1821 Windsor Drive

Off Market

1821 Windsor Drive

Winter Park FL 32789

3042 sq. ft.

10449 sq. ft.

Single-Family

Last sold for $995,000

Chris Creegan Agent, last sold this property on 22 July 2025 after 69 days on market.

Overview

WELCOME to 1821 WINDSOR DR in WINTER PARK, FLORIDA! This is a ONCE IN A LIFETIME OPPORTUNITY to own this BEAUTIFUL CUSTOM-BUILT MASTERPIECE of a HOME in ONE OF THE MOST DESIRED LOCATIONS in TOWN! When you buy this Home, you aren?t just purchasing a NEWLY BUILT CUSTOM HOME FULL OF LUXURIOUS UPGRADES and ARCHITECTURAL FEATURES; you are also buying into the LIFESTYLE that others DREAM OF LIVING in the LAKEMONT AREA of WINTER PARK! The A RATED LAKEMONT ELEMENTARY SCHOOL is just beyond your backyard! Phelps Park is also only ? mile away! The INFAMOUS PARK AVE is LESS THAN A MILE AND A HALF AWAY. There are over 175 LOCAL SHOPPES and RESTAURANTS in the immediate area of PARK AVE, mixed in with NUMEROUS PARKS AND GREEN SPACE! The RENOWNED ROLLINS COLLEGE is also LESS THAN A MILE AND A HALF AWAY! You will LIVE, WORK and PLAY in the MIDDLE of THE PLACE TO BE in TOWN! YOU CANNOT PICK A BETTER LOCATION to LIVE IN if you are wanting the WINTER PARK LIFESTYLE! The Home itself was Built in 2017! The CURRENT OWNERS are the ORIGINAL OWNERS and have IMMACULATELY MAINTAINED THIS HOME! This Home has a STATE-OF-THE-ART PHOTOVOLTAIC SOLAR SYSTEM that is PAID OFF and WILL CONVEY WITH THE HOUSE so the NEW OWNER WILL HAVE MINIMAL POWER COSTS and TOP OF THE LINE SOLAR ENERGY! Structural Upgrades that are above and beyond are: Architectural Features such as the Roof Shape and the Design of the Exterior Walls that are meant to withstand the strongest of hurricane winds. The home is also built up on one extra layer of Cinderblock to avoid any flooding risk! You will notice as soon as you pull up to the house, there is a BEAUTIFUL CURB APPEAL that is emphasized by the mature, but low maintenance landscaping. Walking into the house, your attention is immediately drawn to the BEAUTIFUL WOOD LOOK PORCELAIN TILE that is THROUGHOUT THE ENTIRE MAIN LIVING AREA and BEDROOMS! The house opens up into a very large and modern floor plan! The Main Living Area is a very large area that includes the Living/Family Room, an Oversized Gourmet Kitchen and a nice sized dining room! This entire space is punctuated by lots of perfectly placed windows for tons of natural light, warmth and comfort! The Kitchen has High-End Quartzite Countertops, an oversized island and Custom Walnut Soft-Close Cabinets! Stainless Steel Appliances, recess lighting and under cabinet lights top off what is already a DREAM KITCHEN! The PRIMARY SUITE is OVERSIZED with large windows and lots of space! The Primary Bathroom is the size of a Primary Bathroom you would expect in a home of twice its size! There is a HUGE OVERSIZED CUSTOM SHOWER with MULTIPLE SHOWER HEADS include a RAIN SHOWER HEAD and enough space for you and your significant other to comfortably shower at the same time! There is also an elegant garden tub if you prefer to bathe in relaxation! Lots of floor space, lots of counter space and well-designed dual vanities make the primary bathroom feel like its own little slice of heaven! There is also a very large, custom closet that has built-in ?his & her? shelving. All secondary bedrooms are also a very healthy size!! Out back, you can enjoy the birds, plants and the nice Florida weather on your covered lanai that is over 250 square feet and has an OUTDOOR KITCHEN with a built-in refrigerator, and a built-in grill! Many species of plants in the natural backyard attract all sorts of birds to your home as well! Don't Miss This Opportunity! It's a One-of-a-Kind Home! Book your appointment today!

Features

4 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

3042 sq. ft. floor area

10449 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Winter Park over the last 12 months, the estimated median property value of 1821 Windsor Drive is $1.43m.

Median value

$1.43m

Estimated value range

$315k - $6.3m

Median days on market

Estimated value trend

-5%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Winter Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1821 Windsor Drive

2025

Sold

$995,000

22 Jul 2025 by Chris Creegan Agent, of CREEGAN GROUP

2010

Sold

$215,000

19 Feb 2010 by Farah Novin, of Parkland International Realty

Happy sellers in Winter Park

83%

83% of sellers in Winter Park reported that their sale price either exceeded or met their price expectations.

Winter Park stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 7 reviews in Winter Park over the last 12 months.

Local market activity for 4 bedroom single-family properties in Winter Park

In the last 12 months, 108 four-bedroom single-family properties similar to 1821 Windsor Drive, have been sold.

This represents a 13% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Winter Park for a market analysis.

Lisa Gould

at KELLER WILLIAMS WINTER PARK

(204 reviews)

Get a market analysis

Justin Adams

(145 reviews)

Get a market analysis

Andrew Livingston

at Coldwell Banker Realty - Winter Park

(16 reviews)

Get a market analysis

Jennifer King

at CORCORAN PREMIER REALTY

(6 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winter Park

Lisa Gould

Sellers who recommend Lisa Gould have praised them for being local expert, clear communication, supportive, responsive, patient, reliable, and empathetic