HeaderIcon
  1. Agent Logo

Explore by Metro

  • Atlanta
  • Baltimore
  • Boston
  • Bronx
  • Brooklyn
  • Chicago
  • Los Angeles
  • Manhattan
  • Miami
  • Nashville
  • Orlando
  • Philadelphia
  • Phoenix
  • Queens
  • San Diego
  • San Jose
  • Tampa
  • Washington
HeaderIcon

Explore By Metro

  • Atlanta
  • Baltimore
  • Boston
  • Bronx
  • Brooklyn
  • Chicago
  • Los Angeles
  • Manhattan
  • Miami
  • Nashville
  • Orlando
  • Philadelphia
  • Phoenix
  • Queens
  • San Diego
  • San Jose
  • Tampa
  • Washington
leftArrowBack to Search
OverviewAmenities & PoliciesFinancialsNeighborhood
Add to favoritesAdd to favorites (hover)
Save
  1. Home
  2. /Orlando, FL
  3. /7 - 1429 S CHICKASAW TRAIL
leftArrow
Add to favoritesAdd to favorites (hover)
$299,900est. $1,516 MortgageInfo icon
Date Listed : May 15, 2026 Days on HelloCondo: 26

7- 1429 S CHICKASAW TRAIL, ORLANDO, FL 32825

BEDS

beds

2

BATHS

baths

2

PARKING

parking

-

SQFT

sqft
1732

Description

Welcome to the highly sought-after Country Club Villas of Rio Pinar, an exclusive 14-unit community offering a rare opportunity to own a spacious one-story condominium in one of Orlando’s most desirable locations. Surrounded by mature landscaping and timeless brick exteriors, this beautifully maintained villa combines comfort, privacy, and low-maintenance living with the feel of a single-family home. Step through the private entrance courtyard and into an expansive 1,732-square-foot layout designed for both everyday living and entertaining. Soaring ceilings, recessed lighting, upgraded ceiling fans, and a cozy wood-burning fireplace create a warm and inviting atmosphere, while luxury vinyl plank flooring throughout the main living areas adds both elegance and durability. Upgraded solid rear sliding glass doors enhance the home’s natural light and seamlessly connect the indoor living spaces to the outdoors. The beautifully updated kitchen is thoughtfully designed with upgraded solid wood 42-inch soft-close cabinetry, granite countertops, newer GE appliances, and abundant storage and prep space. A charming breakfast nook highlighted by a bay window fills the area with natural light, creating the perfect place to start your day. The spacious family room and primary suite both open to a large screened and enclosed patio featuring breathtaking 180-degree wooded conservation views, offering a peaceful setting to relax and enjoy Florida living year-round. Rain gutters and thoughtful exterior upgrades add additional convenience and value. The spacious primary retreat offers comfort and privacy with direct patio access, a beautifully upgraded dual-sink vanity, and a walk-in shower in the master bath. A split-bedroom floor plan places the guest bedroom and full bath away from the owner’s suite, while the versatile flex room is ideal for a home office, den, library, or formal dining room. The guest bedroom also features a charming window bench seat that adds both character and functionality. Additional highlights include an indoor laundry room complete with front-load washer and dryer, attached two-car garage, pull-down attic stairs for additional storage, garage door replaced in 2018, LiftMaster garage door opener installed in 2022, HVAC replaced in 2022, and re-roof with gutters in 2023 for added peace of mind. Residents enjoy a truly carefree lifestyle with the association covering landscaping, exterior maintenance, roof care, and building insurance. Perfectly positioned near the renowned Rio Pinar Country Club, residents can enjoy golf, dining, and social activities just moments away. The location also provides quick access to medical facilities, Waterford Lakes Town Center, Valencia College, UCF, Orlando International Airport, world-famous attractions, and major highways including SR 417 and SR 408 for easy commuting throughout Central Florida. Whether you are searching for a primary residence, seasonal retreat, or low-maintenance lifestyle in an established community, this exceptional villa delivers space, location, thoughtful upgrades, and timeless appeal all in one. This is Florida living at its finest.

