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

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

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

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

Preferred Lender rate Incentives available. This beautifully maintained 3-bedroom, 2.5-bath townhome with a one-car garage, located in a newly gated community that offers comfort, style, and convenience. The home features ambient high-hat lighting throughout, creating a warm and modern atmosphere. The spacious kitchen is ideal for everyday living and entertaining, while the open living area is

Irene Navarro LIFESTYLE INTERNATIONAL REALTY

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

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 throughout,

John Hwangbo HONEST REAL ESTATE COMPANY

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

One or more photo(s) has been virtually staged. Price ENHANCEMENT! The best value in the area. Do not miss out on the opportunity to be the next owner of Conifer Avenue!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 2025, HVAC 2020, entire replumb and newer windows throughout. Nestled in

Denise Korrey KORR REALTY CORP

Fully Renovated Home in Winter Park!Beautifully 3-bedroom, 2-bathroom POOL home located in the desirable Eastbrook community of Winter Park. Situated on an oversized .30-acre corner lot in a quiet cul-de-sac with no HOA.This property offers 1,715 sq. ft. of living space, a 1-car garage, and a spacious fenced backyard—the perfect combination of comfort, style, and location. Updates include

Julimar Barreiro Pastrana SERHANT

Discover comfortable Winter Park living in this freshly painted, bright 3-bedroom, 2.5-bath corner-unit townhome located in the gated Grayson Square community. The open-concept living and dining area is filled with natural light and opens to a covered lanai, ideal for everyday enjoyment. The modern kitchen features stainless steel appliances, quartz countertops, ample cabinetry, and generous

Denise Del Castillo LPT REALTY, LLC

Price Reduced | Best Value in Grayson Square! Step into effortless style and modern comfort in this beautifully crafted 2024 townhome, now priced to sell in Winter Park’s gated Grayson Square community. From the moment you arrive, the home’s sleek curb appeal and smart features set the tone, including keypad entry, smart lighting, and thoughtful upgrades throughout. Inside, the open-concept main

Erica Diltz BALDWIN PARK REALTY LLC

Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and

He Gao U S GLORY REALTY

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

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

A Fully Renovated Gem in the Heart of Winter Park Welcome to this stunningly renovated 5-bedroom, 2-bathroom residence, perfectly positioned in one of Winter Park’s most sought-after neighborhoods. Offering over 2,000 square feet of beautifully designed living space, this home seamlessly blends modern elegance, everyday comfort, and an unbeatable Central Florida location—all set on a quiet,

Jose Hernandez LA ROSA REALTY CW PROPERTIES L

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

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

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.

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

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

Welcome home to this immaculately maintained 3-bedroom, 3-bathroom brick home in Winter Park, ideally located in one of Central Florida’s most sought-after areas and offering the freedom of no HOA. Thoughtfully cared for and upgraded, this home blends timeless construction with modern comfort and exceptional functionality, making it perfect for everyday living and entertaining. The heart of the

Joseph Giardino PHOENIX REALTY ADVISORS LLC

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 Bathrooms: Both

Yuleisy Marquez FLORIDA INVESTMENT REALTY GRP

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

SELLER MOTIVATED! 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

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

One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a 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 layout is perfect

Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

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