Homes for sale - 266 CHASE AVE, Winter Park, FL 32789

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Gisselle Amparo

amparogisselle@gmail.com +1(401) 339-8460

$ 3,250,000

Est. payment | -/mo

5 Beds

6 Baths

4,088 SqFt

Save Virtual Tour

$ 3,250,000

Est. payment | -/mo

Save Virtual Tour

5 Beds

6 Baths

4,088 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 4,088 sqft

Price per Sqft $795

Subdivision Gibbs Sub

MLS Listing ID O6296421

Bedrooms 5

Full Baths 5

Half Baths 1

HOA Y/N No

Originating Board Stellar MLS

Year Built 1930

Annual Tax Amount $26,112

Lot Size 0.310 Acres

Acres 0.31

Property Sub-Type Single Family Residence

Property Description

One of Winter Park's Most Iconic and Cherished Homes – Just Steps from Park Avenue. Nestled 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. Located 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 most 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 5-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—perfect for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompasses the perfect 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 fridge. It's a space designed for gatherings, large or small. The expansive and private primary suite is located 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 perfect 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 own neighborhood, this home places you at the very 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...

Location

State FL

County Orange

Community Gibbs Sub

Zoning R-1AA

Rooms

Other Rooms Attic, Family Room, Florida Room, Formal Dining Room Separate

Interior

Interior Features Attic Fan, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s), Wet Bar

Heating Central, Heat Pump, Zoned

Cooling Central Air, Zoned

Flooring Marble, Tile, Wood

Fireplaces Type Living Room

Fireplace true

Appliance Bar Fridge, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, Washer

Laundry Inside, Laundry Room

Exterior

Exterior Feature French Doors, Irrigation System, Rain Gutters, Sidewalk

Parking Features Driveway, Garage Door Opener

Garage Spaces 2.0

Utilities Available BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights, Water Connected

Roof Type Shake

Porch Covered, Deck, Front Porch, Porch

Attached Garage false

Garage true

Private Pool No

Building

Lot Description City Limits, Landscaped, Level, Oversized Lot, Sidewalk, Street Brick

Story 2

Entry Level Two

Foundation Basement, Crawlspace, Slab

Lot Size Range 1/4 to less than 1/2

Sewer Public Sewer

Water Public

Structure Type Wood Frame

New Construction false

Schools

Elementary Schools Audubon Park K8

Middle Schools Audubon Park K-8

High Schools Winter Park High

Others

Pets Allowed Yes

Senior Community No

Ownership Fee Simple

Special Listing Condition None

Virtual Tour https://youtu.be/Avb8_9zvwOY

Listed by PREMIER SOTHEBY'S INTL. REALTY

"My job is to find and attract mastery-based agents to the office, protect the culture, and make sure everyone is happy! "

+1(401) 339-8460

amparogisselle@gmail.com

3309 W Bay To Bay Blvd, Tampa, FL, 33629, USA

266 CHASE AVE Winter Park, FL 32789