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  1. Home
  2. /Kissimmee, FL
  3. /1638 WINDSOR OAK COURT
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$245,000est. $1,239 MortgageInfo icon
Listed: $ 245,000 (Sold on: Sep 15, 2026) Days on Market:66

1638 WINDSOR OAK COURT, KISSIMMEE, FL 34744

BEDS

beds

3

BATHS

baths

3

PARKING

parking

-

SQFT

sqft
1380

Description

Whether you live here year-round or use it as your Florida escape, this property offers the best of both worlds, personal enjoyment and rental income potential when you’re away. Welcome to this beautifully maintained and fully upgraded townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3-bedroom, 2.5-bath home features a flexible layout with two master suites upstairs and a third bedroom on the main level that can also serve as a home office, den, or gym. Major improvements give this home incredible value and peace of mind: the roof was replaced just 8 months ago, the A/C is only 2 years old, the water heater is brand new, the sliding glass door recently installed new, and all appliances including washer and dryer are included.You’ll find a bright and inviting open-concept living and dining area that flows seamlessly into the kitchen. The kitchen has been fully upgraded with new cabinets, modern fixtures, a farmhouse sink, quartz countertops with a beautiful backsplash, and a new garbage disposal. All bathrooms feature new cabinetry and fixtures, while the upstairs and bedrooms are finished with new laminate flooring. Windsor Oaks provides a low HOA, short-term rental approval, and a community pool, making this property ideal for investors and first-time homeowners alike. With shops, restaurants, and entertainment nearby, this home blends modern upgrades with everyday convenience.

Description

Whether you live here year-round or use it as your Florida escape, this property offers the best of both worlds, personal enjoyment and rental income potential when you’re away. Welcome to this beautifully maintained and fully upgraded townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3-bedroom, 2.5-bath home features a flexible layout with two master suites upstairs and a third bedroom on the main level that can also serve as a home office, den, or gym. Major improvements give this home incredible value and peace of mind: the roof was replaced just 8 months ago, the A/C is only 2 years old, the water heater is brand new, the sliding glass door recently installed new, and all appliances including washer and dryer are included.You’ll find a bright and inviting open-concept living and dining area that flows seamlessly into the kitchen. The kitchen has been fully upgraded with new cabinets, modern fixtures, a farmhouse sink, quartz countertops with a beautiful backsplash, and a new garbage disposal. All bathrooms feature new cabinetry and fixtures, while the upstairs and bedrooms are finished with new laminate flooring. Windsor Oaks provides a low HOA, short-term rental approval, and a community pool, making this property ideal for investors and first-time homeowners alike. With shops, restaurants, and entertainment nearby, this home blends modern upgrades with everyday convenience.
listing image
$245,000
est. $1,238.85 MortgageInfo icon
Listed: $ 245,000 (Sold on: Sep 15, 2026)
Days on Market:66

1638 WINDSOR OAK COURT, KISSIMMEE, FL 34744

BEDS

3

BATHS

3

PARKING

-

SQFT

1,380

Description

Whether you live here year-round or use it as your Florida escape, this property offers the best of both worlds, personal enjoyment and rental income potential when you’re away. Welcome to this beautifully maintained and fully upgraded townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3-bedroom, 2.5-bath home features a flexible layout with two master suites upstairs and a third bedroom on the main level that can also serve as a home office, den, or gym. Major improvements give this home incredible value and peace of mind: the roof was replaced just 8 months ago, the A/C is only 2 years old, the water heater is brand new, the sliding glass door recently installed new, and all appliances including washer and dryer are included.You’ll find a bright and inviting open-concept living and dining area that flows seamlessly into the kitchen. The kitchen has been fully upgraded with new cabinets, modern fixtures, a farmhouse sink, quartz countertops with a beautiful backsplash, and a new garbage disposal. All bathrooms feature new cabinetry and fixtures, while the upstairs and bedrooms are finished with new laminate flooring. Windsor Oaks provides a low HOA, short-term rental approval, and a community pool, making this property ideal for investors and first-time homeowners alike. With shops, restaurants, and entertainment nearby, this home blends modern upgrades with everyday convenience.

Description

Whether you live here year-round or use it as your Florida escape, this property offers the best of both worlds, personal enjoyment and rental income potential when you’re away. Welcome to this beautifully maintained and fully upgraded townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3-bedroom, 2.5-bath home features a flexible layout with two master suites upstairs and a third bedroom on the main level that can also serve as a home office, den, or gym. Major improvements give this home incredible value and peace of mind: the roof was replaced just 8 months ago, the A/C is only 2 years old, the water heater is brand new, the sliding glass door recently installed new, and all appliances including washer and dryer are included.You’ll find a bright and inviting open-concept living and dining area that flows seamlessly into the kitchen. The kitchen has been fully upgraded with new cabinets, modern fixtures, a farmhouse sink, quartz countertops with a beautiful backsplash, and a new garbage disposal. All bathrooms feature new cabinetry and fixtures, while the upstairs and bedrooms are finished with new laminate flooring. Windsor Oaks provides a low HOA, short-term rental approval, and a community pool, making this property ideal for investors and first-time homeowners alike. With shops, restaurants, and entertainment nearby, this home blends modern upgrades with everyday convenience.

Glen Gardens Estate Market Stats Last 12 months

LOCKER
Contact Us for Info

POSSESSION
Close Of Esc
HOA FEESinfo
$180 /Monthly

OUTDOOR SPACE
Lighting, Ra
TAXES
$2,008.32 (2024)

BUILDING AGE
27 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$178

Market Stats

HOA FEESinfo
$180 /Monthly

OUTDOOR SPACE
Lighting, Ra
TAXES
$2,008.32 (2024)

BUILDING AGE
27 Years
BASEMENT FEATURE
Contact Us for Info

PRICE PER SQFTinfo
$178

Amenities

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

Amenities

Unit
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
Sep 2026MLS#: S5153418Closed$245,000
Aug 2014MLS#: S4724823Closed$76,000

Unit Price History

$245,000

Closed

Sep 2026MLS#: S5153418

$76,000

Closed

Aug 2014MLS#: S4724823

Monthly Payment Calculator

$1,643 / Monthly

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

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$1,643
Est.
Listing Price
Down Payment
Interest Rate
Terms
Listing Price
Down Payment
Interest Rate
Terms

Monthly Payment Calculator

$1,643
Est.
Listing Price
Down Payment
Interest Rate
Terms
Listing Price
Down Payment
Interest Rate
Terms
$1,643 / Monthly

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

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Monthly Mortgage: $1,239
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The Neighborhood: KISSIMMEE, FL

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  1. Home
  2. /Kissimmee, FL
  3. /1638 WINDSOR OAK COURT
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