22

Chickasaw Homes under $500,000

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  • /68

    $484,900

    • 4 Beds
    • 2.5 Baths
    • 1,742 Sq Ft

    4713 Fort Knox Ct, Orlando, FL 32822

    This stunning home is move-in ready and perfectly located on a quiet cul-de-sac with 1,742 sq. ft. of living space (2,307 sq. ft. total), built in 1993, and a 2-car garage. Major systems provide peace of mind with a newer roof (2021), HVAC (2019), water heater (2022), updated plumbing (2025), and a resurfaced pool (2025) — all in a community with a low HOA of just $22/month

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 467-7999

    4713 Fort Knox Ct, Orlando, FL 32822
  • /31

    $424,900

    • 3 Beds
    • 2 Baths
    • 2,039 Sq Ft

    2023 Gamboge Dr, Orlando, FL 32822

    Welcome to 2023 Gamboge Dr, a beautifully updated Orlando home offering comfort, privacy, and an ideal location. Recent upgrades include a new roof (2024), newer A/C compressor and condenser (2022), water heater (2023), refrigerator (2023), garbage disposal (2022), digital thermostat, sprinkler system, and a high-wind rated garage door. Fresh carpet in the family room (2024) adds warmth, while

    Abby Nelson RE/MAX 200 REALTY

    2023 Gamboge Dr, Orlando, FL 32822
  • /61

    $449,950

    • 4 Beds
    • 2 Baths
    • 1,887 Sq Ft

    8654 San Toccoa Dr, Orlando, FL 32825

    PRICE IMPROVEMENT! Charming 4-Bedroom Pool Home in Rio Pinar Country Club! New A/C 8/13/25Welcome to this spacious and beautifully maintained 4-bedroom, 2-bath home located in the highly sought-after Rio Pinar East community. Perfect for entertaining and everyday living, this home offers both a separate gathering.The kitchen is a chef’s dream with 42-inch maple cabinetry, custom tile

    George Freelove KELLER WILLIAMS WINTER PARK

    8654 San Toccoa Dr, Orlando, FL 32825
  • /29

    $449,000

    • 3 Beds
    • 3 Baths
    • 1,804 Sq Ft

    8850 Pine Bay Ct, Orlando, FL 32825

    These homeowners after decades of raising a family and caring for this desirable three-bedroom, three-bathroom, pool home have decided to move on with the next chapter in their lives. Right away, you'll notice the entire front yard has new sod and along with that a brand-new drain field was recently installed and roof shingles were replaced just last year. And in late 2023 the house was re-piped

    Jeff Lain CHARLES RUTENBERG REALTY ORLANDO

    8850 Pine Bay Ct, Orlando, FL 32825
  • /42

    $457,000

    • 3 Beds
    • 2 Baths
    • 1,828 Sq Ft

    969 Gran Paseo Dr, Orlando, FL 32825

    ASSUMABLE VA LOAN WITH A 4.99% INTEREST RATE! Welcome to your personal slice of paradise in the highly desirable Rio Pinar East near the Golf Course community of Orlando, Florida! Key Features: Roof and Solar panels are 5 years old. Solar panels are PAID OFF keeping your electric bill CHEAP (Last month's bill was under $100, maintaining the interior temperature below 70 degrees). 2020 Lennox 5

    Carolina Taborda MOMENTUM REALTY

    969 Gran Paseo Dr, Orlando, FL 32825
  • /6

    $445,000

    • 4 Beds
    • 2 Baths
    • 1,936 Sq Ft

    8419 Fort Thomas Way, Orlando, FL 32822

    SOLAR PANELED HOME *** Welcome to this stunning, move-in-ready home nestled in the heart of Orlando! This spacious property boasts 4 bedrooms and 2 bathrooms, including a luxurious master suite with a walk-in closet and a private bathroom featuring a relaxing garden tub. The chef’s kitchen is equipped with stainless steel appliances and a charming breakfast area. With a roof that’s just 3 years

    Amy Martinez PR REAL ESTATE SERVICES

    8419 Fort Thomas Way, Orlando, FL 32822
  • /20

    $445,000

    • 4 Beds
    • 3 Baths
    • 2,399 Sq Ft

    8647 Otter Creek Ct, Orlando, FL 32829

    Offered As-Is. This neighborhood is located convenient to Orlando airport, the 528 & 417 expressways and Orange County employers. Spacious and open 4 bedroom 3 bath split plan! The home has formal living and dining rooms plus a huge family room off the eat-in kitchen. Skylight in the family room. A one story home that's one of the largest in the neighborhood. Updates to HVAC and plumbing. Roof

