$4,799,900.00 | 5 bed 4.5 bath 4,582sqft 4,582 square feet 0.42acre lot | 1691 Chestnut Ave, Winter Park, FL 32789.

Listed at Prime Holdings Inc

Email: broker@primeholdings.site

Property Type

Single family

Price Per Sqft.

$1,048

Garage

4 Cars

Year Built

2024

A Mid-Century Modern Masterpiece in the Heart of Winter Park


Welcome to a one-of-a-kind, custom-designed estate by Ferrarini Custom Homes, Inc., completed in February 2024. This architecturally striking Mid-Century Modern residence stands alone in Winter Park, combining timeless design with today’s most sought-after features. Ideally located just steps from Phelps Park and only 1.5 miles from Park Avenue, this home offers both luxury and convenience for the most discerning buyer.


Unmatched Craftsmanship & Design

Spanning 4,582 sq ft of thoughtfully curated living space with over 6,600 sq ft under roof, this home boasts:

  • 5 spacious bedrooms and 4.5 designer bathrooms

  • White oak floors, exposed beams, and natural wood accents throughout

  • A first-floor primary suite, private guest suite, home office, open-concept great room, formal dining, and a dedicated bar area

  • A chef’s gourmet kitchen featuring all Wolf & Sub-Zero appliances, Antolini Italian marble backsplash, exotic quartzite counters, and a hidden scullery behind a secret door

  • Custom cabinetry in white oak with extensive built-in storage

  • Second floor includes three additional bedrooms and two bathrooms with upscale finishes


Smart Living & Energy Efficiency

  • Full smart home integration with wireless controls for audio, lighting, pool, HVAC, cameras, and garage doors

  • Spray foam insulation, gas-powered appliances (range, fireplaces, washer, water heaters)

  • Exterior elevation finished with Cultured Stone, Hardie siding, and a grand Jeld-Wen 10' front entry door


Outdoor Living Like No Other

Situated on an oversized 155’ x 143’ lot, the outdoor space is a true showstopper:

  • 34-foot covered lanai with built-in summer kitchen, gas grill, outdoor fireplace, and porcelain paver flooring

  • Custom-designed pebbletec pool with lounging shelf, fire feature, and swim-out

  • Separate firepit conversation area nestled in mature landscaping

  • Remote screen access to pool deck, outdoor shower, and irrigated rear yard fed by a private well

  • Extensive landscape lighting and privacy hedges for a secluded estate feel


Bonus Features That Elevate the Experience

  • 4-car garage with workbench area

  • Herringbone paver driveway from cobblestone street to front door

  • Additional appliances: 3 beverage refrigerators, wine fridge, ice maker, and secondary 36" refrigerator

  • Cultivated landscaping that rivals any established estate despite being a brand-new construction


This is more than just a home—it’s a turnkey luxury estate, combining high design, functionality, and privacy with no waiting time for new construction. Every detail has been thoughtfully executed, offering an unmatched living experience in Winter Park.

Schedule your private tour today—this rare gem will not last.

Interior:

Other Rooms

  • Total Rooms: 10

  • Den Dimensions: 11 X 14

  • Great Room Dimensions: 19 X 20

  • Den Level: First

  • Great Room Level: First

  • Extra Room-1 Description: Den/Library/Office, Inside Utility

Appliances

  • Bar Fridge

  • Built-In Oven

  • Convection Oven

  • Cooktop

  • Dishwasher

  • Disposal

  • Dryer

  • Gas Water Heater

  • Microwave

  • Range

  • Range Hood

  • Refrigerator

  • Tankless Water Heater

  • Washer

  • Wine Refrigerator

  • Laundry Features: Gas Dryer Hookup, Laundry Room, Washer Hookup

Bedrooms

  • Bedrooms: 5

  • Primary Bedroom Dimensions: 17 X 18

  • Bedroom 2 Dimensions: 11 X 12

  • Bedroom 3 Dimensions: 13 X 13

  • Bedroom 4 Dimensions: 12 X 15

  • Bedroom 5 Dimensions: 13 X 17

  • Primary Bedroom Level: First

  • Bedroom 2 Level: Second

  • Bedroom 3 Level: Second

  • Bedroom 4 Level: Second

  • Bedroom 5 Level: First

Bathrooms

  • Total Bathrooms: 5

  • Full Bathrooms: 4

  • 1/2 Bathrooms: 1

Interior Features

  • Built-In Features

  • Cathedral Ceiling(S)

  • Ceiling Fans(S)

  • High Ceilings

  • Open Floorplan

  • Primary Bedroom Main Floor

  • Smart Home

  • Solid Surface Counters

  • Solid Wood Cabinets

  • Split Bedroom

  • Stone Counters

  • Thermostat

  • Vaulted Ceiling(S)

  • Walk-In Closet(S)

  • Wet Bar

  • Window Treatments

  • Furnished Description: Unfurnished

  • Flooring: Carpet, Tile, Wood

Heating and Cooling

  • Cooling Features: Central Air, Zoned

  • Fireplace Features: Family Room, Gas, Outside, Stone

  • Heating Features: Electric, Zoned

Kitchen and Dining

  • Dining Room Dimensions: 13 X 17

  • Dining Room Level: First

  • Kitchen Dimensions: 15 X 28

  • Kitchen Level: First

Exterior:

Exterior and Lot Features

  • French Doors

  • Irrigation System

  • Lighting

  • Outdoor Grill

  • Outdoor Kitchen

  • Outdoor Shower

  • Private Mailbox

  • Sidewalk

  • Fencing: Vinyl, Wood

  • Road Responsibility: Public Maintained Road

  • Road Surface Type: Brick

Pool and Spa

  • Pool Features: Deck, Gunite, In Ground

  • Pool Private: Yes

Garage and Parking

  • Attached Garage: Yes

  • Garage Spaces: 4

  • Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Open, Split Garage, Workshop In Garage

Land Info

  • Lot Size Acres: 0.42

  • Lot Size Square Feet: 18418

Community

School Information

  • Elementary School: Lakemont Elem

  • High School: Winter Park High

  • Middle School: Maitland Middle

Homeowners Association

  • Calculated Total Monthly Association Fees: 0

  • Pets Allowed: Cats OK, Dogs OK

Rental Info

  • Lease Term: Minimum Lease: No Minimum

Listing:

Other Property Info

  • Annual Tax Amount: 6314.81

  • Source Listing Status: Pending

  • County: Orange

  • Directions: Palmer Ave. To Phelps, Turn North And Phelps Ends At Chestnut. Home Is Straight Ahead.

  • Tax Year: 2024

  • Ownership: Fee Simple

  • Source Property Type: Residential

  • Area: 32789 - Winter Park

  • Source Neighborhood: LAKE KNOWLES TERRACE

  • Parcel Number: 32-21-30-4536-01-010

  • Postal Code Plus 4: 1607

  • Subdivision: LAKE KNOWLES TERRACE

  • Township: 21

  • Zoning: R-1 A

  • Property Subtype: Single Family Residence

  • Source System Name: C 2 C

Features:

Building and Construction

  • Total Square Feet Living: 4582

  • Year Built: 2024

  • Builder Name: Ferrarini Custom Homes

  • Building Area Source: Builder

  • Building Area Total: 6600

  • Construction Materials: Block, Stucco

  • Direction Faces: South

  • Foundation Details: Block, Slab

  • Levels: Two

  • New Construction: Yes

  • Property Age: 1

  • Property Condition: Completed

  • Roof: Shingle

  • Levels Or Stories: 2

  • Building Total Stories: 2

  • Structure Type: End Unit

Utilities

  • Sewer: Public Sewer

  • BB/HS Internet Available

  • Cable Connected

  • Electricity Connected

  • Natural Gas Connected

  • Public

  • Sewer Connected

  • Sprinkler Well

  • Street Lights

  • Water Connected

  • Water Source: Public

💰 Estimated Monthly Payment: $26,635


Based on a 30-year fixed loan at 6.515%

  • Principal & Interest: $24,309

  • Property Tax: $526

  • Home Insurance: $1,800

  • HOA Fees: $0

  • Mortgage Insurance: $0


🏁 Total Due at Closing: $1,151,976

  • Down Payment (20%): $959,980

  • Estimated Closing Costs (4%): $191,996

Today

Mar 3, 2025

Listed

StellarMLS

$4,799,900

+772.71%

$1,048/sqft

2020

Aug 6, 2020

Sold

StellarMLS

$550,000

-12.70%

$445/sqft

2018

Jun 30, 2018

213 days after listed

Listing removed

StellarMLS

$595,000

$482/sqft

Jun 30, 2018

Listing removed

StellarMLS

$595,000

-

May 29, 2018

Price decreased

StellarMLS

$595,000

-$35,000

$482/sqft

May 29, 2018

Price decreased

StellarMLS

$595,000

-$35,000

-

2017

Nov 29, 2017

Listed

StellarMLS

$630,000

$510/sqft

Nov 29, 2017

Listed

StellarMLS

$630,000

-

2024

Built

StellarMLS

-

-

Year

Taxes

Total assessment

equals

Land

added to

Additions

2023

$6,281

$400,000

=

$400,000

+

-

2022

$7,244

$472,504

=

$400,000

+

$72,504

2021

$6,684

$423,818

=

$370,000

+

$53,818

2020

$6,543

$424,880

=

$370,000

+

$54,880

2019

$6,874

$421,372

=

$370,000

+

$51,372

2018

$6,882

$415,656

=

$365,000

+

$50,656

2017

$6,888

$410,439

=

$360,500

+

$49,939

2016

$1,489

$152,400

=

-

+

-

2015

$1,534

$151,341

=

-

+

-

2014

$1,975

$150,140

=

-

+

-

2013

$1,925

$147,921

=

-

+

-

2012

$1,897

$145,448

=

-

+

-

2011

$1,830

$141,212

=

-

+

-

2010

$1,728

$139,125

=

-

+

-

2009

$1,638

$135,467

=

-

+

-

2008

$1,577

$135,332

=

-

+

-

2007

$1,731

$131,390

=

-

+

-

The price and tax history data displayed is obtained from public records and/or MLS feeds from the local jurisdiction.

Date

Type of work

Project type

Project name

Status

Aug 19, 2015

Window replacement

  • Doors and windows

  • Residential

-

Issued

Aug 5, 2015

Re-roof

  • Roofing

-

Issued

Aug 31, 2009

Tree removal permit

  • Landscape

-

Complete

Jun 2, 2006

Tree removal permit

  • Landscape

-

Issued

The permit history displayed is obtained from public records and provided for informational purposes only. It may not represent the complete permit history for the property. Accuracy is not guaranteed.

🌿 Environmental Risk Overview

Risk Factor

Level

Details

Flood

Minimal

This property’s flood risk is not changing.

Fire

Minimal

Wildfire risk remains low and stable.

Heat

Extreme

7 days forecasted above 107°F this year.

Wind

Extreme

High likelihood of severe wind events over the next 30 years.

Air

Minor

Increasing risk of poor air quality.

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