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

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

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 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

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

Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is perfect for entertaining, gardening, or simply relaxing under the Florida sun. With plenty of room

Eric Gross EXP REALTY LLC

NEW REDUCED PRICE BELOW MARKET IN DESIRABLE TANGLEWOOD WINTER PARK COMMUNITY WITH NO HOA! ALLOWS SHORT TERM RENTALS (STR). LOW TAX DISTRICT. This is probably the closet you can get to Winter Park (Park Ave) without having to pay the Winter Park taxes or conform to their restrictions! This property has been extremely well maintained and would be an amazing home for a new family. ROOF IS 2023! All

Michael Cameron CAMERON REALTY GROUP LLC

Don't miss this rare opportunity to own a slice of historic Hannibal Square! This 2 bed 2 bath bungalow showcases an open floorplan with high-vaulted ceilings in the main living areas, plenty of natural light, and a separate indoor laundry room. The paver patio on the side of the home offers a nice added space for dining and entertainment. It is one out of only a handful of lots to have a view of

Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedrooms, 2 full bathrooms and open floor plan. You will notice the enhanced curb appeal from the moment

Jennifer Conrado CHARLES RUTENBERG REALTY ORLANDO

This POOL home is amazing in every way and is truly a must see! Original Owner with incredible pride of ownership. Brand NEW Roof, Brand NEW Water Heater, HVAC 2020, entire replumb and newer windows throughout. Nestled in the highly coveted community of Eastbrook in Winter Park. A perfect location just minutes to everything. This residence boasts an array of desirable features. As you stroll down

Denise Korrey KORR REALTY CORP

Welcome to 824 Garrett Court, a beautifully updated 4-bedroom, 2-bath home located on a quiet cul-de-sac in the highly desirable Winter Park Forest community. This bright and spacious residence is one of the only homes listed in this sought-after neighborhood in 2025. The interior features luxury vinyl flooring throughout, 4inch baseboards, an updated kitchen with stainless steel appliances

Shelby Serrao COMPASS FLORIDA LLC

Discover comfortable Winter Park living in this bright and stylish 3-bedroom, 2.5-bathroom corner-unit townhome located in the gated Grayson Square community. Abundant natural light fills the open-concept living area, which flows seamlessly to a covered lanai that’s perfect for relaxing mornings or quiet evenings. The modern kitchen includes stainless steel appliances, quartz countertops, and

Denise Del Castillo LPT REALTY, LLC

Seller offering $10,000 credit to buyer at closing—may be applied toward buyer’s rate buy-down, closing costs, or prepaid expenses (subject to lender approval).Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features,

Erica Diltz BALDWIN PARK REALTY LLC

Beautiful home in Winter Park, located in a quiet neighborhood with no homeowner association fees. This 4-bedroom, 2-bathroom home has been recently remodeled, including new bathrooms, new flooring, new quartz countertops, new kitchen cabinets, a new 2025 central air conditioning unit, a 2023 roof, and a new 2025 water heater. It features a 2-car garage and ample parking, as well as a renovated

Pia Jijon Garcia AGENT TRUST REALTY CORPORATION

Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and living area—perfect for entertaining. The modern kitchen is equipped with stainless steel appliances, sleek gray cabinets, and elegant quartz countertops. Upstairs, the Primary Bedroom features a spacious walk-in closet and a luxurious en-suite bathroom with a dual-sink quartz vanity and a private water

Monica Puche LPT REALTY, LLC

Welcome to this fully remodeled, move in ready home perfectly situated on a spacious corner lot in Winter Park, just blocks from the Dubsdread Golf Course and close to the shops, restaurants, and charm of College Park and downtown Winter Park. Every inch of this 3 bedroom, 2 bath home has been thoughtfully updated to blend modern comfort with timeless style. Step inside to find a bright, open

Chris Creegan CREEGAN GROUP

One or more photo(s) has been virtually staged. Major Price Reduction! Don’t miss this rare opportunity in sought after Winter Park location —now offered at a significantly lower price. 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

