266 CHASE AVENUE, Winter Park, FL, 32789 | $3,250,000

One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park, ” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5. 5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties.

Features

  • Rooms: 11
  • Bedrooms: 5
  • Baths: 5 full / 1 half
  • Laundry: Inside, Laundry Room
  • Year Built: 1930
  • Garage: 2-car Driveway, Garage Door Opener
  • Heating: Central, Heat Pump, Zoned
  • Cooling: Central Air, Zoned
  • Approx Sq. Feet: 4,088
  • Acreage: 0.31
  • Est. Taxes: $26,112
  • Lot Desc: 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: Bar Fridge, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
  • MLS#: O6296421
  • Days on Market: 4 days
  • Website: https://www.raveis.com
    /eprop/O6296421/266chaseavenue_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 4/11/2025 5:44:54 AM)

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NMLS Mortgage Loan Originator ID 1017266

508.335.8179

Michael.Cartier@raveis.com

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266 CHASE AVENUE, Winter Park, FL, 32789

$3,250,000

Laurie Malcom

Sales Associate

William Raveis Real Estate

Phone: 617.529.5466

Laurie.Malcom@raveis.com

Michael Cartier

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 508.335.8179

Michael.Cartier@raveis.com

NMLS Mortgage Loan Originator ID 1017266

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $2,600,000 $2,600,000 $2,600,000
Term 360 months 360 months 180 months
Initial Interest Rate** 6.250% 6.625% 6.250%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.911% 6.764% 6.435%
Monthly Tax Payment $2,176 $2,176 $2,176
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $16,009 $16,648 $22,293
Total Monthly Payment $18,310 $18,949 $24,594

* 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.