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3-Bedroom Homes for Sale in Winter Park, FL with Private Pool

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  • /54

    $569,999 Open Sat 11AM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,706 Sq Ft

    7730 Broken Arrow Trail, Winter Park, FL 32792

    Welcome to this inviting 3-bedroom, 2-bathroom home, perfectly situated on a spacious lot that offers peace, privacy, and room to breathe. From the moment you arrive, you'll be drawn in by the extended driveway and lush, serene surroundings—ideal for anyone seeking a quiet retreat without sacrificing convenience. Step inside and experience the seamless flow of this thoughtfully designed home,

    Waseem Saedi LA ROSA REALTY PREMIER LLC

    7730 Broken Arrow Trail, Winter Park, FL 32792
  • /33

    $650,000

    • 3 Beds
    • 2 Baths
    • 1,727 Sq Ft

    2855 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2855 Lion Heart Dr, Winter Park — a beautifully remodeled home that seamlessly combines modern comfort with an unbeatable location. This move-in ready residence features a brand-new kitchen with smart stainless steel appliances, completely updated bathrooms, new luxury flooring throughout, and an open-concept layout perfect for entertaining. Major upgrades include a new roof (2025) and

    Kevin Henao MY REALTY GROUP, LLC.

    2855 Lion Heart Rd, Winter Park, FL 32792
  • /46

    $569,900

    • 3 Beds
    • 2 Baths
    • 1,906 Sq Ft

    7584 Lodge Pole Trail, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Beautiful remodeled home. Luxury vinyl plank flooring throughout the entire home with tile in the bathrooms. Spacious living area with open concept floorplan. Upgraded kitchen with stainless steel appliances, granite counters, large kitchen island/bar, and closet pantry. Bathrooms both updated. Primary bathroom has large walk-in shower with dual

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    7584 Lodge Pole Trail, Winter Park, FL 32792
  • /32

    $599,000

    • 3 Beds
    • 2 Baths
    • 2,268 Sq Ft

    701 Denton Rd, Winter Park, FL 32792

    Welcome to this beautifully upgraded home in Winter Park Estates! Nestled on a quarter-acre lot, step into your private creating memories that last! This exceptional property has been meticulously maintained and enhanced with high-end features, making it a true standout. Recent upgrades include a brand-new roof (2024) and a new aluminum fence (2024), adding both durability and curb appeal. The

    Elizabeth Boyce CHARLES RUTENBERG REALTY ORLANDO

    701 Denton Rd, Winter Park, FL 32792
  • /23

    $569,000

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft

    426 S Lakemont Ave, Winter Park, FL 32792

    Winter Park, Outstanding Renovations! 3 BD/2 BT Pool Home! Open concept , single story with a lot of natural light. Lavish Updated Kitchen. Stainless steel appliances. Walk in the pantry. New roof 2018, New energy efficient windows and sliding glass doors, 2020, New Trane AC 2023 and New Attic ventilation fan thermostat / humidistat controlled 2024. New refrigerator. Interior includes fresh

    Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

    426 S Lakemont Ave, Winter Park, FL 32792
  • /27

    $760,000

    • 3 Beds
    • 2 Baths
    • 1,867 Sq Ft

    1312 Golfside Dr, Winter Park, FL 32792

    Experience luxury living in this stunning 3-bedroom, 2-bathroom pool home perfectly positioned on the 3rd hole of the golf course in Winter Park. Thoughtfully upgraded with designer details, this home blends elegance and comfort. A beautifully tiled walkway leads to an inviting interior featuring crown moldings, wood-look porcelain flooring, energy-efficient LED lighting, and stylish fixtures

    Uno Sorlie HOPKEY REALTY

    1312 Golfside Dr, Winter Park, FL 32792
  • /40

    $589,000

    • 3 Beds
    • 2 Baths
    • 1,420 Sq Ft

    274 N Ranger Blvd, Winter Park, FL 32792

    Welcome to your fully renovated home located in the highly sought-after Winter Park Pines Golf Course Community. This beautiful open floor plan residence offers a fresh and modern living experience, perfect for both relaxation and entertaining. Inside you'll find brand-new flooring throughout, along with fully upgraded bathrooms that include stylish new vanities and custom tile work. The kitchen

    Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

    274 N Ranger Blvd, Winter Park, FL 32792
  • /16

    $1,495,000

    • 3 Beds
    • 3 Baths
    • 2,145 Sq Ft

    1644 Hibiscus Ave, Winter Park, FL 32789

    Charming, Well-Maintained Home on a Prime Lot in Winter Park’s Coveted Tree StreetsDon’t miss this rare opportunity to own a beautifully landscaped and meticulously maintained property on one of the most desirable streets in Winter Park. Situated on one of the largest lots in the sought-after Tree Streets, this home is perfect for a buyer or builder ready to create something truly special in an

