Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$414,999 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,022 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, 3.5-bath single-family home perfectly located in South Orlando, offering comfort, space, and serene lake views in a sought-after residential community. This two-story home features a spacious and functional layout ideal for both everyday living and entertaining. Inside, you'll find new flooring throughout, creating a fresh and modern feel. The kitchen is well equipped with appliances and ample counter space, making it the heart of the home for gathering and meal preparation. Generously sized living areas provide flexibility for family living, work-from-home needs, or hosting guests. Step outside and enjoy peaceful lake views, perfect for relaxing mornings or unwinding in the evening. With four bedrooms and three-and-a-half bathrooms, this home offers comfort and privacy for everyone. The property has been well cared for, offering move-in-ready appeal and long-term value. Fairly New roof , NO HOA !! Ideally situated near major highways, Orlando International Airport, shopping, dining, and world-famous attractions, this home combines convenience with a tranquil setting. Whether you're looking for a primary residence or an investment opportunity, this lakefront home delivers space, location, and lifestyle-don't miss your chance to make it yours.

Full Property Details for 397 Chicago Woods Cir

General

  • Price: $414,999
  • Taxes: $6,190 (2024)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: TB8469551
  • Updated: 2/3/2026
  • Added to Site: 26 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 11
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Walk-In Closet(s)
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Furnished
  • Flooring: Tile, Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Common Area, In Garage

Exterior

  • Exterior Features: Balcony, Lighting, Sidewalk, Sliding Doors
  • Deck/Patio: Front Porch, Rear Porch
  • Porch/Patio/Deck: Front Porch, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 32824 - Orlando/Taft / Meadow woods
  • County: Orange
  • Development Name: 32824 - Orlando/Taft / Meadow woods
  • Subdivision: MEADOW WOODS VILLAGE 07 PH 01
  • Driving Directions: From FL-417, take the Landstar Blvd exit and head north. Turn right onto Rhode Island Woods Cir, then left onto Chicago Woods Cir. Continue to 397 Chicago Woods Cir. The home will be on the right.
  • Direction Faces: South

School Information

  • Elementary School: Meadow Woods Elem
  • Middle School: Meadow Wood Middle
  • High School: Cypress Creek High

Community

  • Community Name: 32824 - Orlando/Taft / Meadow woods
  • Pet Restrictions: Please verify with city and county restrictions.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Available, Phone Available, Sewer Available, Water Available

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,022
  • Sq. Ft. Source: Public Records
  • Year Built: 1987

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,620
  • Lot Size: 5620
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Water Features

  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Pond

Financial Considerations

  • Tax Amount: $6,190.81
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: MEADOW WOODS VILLAGE 7 PHASE 1 16/60 LOT29 BLK 141
  • Flood Zone Info: X
  • APN: 292425601841290
  • Property ID: 292425601841290
  • Block/Lot/Section: 141

Listed by Lpt Realty, Llc

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agents

— 397 Chicago Woods Cir —

  • Lpt Realty, Llc

  • Lpt Realty, Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 397 Chicago Woods Cir

School District:Orange County School District
NameGradesDistance
Meadow Woods Elementary School
500 Rhode Island Woods Circle, Orlando, FL 32824
PK-50.6 mi
Meadow Woods Middle School
1800 Rhode Island Woods Circle, Orlando, FL 32824
6-81.5 mi
Cypress Creek High School
1101 Bear Crossing Drive, Orlando, FL 32824
9-120.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 397 Chicago Woods Cir Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/27/2026
Listed
$414,999
118.42%
MLS
4/17/2023
Sold
$190,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 397 Chicago Woods Cir

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,191
—
$388,410
9%
2024
$6,191
22%
$355,422
5%
2023
$5,058
29%
$339,866
50%
2021
$3,933
-11%
$226,544
-19%
2022
$4,421
12%
$279,749
28%
2021
$3,933
10%
$218,083
2%
2019
$3,571
4%
$214,621
2%
2018
$3,423
8%
$210,292
10%
2017
$3,164
8%
$191,052
11%
2016
$2,932
5%
$171,503
36%
2015
$2,804
14%
$125,741
10%
2014
$2,461
13%
$114,310
10%
2013
$2,187
—
$103,918
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 397 Chicago Woods Cir

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Lpt Realty, Llc

Similar Properties near 397 Chicago Woods Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1208 Sandestin Way, Orlando, FL 32824 - Photo 1
$415,000

1208 Sandestin Way  Orlando, FL 32824

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 1,837
    Sq. Ft.
Listed by Century 21 Carioti
14417 Jasmine Glen Dr, Orlando, FL 32824 - Photo 1
$414,990

