$1,899,900
$100K PRICE DROP

1521 Chestnut Ave Winter Park, FL 32789

Estimated payment $12,066/month

Total Views 10,502
4 Beds
3 Baths
2,843 Sq Ft
$668 Price per Sq Ft

Highlights

  • In Ground Pool
  • Open Floorplan
  • Private Lot
  • Winter Park High Rated A+
  • Midcentury Modern Architecture
  • Family Room with Fireplace

About This Home

Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, built in 2023, 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, along with an oversized bonus room.
From the great room, expansive sliding glass doors lead out to the covered lanai, where you'll find an inground 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 multigenerational living.

The original two-car garage has been converted into a 425 sq ft air-conditioned bonus room—perfect as a media room, home gym, or additional 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

Sue Silberbusch

COMPASS FLORIDA LLC License #3124912 Listed on: 05/16/2025

COMPASS FLORIDA LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $20,570

Year Built

  • Built in 2022

Lot Details

  • 7,469 Sq Ft Lot
  • South Facing Home
  • Wood Fence
  • Private Lot
  • Irrigation Equipment
  • Street paved with bricks
  • Property is zoned R-1A

Parking

  • 2 Car Attached Garage
  • Side Facing Garage
  • Driveway

Home Design

  • Midcentury Modern Architecture
  • Slab Foundation
  • Frame Construction
  • Shingle Roof
  • Block Exterior
  • Stucco

Interior Spaces

  • 2,843 Sq Ft Home
  • 2-Story Property
  • Open Floorplan
  • Built-In Features
  • Shelving
  • High Ceiling
  • Ceiling Fan
  • Electric Fireplace
  • Blinds
  • Sliding Doors
  • Family Room with Fireplace
  • Great Room
  • Family Room Off Kitchen
  • Bonus Room
  • Laundry Room

Kitchen

  • Built-In Oven
  • Recirculated Exhaust Fan
  • Microwave
  • Dishwasher
  • Solid Surface Countertops

Flooring

  • Tile
  • Luxury Vinyl Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Primary Bedroom Upstairs
  • En-Suite Bathroom
  • Walk-In Closet
  • 3 Full Bathrooms
  • Split Vanities
  • Bathtub With Separate Shower Stall

Pool

  • In Ground Pool
  • Gunite Pool
  • Pool Lighting

Outdoor Features

  • Balcony
  • Exterior Lighting

Schools

  • Lakemont Elementary School
  • Maitland Middle School
  • Winter Park High School

Utilities

  • Forced Air Zoned Heating and Cooling System
  • Heat Pump System
  • Thermostat
  • Propane
  • Tankless Water Heater
  • High Speed Internet
  • Cable TV Available

Community Details

  • No Home Owners Association
  • Lake Knowles Terrace Subdivision

Listing and Financial Details

Home Details

Home Type

Single Family

Est. Annual Taxes

$20,570

Year Built

Built in 2022

Lot Details

0

Parking

2

Listing Details

  • Property Type: Residential
  • Property Sub Type: Single Family Residence
  • Architectural Style: Mid-Century Modern
  • Construction Materials: Block, Stucco, Frame
  • Fireplace: Yes
  • Living Area: 2843
  • Lot Size Acres: 0.17
  • New Construction: No
  • Year Built: 2022
  • Building Area Total: 3703
  • Lot Size Sq Ft: 7469
  • Directions to Property: Palmer Avenue to north on Phelps. Turn left onto Chestnut to home on the right.
  • Status: Active
  • Ownership: Fee Simple
  • Available for Lease YN: 1
  • Escrow City: Altamonte Springs
  • Escrow Postal Code: 32714
  • Escrow State: FL
  • Escrow Street Name: Douglas Ave.
  • Escrow Street Number: 797
  • List Office Head Office Key Nume: 169647934
  • Minimum Lease: No Minimum
  • RATIO Current Price By Calculate: 668.27
  • Total Acreage: 0 to less than 1/4
  • Unit Number YN: 0
  • Water Access YN: 0
  • MFR_InLawSuiteYN: 0
  • Tax Year: 2024
  • Special Features: VirtualTour

