Orlando/Chickasaw Homes under $400,000

Orlando/Chickasaw Homes under $400,000

Welcome to the enchanting neighborhood of Chickasaw in Orlando, Florida, where vibrant living meets affordability! Nestled in the heart of Orange County, Chickasaw boasts a unique blend of suburban charm and urban convenience. This thriving community is known for its friendly atmosphere, lush green parks, and excellent schools, making it an ideal location for families, first-time homebuyers, and anyone looking to enjoy the sunshine state.

One of the most appealing aspects of Chickasaw is the availability of homes priced under $400,000. Here, you can discover a variety of charming properties, from cozy single-family homes to modern townhouses, all designed to suit diverse lifestyles and budgets. Whether you’re seeking a quaint starter home or a spacious residence to raise your family, Chickasaw offers a wealth of options that won’t break the bank.

Beyond the homes, the neighborhood is surrounded by an array of amenities. You’ll find delightful local shops, dining options, and recreational opportunities just a stone's throw away. Enjoy leisurely afternoons at the nearby parks, or take advantage of the vibrant cultural scene that Orlando has to offer, including world-renowned attractions and entertainment.

Living in Chickasaw means embracing a lifestyle filled with sunshine, community spirit, and endless possibilities. With its affordable housing market and prime location, this neighborhood is the perfect place to call home. Come explore the charm of Chickasaw—your dream home awaits!

Newest Orlando/Chickasaw Homes under $400,000

3548 Benson Park Boulevard, Orlando
$389,000
3 Beds ⋅ 2 Baths ⋅ O6449166 MLS
A wooded conservation backdrop, an established neighborhood, and the appeal of East Orlando suburban living. Welcome to this home in the Young Pine community, where a natural setting complements everyday comfort and convenience. This three-bedroom, two-bathroom home offers comfortable single-story living, a two-car garage, and an outdoor setting designed for relaxation and everyday enjoyment. The spacious backyard features open green space, mature landscaping, and a wooded conservation backdrop. A patio extends your living space outdoors, creating an inviting setting for morning coffee, weekend gatherings, or simply unwinding at the end of the day. Inside, the home offers a comfortable, functional layout that accommodates the rhythm of everyday life, from quiet mornings and relaxed evenings to entertaining friends and gathering around the table. Three bedrooms provide flexibility for a variety of needs, while the single-story design creates a natural connection between indoor comfort and outdoor living. Beyond the property, enjoy the appeal of East Orlando suburban living, where established neighborhoods and residential surroundings offer a welcome retreat from the busier parts of Central Florida. With convenient access to major roadways, shopping and dining at Waterford Lakes, Orlando's theme parks, Downtown Orlando, and Orlando International Airport are all within a manageable drive. It's a location that offers the comfort of suburban living while keeping the area's entertainment, recreation, and everyday conveniences within reach. For buyers exploring homes for sale in East Orlando, this property brings together comfortable single-story living, generous outdoor space, a patio, and a conservation backdrop in an established East Orlando community. Come experience the setting, explore the possibilities, and discover how this East Orlando home could complement your lifestyle. Schedule your private showing.

3548 Benson Park Boulevard, Orlando
2814 Palm Isle Way, Orlando
$385,000
3 Beds ⋅ 2 Baths ⋅ O6448247 MLS
Your own private backyard retreat in the heart of Orlando! Tucked away on a quiet cul-de-sac in the desirable Islands of Curry Ford community, this inviting 3-bedroom, 2-bathroom pool home offers a wonderful combination of privacy, comfort, and convenience—with some special features that make it stand out from the crowd. Step inside and discover an open, welcoming living space highlighted by vaulted ceilings, abundant natural light, and a comfortable floor plan designed for everyday living. With 1,339 square feet of living space, this home makes excellent use of its layout, offering spacious bedrooms, an inviting kitchen with dining space, and plenty of room to relax or entertain. But the real showstopper is waiting out back! Step outside to your private, screened-in swimming pool and backyard entertainment area, where weekends can feel like a vacation without ever leaving home. The recently renovated pool is perfect for cooling off on warm Florida afternoons, while the 16-foot retractable outdoor movie screen transforms your backyard into your very own open-air theater. Imagine movie nights under the stars, weekend barbecues, or simply unwinding poolside after a long day. A retractable awning provides additional shade and comfort, while the fenced backyard and mature landscaping create a peaceful setting for enjoying the Florida lifestyle. Beyond its inviting atmosphere, this home offers several important improvements, including a newer roof, new air conditioning system, newer solar hot water heater, and additional attic insulation. The attached two-car garage also features a screened garage door, adding versatility and allowing you to enjoy fresh air while working on projects or spending time in the garage. Location is another major advantage! Conveniently situated near SR-417 and SR-408, you'll enjoy easy access to Downtown Orlando, UCF, Orlando International Airport, International Drive, and Central Florida's world-famous theme parks. Shopping, restaurants, parks, schools, and everyday conveniences are all nearby. And with an HOA of just $312 annually, you can enjoy the benefits of this established neighborhood without the burden of high association fees. If you've been searching for a home that offers more than just the basics, this one deserves your attention. A quiet cul-de-sac setting, private pool, outdoor movie theater, valuable improvements, and a fantastic Orlando location make this a home you'll want to experience in person.Come see what makes this home special—schedule your private showing today!

