1421 Chapman Cir, Winter Park, FL 32789
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FOR SALE
OPEN SUN, 2-4PM
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1421 Chapman Cir
Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,578 sqft

$1,450,000

Original price: $1,550,000
Est. Mortgage $10,348/mo*
Get Pre-Qualified

$1,450,000

Original price: $1,550,000
Est. Mortgage $10,348/mo*
Get Pre-Qualified
4 Beds
3.5 Baths
3,578 sqft
We estimate this home will sell faster than 94% nearby.

Home Highlights

Parking
2 Car Garage
Outdoor
Porch
Climate Control
Heating & Cooling
HOA
$268/Monthly
Price/Sqft
$405
Listed
43 days ago

Local Information

  • Map ViewExplore the area around 1421 Chapman Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
We estimate this home will sell faster than 94% nearby.

Open House

Sunday, July 26
2:00 PM to 4:00 PM

Home Details for 1421 Chapman Cir

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3578 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Natural Gas ConnectedAppliances: Oven, Dishwasher, Microwave, Range Hood, RefrigeratorDishwasherLaundry: Inside,Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Gas, Living RoomHas a Fireplace
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Engineered Hardwood, Tile
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Engineered Hardwood, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Rear Porch, ScreenedVegetation: Trees/LandscapedExterior: Private Mailbox, SidewalkFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway
Frontage
Waterfront: Lake, Lake PrivilegesRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 41Days on Market: 43

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Mediterranean
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 172230937100170

Price & Status

Price
List Price: $1,450,000Price Per Sqft: $405

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINTER PARKCommunity: WINDSONG ELIZABETHS WALK 43/81
School Information
Elementary School: Brookshire ElemJr High / Middle School: Glenridge MiddleHigh School: Winter Park High

Agent Information

Listing Agent
Listing ID: O6415941

Building

Building Area
Building Area: 4529 Square Feet

Community

Community Features: Fishing, Lake, Deed Restrictions, Park, Playground, Pool, SidewalksNot Senior Community
Other
Playground

HOA

HOA Fee Includes: Manager, Recreational FacilitiesHOA Name: Leland ManagementHOA Phone: 407-781-1836Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $268/Monthly

Lot Information

Lot Area: 6294 sqft

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6415941Showing Advance Notice: 24Showing AttendedShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12095-N-172230937100170-R-N

Additional Information

FishingLakeDeed RestrictionsParkPlaygroundPoolSidewalks
Last check for updates: about 5 hours ago
Listing Provided by: Kelly Price, (407) 645-4321
KELLY PRICE & COMPANY LLC, (407) 645-4321
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6415941
Also Listed on Stellar MLS.
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. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Market trends in Winter Park

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$452K
$7.33KMoM
Sale-to-List Price
97.7%
0.2%MoM
Price per sq ft
$288
$1MoM
Available listings
380
7MoM

Price History for 1421 Chapman Cir

DatePriceEventSource
07/12/2026$1,450,000PriceChange
Stellar MLS #O6415941
06/12/2026$1,550,000Listed For SaleStellar MLS #O6415941
03/30/2004$130,000Sold
N/A
07/31/2003$112,600Sold
N/A

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Property Tax and Assessment

Year2024
Tax$10,269
Assessment$1,433,259
Home facts updated by county records

Comparable Sales for 1421 Chapman Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1429 Chapman Cir, Winter Park, FL
0.02
Single-Family Home
$1,280,000
02/24/26
4
4
3,116
1408 Chapman Cir, Winter Park, FL
0.04
Single-Family Home
$1,475,000
03/16/26
4
4
3,237
1636 Elizabeths Walk, Winter Park, FL
0.06
Single-Family Home
$2,050,000
06/18/26
4
4.5
3,412
1841 Harland Park Dr, Winter Park, FL
0.18
Single-Family Home
$1,635,000
05/11/26
4
3.5
3,470
4184 Oak St, Orlando, FL
0.17
Single-Family Home
$1,000,000
08/06/25
3
2.5
2,735
1713 Elizabeths Walk, Winter Park, FL
0.11
Single-Family Home
$1,850,000
04/15/26
4
4
3,670
1813 Harland Park Dr, Winter Park, FL
0.28
Single-Family Home
$1,755,000
07/24/26
4
3.5
3,551
1705 Elizabeths Walk, Winter Park, FL
0.10
Single-Family Home
$1,688,750
04/01/26
5
5
3,820
1327 Bridgeport Dr, Winter Park, FL
0.16
Single-Family Home
$1,400,000
08/21/25
5
4
4,181
3856 Lower Park Rd, Orlando, FL
0.45
Single-Family Home
$1,400,000
01/06/26
4
3
3,708

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Assigned Schools

These are the assigned schools for 1421 Chapman Cir.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Park

At least 595 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 79 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
    Flag
  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
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  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
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  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
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  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
    Flag
  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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LGBTQ Local Legal Protections

Kelly Price, KELLY PRICE & COMPANY LLC, (407) 645-4321
Agent Phone: (407) 645-4321
1421 Chapman Cir, Winter Park, FL 32789 is a 4 bedroom, 4 bathroom, 3,578 sqft single-family home built in 2005. This property is currently available for sale and was listed by Stellar MLS on Jun 12, 2026. The MLS # for this home is MLS# O6415941.