33

Houses in 32792 under $500,000

Section Image Section Image
  • /50

    $469,900

    • 3 Beds
    • 3 Baths
    • 1,880 Sq Ft

    2835 Bongart Rd, Winter Park, FL 32792

    Seller is Motivated and open to incentives, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard

    Agent Photo

    Claudia Jenkins

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 450-7314

    2835 Bongart Rd, Winter Park, FL 32792
  • /35

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    1660 Tremont Ln, Winter Park, FL 32792

    4 Bedrooms | 2.5 Baths | New Roof | Winter Park’s Country LaneWelcome to this well-cared-for 4-bedroom, 2.5-bath home in the highly desirable Country Lane neighborhood of Winter Park!On the first floor, you’ll find a bright and inviting layout with a kitchen featuring stainless steel appliances, along with ample cabinet and counter space. There’s plenty of room to entertain, with

    Agent Photo

    Jason Howell

    REAL BROKER, LLC

    (321) 325-3575

    1660 Tremont Ln, Winter Park, FL 32792
  • /20

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,071 Sq Ft

    2320 High St, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Enjoy a 1% lower interest rate for your first year with our preferred lender! Located in the highly sought after Winter Park area, this home features 3 Bedrooms, 2 Bathrooms was thoughtfully renovated in 2025 by the current owner. Perfect for a first time homebuyer or investor looking for a move-in ready, low maintenance property! Updates include a

    Jessica Lee THE AGENCY ORLANDO

    2320 High St, Winter Park, FL 32792
  • /32

    $465,000

    • 5 Beds
    • 3 Baths
    • 1,442 Sq Ft

    2181 Linden Rd, Winter Park, FL 32792

    Discover this beautifully remodeled home at 2181 Linden Road, located in the heart of Winter Park. With 5 bedrooms and 3 bathrooms, this property features modern upgrades throughout, including a brand-new kitchen, updated bathrooms, and fresh finishes. Nestled on a spacious lot with no HOA, it offers both privacy and flexibility for homeowners seeking comfort and style.Enjoy living just

    Alejandro Rodriguez AROD PARTNERS REALTY

    2181 Linden Rd, Winter Park, FL 32792
  • /41

    $430,000

    • 4 Beds
    • 2 Baths
    • 1,821 Sq Ft

    2829 Aloma Ave, Winter Park, FL 32792

    Rare Opportunity in Highly Sought-After Winter Park!Don’t miss your chance to own this fantastic ...LISTED WELL BELOW APPRAISED VALUE ! Known for its top-rated schools and unbeatable location as well , this home exudes timeless charm with elegant terrazzo floors throughout. Newer Roof ( 2021) and Newer A/C ( 2019) Too!Step inside to a spacious and inviting layout, featuring a

    Cassie Lamoureux KELLER WILLIAMS CLASSIC

    2829 Aloma Ave, Winter Park, FL 32792
  • /9

    $499,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,515 Sq Ft

    2485 Middleton Ave, Winter Park, FL 32792

    Wait no more! Don’t miss this charming and hard to find 3 bed/ 2 bath PLUS bonus room in Brookshire Heights! Large treed lot walking distance to Brookshire Elementary, Showalter Field, Cady Way Pool and Park and the Advent Health Winter Park Complex. Ready for your personal touches, this well loved home has large living room and dining area, terrazzo floors, vintage cabinetry, great closets

    Lisa Gould KELLER WILLIAMS WINTER PARK

    2485 Middleton Ave, Winter Park, FL 32792
  • /80

    $499,000

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    1339 Monte Ln, Winter Park, FL 32792

    Lovely home with an expanded floor plan in Casa Aloma—one of Winter Park’s most walkable and established neighborhoods! Featuring approx. 2,200 sq ft of living space (permitted addition, buyer to verify), this 3/2 offers a spacious, flexible layout and a relaxing backyard oasis. Enjoy a sparkling pool, screened patio, and mature palm landscaping—perfect for entertaining! Fresh exterior paint,

    Rod Banks ANCHOR FLORIDA REALTY LLC

    1339 Monte Ln, Winter Park, FL 32792
  • /31

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,671 Sq Ft

    1932 Houndslake Dr, Winter Park, FL 32792

    Newly renovated 3 Bedroom 2 Bath in a well establish community of Cedar Ridge. Conveniently located in Winter Park Seminole County Pool home. The office can easily turn into a 4th bedroom if needed. New tile floors throughout. Open, airy and bright. Updated kitchen with quartz countertop. New stainless steel appliances. New roof, new water heater and most of the windows are newly