2814 Palm Isle Way, Orlando
9149 Lee Vista Boulevard Unit 405, Orlando
$230,000
2 Beds ⋅ 2 Baths ⋅ S5157640 MLS ⋅ 9149 BLDG.
Well-located 2-bedroom, 2-bath condo featuring a versatile loft that provides additional space for a home office, guest area, or entertainment room. The functional layout offers comfortable living with the added flexibility of the loft, making this property a great option for a variety of lifestyles. Conveniently located with easy access to shopping, dining, major roads, and everyday essentials. Whether you’re looking for your next home or an investment opportunity, this condo offers space, convenience, and a desirable location. Schedule your showing today! Unit is currently rented a great opportunity for an investor.

9149 Lee Vista Boulevard Unit 405, Orlando
9672 Doris Lane, Orlando
$339,900
3 Beds ⋅ 3 Baths ⋅ A4708513 MLS ⋅ - BLDG.
SPACE, STYLE & FLEXIBILITY! This Mediterranean-style END-UNIT townhome stands out with soaring high ceilings, an impressive grand loft, 2024 A/C system, and approximately 1,659 sq. ft. of versatile living space. Featuring 3 bedrooms, 2.5 baths, a private lanai, and attached 1-car garage, it offers the extra space and flexibility today's buyers are looking for—all within a gated community with a community pool. Inside, enjoy spacious living and dining areas, an eat-in kitchen, and an upstairs loft overlooking the living space—perfect for a home office, media room, playroom, or second living area. The kitchen features Corian countertops and stainless steel appliances, including a glass-top range, refrigerator, and dishwasher. The upstairs primary suite offers a walk-in closet and private bath with walk-in shower, plus two additional bedrooms. INVESTMENT OPPORTUNITY! Currently tenant occupied with tenants in good standing, offering an attractive opportunity for investors seeking an income-producing property. Conveniently located minutes from Downtown Orlando, Lake Nona, Orlando International Airport, shopping, attractions, UCF, and Valencia College. A standout combination of space, style, versatility, and convenience!

9672 Doris Lane, Orlando
5264 Sapling Sprout Drive, Orlando
$399,900
4 Beds ⋅ 3 Baths ⋅ O6444333 MLS ⋅ 5264 BLDG.
Welcome to Pinewood Reserve! Built in 2021 and beautifully maintained, this spacious 4-BEDROOM, 3-BATHROOM townhome offers 1,809 square feet of thoughtfully designed living space, a 2-CAR REAR-ENTRY GARAGE, and upgraded hard-surface flooring throughout. Step inside to a bright, open-concept main living area where the kitchen, dining and family spaces flow together beautifully. The kitchen features STONE COUNTERTOPS and plenty of room for gathering and entertaining. A FIRST-FLOOR BEDROOM AND FULL BATH provide added flexibility for guests, a home office, or multigenerational living. Upstairs, you'll find the spacious PRIMARY SUITE with an en-suite bath featuring dual sinks and a walk-in closet, along with two additional bedrooms, another full bath, a loft area and conveniently located UPSTAIRS LAUNDRY. Updated interior paint, light fixtures and ceiling fans add to the home's fresh, move-in-ready feel. Enjoy Florida living from the home's PRIVATE COURTYARD AND PATIO, with a park and playground conveniently located across the street. Pinewood Reserve offers fantastic community amenities including a POOL, DOG PARK, PLAYGROUND, WALKING TRAILS, SIDEWALKS AND FISHING POND, along with exterior and grounds maintenance included through the association. Conveniently located near SR 417, shopping, dining and everything the Orlando area has to offer, this nearly-new townhome combines space, convenience and low-maintenance living in a great Central Florida location.

