$950,000
250 Cortland Avenue
Winter Park, FL 32789
Listing updated: May 10, 2026 at 3:35 PM ET
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
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
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
- Status: ActiveApr 3, 2026
- Listed$950,000Apr 3, 2026
- 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
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
| Room | Level | Dimensions |
|---|---|---|
| Family Room | First | 17x23 |
| Kitchen | First | 11x15 |
| Living Room | First | 12x20 |
| Primary Bedroom | First | 12x17 |
| Bathroom 2 | First | 12x14 |
| Bathroom 3 | First | 9x13 |
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-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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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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