    Harry Pool, III COLDWELL BANKER RESIDENTIAL RE

    1644 Hibiscus Ave, Winter Park, FL 32789
  • /70

    $498,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,740 Sq Ft

    808 Denton Rd, Winter Park, FL 32792

    **Step Into a Slice of Mid-Century Magic—Your Private Oasis Awaits**Nestled on an oversized *corner lot* with *no rear neighbors*, this one-of-a-kind mid-century gem is more than just a home—it’s an experience. With classic architectural charm, lush landscaping, and thoughtful updates, you’ll feel like you’ve stepped back in time without sacrificing modern-day comforts.Enjoy the tranquility of

    Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

    808 Denton Rd, Winter Park, FL 32792
  • /39

    $525,000 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,408 Sq Ft

    3306 Fishermans Cove, Winter Park, FL 32792

    Beautiful home is the sought-after community of Pelican Bay in Winter Park. Pelican Bay only has 48 homes in the community and has a small HOA of $500 a year. This 3- bedroom, 2-bathroom pool home is full of charm, warmth, and love, and ready to move-in. Located on a corner lot as you enter the community. Extra parking pad to the left of the garage. As you walk up the pathway to the front

    Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

    3306 Fishermans Cove, Winter Park, FL 32792
  • /54

    $478,000

    • 3 Beds
    • 2 Baths
    • 1,919 Sq Ft

    7320 Fieldcrest Ave, Winter Park, FL 32792

    Welcome to your dream home in a quiet neighborhood as you relax by the private pool. Leave all the worry behind! Be the happy owner to enjoy as all the recent improvements, upgrades which are COMPLETELY DONE IN 2024! This beautiful block home features 3 bedrooms 2 baths, Brand New Roof, 3.5 Tons HVAC, Plumbing, Electric Panel, Water Heater, Designer Kitchen with Double Sided Cabinets Island,

    Winnie Mai COLDWELL BANKER REALTY

    7320 Fieldcrest Ave, Winter Park, FL 32792
  • /28

    $434,900

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

    5441 Justine Way, Winter Park, FL 32792

    Pool Home! Whole House Solar!! No HOA!!! This 3 bedroom, 2 bathroom pool home offers a split plan bedroom arrangement and open-concept gathering areas that lead out to a spacious screen-enclosed porch that faces the pool. The absence of a pool cage allows for landscape & gardening opportunities along with cannonballs at a moment’s notice. Enjoy fun in the sun and night swims next to the stone

    Sheri Malin REDFIN CORPORATION

    5441 Justine Way, Winter Park, FL 32792
  • /29

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft

    3214 Lowndes Dr, Winter Park, FL 32792

    Welcome to this stunning 3-bedroom, 2-bathroom pool home, offering 1,200 square feet of beautifully remodeled and updated living space. Nestled in a quiet, friendly neighborhood, this home provides the perfect blend of tranquility and convenience, making it an ideal retreat for families, professionals, or anyone seeking a relaxing, move-in-ready property.From the moment you walk in,

    Crystal Whitehead MARK SPAIN REAL ESTATE

    3214 Lowndes Dr, Winter Park, FL 32792
  • /68

    $1,070,000

    • 3 Beds
    • 2 Baths
    • 2,114 Sq Ft

    250 Cortland Ave, Winter Park, FL 32789

    Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

    Alexandra Nordine EXP REALTY LLC

    250 Cortland Ave, Winter Park, FL 32789
  • /39

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,236 Sq Ft

    1109 Denton Rd, Winter Park, FL 32792

    **This property qualifies for a closing cost credit up to $6,100 through the Seller’s preferred lender.**Look no further than this charming 3-bedroom, 2-bathroom pool home located in the highly desirable Winter Park community of Winter Park Estates. Sitting on ¼ of an acre with no HOA, this home is just what you’ve been searching for! Head inside to find the beautifully updated kitchen featuring

    Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

    1109 Denton Rd, Winter Park, FL 32792
  • /31

    $454,999

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft

    5359 Lanyard Ct, Winter Park, FL 32792

    MOTIVATED SELLER. Meticulously Maintained Corner-Lot Pool Home with Modern Upgrades & No HOA!Pride of ownership shines throughout this beautifully maintained corner-lot home, offering privacy, space, and modern comfort on over a quarter-acre of professionally landscaped grounds—all with NO HOA! Every detail has been thoughtfully cared for, ensuring a move-in-ready retreat for its next

    Nicole Dege REDFIN CORPORATION

    5359 Lanyard Ct, Winter Park, FL 32792
  • /22

    $409,000

    • 3 Beds
    • 2 Baths
    • 1,327 Sq Ft

    927 Mare Bello Dr, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. LOCATION, LOCATION! Welcome to 927 Mare Bello Drive in Winter Park, Florida's highly desirable Eastbrook neighborhood. This peaceful and family-friendly community is renowned for its quiet streets and welcoming atmosphere. TOP-RATED SCHOOLS: Families will appreciate access to excellent educational institutions, including Winter Park High School.

