1421 CHAPMAN CIRCLE, Winter Park, FL 32789
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Property image
FOR SALE
OPEN SAT, 1-4PM
3D VIEW

$1,377,500

Original price: $1,450,000
  • 4 Beds
  • 3.5 Baths
  • 3,578 sqft

1421 CHAPMAN CIRCLE, Winter Park, FL 32789

Est. Mortgage $10,075/mo*
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Home Highlights

Single-Family Home
Built in 2005
$385/sqft
2 Car Garage
HOA $268/mo

Local Information

  • Map ViewExplore the area around 1421 CHAPMAN CIRCLE.
  • 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.
Last check for updates: about 10 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

Open House

Saturday, September 19
1:00 PM to 4:00 PM
Sunday, September 20
1:00 PM to 4:00 PM

Home Details for 1421 CHAPMAN CIRCLE

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: 95Days on Market: 97

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: $1,377,500Price Per Sqft: $385

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

Around this home

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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Market trends in Winter Park

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$455K
$4.03KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$281
$6MoM
Available listings
382
13MoM

Home Value

Trulia Estimate
$1.33M
Since last month
Decreased$47K (-3.4%)
Since last year
Decreased$237K (-15.1%)
Since last sale
Increased$1M (+923.2%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +45% in the last 10 years
MonthEstimated value
2026
September 2026$1.33M
August 2026$1.38M
July 2026$1.39M
June 2026$1.5M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1429 CHAPMAN CIRCLE, Winter Park, FL
0.02
Single-Family Home
$1,280,000
02/24/26
4
4
3,116
1408 CHAPMAN CIRCLE, Winter Park, FL
0.04
Single-Family Home
$1,475,000
03/16/26
4
4
3,237
1347 CHAPMAN CIRCLE, Winter Park, FL
0.09
Single-Family Home
$1,425,000
08/14/26
4
3.5
2,922
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 DRIVE, Winter Park, FL
0.18
Single-Family Home
$1,635,000
05/11/26
4
3.5
3,470
1713 ELIZABETHS WALK, Winter Park, FL
0.11
Single-Family Home
$1,850,000
04/15/26
4
4
3,670
1813 HARLAND PARK DRIVE, 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
3856 LOWER PARK ROAD, Orlando, FL
0.45
Single-Family Home
$1,400,000
01/06/26
4
3
3,708
1817 JESSICA COURT, Winter Park, FL
0.27
Single-Family Home
$540,000
12/29/25
3
2
1,870

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1425 CHAPMAN CIRCLE, Winter Park, FL 32789
0.01
$1,492,900
4
3.5
2,942
Off Market
1429 CHAPMAN CIRCLE, Winter Park, FL 32789
0.02
$1,280,000
4
4
3,116
Recently Sold
1408 CHAPMAN CIRCLE, Winter Park, FL 32789
0.04
$1,475,000
4
4
3,237
Recently Sold
2979 UPPER PARK ROAD, Orlando, FL 32814
0.05
$516,100
2
2.5
1,897
Off Market
2976 SAINT GEORGE STREET, Orlando, FL 32814
0.07
$670,400
3
2
1,472
Off Market
1405 CHAPMAN CIRCLE #OR, Winter Park, FL 32789
0.05
$984,300
3
4
2,950
Off Market
4006 MARKHAM PLACE, Orlando, FL 32814
0.07
$783,000
3
2.5
2,291
Off Market
2959 UPPER PARK ROAD, Orlando, FL 32814
0.07
$589,000
2
2.5
1,897
Recently Sold
1636 ELIZABETHS WALK, Winter Park, FL 32789
0.06
$2,050,000
4
4.5
3,412
Recently Sold
1702 Glenridge Way, Winter Park, FL 32789
0.10
$790,000
2
2
1,832
Recently Sold
1764 ELIZABETHS WALK, Winter Park, FL 32789
0.09
$1,700,000
4
4
3,989
Off Market

Price and Tax history

DateEventPrice
Sep 8, 2026
Source: Stellar MLS #O6415941
PriceChange
$1,377,500
Price decreased by 5%
Jul 12, 2026
Source: Stellar MLS #O6415941
PriceChange
$1,450,000
Price decreased by 6%
Jun 12, 2026
Source: Stellar MLS #O6415941
Listed For Sale
$1,550,000
Mar 30, 2004
Source: N/A
Sold
$130,000
Jul 31, 2003
Source: N/A
Sold
$112,600

LGBTQ Local Legal Protections

Kelly Price, KELLY PRICE & COMPANY LLC, (407) 645-4321
Agent Phone: (407) 645-4321

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Frequently asked questions about 1421 CHAPMAN CIRCLE

  • What is the estimated monthly payment for 1421 CHAPMAN CIRCLE?
    Based on a $1,377,500 list price with 20% down at today's rates, the estimated monthly payment for 1421 CHAPMAN CIRCLE in Winter Park, FL is approximately $9,978 (about $7,458 principal & interest, $2,445 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 1421 CHAPMAN CIRCLE compare to homes in Winter Park?
    1421 CHAPMAN CIRCLE in Winter Park, FL is listed at $1,377,500, about 203% above the $455K median sale price in Winter Park.
  • What do residents say about Winter Park?
    Residents describe Winter Park, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Park, FL.
  • What are the closest schools to 1421 CHAPMAN CIRCLE?
    The closest schools to 1421 CHAPMAN CIRCLE in Winter Park, FL are Brookshire Elementary School (Pre-K, rated 4/10), Glenridge Middle School (rated 7/10), Winter Park High School (rated 7/10).
  • Does 1421 CHAPMAN CIRCLE have air conditioning?
    Yes, 1421 CHAPMAN CIRCLE in Winter Park, FL has air conditioning.
  • Does 1421 CHAPMAN CIRCLE have a pool?
    Yes, 1421 CHAPMAN CIRCLE in Winter Park, FL has a pool.
1421 CHAPMAN CIRCLE, 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.