457 E NEW ENGLAND AVENUE, Winter Park, FL, 32789 | $3,100,000

Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and Sub-Zero appliances, including a 72-bottle Sub-Zero wine tower and refrigerated drawers, making it as functional as it is beautiful. Open to the family room, complete with rich woodwork and a third gas fireplace, this space is ideal for gathering and entertaining. The primary suite is conveniently located on the first floor and features an updated ensuite bath. Upstairs, three additional bedrooms and two renovated baths provide comfortable accommodations for family and guests. A charming “sleeping room, ” now used as a light-filled office, overlooks picturesque New England Avenue. Adding to the property’s appeal is a detached two-story guest house offering a full bedroom, full bath, sitting area, and kitchen—perfect for extended stays or as a private retreat. Outdoor living is equally inviting, with a back porch for grilling, a separate patio for lounging and mature landscaping that enhances the home’s curb appeal. Architectural details available for adding an oversize two-car garage, if desired. Perfectly positioned on the same block as The Alfond Inn and just two short blocks from the renowned Park Avenue district, this home offers not just refined living, but a downtown walkable lifestyle that is truly unmatched. Park Avenue is the cultural heart of Winter Park—a tree-lined promenade alive with award-winning restaurants, boutique shopping, art galleries and historic landmarks. Residents enjoy a vibrant calendar of events, from the Winter Park Farmers’ Market and seasonal art festivals to beloved holiday parades and outdoor movies under the stars. Here, every day is an invitation to experience the best of Central Florida living—whether it’s sipping coffee at a charming café, strolling to or after dinner surrounded by beautiful ambience, or embracing the timeless traditions that make Winter Park so treasured.

Features

  • Rooms: 10
  • Bedrooms: 5
  • Baths: 4 full / 1 half
  • Lot Size: 120 x 170 x 88 x 182
  • Laundry: Inside, Laundry Room
  • Style: Traditional
  • Year Built: 1920
  • Garage: Circular Driveway, Driveway, Parking Pad
  • Heating: Central, Zoned
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 3,847
  • Acreage: 0.41
  • Lot Size: 120 x 170 x 88 x 182
  • Est. Taxes: $3,876
  • Lot Desc: Corner Lot, City Lot, Landscaped, Level, Oversized Lot, Sidewalk
  • Elem. School: Audubon Park K8
  • Middle School: Audubon Park K-8
  • High School: Winter Park High
  • Pet Policy: Yes
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Gas Water Heater, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
  • MLS#: O6345511
  • Days on Market: 85 days
  • Website: https://www.raveis.com
    /eprop/O6345511/457enewenglandavenue_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 1/10/2026 6:47:07 PM)
Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY   Phone: 407-644-3295

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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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457 E NEW ENGLAND AVENUE, Winter Park, FL, 32789

$3,100,000

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 $2,480,000 $2,480,000 $2,480,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.000% 5.750%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.241% 6.110% 5.972%
Monthly Tax Payment $323 $323 $323
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $14,081 $14,869 $20,594
Total Monthly Payment $14,529 $15,317 $21,042

* 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.