Maitland / Eatonville Homes under $500,000

Maitland / Eatonville Homes under $500,000

Welcome to the enchanting region of Maitland and Eatonville, Florida—a hidden gem nestled just north of Orlando. Known for its rich history, vibrant culture, and lush landscapes, this area offers a unique blend of suburban charm and urban convenience. With its picturesque lakes, beautiful parks, and friendly neighborhoods, Maitland and Eatonville are perfect for families, professionals, and retirees alike.

One of the most appealing aspects of this region is the diverse range of homes available, especially for those seeking options under $500,000. Whether you’re looking for a cozy bungalow, a modern townhouse, or a spacious family home, Maitland and Eatonville have something to suit every taste and budget. Many properties boast stunning architectural styles, well-maintained gardens, and easy access to local amenities, making it a desirable choice for homebuyers.

Maitland is known for its excellent schools, thriving arts scene, and a variety of dining and shopping options, from charming boutiques to popular restaurants. The nearby scenic Lake Lily Park is perfect for afternoon strolls or weekend picnics, while the historic Eatonville invites residents to explore its rich heritage and cultural events.

With its affordable housing market and vibrant community spirit, Maitland and Eatonville are ideal for those looking to invest in a home without compromising on quality of life. Discover the beauty and charm of this delightful region—your dream home awaits!

Newest Maitland / Eatonville Homes under $500,000

1931 Michael Tiago Circle, Maitland

1931 Michael Tiago Circle, Maitland

3 Beds ⋅ 3 Baths ⋅ Maitland Village SubDv. ⋅ 32751 Zip Code

Welcome to this beautiful 3-bedroom, 2.5-bath townhome offering approximately 2,100 square feet of comfortable living space in the gated community of Maitland Village. The open floor plan features spacious living and dining areas with abundant natural light, creating an inviting setting for everyday living and entertaining. The kitchen flows seamlessly into the main living areas, while all three bedrooms are located upstairs for added privacy. The generous primary suite provides a relaxing retreat with an en-suite bathroom and ample closet space. Additional features include an interior laundry area, a private outdoor patio, and an attached two-car garage. Maitland Village offers gated access, a community pool, clubhouse, sidewalks, and beautifully maintained surroundings, also includes water, Cable & internet . Conveniently located near I-4, Maitland Center, Winter Park, Downtown Orlando, shopping, dining, and entertainment. Schedule your private showing and discover the space, convenience, and lifestyle this Maitland townhome has to offer!

1931 Michael Tiago Circle, Maitland

2517 Caper Lane Unit 207, Maitland

2517 Caper Lane Unit 207, Maitland

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Virtually Staged. Welcome to this charming 1-bedroom, 1-bathroom second-floor condo in the heart of beautiful Maitland! This well-maintained home offers a fantastic opportunity for both investors and buyers looking for a convenient Central Florida location. The interior has been recently repainted, giving the home a fresh, clean feel. Several major components have also been updated within the past 3-5 years, including the HVAC system, water heater, refrigerator, and oven, providing added peace of mind for the next owner. The community offers desirable amenities including a swimming pool, fitness center, and playground, while the HOA fee includes water, helping simplify monthly expenses. Location is a major plus, with easy access to shopping, restaurants, major roads, and Central Florida's universities, including Full Sail University and UCF. Whether you're looking to add to your investment portfolio or secure a property in a convenient Maitland location, this condo is worth a look. The property is currently tenant occupied, with the existing lease scheduled to expire in March, making this an excellent opportunity for an investor seeking an income-producing property with an established tenant in place. Schedule your showing today and discover all this cute Maitland condo has to offer!

