1521 Chestnut Ave

Winter Park, FL 32789

$1,899,900
Price
4
Beds
2,842 Sq. Ft.
$669 / Sq. Ft.
2,842
Sq. Ft.
$669
per Sq. Ft.
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Listed By Compass
Listed By Compass

Description

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...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!

Listing Agent

  1. Corey Evans

    Corey Evans

    Alternative Listing Agent

    Compass

    corey.evans@compass.com

    P: (407)-721-2116

    CallTextEmail

Property Details for 1521 Chestnut Avenue

Subdivision Name
LAKE KNOWLES TERRACE
Township
21
Garage Spaces
2
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 03/06/2026 06:53 AM

Property Details for 1521 Chestnut Avenue

StatusActive
MLS #A4685113
Days on Market2
Taxes$20,570 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2022
Lot Size0.17 AC / 7,469 SF
CountyOrange County
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Location

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Building Information for 1521 Chestnut Avenue

Stories2Year Built2022Building Size-Lot Size0.17 AC / 7,469 SF

Payment Calculator

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$10,974 per month

30 year fixed, 6.15% Interest

Principal and Interest

$9,260

Property Taxes

$1,714

HOA Dues

$0

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Property Information for 1521 Chestnut Avenue

Summary
Location and General Information
  • Building Area Source: Builder
  • Building Area Total: 3703.0
  • Building Area Units: Square Feet
  • Direction Faces: South
  • Directions: Palmer Avenue to north on Phelps. Turn left onto Chestnut to home on the right.
  • Elementary School: Lakemont Elem
  • Middle Or Junior School: Maitland Middle
  • High School: Winter Park High
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 1521
  • Street Name: CHESTNUT
  • Street Suffix: AVENUE
  • State: FL
  • City: WINTER PARK
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Association: No
  • CDD: No
  • Tax Block: 1
  • Tax Book Number: K-4
  • Tax Legal Description: LAKE KNOWLES TERRACE K/4 LOT 18 BLK 1
  • Tax Lot: 18
  • Tax Year: 2024
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 322130453601180
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: R-1A
  • Living Area: 2842
Property and Assessments
  • Year Built Numeric: 2022
  • Flood Zone Code: x
  • Homestead: No
  • New Construction: No
  • Public Survey Range: 30
  • Public Survey Section: 32
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Connected, Sewer Connected, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Block, Wood Frame
  • Exterior Features: Balcony, Irrigation System, Private Yard, Sliding Doors
  • Fencing: Fenced
  • Foundation Details: Slab
  • Levels: Two
  • Pool Features: Gunite, In Ground, Lighting, Tile
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Spa: No
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Inside Utility
  • Appliances: Built-In Oven, Convection Oven, Cooktop, Refrigerator, Tankless Water Heater
  • Cooling: Central Air, Zoned
  • Fireplace Features: Electric, Family Room
  • Fireplace: Yes
  • Flooring: Tile
  • Heating: Central, Zoned
  • Interior Features: High Ceilings, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Thermostat, Window Treatments
  • Laundry Features: Inside, Laundry Room
  • Living Area Source: Builder
  • Living Area Units: Square Feet
  • Room Count: 7.0
  • Water View: No
  • Bathrooms Half: 0

Property History for 1521 Chestnut Avenue

DateEvent & SourcePriceAppreciation
Mar 6, 2026

Listed (Active)

MFRMLS #A4685113

$1,899,900—
Dec 1, 2025

Withdrawn

MFRMLS #A4651868

$1,899,900—
May 16, 2025

Listed (Active)

MFRMLS #A4651868

$1,999,900—
Apr 30, 2019

Sold (Public Record)

Public Record #644239078

$327,500—
Apr 30, 2019

Sold (Public Record)

Public Record #644239078

$327,500—
Apr 30, 2019

Sold

MFRMLS #O5770197

$327,500—
Apr 30, 2019

Sold

MFRMLS #O5768459

$327,500—
Apr 1, 2019

Pending

MFRMLS #O5770197

—
Apr 1, 2019

Pending

MFRMLS #O5768459

—
Mar 14, 2019

Listed (Active)

MFRMLS #O5770197

$335,000—
Mar 14, 2019

Listed (Active)

MFRMLS #O5768459

$335,000—
DateEvent & SourcePrice
03/06/2026

Listed (Active)

MFRMLS #A4685113

$1,899,900
12/01/2025

Withdrawn

MFRMLS #A4651868

$1,899,900
05/16/2025

Listed (Active)

MFRMLS #A4651868

$1,999,900
04/30/2019

Sold (Public Record)

Public Record #644239078

$327,500
04/30/2019

Sold (Public Record)

Public Record #644239078

$327,500
04/30/2019

Sold

MFRMLS #O5770197

$327,500
04/30/2019

Sold

MFRMLS #O5768459

$327,500
04/01/2019

Pending

MFRMLS #O5770197

—
04/01/2019

Pending

MFRMLS #O5768459

—
03/14/2019

Listed (Active)

MFRMLS #O5770197

$335,000
03/14/2019

Listed (Active)

MFRMLS #O5768459

$335,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1521 Chestnut Avenue

Taxable ValueLand$400,000Additions$992,380Total$1,392,380
Tax Record2024$20,570 ($1,714 / month)
Home Facts
Beds4Total Finished SqFt2,692 SqFtAbove Grade Finished SqFt2,692 SqFtStories2Lot Size7,469 SqFtStyleSingle Family ResidenceYear Built2022ZoningR-1ACountyORANGEAPN32-21-30-4536-01-180

Schools near 1521 Chestnut Avenue

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Lakemont Elementary School
Public - PK to 5
Cornerstone Academy Charter
Charter - K to 8
Maitland Middle School
Public - 6 to 8
Cornerstone Charter Academy High School
Charter - 9 to 12
Rating
School
Distance
Lakemont Elementary School
PublicPK to 5

Cornerstone Academy Charter
CharterK to 8

Maitland Middle School
Public6 to 8

Cornerstone Charter Academy High School
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1521 Chestnut Avenue, Winter Park, FL 32789

1521 Chestnut Avenue is a single family home for sale in Winter Park, FL 32789. This property was listed for sale on March 6, 2026 by Compass, it's currently listed at $1,899,900. It has been on the market for a total of 2 days and was last sold on April 30, 2019. This listing's school district is Orange County Public Schools. Nearby schools include Lakemont Elementary School, Cornerstone Academy Charter and Maitland Middle School. 1521 Chestnut Avenue is a 4-bed, 3-bath, 2,842 sqft single family home built in 2022.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 03/06/2026 06:53 AM