35

Winter Park, FL Homes for Sale under $500,000

Section Image Section Image
  • /58

    $449,900

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

    3463 Arnel Dr, Winter Park, FL 32792

    Your pool home in Winter Park just became one of the best opportunities under $450K. Now priced at $449,900, this home offers 3 bedrooms plus a versatile bonus room, approximately 1,770 sq ft, a 2-car garage, and extended driveway — all in the established Eastbrook community with NO HOA. Major systems are already taken care of: roof 2018, solar panels 2020 (fully paid off), water heater 2019, and

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (689) 356-6537

    3463 Arnel Dr, Winter Park, FL 32792
  • /37

    $419,900 Open Wed 12PM - 2:30PM

    • 4 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    1871 Casselwood St, Winter Park, FL 32792

    Beautifully updated and move-in ready home in Winter Park with BRAND NEW 2026 A/C installed, roof from 2014 (call for more information regarding the roof), and water heater from 2009. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, recessed lighting, updated fixtures, fireplace, screened patio, and a bright functional layout. The upgraded kitchen and

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 252-6747

    1871 Casselwood St, Winter Park, FL 32792
  • /20

    $400,000

    • 2 Beds
    • 1 Bath
    • 913 Sq Ft

    2482 Roxbury Rd, Winter Park, FL 32789

    Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready.But what truly sets this property apart is the location and land. With

    Gary Cohl COLDWELL BANKER REALTY

    2482 Roxbury Rd, Winter Park, FL 32789
  • /17

    $489,990

    • 4 Beds
    • 2 Baths
    • 1,376 Sq Ft

    501 Heritage Blvd, Winter Park, FL 32792

    Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

    Bernardo Carrasquel B EXP REALTY LLC

    501 Heritage Blvd, Winter Park, FL 32792
  • /43

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,676 Sq Ft

    1468 Auburn Green Loop, Winter Park, FL 32792

    Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have

    Jodie Ma COLDWELL BANKER VANGUARD EDGE

    1468 Auburn Green Loop, Winter Park, FL 32792
  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, Winter Park, FL 32792
  • /27

    $470,000

    • 4 Beds
    • 2 Baths
    • 1,787 Sq Ft

    1032 Manchester Cir, Winter Park, FL 32792

    Welcome to this beautifully maintained 4-bedroom, 2-bath pool home nestled in one of the nice neighborhoods in Winter Park, located within Seminole County. Offering the perfect blend of comfort, space, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to discover a spacious, light-filled floor plan featuring generous living areas,

    Nancy Morales BHHS FLORIDA REALTY

    1032 Manchester Cir, Winter Park, FL 32792
  • /45

    $459,000

    • 3 Beds
    • 2 Baths
    • 1,491 Sq Ft

    405 Lake Fair Ln, Winter Park, FL 32789

    One or more photo(s) has been virtually staged. Fully rebuilt, not just renovated. This Winter Park home at 405 Lake Fair Ln has been completely transformed from top to bottom, with all major systems updated and no detail overlooked, enhanced by custom architectural wood paneling that gives the exterior a modern, high-end presence and standout curb appeal. Positioned on a quiet dead-end street

    Donnamarie Leiba Gough EXP REALTY LLC

    405 Lake Fair Ln, Winter Park, FL 32789
  • /28

    $470,000

    • 3 Beds
    • 2 Baths
    • 1,606 Sq Ft

    950 Hanover Ave, Winter Park, FL 32789

    Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with views of Lake Wilderness. Completely updated in 2017, move-in ready so you can lock and leave with peace of mind to enjoy the everyday lifestyle of Winter Park and Central Florida this amazing location offers. Full updates made in 2017 include new roof, plumbing, electrical,

    Michael Domi COMPASS FLORIDA LLC

    950 Hanover Ave, Winter Park, FL 32789
  • /43

    $499,000

    • 4 Beds
    • 3 Baths
    • 1,526 Sq Ft

    731 Bongart Rd, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Completely renovated pool home on a large corner lot, tucked away on a quiet dead-end street in Winter Park. Solid block construction adds peace of mind, and this one has been updated top to bottom—new laminate flooring throughout, recessed lighting, popcorn ceilings removed, and a fresh, clean feel the moment you walk in. The main living area is

    Ed Klein FANNIE HILLMAN & ASSOCIATES

    731 Bongart Rd, Winter Park, FL 32792
  • /30

    $484,000

    • 4 Beds
    • 2 Baths
    • 1,718 Sq Ft

    240 Orange Terrace Dr, Winter Park, FL 32789

    PRICE IMPROVEMENT - SELLER MOTIVATED - MOVE IN READY - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to