    Qiping Shen SMOOTH RIVER REALTY LLC

    8647 Otter Creek Ct, Orlando, FL 32829
  • /26

    $400,000

    • 4 Beds
    • 2 Baths
    • 1,641 Sq Ft

    3826 Peace Pipe Dr, Orlando, FL 32829

    Nestled in the highly desirable Chickasaw Trails community, this beautifully maintained 4-bedroom, 2-bath home perfectly blends comfort, style, and functionality. From the moment you arrive, the well-manicured landscaping, extended driveway, and inviting entryway create a warm and welcoming first impression.Step inside to discover an open, light-filled layout with high ceilings and plenty

    Christina Munkberg COLDWELL BANKER RESIDENTIAL RE

    3826 Peace Pipe Dr, Orlando, FL 32829
  • /42

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    8353 Fort Clinch Ave, Orlando, FL 32822

    Welcome to this beautiful two-story home in the desirable Stonebridge Village community of Orlando! Step inside to a bright foyer that opens to the formal living room, complete with soaring ceilings and a sliding glass door to the backyard. Just beyond is the formal dining room, perfect for hosting special occasions.The heart of the home is the kitchen, featuring granite countertops, a

    Monica Phu CENTURY 21 CARIOTI

    8353 Fort Clinch Ave, Orlando, FL 32822
  • /31

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    2791 Arbor Trail Way, Orlando, FL 32829

    Tucked away on a peaceful cul-de-sac in the desirable Arbor Chase community, this 2016-built home blends modern design with everyday comfort. Step through the grand foyer and take in the soaring 10-foot ceilings, open layout, and natural flow that make this home feel light, bright, and welcoming. All new lighting fixtures and fresh full interior paint enhance the home’s style and move-in ready

    Cristina Porretto THE AGENCY ORLANDO

    2791 Arbor Trail Way, Orlando, FL 32829
  • /52

    $500,000

    • 3 Beds
    • 2 Baths
    • 2,697 Sq Ft

    8688 Palos Verde Dr, Orlando, FL 32825

    Beautiful Home with huge Sparkling Screened Pool with Private newly Fenced yard, and lots of space for Entertaining!! Spacious home features a wonderful Eat-in Kitchen with impressive Custom wood Cabinetry, Corian countertops, and Stainless appliances!! Natural lighting from a peaceful Atrium!! Impressive formal Dining room!! Inviting vaulted Living room features wood-burning Stone fireplace and

    Amy Hodges RE/MAX 200 REALTY

    8688 Palos Verde Dr, Orlando, FL 32825
  • /25

    $419,900

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft

    7337 Marseille Cir, Orlando, FL 32822

    What an opportunity ! A 4 bedroom 2 bath pool home for sale ! This four bedroom has more than you need. As you enter the home, you'll notice the 15" vaulted ceilings, upgraded bedroom, bathroom and closet doors. All of the bathrooms have been remodeled with updated vanities, ceramic tile, you have 15" vaulted ceilings, a walk-in closet; dual sinks, walk-in shower and a separate tub in the

    Pedro Ramos ROCKER'S REAL ESTATE, LLC

    7337 Marseille Cir, Orlando, FL 32822
  • /46

    $475,000

    • 3 Beds
    • 3 Baths
    • 2,637 Sq Ft

    8632 Tarragon Dr, Orlando, FL 32825

    Impeccably maintained and thoughtfully renovated home in the highly-desirable Peppertree community. Situated on a prime corner lot, this property exudes pride of ownership from every angle. A full gut renovation and expansion in 2005 transformed the home into a modern, open-concept space perfect for entertaining and everyday living with incredible natural light. The home includes a

    Stephane Gregory Clear Realty, LLC.

    8632 Tarragon Dr, Orlando, FL 32825
  • /56

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,521 Sq Ft

    124 Cinnamon Dr, Orlando, FL 32825

    Spacious corner lot two story updated home of nearly a quarter acre. Step inside to discover luxurious flooring made of porcelain tile that creates a sleek and modern ambiance. Beautiful quartz countertops are complemented by light cabinetry, making this space ideal for both cooking and entertaining. this 3-bedroom, 2.5-bath home offers a convenient half bath, and a screened back porch—perfect

    Gloria Mejia FLORIDA REALTY INVESTMENTS

    124 Cinnamon Dr, Orlando, FL 32825
  • /47

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,842 Sq Ft

    414 Bonifay Ave, Orlando, FL 32825

    Welcome to this Beautiful totally Remodeled Pool Home, tucked away on a cul-de-sac street in desirable Deerwood!! Every detail of this Home has been Upgraded, providing luxury and comfortable living!! Spacious floor plan featuring Separate Living and Family rooms, plus a formal Dining room that's ideal for both Casual living and Entertaining!! Gorgeous Chef's Kitchen is the Heart of the home,

