN REAL ESTATE LLC

    1120 Palmer Ave, Winter Park, FL 32789

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$600,000
Median Townhouse Sale Price
$457,000
Median 2 Bedroom Sale Price
$205,000
Median 1 Bedroom Sale Price
$154,000
Average Price Per Sq Ft
$370
Number of Homes for Sale
308
Last 12 months Home Sales
1,018
Months of Supply
3.60
Median List Price
$530,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
2%
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