Description

Welcome to the highly sought-after Country Club Villas of Rio Pinar, an exclusive 14-unit community offering a rare opportunity to own a spacious one-story condominium in one of Orlando’s most desirable locations. Surrounded by mature landscaping and timeless brick exteriors, this beautifully maintained villa combines comfort, privacy, and low-maintenance living with the feel of a single-family home. Step through the private entrance courtyard and into an expansive 1,732-square-foot layout designed for both everyday living and entertaining. Soaring ceilings, recessed lighting, upgraded ceiling fans, and a cozy wood-burning fireplace create a warm and inviting atmosphere, while luxury vinyl plank flooring throughout the main living areas adds both elegance and durability. Upgraded solid rear sliding glass doors enhance the home’s natural light and seamlessly connect the indoor living spaces to the outdoors. The beautifully updated kitchen is thoughtfully designed with upgraded solid wood 42-inch soft-close cabinetry, granite countertops, newer GE appliances, and abundant storage and prep space. A charming breakfast nook highlighted by a bay window fills the area with natural light, creating the perfect place to start your day. The spacious family room and primary suite both open to a large screened and enclosed patio featuring breathtaking 180-degree wooded conservation views, offering a peaceful setting to relax and enjoy Florida living year-round. Rain gutters and thoughtful exterior upgrades add additional convenience and value. The spacious primary retreat offers comfort and privacy with direct patio access, a beautifully upgraded dual-sink vanity, and a walk-in shower in the master bath. A split-bedroom floor plan places the guest bedroom and full bath away from the owner’s suite, while the versatile flex room is ideal for a home office, den, library, or formal dining room. The guest bedroom also features a charming window bench seat that adds both character and functionality. Additional highlights include an indoor laundry room complete with front-load washer and dryer, attached two-car garage, pull-down attic stairs for additional storage, garage door replaced in 2018, LiftMaster garage door opener installed in 2022, HVAC replaced in 2022, and re-roof with gutters in 2023 for added peace of mind. Residents enjoy a truly carefree lifestyle with the association covering landscaping, exterior maintenance, roof care, and building insurance. Perfectly positioned near the renowned Rio Pinar Country Club, residents can enjoy golf, dining, and social activities just moments away. The location also provides quick access to medical facilities, Waterford Lakes Town Center, Valencia College, UCF, Orlando International Airport, world-famous attractions, and major highways including SR 417 and SR 408 for easy commuting throughout Central Florida. Whether you are searching for a primary residence, seasonal retreat, or low-maintenance lifestyle in an established community, this exceptional villa delivers space, location, thoughtful upgrades, and timeless appeal all in one. This is Florida living at its finest.
listing image
listing image 2
listing image 3
7 -
$299,900
est. $1,516.46 MortgageInfo icon
Date Listed : May 15, 2026
Days on HelloCondo: 26

7 -

1429 S CHICKASAW TRAIL #7, ORLANDO, FL 32825

BEDS

2

BATHS

2

PARKING

-

SQFT

1,732

Description

Welcome to the highly sought-after Country Club Villas of Rio Pinar, an exclusive 14-unit community offering a rare opportunity to own a spacious one-story condominium in one of Orlando’s most desirable locations. Surrounded by mature landscaping and timeless brick exteriors, this beautifully maintained villa combines comfort, privacy, and low-maintenance living with the feel of a single-family home. Step through the private entrance courtyard and into an expansive 1,732-square-foot layout designed for both everyday living and entertaining. Soaring ceilings, recessed lighting, upgraded ceiling fans, and a cozy wood-burning fireplace create a warm and inviting atmosphere, while luxury vinyl plank flooring throughout the main living areas adds both elegance and durability. Upgraded solid rear sliding glass doors enhance the home’s natural light and seamlessly connect the indoor living spaces to the outdoors. The beautifully updated kitchen is thoughtfully designed with upgraded solid wood 42-inch soft-close cabinetry, granite countertops, newer GE appliances, and abundant storage and prep space. A charming breakfast nook highlighted by a bay window fills the area with natural light, creating the perfect place to start your day. The spacious family room and primary suite both open to a large screened and enclosed patio featuring breathtaking 180-degree wooded conservation views, offering a peaceful setting to relax and enjoy Florida living year-round. Rain gutters and thoughtful exterior upgrades add additional convenience and value. The spacious primary retreat offers comfort and privacy with direct patio access, a beautifully upgraded dual-sink vanity, and a walk-in shower in the master bath. A split-bedroom floor plan places the guest bedroom and full bath away from the owner’s suite, while the versatile flex room is ideal for a home office, den, library, or formal dining room. The guest bedroom also features a charming window bench seat that adds both character and functionality. Additional highlights include an indoor laundry room complete with front-load washer and dryer, attached two-car garage, pull-down attic stairs for additional storage, garage door replaced in 2018, LiftMaster garage door opener installed in 2022, HVAC replaced in 2022, and re-roof with gutters in 2023 for added peace of mind. Residents enjoy a truly carefree lifestyle with the association covering landscaping, exterior maintenance, roof care, and building insurance. Perfectly positioned near the renowned Rio Pinar Country Club, residents can enjoy golf, dining, and social activities just moments away. The location also provides quick access to medical facilities, Waterford Lakes Town Center, Valencia College, UCF, Orlando International Airport, world-famous attractions, and major highways including SR 417 and SR 408 for easy commuting throughout Central Florida. Whether you are searching for a primary residence, seasonal retreat, or low-maintenance lifestyle in an established community, this exceptional villa delivers space, location, thoughtful upgrades, and timeless appeal all in one. This is Florida living at its finest.