2517 Caper Lane Unit 207, Maitland

508 Banyon Tree Circle Unit 200, Maitland

508 Banyon Tree Circle Unit 200, Maitland

Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

MUST SEE! Well-maintained and move-in-ready 2-bedroom, 2-bath, second-floor condo in the desirable Carrington Park community of Maitland. Offering 1,200+ square feet, this spacious split-bedroom floor plan features generously sized bedrooms, an open living and dining area, and a private screened balcony—perfect for enjoying the Florida lifestyle. The unit also includes a private washer/dryer hookup for added convenience. Enjoy an exceptional location near the intersection of Howell Branch Road and SR-436, with Publix, Starbucks, shopping, dining, and everyday conveniences just minutes away. Full Sail University is approximately 10 minutes away, UCF is nearby, and Orlando's major attractions are easily accessible. Carrington Park offers two swimming pools, a large fitness center, a playground, and beautifully maintained green spaces. The HOA provides excellent value by including water, sewer, trash, building insurance, roof maintenance, grounds maintenance, and community pool maintenance. Currently leased through December 31, 2026, at $1,700/month, providing immediate rental income for an investor while preserving future flexibility for an owner-occupant. Seller financing may be available with $50,000 down and acceptable terms. A great opportunity for an owner-occupant or investor looking for space, location, amenities, and value in a desirable Maitland area. Come see it in person—this is one you won't want to overlook. Schedule your showing today and bring your offer!

508 Banyon Tree Circle Unit 200, Maitland

508 Banyon Tree Circle Unit 200, Maitland

508 Banyon Tree Circle Unit 200, Maitland

2 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

MUST SEE! Well-maintained and move-in-ready 2-bedroom, 2-bath second-floor condo in the desirable Carrington Park community of Maitland. Offering 1,200+ square feet, this spacious split-bedroom floor plan features generously sized bedrooms, an open living/dining area, and a private screened balcony—perfect for enjoying the Florida lifestyle. The unit also includes a private washer/dryer hookup for added convenience. Enjoy an exceptional location near the intersection of Howell Branch Road and SR-436, with Publix, Starbucks, shopping, dining, and everyday conveniences just minutes away. Full Sail University is approximately 10 minutes away, UCF is nearby, and Orlando’s major attractions are easily accessible. Carrington Park offers two swimming pools, a large fitness center, playground, and beautifully maintained green spaces. The HOA provides excellent value by including water, sewer, trash, building insurance, roof, grounds maintenance, and community pool maintenance. Currently leased through December 31, 2026 at $1,700/month, providing immediate rental income for an investor while preserving future flexibility for an owner occupant. Seller financing may be available with $50,000 down and acceptable terms. A great opportunity for an owner occupant or investor looking for space, location, amenities, and value in a desirable Maitland area. Come see it in person—this is one you won’t want to overlook. Schedule your showing today and bring your offer!

508 Banyon Tree Circle Unit 200, Maitland

514 Wigman Drive, Maitland

514 Wigman Drive, Maitland

3 Beds ⋅ 2 Baths ⋅ Eaton Estates SubDv. ⋅ 32751 Zip Code

This beautifully renovated three-bedroom, two-bathroom home offers a bright, comfortable layout with stylish modern finishes throughout. Enjoy a spacious enclosed Florida room, a large fenced backyard perfect for entertaining, pets or outdoor activities, and a covered two-car carport with additional driveway parking. Major improvements include an updated exterior A/C unit, new refrigerator, stove, dishwasher and microwave. Conveniently located in Eatonville with no HOA, this move-in-ready home is an excellent opportunity for homeowners and comes fully furnished. Near Wholefoods, LA Fitness, with many restaurants and shopping blocks away.

