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1446 Berkshire Avenue

Winter Park, FL 32789

$1,877,500

  • 5Beds
  • 6Baths6 full
  • 4,612Sq Ft
  • $407Per Sq Ft
  • 0.45Acres
  • 1925Built
Subdivision
Orwin Manor Westminster Sec
County
Orange
MLS®
O6275533

Overview

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

Listing Snapshot

Price
$1,877,500
Days On Site
N/A
Bedrooms
5
Inside Area (SqFt)
4,612 sqft
Total Baths
6
Full Baths
6
Partial Baths
0
Lot Size
0.45 Acres
Year Built
1925
MLS® Number
O6275533
Status
Sold
Property Tax
$17,935.74 (2024)
HOA/Condo/Coop Fees
N/A
Sq Ft Source
Public Records

Property Details

General Features

18 items
Acres
0.45
Attached Garage
Yes
Direction Faces
North
Foundation
Slab
Garage
Yes
Garage Spaces
2
Levels
Two
Number Of Stories
2
Parking
Circular Driveway, Driveway, Garage Door Opener, Guest, On Street, Oversized, Attached
Pets
Yes
Property Sub Type
Single Family Residence
Security
Closed Circuit Camera(s), Security System
Sewer
Public Sewer
SqFt Total
7,963
Style
Mediterranean
Utilities
Natural Gas Available, Cable Available, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected
Water Source
Public
Zoning
R-1A

Interior Features

26 items
Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Range Hood, Refrigerator, Washer
Basement
Crawl Space
Cooling
Central Air
Fireplace
Yes
Fireplace Features
Wood Burning
Flooring
Carpet, Wood
Heating
Central
Interior
Built-in Features, Cathedral Ceiling(s), Coffered Ceiling(s), Crown Molding, Eat-in Kitchen, High Ceilings, Stone Counters, Tray Ceiling(s), Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Spa
Yes
Window Features
Window Coverings, Window Treatments

Rooms

RoomDimensionsLevelFeatures
Bedroom 211x13First
Bedroom 316x14First
Bedroom 49x11Second
Bedroom 513x13Second
Dinette20x9First
Dining Room21x15First
Family Room12x17First
Game Room13x14First
Gym10x17First
Kitchen12x17FirstBreakfast Bar, Granite Counters, Kitchen Island
Laundry9x9First
Living Room25x16First
Master Bedroom23x29SecondCeiling Fan(s), Granite Counters
Media Room10x15First
Studio15x20Second

Exterior Features

13 items
Construction Details
Block, Stucco
Exterior
Balcony, Dog Run, Garden, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters
Fencing
Fenced, Masonry, Other
Lot Features
Landscaped, Level, Paved
Patio And Porch
Covered, Deck, Patio, Porch, Rear Porch
Pool Features
Gunite, Heated, In Ground, Salt Water, Private
Private Pool
Yes
Roof
Membrane, Tile
Spa
Yes
Spa Features
Heated, In Ground
View
Garden, Pool
Waterview
Garden, Pool
Windows/Doors
Window Coverings, Window Treatments

Community Features

5 items
Community Features
Park, Playground, Sidewalks
MLS Area
32789 - Winter Park
Township
22
Financing Terms Available
Cash, Conventional
Roads
Asphalt

Location

1446 Berkshire Avenue, Winter Park, FL 32789 · 32789 - Winter Park

$11M$7M$6M$6M$6M
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Neighborhood & Commute

ZIP Code 32789

Median household income
$110,150
Income per person
$78,898
Households
12,171
Average household size
2.08
Median age
44.5

Source: Walk Score.

Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.

Schools

Elementary School
Killarney Elem
Middle School
College Park Middle
High School
Edgewater High

Price & Status History

  1. Listing updated with changes from the MLS®
  2. Status changed to Closed

Friends & Family

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Listing courtesy of SERHANT (321) 302-2618

Stellar MLS

Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.

Last checked: 2026-11-10 07:40 AM EST

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