Description

Welcome to the highly sought-after Country Club Villas of Rio Pinar, an exclusive 14-unit community offering a rare opportunity to own a spacious one-story condominium in one of Orlando’s most desirable locations. Surrounded by mature landscaping and timeless brick exteriors, this beautifully maintained villa combines comfort, privacy, and low-maintenance living with the feel of a single-family home. Step through the private entrance courtyard and into an expansive 1,732-square-foot layout designed for both everyday living and entertaining. Soaring ceilings, recessed lighting, upgraded ceiling fans, and a cozy wood-burning fireplace create a warm and inviting atmosphere, while luxury vinyl plank flooring throughout the main living areas adds both elegance and durability. Upgraded solid rear sliding glass doors enhance the home’s natural light and seamlessly connect the indoor living spaces to the outdoors. The beautifully updated kitchen is thoughtfully designed with upgraded solid wood 42-inch soft-close cabinetry, granite countertops, newer GE appliances, and abundant storage and prep space. A charming breakfast nook highlighted by a bay window fills the area with natural light, creating the perfect place to start your day. The spacious family room and primary suite both open to a large screened and enclosed patio featuring breathtaking 180-degree wooded conservation views, offering a peaceful setting to relax and enjoy Florida living year-round. Rain gutters and thoughtful exterior upgrades add additional convenience and value. The spacious primary retreat offers comfort and privacy with direct patio access, a beautifully upgraded dual-sink vanity, and a walk-in shower in the master bath. A split-bedroom floor plan places the guest bedroom and full bath away from the owner’s suite, while the versatile flex room is ideal for a home office, den, library, or formal dining room. The guest bedroom also features a charming window bench seat that adds both character and functionality. Additional highlights include an indoor laundry room complete with front-load washer and dryer, attached two-car garage, pull-down attic stairs for additional storage, garage door replaced in 2018, LiftMaster garage door opener installed in 2022, HVAC replaced in 2022, and re-roof with gutters in 2023 for added peace of mind. Residents enjoy a truly carefree lifestyle with the association covering landscaping, exterior maintenance, roof care, and building insurance. Perfectly positioned near the renowned Rio Pinar Country Club, residents can enjoy golf, dining, and social activities just moments away. The location also provides quick access to medical facilities, Waterford Lakes Town Center, Valencia College, UCF, Orlando International Airport, world-famous attractions, and major highways including SR 417 and SR 408 for easy commuting throughout Central Florida. Whether you are searching for a primary residence, seasonal retreat, or low-maintenance lifestyle in an established community, this exceptional villa delivers space, location, thoughtful upgrades, and timeless appeal all in one. This is Florida living at its finest.

Glen Gardens Estate Market Stats Last 12 months

LOCKER
Contact Us for Info

POSSESSION
Close Of Esc
HOA FEESinfo
Contact Us for Info

OUTDOOR SPACE
Courtyard, R
TAXES
$1,666.53 (2025)

BUILDING AGE
43 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$173

Market Stats

HOA FEESinfo
Contact Us for Info

OUTDOOR SPACE
Courtyard, R
TAXES
$1,666.53 (2025)

BUILDING AGE
43 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$173

Amenities

Parking
Parking
-
Locker
Locker
Concierge
Concierge
-
Elevator(s)
Elevator(s)
-
Central AC
Central AC
Check Icon
Pool
Pool
-
Fitness Center
Fitness Center
-
Visitors Parking
Visitors Parking
-