514 Wigman Drive, Maitland

180 E Faith Terrace, Maitland

180 E Faith Terrace, Maitland

2 Beds ⋅ 2 Baths ⋅ Northwood Heights SubDv. ⋅ 32751 Zip Code

Welcome home to this charming and beautifully updated 2 bedroom, 2 bathroom property in the heart of Maitland. Thoughtfully renovated in 2016, this inviting residence offers a wonderful blend of character, comfort, and modern finishes. Step inside to discover updated wood flooring, fresh interior paint, and a completely renovated kitchen featuring stainless steel appliances and stone countertops. The two generously sized bedrooms provide a comfortable living space, while both bathrooms have been tastefully renovated. Stone countertops can be found throughout the home, adding a cohesive and timeless touch. Peaceful water views of Lake Seminary, create a lovely backdrop for morning coffee, entertaining, or simply relaxing at home. Additional highlights include a new well installed 2022, a new septic tank installed in 2024, and a new grey water tank in 2026. The backyard was also freshly resodded, providing a beautiful outdoor space to enjoy Florida's year-round sunshine. Located in desirable Maitland, the home is close to shopping, dining, parks, Winter Park, and major roadways, making it easy to enjoy everything Central Florida has to offer.

180 E Faith Terrace, Maitland

559 Flemming Way Unit 203, Maitland

559 Flemming Way Unit 203, Maitland

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Virtually Staged. Welcome to this well-maintained and move-in-ready second-floor condo, offering comfort, convenience, and a great location! This charming 1-bedroom, 1-bathroom unit features a spacious layout, a large walk-in closet, and a private outdoor patio where you can enjoy your morning coffee or relax after a long day. The property is currently vacant and ready to show, making it an excellent opportunity for a first-time homebuyer, seasonal resident, or investor looking for a low-maintenance property. The community offers a variety of desirable amenities, including a beautiful swimming pool, playground, and green spaces, and a great fitness/exercise room for residents to enjoy. The low HOA fee makes this property even more attractive for those looking for an affordable and convenient lifestyle. Laundry facilities are conveniently located outside across from the building. Located in a convenient area close to public transportation, stores, shops, restaurants, and everyday necessities, this condo provides easy access to everything you need. Whether you are looking for a comfortable place to call home or a great investment opportunity, this property offers an excellent combination of location, amenities, affordability, and convenience. Don't miss the opportunity to see this beautiful second-floor condo. The unit is vacant, in good condition, and ready for its new owner. Schedule your showing today!

559 Flemming Way Unit 203, Maitland

2313 Haywood Court Unit 201, Maitland

2313 Haywood Court Unit 201, Maitland

2 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Welcome to Carrington Park Condominiums! This 2-BEDROOM, 2-BATHROOM condo is located on the TOP FLOOR, (only1 flight of stairs) offering added privacy with no neighbors above. The comfortable floor plan provides plenty of space for everyday living, while the SCREENED-IN BALCONY is the perfect spot to relax and enjoy the Florida weather. A STACKABLE WASHER-DRYER is conveniently located inside the unit, and the REFRIGERATOR CONVEYS for added convenience. The condo building is ideally situated NEXT to the COMMUNITY POOL, making it easy to take advantage of one of the communities most popular amenities. The community also features a LARGE FITNESS CENTER and PLAYGROUND, providing something for everyone. Conveniently located in Maitland with easy access to major highways, shopping, dining, and everyday necessities, this condo offers a great combination of location and low-maintenance living. Whether you're searching for a PRIMARY RESIDENCE OR INVESTMENT/RENTAL PROPERTY, this Carrington Park condo is a wonderful opportunity!

2313 Haywood Court Unit 201, Maitland

1225 Lake Shadow Circle Unit 14102, Maitland

1225 Lake Shadow Circle Unit 14102, Maitland

2 Beds ⋅ 2 Baths ⋅ Building 14 Visconti West SubDv. ⋅ 32751 Zip Code

Auction Property. Auction Property. AUCTION/OCCUPIED. Buyers will be required to sign a occupancy declaration. 2-bedroom 2-bathroom condominium in gated community of Visconti West situated off Lake Shadow. Quick access to interstate 4 and Florida turnpike. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or guarantee occupancy status. NO VIEWINGS of this property. Please DO NOT DISTURB the occupant. Buyer is responsible for obtaining possession of the property upon closing.