Mystique Barba CENTURY 21 CARIOTI

Gorgeous 2-Story Townhome, newly built in 2024. Located in upscale Winter Park, Florida, close to fine dining, shopping and entertainment. Not far from downtown Orlando and Orlando theme parks, this manicured gated community showcases beautiful landscaping and a sparkling pool surrounded by coveted modern architecture. The home contains the high-end Lux Fresh interior package, and owner has added

Steven Koleno BEYCOME OF FLORIDA LLC

RARE OPPORTUNITY TO OWN A GREAT HOME IN WINTER PARK! MOTIVATED SELLER! Check out this spacious 3 bedroom, 3 bathroom home almost 1800 sq. ft. The home offers a great layout with abundant natural light, comfortable living spaces and timeless design elements. Enjoy central Florida living in one of Winter Park's most established neighborhoods, walking distance to dining, shopping, parks and

Tori Alexander LEGACY REALTY & BROKERS LLC

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 steel

Trisha Deokinandan ALORA REALTY GROUP INC

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 2024, new water heater 2024, whole house plumbing re-piped 2025,

Trung Nguyen LA ROSA REALTY LLC

Welcome home to this charming 3-bedroom, 3-bathroom single-family residence nestled in the quiet, established neighborhood of Winter Park Estates. Boasting the highly desirable Winter Park school district, this location offers both prestige and tranquility, yet is conveniently located near major roads which make getting around town a snap! Nearby restaurants and entertainment include Aloma Bowl,

Lauren Lester COLONIALTOWN REALTY

Exceptional opportunity This 4-bedroom, 2-bath property offers approximately 1,490 square feet of living space features a spacious backyard and is ideally located just minutes from Downtown Winter Park, within the highly desirable 32789 zip code. It is within close distance to Mead Botanical Garden and just over one mile from Rollins College. With ongoing redevelopment in the area this property

Ken Sheldon SHELDON PROFESSIONALS INC

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 THE PALMS PROPERTY GROUP

Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potential. Updated with original hardwood floors, gas fireplace, granite kitchen, and bath. The 3rd BR functions as a guest room or office. Spacious fenced yard with wood deck and room for a pool. Deep garage offers space to add a second bath or storage. Original plan was to remove back -to-back closets in LR to

Julie Wright CHARLES RUTENBERG REALTY ORLANDO

Welcome to this beautifully designed, move-in-ready townhome— the largest end-unit in one of Winter Park’s most sought-after gated communities! This spacious townhome is conveniently located in the gated community of Hawks Crest, offering 2,312 sq ft of low-maintenance living. With 3 bedrooms, 2.5 bathrooms, a 2-car garage, filled with natural light thanks to abundant windows and soaring

Kristan Hayden ATRIUM REALTY, LLC

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

Welcome to this beautifully renovated 3-bedroom, 2-bath home located in Seminole County — a rare find in Winter Park with NO HOA OR CDD! This delightful residence offers a perfect blend of modern updates and practical features throughout. Enjoy bright, inviting living spaces, a functional layout, and a master suite featuring its own private exterior door, offering added convenience for guests,

Aracelis Batista NORTHGROUP REAL ESTATE, INC

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

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

Bo Zhang CENTURY 21 CARIOTI

**Take advantage of a seller paid promotion towards closing costs or rate buy down.** This 3-bedroom, 2.5-bath townhome combines style, functionality, and low-maintenance living and is ready for you to move right in. It features a paver driveway and walkway framed by lush landscaping. As you step inside the home, you will find a versatile flex space, which is perfect as a home office, or

Gaelle Cenord FOWLKES REALTY CO

Get ready to fall in love with this stunning Winter Park home! Tucked away in a peaceful cul-de-sac, this fully renovated 3-bedroom, 2-bath beauty blends modern style with everyday comfort. Step into the family room and instantly feel the openness of the bright, airy layout. The open floor plan creates a seamless flow from the living area to the brand-new kitchen, making the entire space feel

Linda Jokbengboon COMPASS FLORIDA LLC

Location, Location, Location!Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz.Enjoy a

David Auerbach PARK TOWN REAL ESTATE LLC