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1421 CHAPMAN CIRCLE

House For Sale
$1,550,000

BTC: 24.21875000

ETH: 916.61738616

1 days
4 bds
3 ba
3,578 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Driveway
Year Built:
2005
Lot:
0.14 Acres
Heating:
Central / Electric
Price/sqft:
$433
Cooling:
Central Air
HOA:
$805

Valuation

Our model vs. what's actually selling nearby.
Estimate
$1,095,000
$763K – $1.5M
Confidence Low
List vs. estimate
$455K above estimate
List $1,550,000 · +41.6%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$433
-6.8% vs. city median $464
Based on
5 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$10,592
2025
HOA
$805/qtr
Manager, Recreational Facilities
Garage
2 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Engineered Hardwood

    • Tile

    Heating

    • Central

    • Electric

    Cooling

    • Central Air

    Appliances

    • Built-In Oven

    • Dishwasher

    • Microwave

    • Range Hood

    • Refrigerator

    Other interior features

    • Ceiling Fan(s)

    • Crown Molding

    • Eating Space In Kitchen

    • High Ceilings

    • Open Floorplan

    • Primary Bedroom Main Floor

    • Split Bedroom

    • Stone Counters

    • Thermostat

    • Walk-In Closet(s)

    Bedrooms and bathrooms

    • Bedrooms: 4

    • Bathrooms: 1

    • Full bathrooms: 3

  • Parking

    • Driveway

    Property

    • Levels: Two

    • Exterior Features: French Doors / Private Mailbox / Sidewalk

    Lot

    • Lot: 0.14 Acres

    Other Property Information

    • Parcel Number: 172230937100170

    • Zoning: PURD

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • BB/HS Internet Available

    • Cable Available

    • Natural Gas Connected

  • Other financial information

    • HOA: $805

    • HOA Frequency: Quarterly

    • Annual tax amount: $10,592

  • Source details

    • MLS ID: O6415941

    Other facts

    • Construction Materials: Block / Stucco

    • Foundation Details: Slab

    • Fireplace Features: Gas / Living Room

    • Laundry Features: Inside / Laundry Room

    • Patio And Porch Features: Rear Porch / Screened

    • Window Features: Blinds

    • Direction Faces: North

    • Architectural Style: Mediterranean

    • Fireplace: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 3578

    • Water Source: Public

    • Subdivision Name: WINDSONG ELIZABETHS WALK 43/81

Private inquiry
Talk to the advisor on this listing.
Floor plans, HOA docs, off-market comparables, scheduling a private showing — one message, direct to the local specialist.

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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: KELLY PRICE & COMPANY LLC