1225 Lake Shadow Circle Unit 14102, Maitland

2308 Haywood Court Unit 100, Maitland

2308 Haywood Court Unit 100, Maitland

3 Beds ⋅ 2 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

Need Room! Welcome home to this spacious 1612 S.F. first-floor condominium featuring three bedrooms and two full baths in a well-maintained community conveniently located near shopping, dining, and Full Sail University. Step inside to find brand-new luxury plank flooring throughout the living and bedroom areas, ceramic tile in the kitchen and bathrooms, and absolutely no carpet! Blinds on all windows and ceiling fans add to the comfort and convenience of this inviting home. The kitchen comes complete with refrigerator, range, microwave, and dishwasher, while a brand-new washer and dryer are also included. Relax and enjoy Florida's beautiful weather year-round from your private screened-in lanai, with the community pool and playground conveniently located nearby. The HOA offers exceptional value by covering water, sewer, trash, building insurance, roof, grounds maintenance, and the community pool. With its desirable first-floor location, fresh updates, generous three-bedroom floor plan, and convenient location, this condo offers easy Florida living and is ready for you to make it home!

2308 Haywood Court Unit 100, Maitland

27 N Calhoun Avenue, Maitland

27 N Calhoun Avenue, Maitland

4 Beds ⋅ 2 Baths ⋅ Coopers Sub SubDv. ⋅ 32751 Zip Code

BRAND-NEW CONSTRUCTION IN MAITLAND, FL! Welcome to this beautifully designed 4-bedroom, 2-bath home offering 1,809 sq. ft. under air and 2,359 total sq. ft., with NO HOA and an oversized driveway providing plenty of parking. Step inside to a bright, open-concept floor plan where the family and dining areas flow seamlessly into a spacious modern kitchen designed for both everyday living and entertaining. The kitchen features a large center island with generous seating, 42” wood cabinetry with soft-close doors, stylish hardware and crown molding, beautiful pendant lighting, sleek quartz countertops, and stainless-steel appliances. The private primary suite offers a spacious walk-in closet and a beautifully appointed bathroom featuring upgraded porcelain tile details and quartz countertops. Three additional bedrooms provide comfortable living space and generous closets, making the layout ideal for family, guests, or a home office. Additional upgrades include tile flooring, 5¼” baseboards, ceiling fans, upgraded fixtures throughout, and an attractive modern exterior elevation. The kitchen and family room open to a spacious patio, extending the living space outdoors and creating the perfect setting for relaxing or entertaining. The oversized driveway offers ample room for multiple vehicles, while the Maitland location puts you close to shopping, dining, entertainment, and everything Central Florida has to offer. Enjoy convenient access to Downtown Orlando, area beaches, and major roadways including SR-417, SR-408, and I-4. Brand-new construction, modern finishes, generous living spaces, NO HOA, and a highly convenient Maitland location—this home brings together style, functionality, and location in one exceptional property.

27 N Calhoun Avenue, Maitland

2520 Caper Lane Unit 204, Maitland

2520 Caper Lane Unit 204, Maitland

1 Beds ⋅ 1 Baths ⋅ Carrington Park A Condo SubDv. ⋅ 32751 Zip Code

**LOCATION, LOCATION!** Welcome to this charming and cozy 1-bedroom, 1-bathroom condo, ideally located in a convenient and desirable area near Semoran Blvd and Howell Branch Rd. This move-in-ready second-floor unit offers comfort, convenience, and easy access to everything you need. Enjoy being just walking distance from shopping, restaurants, supermarkets, and everyday essentials. The community offers a refreshing swimming pool, perfect for relaxing or enjoying quality time with family and friends, as well as ample parking for residents and guests. The property is also conveniently located near schools and educational institutions, including Rollins College, making it an excellent opportunity for professionals, or anyone looking for a convenient Central Florida location. HOA includes water, adding even more value and convenience. Whether you're looking for your next home, a low-maintenance place to live, or an investment opportunity, this condo is one you won't want to miss! Schedule your showing today and come see all this property has to provide.

2520 Caper Lane Unit 204, Maitland

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