440 CHEROKEE DRIVE, Orlando, FL, 32801 | $989,900

Under contract-accepting backup offers. Multiple Offer Situation. Highest & Best Offers Due by Noon on Monday 6/15. Welcome to one of downtown Orlando's most distinctive homes, perfectly positioned across from Lake Cherokee in the heart of the Historic Lake Cherokee District. With sweeping lake views and the downtown skyline as your backdrop, this property offers a lifestyle that is truly difficult to replicate.

Designed with a blend of timeless Key West charm and open, airy living spaces, the home is filled with architectural character and natural light. Transom windows, French doors, soaring ceilings, and 125-year-old reclaimed heart pine floors create a warm and inviting atmosphere throughout.

The kitchen has been thoughtfully updated with newer quartz countertops and features custom wood cabinetry, stainless steel appliances, and a gas range. Additional recent improvements include a newer refrigerator, dishwasher, water heater, lighting fixtures, and fresh interior paint throughout much of the home. The primary bathroom has also been updated with beautiful quartz countertops.

One of the home's most appealing features is its flexible floor plan. The spacious primary suite occupies the entire second floor and opens to a private balcony overlooking Lake Cherokee and the downtown skyline. A second en-suite bedroom on the first floor features french doors leading directly to the covered porch, making it ideal for guests or multigenerational living. Need additional space? The large downstairs office could easily function as a fourth bedroom.

Outdoor living takes center stage with nearly 1, 400 square feet of wraparound porch space designed for relaxing, entertaining, and enjoying the picturesque lake views. Whether you're sipping coffee while watching the swans glide across the water or gathering with friends on a cool evening, this home was designed to embrace its surroundings. A custom pergola over the parking area creates a spacious covered carport while enhancing the beautiful backyard.

Located just blocks from Lake Eola, Thornton Park, the Dr. Phillips Center for the Performing Arts, Orlando Health, and Delaney Park, you'll enjoy the convenience of downtown living while being surrounded by one of Orlando's most charming historic neighborhoods. Zoned for highly regarded Blankner K-8 and Boone High School.

If you've been searching for a home with character, flexibility, and unforgettable views, this Lake Cherokee gem is one you won't want to miss.

Features

  • Rooms: 11
  • Bedrooms: 4
  • Baths: 3 full
  • Laundry: Inside, Laundry Closet
  • Style: Key West
  • Year Built: 1997
  • Garage: On Street, Parking Pad
  • Heating: Central, Electric
  • Cooling: Central Air
  • Approx Sq. Feet: 3,010
  • Acreage: 0.19
  • Est. Taxes: $12,075
  • Lot Desc: Historic District, City Lot, Sidewalk
  • View: Water
  • Water Front: Yes
  • Elem. School: Blankner Elem
  • Middle School: Blankner School (K-8)
  • High School: Boone High
  • Pet Policy: Yes
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Refrigerator, Washer
  • MLS#: O6415169
  • Days on Market: 4 days
  • Website: https://www.raveis.com
    /prop/O6415169/440cherokeedrive_orlando_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is 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. (last updated 6/28/2026 4:28:35 AM)
Listing courtesy of EXP REALTY LLC   Phone: 407-305-4300

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

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440 CHEROKEE DRIVE, Orlando, FL, 32801

$989,900

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $791,920 $791,920 $791,920
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.000% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.251% 6.086% 6.183%
Monthly Tax Payment $1,006 $1,006 $1,006
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $4,621 $4,748 $6,683
Total Monthly Payment $5,719 $5,846 $7,781

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.