    Trung Nguyen LA ROSA REALTY LLC

    1932 Houndslake Dr, Winter Park, FL 32792
  • /32

    $480,000

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft

    2831 Lion Heart Rd, Winter Park, FL 32792

    Welcome to your Winter Park retreat! This spacious single-story ranch offers nearly 2,000 sq. ft. of living space with 3 bedrooms, 2 baths, and a versatile bonus room. The updated kitchen boasts granite counters, stainless steel appliances, and a cozy breakfast area, opening into a bright Florida room perfect for entertaining. The split floor plan ensures privacy, with a generous primary suite

    Joyce Tang JOY ESTATE ENTERPRISE INC

    2831 Lion Heart Rd, Winter Park, FL 32792
  • /32

    $469,900

    • 4 Beds
    • 2 Baths
    • 1,778 Sq Ft

    7104 Wrenwood Way, Winter Park, FL 32792

    This beautifully updated 4 bedroom, 2 bathroom, 2 car garage home offers modern style, thoughtful upgrades, and a prime location just steps from the neighborhood elementary school. From the moment you arrive, you’ll notice the curb appeal of the corner lot framed by mature trees and a newer white vinyl fence. Inside, the home features a spacious split floor plan with wood-grain laminate flooring,

    Jennah LeBruno, LLC THE WILKINS WAY LLC

    7104 Wrenwood Way, Winter Park, FL 32792
  • /73

    $489,900

    • 5 Beds
    • 2 Baths
    • 2,044 Sq Ft

    1028 Princess Gate Blvd, Winter Park, FL 32792

    The seller is offering a $15,000 concession to the buyer, to be applied toward allowable closing costs and/or prepaid expensesA Fully Renovated Gem in the Heart of Winter ParkStep into this beautifully updated 5-bedroom, 2-bathroom home located in one of Winter Park’s most sought-after neighborhoods. With over 2,000 square feet of stylish and functional living space, this residence offers

    Jose Hernandez LA ROSA REALTY CW PROPERTIES L

    1028 Princess Gate Blvd, Winter Park, FL 32792
  • /70

    $472,000

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft

    2648 Amsden Rd, Winter Park, FL 32792

    Beautiful Pool Home in Desirable Winter Park EstatesWelcome to this charming and thoughtfully updated pool home in the highly sought-after Winter Park Estates subdivision—zoned for top-rated schools, including Winter Park High School. This mid-century gem blends modern comfort with timeless style, located in one of Central Florida’s most beloved neighborhoods.Property

    Mary Dees CHOICEPOINTE REALTY, INC.

    2648 Amsden Rd, Winter Park, FL 32792
  • /49

    $439,000

    • 4 Beds
    • 2 Baths
    • 1,836 Sq Ft

    1842 Puritan Ave, Winter Park, FL 32792

    Modern design, Open concept layout, Sleek quartz counter top, All new appliances, New luxury vinyl plank flooring, New lanai upgrade. This beautiful 4 bedrooms and 2 full bath is situated on a 8,250 square feet lot was newly fenced in 2024 which gives a sense of privacy and spaciousness as you enter into the lanai. There is two detached sheds for your storage convenience. This beautiful done was

    Derek Eisenberg CONTINENTAL REAL ESTATE GROUP

    1842 Puritan Ave, Winter Park, FL 32792
  • /33

    $450,000

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

    1914 Bonanza Ct, Winter Park, FL 32792

    Welcome to your winter Park retreat!Step into this beautifully renovated 3 bedroom, 2 bathroom home where modern meets timeless comfort. Designed with an open floor plan, the living space flows seamlessly, making it perfect for both entertaining and everyday living.The brand new kitchen shines with contemporary finishes, while the new flooring throughout the home adds warmth and

    William Moxey WYNNMORE REALTY LLC

    1914 Bonanza Ct, Winter Park, FL 32792
  • /29

    $455,000

    • 5 Beds
    • 3 Baths
    • 1,945 Sq Ft

    3642 Periwinkle Dr, Winter Park, FL 32792

    Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income.The main home features a freshly painted interior and exterior, new LVP flooring

    John Hwangbo HONEST REAL ESTATE COMPANY

    3642 Periwinkle Dr, Winter Park, FL 32792
  • /39

    $419,900

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    5346 Cypress Dr, Winter Park, FL 32792

    Impeccably cared for and ready for its next chapter, this Winter Park home blends timeless charm with essential modern updates. The property features a premium paver driveway, double-pane windows, offering both curb appeal and efficiency. Inside, the home has been kept in clean original condition, reflecting years of consistent maintenance and pride of ownership. Major systems have been

    Kristy Kesterson KELLER WILLIAMS ADVANTAGE REALTY

    5346 Cypress Dr, Winter Park, FL 32792
  • /45

    $440,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 2,179 Sq Ft

    1362 Tierra Cir, Winter Park, FL 32792

    Welcome to this unique 4-bedroom ranch-style home in the heart of Winter Park! This residence offers flexibility and comfort for today’s lifestyle. The converted two-car garage has been transformed into an additional bedroom with separate entrance, perfect for guests or an in-law suite. Inside, the kitchen flows seamlessly into the bright family room. Entertain with ease in the large dining and

