Maitland, FL Homes for Sale under $500,000

One or more photo(s) has been virtually staged. Mortgage savings may be available for buyers of this listing. Welcome to this beautifully updated single-family home in the heart of Maitland, offering 3 bedrooms, 1 bathroom, and 1,848 square feet of comfortable living space. Set on over a quarter of an acre, this property blends modern upgrades with everyday functionality. From the moment you

David Zambrano REDFIN CORPORATION

Rates have DROPPED and with the FREE 1 year interest rate buy down, it's time to BUY. This four-bedroom, two-bath, split-floor plan home is move-in ready and ready for your personal touches. The home offers a large living room, open floor plan kitchen and den all with soaring ceilings. The fourth bedroom is in front of the house and is great for a home office or guest bedroom. The Winfield

Erik Baum PREMIER SOTHEBYS INT'L REALTY

Welcome! This well-maintained ranch-style home features a functional single-level design with a newer roof (2024) encompassing 1,523 square feet of living space, plus you get to enjoy an additional 255ft' of expanded living space on the enclosed florida room which is under AC. The main living area includes three bedrooms and one and a half baths. a stunning kitchen (remodeled 2025), open floor

Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Welcome to 1241 Manchester Road, a spacious 3-bedroom, 2-bath home with over 2,000 sq ft of livingspace in the heart of Maitland. This solid block construction home, situated on a corner lot,offers incredible potential for new owners to bring their vision to life and make it their own.Inside, you’ll find generous living areas, a glassed Florida room, a breakfast nook adjacent

Suzy Masson OLDE TOWN BROKERS INC

Charming 3BR/2BA Home with Updated InteriorThis move-in ready home features 3 bedrooms, 2 bathrooms, and a bright open layout with stylish updates throughout. Enjoy fresh interior paint, updated flooring, and modern touches in both the kitchen and baths. The timeless exterior offers great curb appeal with fresh paint, dark shutters, and stone accents. A spacious backyard provides plenty

Brett Wright FLORIDA HOMES REALTY & MORTGAGE

One or more photos was virtually staged. Welcome to this generously sized home offering a rare opportunity to create the space you’ve always dreamed of. Situated in a desirable Maitland neighborhood, this property features 3 bedrooms, 2 bathrooms, a 2-car garage, and a private pool — all on a fully fenced lot with NO HOA. Inside, you’ll find a traditional layout with a formal living and dining

Dione Collier-Larkin ADAIR REALTY INC

Breathtaking views of Lake Maitland, the largest lake of the desirable Winter Park Chain of Lakes. Enjoy sunrises across the lake from the privacy of your balcony overlooking the pool. This 2-bedroom, 2-bath condo within West Cove Condos is centrally located in close proximity to a variety of restaurants, Lake Lily Park, Enzian Theater and easy access to I-4 and Maitland Blvd. Your association

Jeff Crandall SHORESTONE PROPERTY GROUP

Charming and Spacious Townhome in Maitland!Welcome to 1938 Michael Tiago a beautifully maintained 4-bedroom, 2.5 bathroom home located in the desirable Maitland Village Community with a POND VIEW and END UNIT. This stunning property offers a perfect blend of classic charm and modern convenience, making it an ideal place to call home.As you approach this inviting residence, you’ll

Robin Mitchell ROBIN MITCHELL REALTY

Something is very special about Lakefront Living! Come visit this beautiful Lakefront Condo located at The Moorings On Lake Maitland, part of the Winter Park chain of lakes. Enjoy the Florida lifestyle in a carefree home with lake front amenities. Imagine Entertaining Family & Friends at the Pool or Heated Spa and the Clubhouse of the Moorings on Lake Maitland. Enjoy relaxing on the Lake Front

Beatrice Palladino GALLERY PROPERTIES INTERNATIONAL

Build Your Dream Home in Prime Maitland Location! A rare opportunity awaits at 1550 Ridgewood Avenue — located just steps from the Enzian Theater, Park Maitland School, and minutes from Whole Foods Market. Zoned for highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High School, this property offers the perfect foundation for your next custom build. With a lot size of 77'

Justin Pekarek ORLANDO PROPERTY ADVISORS

Lovely direct waterfront condominium with large screen porch overlooking beautiful 451 acre Lake Maitland. Screened terrace is wonderful for enjoying the lake. Share the same view as multimillion dollar homes. Updated floor plan with open kitchen, tile throughout, French doors. Maitland is a very central community of greater Orlando. Close to many great restaurants along Orlando Avenue and

Jack Keller JACK KELLER INC

One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 2-bathroom pool home nestled in the heart of Maitland, within sought-after Seminole County. Offering over 1,600 square feet of bright and open living space, this home is designed for comfort and functionality. The sun-filled floor plan features an inviting layout with large windows that bathe the

Dominick Florio RE/MAX TOWN & COUNTRY REALTY

Welcome to Your Family's Next Chapter in Beautiful Maitland!Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend ofmodern comfort and timeless charm, ideal for families ready to make new memories.From the moment you step inside, you're greeted by an abundance of natural light and an open, airy layout

Khamhack Shilling COLDWELL BANKER RESIDENTIAL RE

Welcome to your Lakefront Gem at Lake Lovely Estates!This fully remodeled 3 bedroom, 2 bathroom home on .54 acres is the epitome of modern lakefront living! Step directly into high-end finishes that elevate every corner of this privately fenced retreat. The newly updated kitchen dazzles with sleek quartz countertops, stainless steel appliances, and abundant cabinetry. Waterproof

Laura Heidrich COLDWELL BANKER RESIDENTIAL RE

Motivated Seller – Stylishly Renovated 4-Bedroom Home in Prime Maitland Location! Don’t miss this opportunity - seller is highly motivated and ready to make a deal! This beautifully updated 4-bedroom, 2-bathroom home offers a rare combination of modern upgrades and timeless charm in one of Maitland’s most desirable neighborhoods. Major renovations include a brand-new kitchen, bathrooms, and

Jonathan Minerick HOMECOIN.COM