1429 Chapman Cir

Off Market

1429 Chapman Cir

Winter Park FL 32789

3774 sq. ft.

6294 sq. ft.

Single-Family

Last sold for $1,280,000

Greg Martinez, last sold this property on 24 February 2026 after 465 days on market.

Overview

Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophisticated 4-bedroom, 4-bathroom residence seamlessly blends modern luxury with practical living across two thoughtfully planned levels. The striking exterior features geometric lines, stacked stone accents, and dramatic double entry doors, setting the tone for the remarkable interior. A grand foyer with continuing stone elements welcomes you into an open-concept main level, perfect for both entertaining and daily living. Walls of 8-foot sliding glass doors blur the lines between indoor and outdoor spaces, opening to a covered 12' x 25' lanai. The showstopping gourmet kitchen serves as the heart of the home, featuring a commanding 6' x 6' granite island, KitchenAid stainless steel appliances including a professional 6-burner gas cooktop, generous walk-in pantry, and sleek dark cabinetry contrasting with the subway tile backsplash and white countertops. A sophisticated blue ceiling detail and sunburst light fixture add artistic flair to this culinary haven. The main level includes a private en-suite guest room, while the upper level houses the primary suite, two additional en-suite bedrooms, a versatile loft workspace, and laundry facilities. Recent premium upgrades include a whole-home generator, surge protection system, EV charging outlet, hardwood flooring in upstairs guest rooms, home theater electronics, whole-home audio, and security system with integrated smoke detection. Located in the amenity-rich Windsong community, residents enjoy chain of lakes access, multiple community pools, and playground facilities. Minutes from the vibrant dining scenes of Audubon Park Garden District, Mills 50, and Winter Park's renowned Park Avenue. This masterfully designed residence offers the perfect balance of sophisticated style, modern convenience, and prime location.

Features

4 bedrooms

4 bathrooms

2 carspaces

2 garage spaces

3774 sq. ft. floor area

6294 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 1429 Chapman Cir is $1.52m.

Median value

$1.52m

Estimated value range

$315k - $6.3m

Median days on market

Estimated value trend

increase 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 1429 Chapman Cir

2026

Sold

$1,280,000

24 Feb 2026 by Greg Martinez, of CORCORAN PREMIER REALTY

2018

Sold

$860,000

11 Dec 2018 by Kelly Price, of KELLY PRICE & COMPANY LLC

2014

Sold

$403,700

23 Jul 2014 by Kelly Price, of KELLY PRICE & COMPANY LLC

Happy sellers in Winter Park

80%

80% 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, 112 four-bedroom single-family properties similar to 1429 Chapman Cir, have been sold.

This represents a 8% 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

(206 reviews)

Get a market analysis

Justin Adams

(146 reviews)

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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

5 (206 reviews)
2 Reviews in Winter Park
4 Sales in Winter Park

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Justin Adams

Sellers who recommend Justin Adams have praised them for being local expert, clear communication, responsive, supportive, detail-oriented, reliable, and friendly