    Susan Pinnock A+ REALTY PROFESSIONALS, INC

    240 Orange Terrace Dr, Winter Park, FL 32789
  • /31

    $429,000 Open Sun 12PM - 5PM

    • 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 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your

    Karan Jodha MOBED REALTY, P.A

    1842 Puritan Ave, Winter Park, FL 32792
  • /29

    $439,000

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

    2779 Sanbina St, Winter Park, FL 32789

    Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a

    Caroline Fiore MAINFRAME REAL ESTATE

    2779 Sanbina St, Winter Park, FL 32789
  • /37

    $420,000

    • 3 Beds
    • 2.5 Baths
    • 1,533 Sq Ft

    3440 Allston Ln, Winter Park, FL 32792

    Exceptional Single-Family Home in Winter Park, FLThis beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC

    Hugo Hernandez EXIT GLOBAL REALTY

    3440 Allston Ln, Winter Park, FL 32792
  • /55

    $495,000

    • 2 Beds
    • 2.5 Baths
    • 1,428 Sq Ft

    630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

    Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half

    Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

    630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
  • /29

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,197 Sq Ft

    1518 Pinewood Dr, Winter Park, FL 32789

    Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

    Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

    1518 Pinewood Dr, Winter Park, FL 32789
  • /64

    $444,900

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft

    1951 Canny Cove, Winter Park, FL 32792

    Welcome to easy, light-filled living in this beautifully maintained 3-bedroom, 2.5-bath corner townhome in the gated Grayson Square community. Freshly painted and designed for comfort, the open living and dining spaces feel bright and inviting, flowing effortlessly to a covered lanai—perfect for relaxing evenings or casual gatherings. The kitchen offers a clean, modern look with stainless steel

    Denise Del Castillo LPT REALTY, LLC

    1951 Canny Cove, Winter Park, FL 32792
  • /24

    $425,000

    • 4 Beds
    • 2 Baths
    • 1,610 Sq Ft

    814 Densmore Dr, Winter Park, FL 32792

    Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home.Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for

    Liz Jones ORANGE SLICE PROPERTIES

    814 Densmore Dr, Winter Park, FL 32792
  • /11

    $430,000

    • 4 Beds
    • 2 Baths
    • 1,296 Sq Ft

    Unlisted Address

    Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal

    Arlenys Oviedo EXP REALTY LLC

    Unlisted Address
  • /35

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,402 Sq Ft

    7532 Azurebrook Ct, Winter Park, FL 32792

    Located on a quiet cul-de-sac with NO HOA, this adorable Winter Park home sits on an oversized lot with an incredible backyard and endless room for entertaining, relaxing, or play. With a mid-century modern feel and charming curb appeal, this 3-bedroom, 2-bath home is full of character and functionality.As you enter through the foyer, you’re welcomed by an oversized living room to the left,

    Christina Frucci RE/MAX TOWN & COUNTRY REALTY

    7532 Azurebrook Ct, Winter Park, FL 32792
  • /19

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,088 Sq Ft

    2231 Nairn Dr, Winter Park, FL 32792

    Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

    David Auerbach PARK TOWN REAL ESTATE LLC

    2231 Nairn Dr, Winter Park, FL 32792
  • /22

    $499,000

    • 4 Beds
    • 2 Baths
    • 1,514 Sq Ft

    2560 Franklin Ave, Winter Park, FL 32789

    Come see this charming 4 bed, 2 bath, 2 story home in Winter Park/ Lake Killarney location, 6 mins to downtown Winter park & Winter Park Village with an outdoor shopping center featuring many shops & restaurants. Convenience to Wholefood & Publix Supermarket. Quiet neighborhood with No HOA fees. Its stone elevation gives a captivating curb appeal. Situated on a generous 0.34 acres lot. The

    Jiraporn Wasserman LoKation

    2560 Franklin Ave, Winter Park, FL 32789
  • /27

    $427,500

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

    3054 Bluebrook Dr, Winter Park, FL 32792

    "Open the Doors to Your Dreams" of owning an Affordable Home with a pool in Winter Park. The home features a Spacious Kitchenwith Upgraded Cabinets, and stone countertops; Primary bedroom suite is amazing. You will love the layout and upgraded primary bathroom; Beautiful Porcelain tile flooring throughout the home; Large family room with fireplace; Large screened back porch/LANAI.And

