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104 Cortland Avenue

Winter Park, FL 32789

4 beds
3 baths
3,182 sqft
12,110 sqft lot
$746 per sqft
1926 build
– on site

Commanding an elevated position with tranquil views of Lake Mizell, this quintessential 1926 estate artfully fuses period elegance with refined, modern enhancements. Moments from the boutiques and restaurants of Park Avenue, the residence welcomes with a paver circular drive and a private, gated side entry leading to a detached two-car garage. A brick-clad front porch and mature landscaping frame the formal entry, setting a tone of architectural distinction. Inside, a gallery-style foyer showcases designer wallpaper and salvaged pew rail detailing from a New York City church. The formal living room offers a stately gas fireplace, bespoke built-ins, and a large fixed window framing the lake, ideally suited for a quiet reading nook. The adjacent sunroom, encased in fixed glass, captures the surrounding canopy and lake vistas in all seasons. A generous dining room with custom dry bar, underlit floating shelving, and beverage refrigeration provides an ideal setting for elegant entertaining. The gourmet kitchen is thoughtfully appointed with paneled appliances including refrigerator and freezer columns, refrigerator drawers and a microwave drawer. Additional features include natural gas cooking, double ovens, and a sun-drenched breakfast room opening to the rear terrace and lap pool. A Dutch door entry offers functional access for daily living, while the basement below presents an opportunity for climate-controlled wine storage. The upstairs primary suite exudes comfort and sophistication with its gas fireplace, walk-in closet illuminated by a lake-facing window, a private covered balcony, and a spa-inspired bath with dual vanities, soaking tub, steam shower and private water closet. Two additional guest rooms with a Jack and Jill bath complete the upper level. Extensive renovations include a newer roof, Andersen windows and doors, two HVAC systems, full re-piping and rewiring, fresh paint, lighting, a newly installed pool heater and Hardie board siding—all executed within the last five years. The walk-up attic and pristine basement offer rare additional storage. Refinished hardwood floors throughout provide a consistent, elegant backdrop. This residence is a compelling blend of character, craftsmanship and contemporary living.

Listing courtesy of STELLAR_MLS / PREMIER SOTHEBY'S INTL. REALTY

Last checked: Checking… • Last updated May 21, 2025 •

MLS# O6307403 —

The Building

Year Built:

1926
New Construction:

false
Architectural Style:

Colonial
Construction Materials:

Block
Levels:

Two
Roof:

Built-Up
Basement:

Partial
Foundation Details:

Crawlspace
Window Features:

Shades
Patio And Porch Features:

Covered
Security Features:

Security System Owned
Building Area Total:

4595
Building Area Units:

Square Feet
Building Area Source:

Public Records

Interior

Interior Features:

Built-in Features
Furnished:

Negotiable
Flooring:

Marble
Additional Rooms:

Attic
Fireplace:

true
Fireplace Features:

Gas

Room Dimensions

Living Area:

3182
Living Area Units:

Square Feet
Living Area Source:

Public Records

Location

Directions:

From Park Avenue, head south and make a left onto Fairbanks Avenue. Continue as Fairbanks transitions into Osceola Avenue and then into Brewer Avenue. Follow Brewer as it curves slightly right and becomes Aloma Avenue. Turn right onto Cortland Avenue, and the home will be on the left.
Latitude:

28.597741
Longitude:

-81.337499
Coordinates:

-81.337499, 28.597741

The Property

Parcel Number:

052230175202181
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Features:

City Lot
Lot Size Acres:

0.28
Lot Size Area:

12110
Lot Size SqFt:

12110
Lot Size Dimensions:

76 x 166 x 70 x 166
Lot Size Units:

Square Feet
Total Acres:

1/4 to less than 1/2
Zoning:

R-1A
Direction Faces:

Southwest
View:

Water
View:

true
Exterior Features:

Awning(s)
Fencing:

Fenced
Vegetation:

Mature Landscaping
Water Source:

Public
Road Responsibility:

Public Maintained Road
Road Surface Type:

Brick
Road Frontage Type:

Street Brick
Flood Zone Code:

X
Flood Zone Panel:

12095C0255F
Additional Parcels:

false
Homestead:

false
Lease Restrictions:

true
Land Lease:

false

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Lot:

18
Tax Block:

B
Tax Legal Description:

CORTLAND PARK J/73 THE S 1/2 OF LOT 18 & LOT 19 BLK B
Tax Book Number:

J-73
Tax Annual Amount:

$23,465.21

Beds

Bedrooms Total:

4

Baths

Total Baths:

3
Total Baths:

3
Full Baths:

3

The Listing

Special Listing Conditions:

None

Heating & Cooling

Heating:

Central
Heating:

true
Cooling:

Central Air
Cooling:

true

Utilities

Utilities:

Cable Connected
Sewer:

Public Sewer

Appliances

Appliances:

Bar Fridge
Laundry Features:

Inside

Schools

Elementary School:

Brookshire Elem
Middle Or Junior School:

Glenridge Middle
High School:

Winter Park High

The Community

Subdivision Name:

CORTLAND PARK
Senior Community:

false
Waterview:

Lake
Waterview:

true
Water Access:

false
Water Body Name:

LAKE MIZELL
Waterfront:

false
Spa:

false
Pool Private:

true
Pool Features:

Gunite
Pets Allowed:

Yes
Pet Restrictions:

Buyer to independently verify all pet restrictions directly with the City of Winter Park.
Association:

false
Ownership:

Fee Simple

Parking

Garage:

true
Attached Garage:

false
Garage Spaces:

2
Garage Dimensions:

22x22
Carport:

false
Covered Spaces:

2
Open Parking:

true
Parking Features:

Circular Driveway

Monthly cost estimate

Asking price

$2,375,000

Expense	Monthly cost
Mortgage	$12,717
Taxes	$1,955
Insurance	$653
Utilities	$253 See report
Total	$15,578/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

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Provided by WalkScore® Inc.

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Sale history

Date	Event	Source	Price	% Change
5/15/25 May 15, 2025	Listed / Active	STELLAR_MLS	$2,375,000	109.6% (23.7% / YR)
9/28/20 Sep 28, 2020		STELLAR_MLS	$1,133,000	41.6% (18.2% / YR)
6/15/18 Jun 15, 2018		STELLAR_MLS	$800,000

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This house located in Windsong, Winter Park, FL 32789 is currently for sale for $2,375,000. 104 Cortland Avenue is a 3,182 square foot house with 4 beds and 3 baths that has been on Estately for 7 days. 104 Cortland Avenue is in the Windsong neighborhood of Winter Park and has a WalkScore® of 24, making it car-dependent. This house is in the attendance area of Brookshire Elementary School, Glenridge Middle School, Winter Park High School, Cornerstone Charter Academy High School, and Cornerstone Charter Academy K-8.

Listing Courtesy of: STELLAR_MLS and PREMIER SOTHEBY'S INTL. REALTY.

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.