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1446 Berkshire Avenue

Winter Park, FL 32789

5 beds
6 baths
4,612 sqft
~1/2 acre lot
$477 per sqft
1925 build
– on site

Under contract-accepting backup offers. 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 courtesy of STELLAR_MLS / SERHANT

Last checked: Checking… • Last updated Feb 16, 2025 •

MLS# O6275533 —

The Building

Year Built:

1925
New Construction:

false
Architectural Style:

Mediterranean
Construction Materials:

Block
Levels:

Two
Stories Total:

2
Roof:

Membrane
Foundation Details:

Crawlspace
Window Features:

Window Treatments
Patio And Porch Features:

Covered
Security Features:

Closed Circuit Camera(s)
Building Area Total:

7963
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Built-in Features
Flooring:

Carpet
Additional Rooms:

Bonus Room
Fireplace:

true
Fireplace Features:

Wood Burning

Room Dimensions

Living Area:

4612
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From the Princeton I4 exit head east and take a left onto Orange Ave. From Orange ave take a left onto Berkshire Ave. The house will be the first property on the left.
Latitude:

28.582549
Longitude:

-81.36985
Coordinates:

-81.36985, 28.582549

The Property

Parcel Number:

122229643213190
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Features:

City Lot
Lot Size Acres:

0.45
Lot Size Area:

19421
Lot Size SqFt:

19421
Lot Size Units:

Square Feet
Total Acres:

1/4 to less than 1/2
Zoning:

R-1A
Direction Faces:

North
View:

Garden
View:

true
Exterior Features:

Balcony
Fencing:

Fenced
Vegetation:

Bamboo
Water Source:

Public
Road Surface Type:

Paved
Road Frontage Type:

Street Paved
Flood Zone Code:

X
Additional Parcels:

false
Homestead:

true
Lease Restrictions:

false
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

19
Tax Block:

13
Tax Legal Description:

ORWIN MANOR WESTMINSTER SEC J/118 LOTS 19 & 20 BLK 13
Tax Book Number:

J-118
Tax Annual Amount:

17935.74

Beds

Bedrooms Total:

5

Baths

Total Baths:

6
Total Baths:

6
Full Baths:

6

The Listing

Virtual Tour URL Branded:

https://www.tourdrop.com/dtour/389364
Virtual Tour URL Unbranded:

https://www.tourdrop.com/dtour/389364/Zillow-3D-MLS
Virtual Tour URL Unbranded 2:

https://www.zillow.com/view-imx/ee537546-b959-4364-bdc1-f893eaecd0fa?wl=true&initialViewType=pano
Special Listing Conditions:

None
Home Warranty:

false

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Available
Sewer:

Public Sewer

Appliances

Appliances:

Dishwasher
Laundry Features:

Inside

Schools

Elementary School:

Killarney Elem
Middle Or Junior School:

College Park Middle
High School:

Edgewater High

The Community

Subdivision Name:

ORWIN MANOR WESTMINSTER SEC
Senior Community:

false
Community Features:

Park
Waterview:

false
Water Access:

false
Waterfront:

false
Spa:

true
Spa Features:

Heated
Pool Private:

true
Pool Features:

Gunite
Pets Allowed:

Yes
Association:

false
Amenities Additional Fees:

Home is located within the Orwin Manor Westminster Voluntary Community Association. The community association is not an HOA. A resident may become a member for a $35 fee. Please visit https://orwinmanor.org for details.
Ownership:

Fee Simple

Parking

Garage:

true
Attached Garage:

true
Garage Spaces:

2
Carport:

false
Covered Spaces:

2
Open Parking:

true
Parking Features:

Circular Driveway

Monthly cost estimate

Asking price

$2,200,000

Expense	Monthly cost
Mortgage	$11,780
Taxes	$1,494
Insurance	$605
Utilities	$321 See report
Total	$14,200/mo.^*
	^*This is an estimate

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Sale history

Date	Event	Source	Price	% Change
2/15/25 Feb 15, 2025	Pending	STELLAR_MLS	$2,200,000
2/10/25 Feb 10, 2025	Listed / Active	STELLAR_MLS	$2,200,000	308.2% (15.7% / YR)
6/22/05 Jun 22, 2005		STELLAR_MLS	$539,000

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This house located in Orwin Manor, Winter Park, FL 32789 is currently pending sale for $2,200,000. 1446 Berkshire Avenue is a 4,612 square foot house with 5 beds and 6 baths that has been on Estately for 31 days. 1446 Berkshire Avenue is in the Orwin Manor neighborhood of Winter Park and has a WalkScore® of 60, making it somewhat walkable. This house is in the attendance area of Edgewater High School, Cornerstone Charter Academy High School, College Park Middle School, Cornerstone Charter Academy K-8, and Killarney Elementary School.

Listing Courtesy of: STELLAR_MLS and SERHANT.

Based on information from the My Florida Regional MLS DBA Stellar MLS 2025.

All information provided is deemed reliable but is not guaranteed and should be independently verified. Stellar MLS, Estately and their affiliates provide the MLS and all content therein “AS IS” and without any warranty, express or implied. The information included in this listing is provided exclusively 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. The information on each listing is furnished by the owner and deemed reliable to the best of his/her knowledge, but should be verified by the purchaser. Stellar MLS and Estately assume no responsibility for typographical errors, misprints or misinformation. This property is offered without respect to any protected classes in accordance with the law. For any questions please call (407) 499-8911.