    John Muccigrosso RE/MAX 200 REALTY

    1362 Tierra Cir, Winter Park, FL 32792
  • /27

    $449,900

    • 4 Beds
    • 2 Baths
    • 1,627 Sq Ft

    1849 Viburnum Ln, Winter Park, FL 32792

    Nestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom, 2-bath concrete block home has been recently renovated and features new appliances, stunning waterfall countertops, all-new bathrooms, fresh interior and exterior paint, brand-new flooring, granite countertops, a stylish backsplash, and updated plumbing throughout. Enjoy the spacious backyard, a 2-car

    Lesly Hijar REAL BROKER, LLC

    1849 Viburnum Ln, Winter Park, FL 32792
  • /30

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft

    2774 Banchory Rd, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom block ranch home in Winter Park Pines. Nestled behind a stunning mature oak tree, this home offers comfort, charm, and convenience in one of Central Florida’s most desirable communities. The large driveway leads to a 2-car garage ensuring plenty of space to park for you and your guests. Step onto the covered front porch and into a

    Nicholas Masi KELLER WILLIAMS REALTY AT THE PARKS

    2774 Banchory Rd, Winter Park, FL 32792
  • /41

    $410,000

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

    3415 N Goldenrod Rd, Winter Park, FL 32792

    THIS HOME HAS IT ALL! Private lot with NO rear neighbors and NO HOA. Features 4 bedrooms, 3 bathrooms, including a potential mother-in-law suite, PLUS a huge oversized bonus room perfect for a game room, office, or home gym! Tile floors throughout, brand new granite countertops and new cabinets in the kitchen and bathrooms, and brand new stainless steel appliances.Enjoy the open floor plan with a

    Maria Borges Jaime BORGES & JAIME REAL ESTATE , LLC

    3415 N Goldenrod Rd, Winter Park, FL 32792
  • /25

    $420,100

    • 3 Beds
    • 2 Baths
    • 1,516 Sq Ft

    3425 Ferndell Dr, Winter Park, FL 32792

    Fully Renovated Gem in Winter Park!Welcome to your dream home in one of Central Florida’s most sought-after neighborhoods—Winter Park. This beautifully renovated 3-bedroom, 2-bathroom residence blends timeless charm with modern updates, offering the perfect move-in-ready sanctuary for today’s lifestyle.Step inside and fall in love with the light-filled open layout, anchored by a stunning

    Ivanhoe Alvarez LOKATION

    3425 Ferndell Dr, Winter Park, FL 32792
  • /34

    $482,900

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

    1173 Valley Creek Run, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2-bath home offering 1,906 square feet of comfortable living space in the heart of Winter Park. Built in 1995, this home features a desirable split-bedroom floor plan, high ceilings, and tile flooring throughout the main living areas—perfect for everyday living and entertaining. The spacious layout includes both a formal living room and a separate

    Rebeka Weeks LUKER & CO REAL ESTATE LLC

    1173 Valley Creek Run, Winter Park, FL 32792
  • /24

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,518 Sq Ft

    3107 Ash Park Loop, Winter Park, FL 32792

    Sellers willing to consider assistance with closing costs based on acceptable offer!The popular Hyde Park community welcomes you to your new home. If you are looking for a private, 3/2 with enclosed backyard with view of trees, then look no further. Ideally located to Downtown Winter Park, UCF, Casselberry, and Winter Springs. Restaurants and shopping nearby as well. Enjoy the community

    Jean Miller COLDWELL BANKER REALTY

    3107 Ash Park Loop, Winter Park, FL 32792
  • /40

    $500,000

    • 4 Beds
    • 2.5 Baths
    • 2,075 Sq Ft

    Unlisted Address

    Welcome to this beautifully maintained 4-bedroom, 2.5-bath pool home nestled in a peaceful neighborhood. This two-story gem offers a spacious and functional layout perfect for both relaxing and entertaining. The 1st floor master is spacious and inviting. Enjoy peace of mind with a newer roof and windows, as well as brand-new laminate flooring throughout the main living areas. Upstairs, a

    Luke Lewis TREASURE COAST REALTY GROUP, LLC

    Unlisted Address
  • /60

    $490,000

    • 4 Beds
    • 2.5 Baths
    • 2,616 Sq Ft

    7679 Bent Bow Trail, Winter Park, FL 32792

    Back on the market with fresh updating! Spacious 4 bedroom 2.5 bath 2600+ Sq. Ft. Winter Park home within the desirable Arrowhead Cove subdivision. As you enter the home, you are greeted by a large living room / dining room area, with engineered hardwood floors, and a beautiful stacked stone electric fireplace at the center. The fully updated kitchen is complete with granite counters, wood

