1429 Chickasaw Trail, FL
Stellar MLS

$299,900

1429 Chickasaw Trail

Orlando, FL 32825

Listing updated: May 17, 2026 at 2:16 PM ET

Active
2
Beds
2
Baths
1,732
Sq Ft
3.02
Acres
1983
Built
Fireplace3.02 acres$173/sqft
Condominium

Property type

1983

Year built

131,633 sqft

Lot size

$173

Price / sq ft

No HOA

HOA dues

2

Days on market

2

Garage spaces

X

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$1,516
Property taxes$139
Home insurance (est.)$137

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history2 days on market

  1. Status: Active
    May 15, 2026
  2. Listed$299,900
    May 15, 2026
  3. Price increased$299,900

Facts & features

Property type
Residential
Sub type
Condominium
Status
Active
Days on market
2
Subdivision
Country Club Villas Rio Pinar
County
Orange
Year built
1983
Living area
1,732 sq ft
Price/sq ft
$173
Lot size
131,633 sq ft
Flood zone
X (12095C0270)
Garage
2 spaces
Annual taxes
$1,667 (2025)
Parcel #
01-23-30-1810-02-070
Zoning
P-D
MLS #
O6405968

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Interior Details

Bedrooms
2
Full bathrooms
2
Flooring
Ceramic Tile, Laminate
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator, Washer
Interior features
Eat-in Kitchen, Primary Bedroom Main Floor
Laundry
Inside, Laundry Room
Stories / Levels
One
Direction faces
West
Fireplace
Yes

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Garage Door Opener

HOA & Financial

Total monthly fees
$681/mo
Total annual fees
$8,168
HOA name
Country Club Villas of Rio Pinar
CDD
No
Homestead exemption
Yes
Min lease term
6 Months
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Buyer to verify with HOA
Approval process
Buyer must fill submit an approval application to the HOA

Exterior & Construction

Exterior features
Courtyard, Rain Gutters, Sidewalk, Sliding Doors
Construction materials
Block
Roof
Shingle
Foundation
Brick/Mortar
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Cable Connected, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected

Community

Pets allowed
Cats OK, Dogs OK

Room Details

RoomLevelDimensions
Living RoomFirst16x17
Dining RoomFirst16x9
KitchenFirst13x13
DinetteFirst9x9
Primary BedroomFirst13x16
Primary BathroomFirst9x11
Bedroom 2First13x13
Bathroom 1First9x5
FoyerFirst6x6
DenFirst13x13
LaundryFirst5x9
Balcony/Porch/LanaiFirst24x10

Listing Details

Listing date
2026-05-15
On market date
2026-05-15
Original list price
$299,900
Occupant type
Owner
MLS area
32825 - Orlando/Rio Pinar / Union Park
Listing AOR
Sarasota - Manatee
Status changed
2026-05-15
Tax legal description
COUNTRY CLUB VILLAS OF RIO PINAR CONDO CB 7/138 BLDG 2 UNIT 7

Flood risk

Minimal riskFEMA Zone XPanel 12095C0270

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From 417 head west on Curryford Rd, Right on Chicksaw Trail, Entrance on the right just before the 3 way stop signs

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 17, 2026 at 2:16 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA