CONTACT
FAVORITE
SHARE
CLAIM

1421 CHAPMAN CIRCLE WINTER PARK FL 32789

$1,550,000
USD CAD EUR GBP BTC
1421 CHAPMAN CIRCLE, WINTER PARK, FL 32789 - MLS#MFRO6415941 1421 CHAPMAN CIRCLE, WINTER PARK, FL 32789 - MLS#MFRO6415941 1421 CHAPMAN CIRCLE, WINTER PARK, FL 32789 - MLS#MFRO6415941 1421 CHAPMAN CIRCLE, WINTER PARK, FL 32789 - MLS#MFRO6415941

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Request Info, you are registering to this website and agreeing that BEX Realty, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

Overview of 1421 Chapman Cir

4 Bedrooms
3/1 Bathrooms
2 Car Garage
4,529 Square Feet
3,578SF Living Area
Pool:
No
Water: None
Year Built 2005
Listed For 8 Days

Don't miss this home for sale in Windsong! Welcome to 1421 chapman circle, an elegant spanish-mediterranean home nestled within the highly coveted Windsong community in the heart of winter park. From the moment you arrive, the classic barrel tile roof and timeless architectural character set the tone for what awaits inside — a home with enduring style, gracious proportions, and tremendous potential to be personalized for its next chapter. spanning over 3,500 square feet, this 4-bedroom, 3.5-bath residence offers a formal, well-appointed layout with soaring high ceilings, rich crown molding, and a thoughtful floor plan designed for both comfortable daily living and effortless entertaining. A dedicated first-floor office provides the ideal work-from-home space, while the separate formal dining room adds an air of sophistication perfect for hosting family and friends. the gourmet kitchen is the heart of the home, featuring granite countertops, premium thermador appliances, and bartop seating — a space equally suited for casual mornings and lively gatherings. The living room opens through french doors to a generous wrap-around screened patio, seamlessly blending indoor and outdoor living in true florida fashion. the first-floor primary suite is a private retreat, complete with french door access to the patio, a spacious walk-in closet, and a well-appointed en suite bath featuring a double sink vanity, a separate soaking tub, and a walk-in shower. Upstairs, three generously sized guest bedrooms share a hall bath, and a large bonus room and landing offer flexible space for a playroom, media room, or additional lounge area. A large upstairs utility room and additional walk-in storage beneath the stairs ensure that function is never sacrificed. The home is served by two hvac units, both dated 2017. beyond the front door, the Windsong community is nothing short of exceptional. Residents enjoy access to two resort-style pools, a splash pad for the little ones, scenic parks, a fishing dock, and coveted chain-of-lakes access complete with use of a community boat — a lifestyle that truly sets Windsong apart. Zoned for a-rated schools and ideally situated just minutes from the vibrant energy of baldwin park, audubon park, the mills district, downtown orlando, and all that winter park has to offer, this address places you at the center of everything. whether you're drawn to its classic architecture, its unmatched community amenities, or the incredible opportunity to update and truly make it your own, 1421 chapman circle is a rare find in one of central florida's most beloved neighborhoods.

This luxury single family home was built in 2005 and features 4 bedrooms, and 3 full bathrooms plus 1 half bath. This home for sale is 4,529 square feet, with 3,578 sq ft being air conditioned living space. The home has a 2 car garage and does not have a private swimming pool.

Directions to this property are as follows: From Glenridge: Turn Onto Preserve Point Drive. Turn Right Onto Elizabeths Walk. Turn Right Onto Chapman Circle. Home Is On Right Side.

Please contact your BEX agent for more information about MLS# MFRO6415941 or any other homes for sale in Winter Park or elsewhere in the Orange County area.

Features & Amenities

Appliances

Built-In Oven, Dishwasher, Microwave, Range Hood, Refrigerator

Architecture

Mediterranean

Cooling

Central Air

Heating

Central, Electric

Flooring

Hardwood, Tile

Parking

Driveway

Lot Size

6294

View

view

Construction Materials

Block, Stucco

Interior Features

Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)

Furnished

Unfurnished

Exterior Features

French Doors, Private Mailbox, Sidewalk

Patio And Porch Features

Rear Porch, Screened

Roof

Tile

Window Features

Blinds

Utilities

B B/H S Internet Available, Cable Available, Natural Gas Connected

Laundry

Inside, Laundry Room

Fireplace

Gas, Living Room

Zoning

P U R D

Year Built

2005

Pets Allowed

Yes

Annual Real Estate Taxes

$10,592 (2025)

Legal Description

Windsong -Elizabeths Walk 43/81 Lot 17

Property Type

Single Family Home

HOA Fees

$805 /Quarterly

Association Fee Includes

Management, Recreational Facilities

Community Features

Deed Restrictions, Park, Playground, Pool, Sidewalks

Direction Faces

North

MLS Number

MFRO6415941

Universal Property Id

U S-12095-N-172230937100170-R-N

Days On Market

8

Community Name

Windsong Elizabeths Walk 43/81

Property Manager

Leland Management (407) 781-1836

1421 Chapman Circle Price Calculator

Get Mortgage Quote For This Home

The payment calculator figures for 1421 Chapman Cir should be used as an estimate only. Loan terms including interest rate, and required downpayment will vary with each lender and/or individual. RE taxes for this home for sale are estimated based on the actual property taxes for this property for the tax year 2025 which are $10,592 but will likely change when this home sells. These estimations are calculated from a list price of $1,550,000 and a 25% down payment and do not include homeowners insurance which will vary greatly depending on the home characteristics and location.

Recent Home Sales near 1421 Chapman Circle

Address Sale Price Bed Bth Size Location Sale Date
2607 Lafayette Ave $Log in to view 4 3/1 3,884SF Winter Park Village 04/01/2026

MLS# MFRO6415941 Listing History

06/12/2026 Listed for sale by KELLY PRICE & COMPANY LLC with MLS# MFRO6415941 with a list price of $1,550,000.

Orange County Schools

Elementary School

Middle School

This listing of 1421 Chapman Circle Winter Park FL 32789 was last updated on 2026-06-20 15:12:32. Listing courtesy of KELLY PRICE & COMPANY LLC.
MLS

Map of 1421 Chapman Circle Winter Park FL 32789

Similar Homes For Sale

948 Poinciana Ln, WINTER PARK
Reduced
$2,899,900
$3,599,000

MLS#MFRO6372165

948 Poinciana Ln
Winter Park, FL 32789

4

4

2

4,529 SqFt

0.3 Acres

2299 Via Tuscany, WINTER PARK
Reduced
$2,150,000
$2,345,000

MLS#MFRO6355858

2299 Via Tuscany
Winter Park, FL 32789

4

4

2

5,353 SqFt

0.4 Acres

2240 Venetian Way, WINTER PARK
$3.5 Million

MLS#MFRO6413398

2240 Venetian Way
Winter Park, FL 32789

4

4

2

5,165 SqFt

Water Front

0.31 Acres

1840 Bryan Ave, WINTER PARK
Reduced
$1,725,000
$1,899,500

MLS#MFRO6391922

1840 Bryan Ave
Winter Park, FL 32789

4

4

2

4,665 SqFt

0.29 Acres

1813 Harland Park Dr, WINTER PARK
Reduced
$1,875,000
$1,995,000

Windsong

1813 Harland Park Dr
Winter Park, FL 32789

4

4

2

4,659 SqFt

0.25 Acres

2614 Parkland Dr, WINTER PARK
Reduced
$1,890,000
$2,295,000

MLS#MFRO6301489

2614 Parkland Dr
Winter Park, FL 32789

4

4

2

4,610 SqFt

0.23 Acres

Zev Freidus Broker / President
Zev Freidus
Broker / President
561-235-2161
Call Me
Text Me
Email Me
When clicking Submit Request, you are registering to this website and agreeing that ZFC Real Estate, its affiliates or associated third parties may contact you, including with calls or texts by automated means. You also agree to our Terms of Use and Privacy Policy

The data relating to homes for sale or lease or other real estate for sale or for rent on the BEX Realty website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. BEX Realty, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Currency