Interior Features

  • Fireplace Features: Electric, Family Room
  • Living Area Units: Square Feet
  • Flooring: Tile
  • Full Bathrooms: 3
  • Interior Amenities: Built-in Features, Ceiling Fans(s), High Ceilings, Kitchen/Family Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Thermostat, Walk-In Closet(s)
  • Appliances Included: Built-In Oven, Dishwasher, Exhaust Fan, Microwave, Refrigerator, Tankless Water Heater
  • Foundation Details: Slab
  • Total Bedrooms: 4
  • Levels: Two
  • Other Equipment: Irrigation Equipment
  • Spa Yn: No
  • Stories: 2
  • Window Features: Blinds
  • Street Number Modifier: 1521
  • Living Area Meters: 264.12
  • Room Count: 7

Exterior Features

  • Direction Faces: South
  • Pool Features: Gunite, In Ground, Lighting
  • Exterior Features: Balcony, Lighting, Sliding Doors
  • Roof: Shingle
  • Pool Private: Yes
  • Waterfront: No
  • Road Surface Type: Brick
  • Water Extras YN: 0
  • Water View YN: 0
  • Waterfront Feet Total: 0

Garage/Parking

  • Attached Garage: Yes
  • Carport Y N: No
  • Garage Spaces: 2
  • Garage Yn: Yes
  • Parking Features: Driveway, Garage Faces Side

Utilities

  • Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, Sewer Connected, Water Connected
  • Cooling: Central Air, Ductless, Zoned
  • Heating: Central, Heat Pump, Zoned
  • Laundry Features: Inside, Laundry Room
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Association: No
  • Senior Community: No
  • Association 2 YN: 0
  • Association Approval Required YN: 0

Fee Information

  • Total Annual Fees: 0.00
  • Total Monthly Fees: 0.00

Schools

  • Elementary School: Lakemont Elem
  • High School: Winter Park High
  • Middle Or Junior School: Maitland Middle

Lot Info

  • Zoning: R-1A
  • Parcel Number: 32-21-30-4536-01-180
  • Additional Parcels: No
  • Fencing: Wood
  • Lot Features: Private, Street Brick
  • Property Attached Yn: No
  • Flood Zone Code: X
  • Homestead YN: 1
  • Lot Size Square Meters: 694
  • Zoning Compatible YN: 1

Rental Info

  • Furnished: Unfurnished
  • Lease Restrictions YN: 0

Tax Info

  • Tax Annual Amount: 20569.64
  • Tax Block: 1
  • Tax Book Number: K-4
  • Tax Lot: 18

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $20,570 $1,392,380 $400,000 $992,380
2024 $18,116 $1,346,890 $400,000 $946,890
2023 $18,116 $1,189,210 $400,000 $789,210
2022 $5,022 $325,000 $325,000 $0
2021 $4,732 $300,000 $300,000 $0
2020 $5,185 $336,671 $300,000 $36,671
2019 $5,218 $363,582 $300,000 $63,582
2018 $4,908 $342,656 $280,000 $62,656
2017 $4,386 $292,440 $230,720 $61,720
2016 $4,153 $284,521 $224,000 $60,521
2015 $3,866 $253,988 $196,000 $57,988
2014 $3,316 $199,744 $149,000 $50,744
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/22/2025 07/22/25 Price Changed $1,899,900 -5.0% $668 / Sq Ft
05/16/2025 05/16/25 For Sale $1,999,900 +510.7% $703 / Sq Ft
04/30/2019 04/30/19 Sold $327,500 -2.2% $263 / Sq Ft
04/01/2019 04/01/19 Pending -- -- --
03/28/2019 03/28/19 For Sale $335,000 0.0% $269 / Sq Ft
03/25/2019 03/25/19 Pending -- -- --
03/14/2019 03/14/19 For Sale $335,000 -- $269 / Sq Ft
Source: Stellar MLS

Purchase History

Date Type Sale Price Title Company
Warranty Deed $327,500 Fidelity Natl Ttl Of Fl Inc
Source: Public Records

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Source: Stellar MLS

MLS Number: A4651868

Stellar MLS

APN: 32-2130-4536-01-180