    Amy Hodges RE/MAX 200 REALTY

    414 Bonifay Ave, Orlando, FL 32825
  • /46

    $429,900

    • 4 Beds
    • 2 Baths
    • 1,645 Sq Ft

    7 Madeira Ave, Orlando, FL 32825

    Updated 4/2 Home Near UCF – No HOA, Huge Yard, Tons of Potential!Beautifully updated home on a quiet cul-de-sac just minutes from UCF, Valencia, and major highways. Located in a no-HOA community with no rear neighbors, this 4-bedroom, 2-bath home offers privacy, flexibility, and room to grow.Features include quartz countertops, updated cabinetry, new flooring, and refreshed

    Junio Jean Charles YOUNG REAL ESTATE

    7 Madeira Ave, Orlando, FL 32825
  • /40

    $410,000

    • 3 Beds
    • 2 Baths
    • 2,125 Sq Ft

    9311 Sonia St, Orlando, FL 32825

    Welcome to 9311 Sonia Street. This beautiful home has tile floors throughout most of it. Formal living room, dining room, family room, and huge 30'x10' Florida room give you plenty of space for entertaining. Fireplace in the family room for those cozy Winter days. Spacious primary bedroom with walk-in closet and plenty of room. Split bedroom plan. Roof replaced 2022; water heater replaced

    Robert Arnold SAND DOLLAR REALTY GROUP INC

    9311 Sonia St, Orlando, FL 32825
  • /22

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,447 Sq Ft

    308 S Shadow Bay Dr, Orlando, FL 32825

    Charming Single-Family Home in the heart of Orlando – Endless Potential! Welcome to 308 Shadow Bay, a hidden gem in the heart of Orlando, FL. This quaint 3-bedroom, 2-bath single-family home offers a unique opportunity for those with a vision and a passion for renovation and investment. Built in 1982, this one-story property retains its classic charm with a private pool and is being sold

    Emibeth Aviles PREMIUM PROPERTIES REAL ESTATE

    308 S Shadow Bay Dr, Orlando, FL 32825
  • /14

    $403,000

    • 3 Beds
    • 2 Baths
    • 1,225 Sq Ft

    4749 Hopespring Dr, Orlando, FL 32829

    Stunning home with Beautiful Conservation view in an established community with a LOW HOA. Experience the perfect blend of comfort and nature in this lovely 3 bedroom and 2 bath home, features a comfortable open floor plan with a wood and gas fireplace that adds warmth and charm to your living space. The modern kitchen offers new shaker cabinets with stainless steel appliances, quartz

    Fabiola Matos LARIMAR REALTY

    4749 Hopespring Dr, Orlando, FL 32829
  • /24

    $429,000

    • 3 Beds
    • 2 Baths
    • 2,007 Sq Ft

    444 S Deerwood Ave, Orlando, FL 32825

    This beautifully updated home offers the perfect blend of modern upgrades and family-friendly features. The kitchen is a true centerpiece, featuring brand-new cabinets, sleek granite countertops, and an infrared stove, all complemented by a Samsung smart fridge and other kitchen appliances, all within three years of purchase. The adjacent dining room offers additional granite surfaces, built-in

    Richard Sarta COMWIRE REALTY INC

    444 S Deerwood Ave, Orlando, FL 32825
  • /38

    $425,000

    • 4 Beds
    • 2.5 Baths
    • 1,890 Sq Ft

    2213 Rio Pinar Lakes Blvd, Orlando, FL 32822

    **Price Adjustment**Welcome to Rio Pinar Lakes, 4 beds 2.5 baths house for sale in a great Location, and its upgraded, roof was installed in 2021, half bathroom was added, fully fenced in yard , No HOA. home is minutes away from 417 and 408 expressways, Goldenrod road, Curry Ford road, restaurants, gas stations, fire department, schools, shopping centers, etc. the perfect location for you.

    Antonio Bayron CENTURY 21 WOLF'S CROSSING REALTY

    2213 Rio Pinar Lakes Blvd, Orlando, FL 32822
  • /22

    $485,000 New Construction

    • 4 Beds
    • 2 Baths
    • 1,768 Sq Ft

    7616 Carolyn Ave, Orlando, FL 32807

    BIG INCENTIVE!! FOR A LIMITED TIME, GET A 10K CREDIT TOWARDS CLOSING COSTS, TAKE ADVANTAGE OF IT NOW!! Step into magnificence and comfort with this brand new, architecturally stunning residence nestled in the heart of one of the most sought-after neighborhoods. Meticulously crafted with an eye for detail and an emphasis on modern living, this home offers a seamless blend of elegance and

    Kimberly Adams PREFERRED SHORE LLC

    7616 Carolyn Ave, Orlando, FL 32807

Home Trends in Chickasaw, FL

Housing Trends

Median Sale Price
$370,000
Median Single Family Sale Price
$390,000
Median Townhouse Sale Price
$282,500
Median 2 Bedroom Sale Price
$187,750
Median 1 Bedroom Sale Price
$162,500
Average Price Per Sq Ft
$244
Number of Homes for Sale
87
Last 12 months Home Sales
337
Months of Supply
3.10
Median List Price
$389,900
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
0%
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