250 Cortland Avenue, FL
Stellar MLS

$950,000

250 Cortland Avenue

Winter Park, FL 32789

Listing updated: May 10, 2026 at 3:35 PM ET

Active
3
Beds
2
Baths
2,114
Sq Ft
0.19
Acres
1981
Built
Private pool$449/sqft360° tour
Single Family Residence

Property type

1981

Year built

8,279 sqft

Lot size

$449

Price / sq ft

No HOA

HOA dues

37

Days on market

2

Garage spaces

X

Flood zone

About this home

One or more photo(s) has been virtually staged. Introducing 250 Cortland Ave — a refined expression of Winter Park living, ideally positioned on one of the area’s most picturesque brick-lined streets, surrounded by established luxury homes and mature canopy trees. From the moment you arrive, the home exudes a quiet sophistication, with manicured, low-maintenance landscaping and a sense of privacy that carries throughout the property. An oversized two-car garage and thoughtfully designed exterior set the tone for what awaits inside. Step through the entry and into a light-filled interior where volume ceilings and an open-concept layout create an immediate sense of space and flow. The home is designed to draw your eye outward — through expansive living areas, beyond the enclosed lanai, and into the serene pool and spa, creating a seamless connection between indoor and outdoor living. Every detail has been carefully curated to balance warmth and modern refinement. Rich Brazilian rosewood flooring anchors the main living spaces, while durable quarry tile provides both style and functionality in the kitchen and transitional areas. The kitchen itself has been reimagined with updated cabinetry and modern appliances, offering a clean, sophisticated space that remains highly functional for everyday living and entertaining. The split floor plan provides both comfort and privacy, with a spacious primary suite and well-appointed secondary bedrooms. Both bathrooms have been tastefully updated with contemporary finishes, while additional enhancements throughout the home — including updated lighting, hardware, flooring, and fresh interior touches — contribute to its move-in-ready appeal. Designed for the Florida lifestyle, the home truly comes to life when the expansive sliding glass doors are opened, blending the interior with the screened outdoor living space. The pool and spa become a natural extension of the home — perfect for quiet mornings, entertaining guests, or simply enjoying the year-round sunshine in complete privacy. Located just moments from Lake Mizell, part of the highly sought-after Winter Park Chain of Lakes, the property offers not only a beautiful home, but a lifestyle defined by scenic surroundings, walkability, and timeless charm. 250 Cortland Ave is more than a home — it is a rare opportunity to own a thoughtfully designed residence in one of Winter Park’s most desirable and established neighborhoods.

Local Insight

At $949k for a 1981 home on a modest 0.19-acre lot in Cortland Park, you're paying solid Winter Park pricing but without the lakefront cachet or walkability of Park Avenue—this is a neighborhood street with character but less of the historic prestige that typically anchors values here. The private pool and 360° tour suggest the sellers are banking on that amenity to justify the per-square-foot premium, so you'll want to scrutinize whether the pool's condition and any associated maintenance costs actually move the needle on value, or if you're simply absorbing dated construction at a modern Winter Park price. For serious buyers, the real question is whether you'd rather be in this established town—with its schools, Rollins proximity, and old-money roots—or if similar sqft and a pool elsewhere in Central Florida gets you materially more land and updates for comparable money.

AI-generated insight based on listing data and neighborhood context. Verify independently.

Estimated monthly payment

Principal & interest$4,804
Property taxes$364
Home insurance (est.)$435

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history37 days on market

  1. Status: Active
    Apr 3, 2026
  2. Listed$950,000
    Apr 3, 2026
  3. Price increased$950,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
37
Cumulative DOM
375
Subdivision
Cortland Park
County
Orange
Year built
1981
Living area
2,114 sq ft
Price/sq ft
$449
Building area
2,766 sq ft (Public Records)
Lot size
8,279 sq ft
Lot category
0 to less than 1/4
Flood zone
X
Garage
2 spaces
Pool
Private pool
Annual taxes
$4,370 (2024)
Parcel #
05-22-30-1752-02-040
Zoning
R-1A
MLS #
O6395137

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Interior Details

Bedrooms
3
Full bathrooms
2
Flooring
Ceramic Tile, Vinyl, Wood
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator
Interior features
Open Floorplan, Split Bedroom, Walk-In Closet(s)
Laundry
Inside
Stories / Levels
One
Direction faces
Northwest

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
No Minimum
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Confirm with local rules

Exterior & Construction

Exterior features
Courtyard, Sidewalk, Sliding Doors
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Block, Slab
Pool
Private pool
Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Public

Schools

ElementaryCBrookshire ElemGreatSchools ↗
MiddleAGlenridge MiddleGreatSchools ↗
High SchoolAWinter Park HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Family RoomFirst17x23
KitchenFirst11x15
Living RoomFirst12x20
Primary BedroomFirst12x17
Bathroom 2First12x14
Bathroom 3First9x13

Listing Details

Listing date
2026-03-29
On market date
2026-04-03
Original list price
$950,000
Occupant type
Owner
MLS area
32789 - Winter Park
Listing AOR
Orlando Regional
Status changed
2026-04-03
Tax legal description
CORTLAND PARK J/73 LOT 4 BLK B

Flood risk

Minimal riskFEMA Zone X

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

?? From Winter Park / Orlando Area Get onto I-4 East Take Exit 87 for Fairbanks Ave (FL-426) Turn left onto Fairbanks Ave Continue straight, then turn right onto Denning Dr Turn left onto Palmer Ave Turn right onto Cortland Ave The home will be on your left

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information 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.

Based on information submitted to the MLS GRID as of May 10, 2026 at 3:35 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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