    Susana Moor LA ROSA REALTY KISSIMMEE

    927 Mare Bello Dr, Winter Park, FL 32792
  • /12

    $475,000 Open Sun 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,910 Sq Ft

    3458 Balsam Dr, Winter Park, FL 32792

    Seller motivated! Seller to offer, $2500 towards buyers closing cost, and prepaid items at closing. Come see this charming 3 bedroom, 2 bath pool home, located in Winter Park, FL. Home is centrally located and easily accessible to major highways, downtown Orlando, UCF, Rollins College, entertainment, restaurants, shopping and much more. The driveway has an extended parking pad, for extra

    Marquita Shiever, PA CENTURY 21 BE3

    3458 Balsam Dr, Winter Park, FL 32792
  • /30

    $489,900

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    1710 Aster Dr, Winter Park, FL 32792

    Price improvement!!! Renovated Winter Park home offering 3 bedrooms 2 baths with 1646 sq feet. Nice size lot .24 acre, fenced with a large open pool featuring brand new pool equipment & newly screened patio. 2024 Updates include: NEW Roof, Luxury vinyl flooring, 5 1/4 in. baseboards, popcorn ceilings removed & retextured, Full Kitchen renovation with SS appliances, Soft close cabinets & Quartz

    Dora Siler FOLIO REALTY LLC

    1710 Aster Dr, Winter Park, FL 32792
  • /38

    $1,295,000

    • 3 Beds
    • 2 Baths
    • 2,342 Sq Ft

    632 Country Club Dr, Winter Park, FL 32789

    Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this

    Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

    632 Country Club Dr, Winter Park, FL 32789
  • /35

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,301 Sq Ft

    5418 S Bracken Ct, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. SOLAR PANELS WILL BE PAID OFF AT CLOSING!! Welcome to this move-in ready Winter Park pool home, tucked away in a peaceful cul-de-sac! This gem has been thoughtfully updated with significant renovations, including a composition shingle roof (2019), custom gutters with in-ground drain lines (2019), a Trane HVAC with hurricane slab foundation (2019),

    Chelsea Feinberg EXP REALTY LLC

    5418 S Bracken Ct, Winter Park, FL 32792
  • /40

    $1,258,700

    • 3 Beds
    • 3 Baths
    • 2,460 Sq Ft

    1901 Lake Sue Dr, Orlando, FL 32803

    Chic and tastefully designed, this exceptional 3-bedroom, 3 bath, home has everything that an indoor/outdoor Florida lifestyle home has. An Open floor plan with lots of natural light flowing throughout, a modern kitchen with marble counter tops, stainless-steel appliances and a Breakfast Bar. Through the home, there is an inviting atmosphere that flows effortlessly throughout, and glass doors

    Pamela Stewart REALCOM REAL ESTATE SERVICES INC

    1901 Lake Sue Dr, Orlando, FL 32803
  • /47

    $1,525,000

    • 3 Beds
    • 2.5 Baths
    • 2,960 Sq Ft

    3308 Middlesex Rd, Orlando, FL 32803

    This breathtaking Spanish-style home, winner of First Place for Design by the American Society of Interior Designers in 2020, is a true masterpiece. Designed by HGTV Designer of the Year John McClain, it blends modern luxury with timeless charm.The magazine-worthy kitchen—featured on Southern Living’s website—boasting Sherwin William's 2021 color of the year, the custom Urbane Bronze

    Julie Bettosini STOCKWORTH REALTY GROUP

    3308 Middlesex Rd, Orlando, FL 32803

Home Trends in Winter Park, FL

Home Trends

Median Price (12 Mo)
$599,500
Median Single Family Price
$785,000
Median Townhouse Price
$607,000
Median 2 Bedroom Price
$240,000
Median 1 Bedroom Price
$160,000
Average Price Per Sq Ft
$403
Number of Homes for Sale
234
Last 12 months Home Sales
694
Months of Supply
4.00
Median List Price
$649,000
Median Discount From 1st List Price
6%
Median Home Sale Price YoY Change
0%
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