5264 Sapling Sprout Drive, Orlando
3423 Wilshire Way Road Unit 27, Orlando
$229,900
2 Beds ⋅ 3 Baths ⋅ O6441767 MLS ⋅ 3423 BLDG.
Welcome to this 2-bedroom, 2.5-bathroom condo tucked inside the gated community of Victoria Pines. High ceilings create an open, airy feel throughout, while luxury vinyl plank flooring flows through the main living areas. Recent upgrades include a newly tiled primary bathroom shower, new AC 2026, fresh interior paint, updated blinds, new fans and light fixtures, a newer washer and dryer, a 2023 roof, and fresh exterior paint. Ideally located near top-rated schools, shopping, and dining, this condo offers the perfect blend of comfort, style, and low-maintenance living. Don't miss your chance to make it yours!

3423 Wilshire Way Road Unit 27, Orlando
8775 Sartori Street Unit 301, Orlando
$240,000
3 Beds ⋅ 2 Baths ⋅ O6444022 MLS ⋅ Horizons At Vista Lake BLDG.
Beautifully situated 3-bedroom, 2-bath apartment featuring a new 2026 AC, stainless steel appliances, no carpet, and a spacious third-floor corner location. Enjoy peaceful views of the lush greenery, landscaped walkways, and scenic pond. The gated community offers excellent amenities, including a resort-style pool, tennis courts, and a fitness center. The unit also includes one assigned parking space, with additional guest parking available. Conveniently located with easy access to SR 417 and SR 528, and just minutes from Orlando International Airport, UCF, Lake Nona Medical City, and Downtown Orlando. Disclaimer: The information provided in this listing is for general informational purposes only and is not guaranteed or warranted to be accurate, complete, or current. Buyers are encouraged to independently verify all information before making any decisions.

8775 Sartori Street Unit 301, Orlando
8625 Redskin Court, Orlando
$370,000
3 Beds ⋅ 2 Baths ⋅ O6442696 MLS
VERSATILE BONUS SPACE + BACKYARD ENTERTAINING + CONVENIENT ORLANDO LOCATION! This well-designed home combines a functional layout, low-maintenance finishes, and flexible living spaces in the established Chickasaw Trails neighborhood. The split-bedroom floor plan offers comfortable separation between the primary and secondary bedrooms, while the L-shaped living and dining areas provide flexibility for everyday living and entertaining. Wood-plank vinyl flooring flows throughout the main living areas for a clean, cohesive look. A standout feature is the spacious, air-conditioned Florida/bonus room with tile flooring, offering valuable additional living space ideal for a home office, fitness area, hobby space, playroom, or entertainment room. Outside, the backyard is ready for relaxing and entertaining, featuring a recently upgraded deck perfect for weekend barbecues, outdoor gatherings, or enjoying the Florida sunshine. Enjoy the neighborhood conveniently located near Chickasaw Trail shopping and dining, Vista Lakes shopping center, and everyday essentials, with access to SR 417 via Curry Ford Road for travel throughout Central Florida. Orlando International Airport and Lake Nona are also within convenient driving distance, while Waterford Lakes Town Center offers additional shopping, dining, and entertainment options. Enjoy a blend of flexible living space, outdoor enjoyment, and convenient access to Orlando-area amenities. Schedule your showing today!

8625 Redskin Court, Orlando
9743 Biscotti Avenue, Orlando
$343,900
3 Beds ⋅ 3 Baths ⋅ O6435592 MLS ⋅ 9743 BLDG.
PRICED TO SELL! WELL-MAINTAINED TOWNHOME WITH DIRECT VIEW OF THE COMMUNITY POND, NEW AC & NEW WATER HEATER! Welcome to this beautiful and well-maintained two-story townhome located in a highly desirable gated community with a community swimming pool! Enjoy a direct view of the community pond from the covered front entry as you arrive at this spacious and inviting home. Featuring 3 bedrooms, 2.5 bathrooms, and a versatile loft, this townhome offers a comfortable and functional layout, with all bedrooms conveniently located upstairs. The open floor plan features hardwood flooring in the dining room and tile flooring in the living room, kitchen, bathrooms, creating a clean and inviting living space. The well-appointed kitchen includes a convenient breakfast bar, perfect for casual dining and entertaining, while the interior laundry room adds everyday convenience. The spacious primary suite features a walk-in closet, dual vanities, relaxing garden tub, and separate shower, creating a comfortable retreat at the end of the day. Additional highlights include a NEW AC system, NEW WATER HEATER, one-car garage, paver driveway, covered entry, direct community pond view, and access to the community swimming pool perfect for relaxing and enjoying Florida's year-round lifestyle. Ideally located just minutes from UCF, Orlando International Airport, shopping, dining, entertainment, and major highways, this home offers the perfect combination of comfort, convenience, and community amenities. Priced to sell and ready for its new owner! Don't miss this opportunity to own a beautiful townhome in a desirable gated community with desirable updates already in place. Schedule your private showing today! Disclaimer: All property information, including measurements, HOA fees, lot sizes, and property taxes, is deemed approximate and should be independently verified by the buyer or buyer’s agent.

