# 1421 CHAPMAN Circle, Winter Park, FL 32789 > **TL;DR:** 4bd/4ba single family, $1,377,500 ($385/sqft), built 2005, 3,578 sqft. > Fireplace, Hardwood, A/C, 2-car garage. Est. $7,367/mo. Listed 106 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $1,377,500 | | Price/sqft | $385 | | Bedrooms | 4 | | Bathrooms | 3 full, 1 half | | Square Feet | 3,578 | | Year Built | 2005 | | Lot Size | 6,098 sqft (0.14 acres) | | Stories | 2 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 106 | ## Why This Home Stands Out - **Hardwood Floors** - Hardwood flooring listed ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $6,965 | | Estimated Insurance | $402 | | **Total** | **$7,367** | ## Nearby Schools - **Elementary:** Brookshire Elem - **Middle:** Glenridge Middle - **High:** Winter Park High ## Key Amenities - Fireplace - Hardwood - A/C - 2-car garage ## Property Highlights - Built in 2005 - 0.14 acre lot - 2 stories - Fireplace ## Description ### Agent 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. ## Location - **Address:** 1421 CHAPMAN Circle, Winter Park, FL 32789 - **County:** Orange - **Neighborhood:** WINDSONG ELIZABETHS WALK 43/81 - **Coordinates:** 28.579103, -81.334206 - **Google Maps:** https://www.google.com/maps?q=28.579103,-81.334206 ## Virtual Tour & Media - **Video Tour:** https://www.youtube.com/watch?v=61JNeSgLD0E ## Listing Agent - **Name:** Kelly Price - **Brokerage:** Kelly Price & Company - **Phone:** 4076454321 - **Broker Phone:** (407) 645-4321 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1421-Chapman-Cir_Winter-Park_FL_32789_M63483-66426?f=listhub&s=MFRMLSFL&m=O6415941&c=propsimple) ## Photos ![1421 CHAPMAN Circle - Photo 1](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1813302477r.jpg) ![1421 CHAPMAN Circle - Photo 2](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3675900550r.jpg) ![1421 CHAPMAN Circle - Photo 3](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1207264107r.jpg) ![1421 CHAPMAN Circle - Photo 4](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f628531579r.jpg) ![1421 CHAPMAN Circle - Photo 5](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f943895226r.jpg) ![1421 CHAPMAN Circle - Photo 6](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3308453960r.jpg) ![1421 CHAPMAN Circle - Photo 7](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2691379736r.jpg) ![1421 CHAPMAN Circle - Photo 8](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f397911906r.jpg) ![1421 CHAPMAN Circle - Photo 9](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1662622642r.jpg) ![1421 CHAPMAN Circle - Photo 10](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f473991419r.jpg) ![1421 CHAPMAN Circle - Photo 11](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2466415050r.jpg) ![1421 CHAPMAN Circle - Photo 12](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f101729478r.jpg) ![1421 CHAPMAN Circle - Photo 13](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3277304183r.jpg) ![1421 CHAPMAN Circle - Photo 14](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2953837744r.jpg) ![1421 CHAPMAN Circle - Photo 15](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3502890421r.jpg) ![1421 CHAPMAN Circle - Photo 16](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f877249409r.jpg) ![1421 CHAPMAN Circle - Photo 17](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f772129866r.jpg) ![1421 CHAPMAN Circle - Photo 18](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1933552071r.jpg) ![1421 CHAPMAN Circle - Photo 19](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f672544534r.jpg) ![1421 CHAPMAN Circle - Photo 20](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3310856240r.jpg) ![1421 CHAPMAN Circle - Photo 21](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1081459123r.jpg) ![1421 CHAPMAN Circle - Photo 22](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1056878971r.jpg) ![1421 CHAPMAN Circle - Photo 23](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1898275322r.jpg) ![1421 CHAPMAN Circle - Photo 24](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2134878434r.jpg) ![1421 CHAPMAN Circle - Photo 25](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f824688365r.jpg) ![1421 CHAPMAN Circle - Photo 26](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2251923660r.jpg) ![1421 CHAPMAN Circle - Photo 27](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f891157856r.jpg) ![1421 CHAPMAN Circle - Photo 28](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f263291390r.jpg) ![1421 CHAPMAN Circle - Photo 29](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f4009167904r.jpg) ![1421 CHAPMAN Circle - Photo 30](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2448202299r.jpg) ![1421 CHAPMAN Circle - Photo 31](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1214717506r.jpg) ![1421 CHAPMAN Circle - Photo 32](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3844738533r.jpg) ![1421 CHAPMAN Circle - Photo 33](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2274152500r.jpg) ![1421 CHAPMAN Circle - Photo 34](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2136411167r.jpg) ![1421 CHAPMAN Circle - Photo 35](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1304589144r.jpg) ![1421 CHAPMAN Circle - Photo 36](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f4020556615r.jpg) ![1421 CHAPMAN Circle - Photo 37](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f311814487r.jpg) ![1421 CHAPMAN Circle - Photo 38](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2587427229r.jpg) ![1421 CHAPMAN Circle - Photo 39](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2701664979r.jpg) ![1421 CHAPMAN Circle - Photo 40](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f3090608874r.jpg) ![1421 CHAPMAN Circle - Photo 41](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f630873577r.jpg) ![1421 CHAPMAN Circle - Photo 42](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f189452226r.jpg) ![1421 CHAPMAN Circle - Photo 43](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f989694645r.jpg) ![1421 CHAPMAN Circle - Photo 44](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f4001671279r.jpg) ![1421 CHAPMAN Circle - Photo 45](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f188819371r.jpg) ![1421 CHAPMAN Circle - Photo 46](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1176963186r.jpg) ![1421 CHAPMAN Circle - Photo 47](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f2368808333r.jpg) ![1421 CHAPMAN Circle - Photo 48](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f1486012923r.jpg) ![1421 CHAPMAN Circle - Photo 49](http://lh.rdcpix.com/7436c3d452c2b48345b46df70ea2db83l-f590328585r.jpg) --- **MLS#:** O6415941 | **Updated:** 2026-09-25 **Source:** listhub *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.* [View on PropertySimple](https://www.propertysimple.ai/listing/1421-chapman-circle-winter-park-fl-32789-o6415941) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/1421-chapman-circle-winter-park-fl-32789-o6415941#listing", "url": "https://www.propertysimple.ai/listing/1421-chapman-circle-winter-park-fl-32789-o6415941", "name": "1421 CHAPMAN Circle, Winter Park, FL 32789", "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. 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