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Front Exterior
Front Exterior
Front Door
Side Entry to Main House
Drive/Side Exterior
Detached Garage/Guest House
Foyer/Living Room
Foyer/Living Room with Fireplace
Living Room with Fireplace
Florida/Sun Room
Dining Room
Dining Room
Kitchen
Kitchen
Wet Bar in Family Room/Kitchen
Half Bath
Laundry Room
Side Entryway
Primary Suite
Primary Custom Walk-in Closet
Primary Bath
Primary Bath
Staircase to Second Floor
Bedroom 2/Secondary Primary Suite
Bedroom 2 Ensuite Bath
Bedroom 2 French Doors to Covered Balcony
Bedroom 2 Covered Balcony
Bedroom 3
Bedroom 3 Ensuite Bath
Bedroom 4
Bedroom 4 Ensuite Bath
Guest House
Guest House
Guest House Kitchenette
Guest House Full Bath
Aerial
Aerial - 2 Blocks to Park Avenue
$3,250,000
5
beds
6
baths
4,088
sqft
2
cars
For Details, Contact
Sea Glass Florida Properties

Description

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.


Listed by Mick Night, .

Property Highlights

  • Patio/Deck: Covered, Deck, Front Porch, Porch
  • Heating / Cooling: Central
  • Property Type: Single Family, Single Family Residence
  • MLS #: O6296421

General Information

Area 32789 - Winter Park
Elementary School Audubon Park K8
High School Winter Park High
Middle School Audubon Park K-8
Property Subtype Residential
Property Type Single Family Residence
Subdivision Gibbs Sub
Taxes $26,112
Utilities Cable Available, Natural Gas Available, Cable Connected, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected

Room Information

Fireplace Features Living Room
Flooring Marble, Tile, Wood
Full Baths 5
Garage Yes
Garage Spaces 2
Half Baths 1
Laundry Inside, Laundry Room
Total Baths 6
Total Beds 5

Property Features

Appliances Bar Fridge, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer
Basement Crawl Space, Partial
Construction Materials Frame
Cooling Central Air, Zoned
Direction Faces West
Exterior Features Rain Gutters
Heating Central, Heat Pump, Zoned
Interior Features Crown Molding, Eat-in Kitchen, Stone Counters, Walk-In Closet(s), Wet Bar
Interior Square Footage 4,088
Lot Size Acres 0.31
Lot Size Square Feet 13,294
Other Structures Guest House
Patio Features Covered, Deck, Front Porch, Porch
Roof Shake
Rooms 11
Sewer Public Sewer
Stories Two
Water Source Public
Windows Shutters
$3,250,000
5
beds
6
baths
4,088
sqft
2
cars
For Details, Contact
Sea Glass Florida Properties
Location
266 Chase Avenue, Winter Park, FL 32789 Driving Directions
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Listed by Mick Night, Premier Sotheby's Intl. Realty.
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