Skip To Content

266 Chase Avenue

Winter Park, FL 32789
  • $3,250,000
  • STATUS: Active
  • ON SITE: 17 Days
  • ID#: O6296421
UPDATED: 88 min ago
$3,250,000
  • 5
    BEDS
  • 0.31
    ACRES
  • 5
    BATHS
  • 1
    1/2 BATHS
  • 4,088
    SQFT
  • $795
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1930
County:
Area:

School Information

Elementary School:
Middle School:
High School:

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 caf 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.

Monthly Payment Calculator




© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2025-04-21T08:44:42.01.
www.swflregroup.com/homes/162210189
Print Image

266 Chase Avenue Winter Park, FL 32789

  • Price: $3,250,000
  • Status: Active
  • On Site: 17 Days
  • Updated: 88 min ago
  • ID#: O6296421
5
Beds
5
Baths
1
½ Baths
0.31
Acres
4,088
SQFT
$795
$/SQFT
1930
Built
Neighborhood:
Gibbs Sub
County:
Orange
Area:
Winter Park
Elementary School:
Audubon Park K8
Middle School:
Audubon Park K-8
High School:
Winter Park High
Property 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 caf 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.
Exterior Features

Attached Garage Yn No Carport Yn No Construction Materials Wood Frame Covered Spaces 2 Direction Faces West Exterior Features French DoorsIrrigation SystemRain GuttersSidewalk Foundation Details BasementCrawlspaceSlab Lot Features City LotLandscapedLevelOversized LotSidewalk Open Parking YN Yes Other Structures Guest House Parking Features DrivewayGarage Door Opener Patio And Porch Features CoveredDeckFront PorchPorch Pool Private Yn No Road Frontage Type Street Brick Road Surface Type Brick Roof Shake Water Access Yn No Water Extras Yn No Water View Yn No Waterfront Feet Total 0 Waterfront Yn No

Interior Features

Additional Rooms AtticFamily RoomFlorida RoomFormal Dining Room Separate Appliances Bar FridgeDishwasherDisposalDryerRangeRange HoodRefrigeratorWasher Basement Partial Building Area Total 4662 Cooling Central AirZoned Cooling YN Yes Fireplace Features Living Room Fireplace Yn Yes Flooring MarbleTileHardwood Heating CentralHeat PumpZoned Heating YN Yes Interior Features Attic FanCeiling Fan(s)Crown MoldingEating Space In KitchenKitchen/Family Room ComboPrimary Bedroom Main FloorSolid Wood CabinetsStone CountersWalk-In Closet(s)Wet Bar Laundry Features InsideLaundry Room Levels Two Rooms Living Room Dining Room Florida Room Kitchen (Breakfast BarKitchen IslandStone Counters) Family Room Primary Bathroom (Dual SinksShower No TubWater Closet/Priv Toilet) Primary Bedroom (En Suite BathroomWalk-In Closet(s)) Primary Bedroom 2 (En Suite BathroomBuilt-in Closet) Bedroom 3 (Built-in Closet) Bathroom 4 (En Suite BathroomBuilt-in Closet) Bedroom 5 (En Suite BathroomWalk-In Closet(s)) Sewer Public Sewer Stories Total 2 Water Source Public Window Features Shutters

Property Features

Additional Lease Restrictions Please verify with City of Winter Park regarding any leasing restrictions. Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Minimum Lease 6 Months New Construction Yn No Ownership Fee Simple Pet Restrictions Please verify with City of Winter Park regarding any pet restrictions. Pets Allowed Yes Property Sub Type Single Family Residence Security Features Security SystemSecurity System OwnedSmoke Detector(s) Senior Community Yn No Special Listing Conditions None Tax Annual Amount 26112.37 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailableCable ConnectedElectricity ConnectedNatural Gas ConnectedPublicSewer ConnectedStreet LightsWater Connected Zoning R-1AA


Listing information © 2025 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of PREMIER SOTHEBY'S INTL. REALTY: 407-644-3295.



© 2025 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2025-04-21T08:44:42.01.
 
https://bt-photos.global.ssl.fastly.net/mfr/orig_boomver_3_O6296421-2.jpg https://bt-photos.global.ssl.fastly.net/mfr/orig_boomver_3_O6296421-2.jpg https://bt-photos.global.ssl.fastly.net/mfr/orig_boomver_3_O6296421-2.jpg
Logo
Southwest Florida R.E. Group LLC | Realty Once Group MVP
1495 Pine Ridge Rd #1
Naples FL, 34109