9743 Biscotti Avenue, Orlando
9863 Tivoli Villa Drive, Orlando
$341,900
3 Beds ⋅ 3 Baths ⋅ S5157082 MLS ⋅ 1 BLDG.
$5,500 SELLER FLEX CASH! Seller is offering buyers the flexibility to use up to $5,500 toward allowable closing costs/prepaids OR toward replacement of the A/C and water heater. COMPLETELY FURNISHED AT NO ADDITIONAL COST TO THE BUYER, making it an exceptional move-in-ready opportunity. LOCATION, VIEWS & PRIVACY! Welcome to 9863 Tivoli Villa Drive, a beautifully maintained 3-bedroom, 2.5-bath corner unit offering 1,809 sq. ft. of comfortable living space in a gated Orlando community. What truly sets this home apart is its exceptional location within the community. Ideally positioned just steps from the pool and amenities, the unit offers beautiful garden and pool views, creating a relaxing setting right outside your door. As a corner unit, it also provides additional privacy and natural light. The home features TWO BALCONIES—a welcoming front balcony and a private balcony off the primary bedroom overlooking the lake, perfect for enjoying your morning coffee or unwinding at the end of the day with a peaceful water view. The spacious floor plan includes two convenient laundry areas and has been well cared for and maintained. The community roof was replaced in 2021, providing another valuable update for future ownership. The location is hard to beat! Conveniently located near Lee Vista, Orlando International Airport, Lake Nona, major highways, shopping, dining, employment centers, and everyday conveniences. Enjoy the benefits of a gated community, low property taxes and NO CDD. Corner location, lake view, pool and garden views, two balconies, and a prime location within the community make this property a standout. Schedule your private showing and experience the setting and views for yourself!

9863 Tivoli Villa Drive, Orlando
6149 Apollos Corner Way, Orlando
$344,900
3 Beds ⋅ 3 Baths ⋅ O6439376 MLS ⋅ 6149 BLDG.
Discover the perfect blend of comfort, style, and convenience in this beautifully maintained townhome located in the desirable community of Tivoli Gardens. Featuring an inviting open layout, spacious living areas and abundant natural light. This property offers the ideal setting for relaxation and entertaining. The kitchen boasts ample counter space and overlooks the main living area for effortless hosting. Upstairs, generously sized bedrooms provide privacy and comfort, including a serene primary suite with a walk in closet. Enjoy peaceful outdoor living with a private patio. Just a short walk tho access community amenities including pool, basketball court, and walking trails. Conveniently located near top-rated schools, major highways, shopping and dining.

6149 Apollos Corner Way, Orlando
10332 Manderley Way Unit 111, Orlando
$229,000
2 Beds ⋅ 3 Baths ⋅ O6432594 MLS ⋅ 10332 BLDG.
MOVE-IN READY | 2 BEDROOMS | 2.5 BATHROOMS | GATED COMMUNITY | COMMUNITY POOL | LOW-MAINTENANCE LIVING Welcome to easy, low-maintenance living in the gated community of Victoria Pines in East Orlando. This move-in-ready, two-story condo offers an open-concept layout with 2 bedrooms, 2 full bathrooms, and a convenient half bath, making it an ideal home for first-time buyers, professionals, investors, or anyone looking for a lock-and-leave lifestyle. The main level features a bright, open-concept living and dining area that flows into the kitchen, along with a convenient half bath for guests. Sliding doors lead to the enclosed screened porch, providing an additional space to enjoy your morning coffee or unwind at the end of the day, overlooking a peaceful green area with no rear neighbors. Upstairs, you'll find two spacious bedrooms, each with its own ensuite bathroom, offering privacy and convenience for residents or guests. A second-floor laundry closet keeps everyday chores tucked away and easily accessible. Residents of Victoria Pines enjoy the convenience of a gated community, community pool, sidewalks, and low-maintenance living. The location puts you close to SR 417 and SR 408 with easy access to UCF, Valencia College, Waterford Lakes Town Center, Avalon Park, shopping, dining, entertainment, and everyday conveniences. If you're looking for a move-in-ready Orlando condo with an open floor plan, screened porch, private rear setting, and resort-style community amenities, this Victoria Pines home is ready to welcome you.

10332 Manderley Way Unit 111, Orlando
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