Amenities

Unit
Parking GarageParking Garage
Building

Policies

Pet Allowed
Check
Pet Allowed Info icon
Check Icon
BBQ Permitted
BBQ Permitted
Sublet Allowed
Sublet Allowed
Short-term Rental Allowed
Short-term Rental Allowed

Unit Price History

DateMLSStatusPrice
Unit Price History for this Listing is not available

Unit Price History

Unit Price History for this Listing is not available

Monthly Payment Calculator

$1,711 / Monthly

All calculations are estimates and provided by HelloCondo.com
for informational purposes only. Actual amounts may vary.

DropDown
$1,711
Est.
Listing Price
Down Payment
Interest Rate
Terms
Listing Price
Down Payment
Interest Rate
Terms

Monthly Payment Calculator

$1,711
Est.
Listing Price
Down Payment
Interest Rate
Terms
Listing Price
Down Payment
Interest Rate
Terms
$1,711 / Monthly

All calculations are estimates and provided by HelloCondo.com for informational purposes only. Actual amounts may vary.

view source
DropDown

Monthly Payment Calculator

Mortgage calculator

Monthly Mortgage: $1,516
DropDown

The Neighborhood: ORLANDO, FL

Get the HelloCondo Newsletter
Real-estate tips, insights, and market reports in your inbox.
Newsletter
  1. Home
  2. /Orlando, FL
  3. /7 - 1429 S CHICKASAW TRAIL
Nearby Cities
Montverde

Buildings

2500 Woodgate Blvd
2504 Woodgate Blvd
2508 Woodgate Blvd
2512 Woodgate Blvd
2524 Woodgate Blvd
2532 Woodgate Blvd
2536 Woodgate Blvd
2540 Woodgate Blvd
2544 Woodgate Blvd
2548 Woodgate # 104th Blvd
2552 Woodgate Blvd
2556 Woodgate Blvd
2560 Woodgate Blvd
2564 Woodgate Blvd
2568 Woodgate Blvd
2572 Woodgate Blvd
8112 Claire Ann Dr
8124 Claire Ann Dr
8213 Claire Ann Dr
8225 Claire Ann Dr

Neighborhoods

Alafaya WoodsAzalea ParkLawson / Fern Creek
LockhartMalibu GrovesMidwayNew MalibuNorth OrlandoParkstPrimeraPrinceton / Silver StarRandal ParkReunionRio Grande ParkRoosevelt ParkRosemontSeaboard IndustrialSky LakeVista EastWindhover

ZIP Codes

321023215932726
3273232757327983280432805328093281032811328183282432839347113474734748347563477134797

Community

Adair CondominiumsAlomaAloma Park
Ambassador House CondominiumsAshford Park TownhomesAtha Urban Flats CondominiumsAtherton Park CondominiumsAvanzar CondominiumsAzalea Lane CondominiumsBacchus GardensBradford CoveBranch TreeBrandywine DubsdreadCabana Key CondominiumsCambridge Circle TownhomesCamelot by The Lake CondominiumsCandlewyck EastCarmel by the LakeCarmel ParkCarrington Park
Hellocondo Logo
HelloCondo Is The #1 Condo Search Platform And Real Estate Recommendation Engine. Search, Find And Buy The Perfect Condo And Get Matched With The Best Agents. Finding A Condo Has Never Been So Easy.

HelloCondo is a division of HelloCasa, LLC

FacebookIconInstagramIconXIconRedditIcon

HelloCondo

Find A RealtorTerms of UsePrivacy PolicyCalifornia Privacy NoticeAccessibility PolicyCCPA Notice on CollectionDMCABrowseBlogsNYS Standard Operating ProcedureNYS Fair Housing Notice

Contact

LocationIcon
300 Galleria Pkwy SE, Suite 1500,
Atlanta, GA 30339
PhoneICon
(855) 625-0319
EmailIConhello@hellocondo.com
Contact Us

For Sale

Condos for saleTownhomes for sale
AgentIcon
LocationIcon

Julie's Realty, LLCYuliya "Julie" Sidorevskaya1700 79th Street CSWY STE#160,North Bay VIllage, FL, 33141

PhoneICon305-340-1857
EmailIConJulie@JuliesRealty.net
© HelloCondo 2026. All Rights Reserved.