1408 CHAPMAN CIRCLE, Winter Park, FL, 32789 | $1,495,000

Under contract-accepting backup offers. Opportunity awaits in the most desirable neighborhood! Buyers have cold feet. Nestled in the Elizabeth’s Walk subdivision in the highly coveted Windsong community of Winter Park, this renovated four-bedroom, four-bathroom pool home offers exceptional privacy and refined updates. Quiet interior street and mature landscaping the home feels secluded. Recent improvements include a new roof (2023), two new AC systems 4-ton Carrier Infinity downstairs and a 2. 5-ton Trane upstairs (2025) and fresh exterior and interior paint in the kitchen and bathroom. The updated kitchen features a butcher block island and new cabinetry hardware. Beautiful wine storage room to showcase your finest wines. The newly redesigned powder bath includes hidden storage and a full shower. The living areas are open and welcoming, highlighted by recessed ceilings in the informal living room with distinctive wood beams in the family room giving the home character. The primary suite features dual closets plus a linen closet, fresh paint, new mirrors, tv, lighting, and UV film on doors to keep the suite very cool and save on electrical. The nursery showcases new paint, custom wallpaper, drapes, and remote shades, basically every detail thoughtfully considered. Upstairs, a generous loft serves perfectly as a playroom, exercise room or home office, along with two ensuite bedrooms and a large AC storage room. Outdoor living is private and inviting, with a newly refinished PebbleTec pool finish, new pool coping, gas fireplace, new screen enclosure and professionally updated landscaping (2024). The backyard feels like a personal retreat -quiet, enclosed, and perfect for both relaxing and entertaining. Other features include new insulation (2024), custom aluminum privacy gates with locks, Wi-Fi-enabled Schlage front door lock, touchscreen garage access, Ring cameras, and new thermostats. Living in Windsong offers a sense of community, exclusivity with access to the Winter Park Chain of Lakes, pools, a kids water park area, and playgrounds. Pontoon boat available for residents use. Just minutes from Park Avenue’s shops and restaurants, Baldwin Park, and top-rated schools including Brookshire Elementary, Glenridge Middle, Winter Park High. Great location for private schools- Lake Highland Prep and Trinity Prep.

Features

  • Amenities: Playground, Pool
  • Rooms: 10
  • Bedrooms: 4
  • Baths: 4 full
  • Laundry: Inside, Laundry Room
  • Style: Mediterranean
  • Year Built: 2003
  • Garage: 2-car Garage Door Opener, Garage Faces Side
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 3,237
  • Acreage: 0.18
  • Est. Taxes: $14,649
  • HOA Fee: $785 Quarterly
  • Lot Desc: City Lot, Sidewalk
  • Elem. School: Brookshire Elem
  • Middle School: Glenridge Middle
  • High School: Winter Park High
  • Pool: In Ground
  • Pet Policy: Yes
  • Appliances: Built-In Oven, Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator
  • MLS#: O6357486
  • Days on Market: 81 days
  • Website: https://www.raveis.com
    /eprop/O6357486/1408chapmancircle_winterpark_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 2/26/2026 4:47:07 PM)
Listing courtesy of Compass Florida LLC   Phone: 407-203-9441

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

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1408 CHAPMAN CIRCLE, Winter Park, FL, 32789

$1,495,000

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $1,196,000 $1,196,000 $1,196,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.250% 5.750% 5.625%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.069% 5.858% 5.806%
Monthly Tax Payment $1,221 $1,221 $1,221
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $6,604 $6,980 $9,852
Total Monthly Payment $7,950 $8,326 $11,198

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.  The Total Monthly Payment does not include the estimated HOA/Common Charge payment.