About This Home

This 4-bedroom, 4-bathroom single family at 1421 CHAPMAN Circle in Winter Park, FL is listed for $1,377,500 ($385 per sqft). Built in 2005, the home offers 3,578 sqft of living space on a 0.14 acres lot.

Key Features

  • Built in 2005
  • 0.14 acre lot
  • 2 stories
  • Fireplace

Property Details

2 stories
3 full, 1 half
2-car garage
2005

Amenities

FireplaceHardwoodA/C
Listing Description

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.

Monthly Cost Estimate

$7,367/mo

20% down · 6.5% · 30 years

Principal$996
Interest$5,969
Insurance$402

Estimates only. Actual payments may vary.

Location

1421 CHAPMAN Circle

Winter Park, FL 32789

WINDSONG ELIZABETHS WALK 43/81

Features & Amenities

Interior Features

Ceiling Fans(s)Crown MoldingEat-in KitchenHigh CeilingsOpen FloorplanPrimary Bedroom Main FloorSplit BedroomStone CountersThermostatWalk-In Closet(s)

Exterior Features

Private MailboxSidewalk

Property Details

Flooring

TileHardwood

Construction

Block Stucco

Outdoor Features

Porch

Parking

Driveway

Heating

Electric (Heating)Central

Cooling

Central Air

Appliances

Built-In OvenDishwasherMicrowaveRange HoodRefrigerator

Questions & Answers

This 4-bedroom, 4-bathroom single family at 1421 CHAPMAN Circle is listed at $1,377,500 ($385/sqft). The estimated monthly payment is $7,367 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 2005, 0.14 acre lot, 2 stories, Fireplace. Interior Features: Ceiling Fans(s), Crown Molding, Eat-in Kitchen. Exterior Features: Private Mailbox, Sidewalk.

This property is listed by Kelly Price and can be reached at 4076454321.

KP

Kelly Price

Agent at Kelly Price & Company

(407) 645-4321
Agent website

Listed by Kelly Price & Company · Broker phone: (407) 645-4321 · View on Broker Site · Broker website

MLS# O6415941· Source: Stellar MLS· 82 days on PropertySimple

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

1421 CHAPMAN Circle, Winter Park, FL 32789

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