1521 CHESTNUT AVENUE, Winter Park, FL, 32789 | $1,799,900

Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept main floor features a beautifully appointed kitchen, a spacious dining area, and a light-filled living room complete with a designer fireplace and custom built-in shelving. The stunning kitchen boasts quartz counters, spacious cabinetry, KitchenAid appliances, and designer lighting. A fourth bedroom (currently used as a study) is also located on the main level. From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an in-ground pool, a fully fenced yard, tongue-in-groove wood ceiling, and pre-plumbing in place for your dream summer kitchen—ideal for entertaining year-round. Upstairs, the luxurious primary suite provides a peaceful retreat with an oversized balcony overlooking the pool and rear yard. Two additional bedrooms are also featured on the second level, along with a second full bath. The first-floor office doubles as a fourth bedroom, with an adjacent full bath for guests or multi-generational living. The side entry two-car garage was once converted into a 425 sq ft air-conditioned bonus room—perfect as a media room, home gym, or additional living space. This could easily be converted back if the next owner requires more living space. This home boasts well-thought-out upgrades, including beautiful wood inlays in niches, open shelving, quartz countertops, slat wall features, and stunning light fixtures throughout. The work has been done for you in this like-new home! Located just steps from Phelps Park, and minutes from the shops and dining of Park Avenue and the Winter Park Chain of Lakes, this home offers the perfect blend of modern design, comfort, and convenience. Don't miss your chance to own this exceptional home in the heart of Winter Park!

Features

  • Rooms: 7
  • Bedrooms: 4
  • Baths: 3 full
  • Laundry: Inside, Laundry Room
  • Year Built: 2022
  • Garage: 2-car
  • Heating: Central, Zoned
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 2,842
  • Acreage: 0.17
  • Est. Taxes: $20,570
  • Elem. School: Lakemont Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High
  • Pool: Gunite, In Ground, Lighting, Tile
  • Appliances: Built-In Oven, Convection Oven, Cooktop, Refrigerator, Tankless Water Heater
  • MLS#: A4685113
  • Days on Market: 37 days
  • Website: https://www.raveis.com
    /eprop/A4685113/1521chestnutavenue_winterpark_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 4/14/2026 12:14:16 AM)
Listing courtesy of Compass Florida LLC   Phone: 941-279-3630

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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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1521 CHESTNUT AVENUE, Winter Park, FL, 32789

$1,799,900

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 $1,439,920 $1,439,920 $1,439,920
Term 360 months 360 months 180 months
Initial Interest Rate** 5.875% 6.125% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.289% 6.235% 6.183%
Monthly Tax Payment $1,714 $1,714 $1,714
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $8,518 $8,749 $12,151
Total Monthly Payment $10,357 $10,588 $13,990

* 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.