Moving to Longwood, FL

Where Longwood is and how it connects

Longwood sits between Altamonte Springs and Lake Mary, north of Orlando. State Road 434 runs through the city and meets I-4 at its western side, and US 17-92 crosses on the east. Longwood has its own SunRail commuter station, which gives a rail option toward Winter Park and downtown Orlando.

The city has a small historic district near the old downtown, and Big Tree Park, once home to the giant cypress known as The Senator, is in Longwood. Most of the city, though, is residential streets and subdivisions, with shopping along 434 and 17-92. Orlando Sanford International Airport is the closer of the two major airports.

Daily life is car-based. Errands mean short drives, and the corridors to I-4 get crowded at rush hour.

The housing: detached houses from the 1970s and 1980s

Census data shows 67.5% of Longwood homes are single-family detached, more than in Altamonte Springs, Casselberry or Lake Mary. Only 15.5% are in buildings with 10 or more units, and mobile homes are 1.4%. The median year built is 1983.

Zillow's prices by size:

• 2 bedrooms: about $227,083
• 3 bedrooms: about $383,091
• 4 bedrooms: about $569,166
• 5 or more bedrooms: about $914,269

The big jumps between sizes are typical of an area where larger homes often come with larger lots, lake frontage or custom construction. A typical single-family house is $474,963, up 1.1% over the past year. Condos are a small, softer piece of the market at about $184,963, down 7.2%.

The upper third of the market starts around $717,025, while the lower third tops out near $312,492, which is mostly condos, townhomes and smaller older houses.

Who lives in Longwood

Longwood is a small, year-round city of 16,337 people. The median age is 40.7, about one in five residents (19.9%) is 65 or older, and only 0.3% of homes are seasonal. Owners tend to stay a long time, which keeps turnover low.

For a buyer, low turnover means fewer listings in any given month, especially for well-kept 3 and 4-bedroom homes. It also means many houses come to market with long-time owners who maintained them well but never updated kitchens, baths or systems. Budget for renovation even on clean-looking homes.

Pros and cons for a buyer

Pros:

• Mostly detached homes, often on bigger lots than in neighboring suburbs
• SunRail station and quick I-4 access
• Strong five-year price performance, with values holding this year
• Many established neighborhoods with mature trees and little through traffic

Cons:

• Higher prices than Altamonte Springs, Casselberry or Sanford
• Older houses with the inspection and insurance issues that come with them
• Very little new construction
• Traffic on 434 and 17-92 at peak times

The mistake I see most from people relocating here is judging Longwood by the citywide number. At $455,153, it looks close to Lake Mary, and on paper the two seem interchangeable. They are different purchases. In Lake Mary that money tends to buy a 1990s house in an HOA community with a smaller yard. In Longwood it more often buys an older house with more land, fewer rules and more work ahead. Decide which of those you want before you start touring, or you will spend weekends seeing houses that were never going to fit.

Inspections and costs specific to older Longwood homes

• Roof and insurance. Roof age is the first thing Florida insurers ask about. On a 1980s house, expect a 4-point inspection and get a wind mitigation report as well.
• Plumbing and sewer. Houses from the late 1970s to mid-1990s may have polybutylene water lines, which many insurers won't cover. Also confirm whether the house is on city sewer or a septic system. A septic inspection is a separate, worthwhile cost.
• Trees. Mature oaks are part of the appeal. They also mean root and roof issues, and storm risk. Look at limbs over the roof.
• Flood. No storm surge this far inland, but lakes, creeks and low areas can flood in heavy rain. Look up the FEMA zone and ask the seller about past water.
• Sinkhole coverage. Florida policies include catastrophic ground cover collapse, and broader sinkhole coverage is often an add-on. Ask what's in your quote.

Get all of this done inside the inspection period. The insurance quote is often what decides whether the price works.

Taxes and how Longwood compares nearby

Florida has no state income tax. A buyer who makes Longwood their permanent home can file for homestead, which in 2026 takes up to $51,411 off assessed value and limits later increases to 3% a year. Remember that the seller's assessment doesn't transfer; your bill starts from the price you pay.

Zillow's typical values nearby: Altamonte Springs $289,149, Sanford $339,925, Casselberry $344,012, Winter Springs $423,358, Lake Mary $466,012, Oviedo $504,529 and Geneva $582,421. Longwood prices near Lake Mary's but with older homes and often more land. If you want to compare a Longwood lot against a Lake Mary or Winter Springs house at the same price, a shortlist will put them side by side.