14417 Jasmine Glen Dr  Orlando, FL 32824

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 1,896
    Sq. Ft.
Listed by Home Sold Realty Llc
1348 Heather Lake Dr, Orlando, FL 32824 - Photo 1 Price Reduced
-$3,500 (-0.83%)
$416,000

1348 Heather Lake Dr  Orlando, FL 32824

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,863
    Sq. Ft.
Listed by Compass Florida Llc
15101 Braywood Trail, Orlando, FL 32824 - Photo 1
$420,000

15101 Braywood Trail  Orlando, FL 32824

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 1,905
    Sq. Ft.
Listed by Lpt Realty, Llc

Just Listed near 397 Chicago Woods Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1183 Wildmeadow Run, Winter Park, FL 32792 - Photo 1 Just Listed
$830,000

1183 Wildmeadow Run  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,020
    Sq. Ft.
Listed by Kara Lushear (321) 663-5550
223 Sandlewood Trail, Winter Park, FL 32789 - Photo 1 Just Listed
$349,890

223 Sandlewood Trail  Winter Park, FL 32789

  • Townhouse
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 1,132
    Sq. Ft.
Listed by Homecoin.Com
2412 Chantilly Ave, Winter Park, FL 32789 - Photo 1 Just Listed
$7,150,000

2412 Chantilly Ave  Winter Park, FL 32789

  • Triplex
  • Active
  • Updated 2 days ago
  • 12,500
    Sq. Ft.
Listed by Real Broker, Llc
1695 Lee Rd, Winter Park, FL 32789 - Photo 1 Just Listed
$159,990

1695 Lee Rd  #E215  Winter Park, FL 32789

  • Condo
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,149
    Sq. Ft.
Listed by Fowlkes Realty Co

Price Reduced near 397 Chicago Woods Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1518 Pinewood Dr, Winter Park, FL 32789 - Photo 1 Price Reduced
-$14,900 (-3.39%)
$425,000

1518 Pinewood Dr  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,197
    Sq. Ft.
Listed by Keller Williams Realty At The Parks
1802 Arbor Park Dr, Winter Park, FL 32789 - Photo 1 Price Reduced
-$25,000 (-2.17%)
$1,125,000

1802 Arbor Park Dr  Winter Park, FL 32789

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,808
    Sq. Ft.
Listed by Tbro Realty Llc
1518 Pinewood Dr, Winter Park, FL 32789 - Photo 1 Price Reduced
-$14,900 (-3.39%)
$425,000

1518 Pinewood Dr  Winter Park, FL 32789

  • Duplex
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,197
    Sq. Ft.
Listed by Keller Williams Realty At The Parks
1792 Chilean Ln, Winter Park, FL 32792 - Photo 1 Price Reduced
-$10,000 (-2.9%)
$335,000

1792 Chilean Ln  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 1
    Total Bath
  • 984
    Sq. Ft.
Listed by Bhhs Florida Realty

Recent Sales near 397 Chicago Woods Cir

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

13026 Baltimore Woods Ln, Orlando, FL 32824 - Photo 1 Sold
$395,000

13026 Baltimore Woods Ln  Orlando, FL 32824

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,369
    Sq. Ft.
Listed by Keller Williams Realty At The Lakes
Sold by Exp Realty Llc
478 Chicago Woods Cir, Orlando, FL 32824 - Photo 1 Sold
$425,500

478 Chicago Woods Cir  Orlando, FL 32824

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 2,493
    Sq. Ft.
Listed by Exp Realty Llc
Sold by Exp Realty Llc
13110 Philadelphia Woods Ln, Orlando, FL 32824 - Photo 1 Sold
$390,000

13110 Philadelphia Woods Ln  Orlando, FL 32824

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,648
    Sq. Ft.
Listed by Preferred Real Estate Brokers
Sold by Hometrust Realty Group
219 Iowa Woods Cir W, Orlando, FL 32824 - Photo 1 Sold
$420,000

219 Iowa Woods Cir W  Orlando, FL 32824

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 1,803
    Sq. Ft.
Listed by Keller Williams Advantage Iii
Sold by Urban Nest Club Inc

397 Chicago Woods Circle, Orlando, FL 32824 (MLS# TB8469551) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 397 Chicago Woods Circle is currently listed for $414,999 and was received on January 27, 2026. Want to learn more about 397 Chicago Woods Circle? Do you have questions about finding other Single Family real estate for sale in Orlando? You can browse all Orlando real estate or contact a Coldwell Banker agent to request more information.

Tour this property