    Jason Gilkey GILKEY REAL ESTATE

    7679 Bent Bow Trail, Winter Park, FL 32792
  • /42

    $480,000

    • 4 Beds
    • 2 Baths
    • 2,313 Sq Ft

    1742 Willa Cir, Winter Park, FL 32792

    some photos are virtually staged!Nestled on one of the largest pie-shaped lots in Willa Grove, this 4-bedroom, 2-bathroom home offers over 2,300 sq. ft. of versatile living space. Designed with a split-bedroom layout for enhanced privacy, the home features an open-concept family, dining, and kitchen area perfect for entertaining. The family room opens onto a large enclosed lanai overlooking a

    Xiaobo Zhang CENTURY 21 CARIOTI

    1742 Willa Cir, Winter Park, FL 32792
  • /34

    $479,900

    • 3 Beds
    • 2 Baths
    • 1,939 Sq Ft

    3054 Bluebrook Dr, Winter Park, FL 32792

    Step into your dream home located in the charming Winter Park, Florida. This stunning property boasts 3 bedrooms and 2 bathrooms, perfect for a growing family or those who love to entertain.As you enter, you are greeted by a cozy fireplace, ideal for chilly Florida evenings. The spacious living room flows seamlessly into the gourmet kitchen, complete with granite countertops and stainless

    Trisha Deokinandan ALORA REALTY GROUP INC

    3054 Bluebrook Dr, Winter Park, FL 32792
  • /37

    $489,500

    • 4 Beds
    • 2 Baths
    • 2,195 Sq Ft

    5338 Tangerine Ave, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Seller is motivated and open to creative solutions — bring your offer today! – Your Dream Home Just Got Closer! Completely Renovated 4-Bedroom Pool Home in the Heart of Winter Park! 2,195 Sq Ft of Modern Living! Welcome to 5338 Tangerine Ave, a beautifully updated 4-bedroom, 2-bathroom home offering 2,195 square feet of thoughtfully redesigned

    Mystique Barba CENTURY 21 CARIOTI

    5338 Tangerine Ave, Winter Park, FL 32792
  • /54

    $485,000

    • 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
  • /31

    $449,900

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

    1354 Tierra Cir, Winter Park, FL 32792

    Located in the highly sought-after Casa Aloma community, this charming 1960s home offers the perfect blend of comfort, style, and convenience. Situated within a one-mile radius of all that Winter Park has to offer, this well-maintained home truly stands out in terms of location, location, location! The open floor plan is ideal for entertaining, with a spacious living room providing ample space

    Carl Mataushek REAL ESTATE FIRM OF ORLANDO

    1354 Tierra Cir, Winter Park, FL 32792
  • /38

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,807 Sq Ft

    1608 Bomi Cir, Winter Park, FL 32792

    Your beautifully upgraded home in Winter Park with NO HOA is waiting for you! Centrally located with walking distance to nearby schools this 3 bedroom, 2.5 bath single family home is ready for its new owner. Offering over 1,800 square feet of thoughtfully designed living space, while sitting on over an acre of land, this home combines modern comfort with the charm of one of Central Florida's most

    Suzette Berkhalter KELLER WILLIAMS ADVANTAGE III

    1608 Bomi Cir, Winter Park, FL 32792
  • /34

    $440,000

    • 4 Beds
    • 2 Baths
    • 1,765 Sq Ft

    1621 Puritan Ave, Winter Park, FL 32792

    Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated pool home located in the highly desirable Winter Park area on the Seminole County side. This property qualifies for multiple down payment assistance programs, making it an excellent opportunity for first-time buyers. Recent upgrades include a new roof (2023), resurfaced pool (2023), and an updated A/C system

    Alejandro Colon PREFERRED REAL ESTATE BROKERS

    1621 Puritan Ave, Winter Park, FL 32792
  • /2

    $419,900

    • 3 Beds
    • 2 Baths
    • 1,405 Sq Ft

    616 Ellendale Dr, Winter Park, FL 32792

    Desirable Winter Park Estates - close to everything! Beautifully updated 3 Bedroom 2 Bath POOL home which is located in a highly desirable school district! Updated Contemporary Kitchen has newer Cabinetry, newer Stainless-Steel appliances, and Granite countertops which connect with the open Living room. Dining area extends to the generous size Family room - Ideal for Entertaining. The home

    David Ruiz CENTRAL REALTY

    616 Ellendale Dr, Winter Park, FL 32792
How to Buy a Home How to Finance a Home How to Sell a Home