    Eugene Weatherspoon WEATHERSPOON REALTY INC

    3054 Bluebrook Dr, Winter Park, FL 32792
  • /31

    $485,000

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

    3207 Lowndes Dr, Winter Park, FL 32792

    3 bedrooms PLUS an office (or 4th bedroom) AND a "flex space". 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

    Courtney Pelfrey MILLER GRANT AND COMPANY

    3207 Lowndes Dr, Winter Park, FL 32792
  • /29

    $450,000

    • 3 Beds
    • 2 Baths
    • 1,815 Sq Ft

    1205 Valley Creek Run, Winter Park, FL 32792

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom home offering 1,815 square feet of comfortable living in the established Lost Creek community of Winter Park. This light-filled residence features a thoughtfully designed split floor plan with vaulted ceilings, fresh interior paint (2026), and a blend of formal and casual living spaces. The formal living and dining rooms provide an

    Amy Turner KELLER WILLIAMS WINTER PARK

    1205 Valley Creek Run, Winter Park, FL 32792
  • /7

    $489,000

    • Land
    • 9,147 Sq Ft
    • $2,328,571 per Acre

    3601 Midiron Dr, Winter Park, FL 32789

    Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a

    Juliana Usquiano EMPIRE NETWORK REALTY

    3601 Midiron Dr, Winter Park, FL 32789
  • /27

    $425,000

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

    1849 Viburnum Ln, Winter Park, FL 32792

    This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor

    Lesly Hijar REAL BROKER, LLC

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

    $450,000 Open Tue 9AM - 7PM

    • 4 Beds
    • 2 Baths
    • 2,264 Sq Ft

    2052 Leanne Ct, Winter Park, FL 32792

    Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample

    Karen Albright OPENDOOR BROKERAGE LLC

    2052 Leanne Ct, Winter Park, FL 32792
  • /26

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 1,907 Sq Ft

    2774 Bright Bird Ln, Winter Park, FL 32792

    Motivated seller! Brand new townhouse professionally decorated, and available today! Built in 2024, this property offers a great floorplan: with a lot of natural light and coziness. Fall in love with the modern and spacious house located in a prestigious area! Close to shops and markets this is an amazing opportunity for those looking for a quiet neighborhood but close to everything at the same

    Priscilla Triska FLORIDA CONNEXION PROPERTIES

    2774 Bright Bird Ln, Winter Park, FL 32792
  • /41

    $470,000

    • 3 Beds
    • 2 Baths
    • 1,703 Sq Ft

    1052 Manchester Cir, Winter Park, FL 32792

    PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious

    Yuleisy Marquez FLORIDA INVESTMENT REALTY GRP

    1052 Manchester Cir, Winter Park, FL 32792
  • /12

    $499,000

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    230 Strathy Ln, Winter Park, FL 32792

    Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

    David Auerbach PARK TOWN REAL ESTATE LLC

    230 Strathy Ln, Winter Park, FL 32792
  • /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
  • /31

    $485,000

    • 3 Beds
    • 2 Baths
    • 1,592 Sq Ft

    346 S Ranger Blvd, Winter Park, FL 32792

    PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

    Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

    346 S Ranger Blvd, Winter Park, FL 32792
  • /25

    $450,000

    • 2 Beds
    • 1 Bath
    • 988 Sq Ft

    220 Alpine Dr, Maitland, FL 32751

    Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida.The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners,

    Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

    220 Alpine Dr, Maitland, FL 32751
  • /30

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,707 Sq Ft

    612 Green Meadow Ave, Maitland, FL 32751

    Welcome to a home that doesn’t just check boxes — it supports your lifestyle. Tucked into one of Maitland’s beloved neighborhoods, Forest Brook, this delightful property blends comfort, practicality, and a little everyday serenity. *Lots of new since 2023: Whole house generator, 20’x12’ shed, front and back sod (just completed 4/2026), renovated driveway, gutters, vinyl fence in backyard & so

    Stacy Wayne FLORIDA HOME TEAM REALTY LLC

    612 Green Meadow Ave, Maitland, FL 32751

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$616,950
Median Townhouse Sale Price
$452,500
Median 2 Bedroom Sale Price
$199,450
Median 1 Bedroom Sale Price
$150,000
Average Price Per Sq Ft
$367
Number of Homes for Sale
296
Last 12 months Home Sales
979
Months of Supply
3.60
Median List Price
$530,000
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