Longwood is a short run up I-4 or SunRail from Winter Park, and it’s an area I know well. I’ve lived in Central Florida since 1978, and I’ve watched Longwood’s neighborhoods from the historic downtown out to Markham Woods Road for a long time. On the business side: Over 37 years in the Real Estate Industry · licensed in Florida since 1989.

City of Longwood vs. a Longwood address

This is the first thing to understand. The City of Longwood is a fairly small city built around its historic downtown. Many of the neighborhoods people mean when they say “Longwood,” including The Springs, Sweetwater Oaks and the Markham Woods Road corridor, are in unincorporated Seminole County with a Longwood mailing address. That affects which government handles your permits and services, so check any parcel with the Seminole County Property Appraiser.

Housing stock and architecture

• Historic downtown. Longwood was settled in the 1870s, got its post office in 1876, and was incorporated as a city in 1923, during the land boom. The Longwood Historic District preserves buildings from roughly 1880 to 1926.
• 1970s and 1980s neighborhoods. The city’s own history notes that Longwood grew into a mostly residential community during the 1970s and 1980s. That era is the bulk of the resale stock today: single-family homes and some condominiums on established, tree-covered lots.
• Estate lots. Along Markham Woods Road, Seminole County land-use rules generally hold density to about one home per net buildable acre, which is why you’ll find acreage and custom homes there.

Homes from the 1970s and 1980s are now old enough that the roof, the electrical panel, the plumbing and the water heater matter to the buyer’s insurance company. I look at those before I look at the kitchen.

Neighborhoods and streets

• The Springs. A gated community built around Sanlando Springs, a natural spring that was a public park until 1970. Construction started in 1971. The spring is private to residents and their guests. Housing includes single-family homes and condominiums.
• Sweetwater Oaks. A large established neighborhood along Wekiva Springs Road, mostly built in the 1970s and 1980s. It isn’t gated, and it has a mandatory homeowners association.
• Markham Woods Road. The estate corridor described above, where lots are often an acre or more.
• Historic district and Columbus Harbor. Older homes near Church Avenue and the downtown core, and Columbus Harbor, on the lake early settlers knew as Fairy Lake.

Lifestyle and amenities

• Big Tree Park. On General Hutchison Parkway. It was home to The Senator, a bald cypress estimated at about 3,500 years old that was lost to fire in 2012. Lady Liberty, another ancient cypress, still stands, and a clone of The Senator was planted in 2013.
• Historic Longwood. Christ Episcopal Church on Church Avenue was founded by some of Longwood’s earliest settlers. The Bradlee-McIntyre House, an 1885 winter cottage, was moved to West Warren Avenue in 1973 and is now part of the historic district.
• Seminole Wekiva Trail. A Seminole County trail with a trailhead on Markham Woods Road.
• Wekiwa Springs State Park. Just west of the Longwood area, in Apopka, with a spring-fed swimming area.

Commute and getting around

• SunRail. The Longwood station is on East Church Avenue, between Altamonte Springs and Lake Mary. Trains run south through Maitland and Winter Park to downtown Orlando.
• I-4 and SR 434. SR 434 is the main east-west road through Longwood and connects to I-4. From the Markham Woods side, check your route to I-4 at the hour you’d actually drive it.
• CR 427. Ronald Reagan Boulevard runs north-south near the historic downtown, close to where the old Dixie Highway ran in the 1920s.

Working with Will in Longwood

I know these neighborhoods well: which streets back up to what, how the HOAs work, and what buyers ask about. I’ve also spent a long stretch in valuation work, so I price homes on adjusted closed sales, not online estimates. My credentials, stated plainly: 2026 RealTrends Verified, ranked #10 in Winter Park by transactions; RE/MAX Hall of Fame; and Golf Community Certified through RE/MAX Golf Lifestyles.

If you’re selling a house you’ve owned for a long time, I’ll walk you through what the market will pay for it as it stands and what’s worth fixing first.

Longwood FAQ

Is The Springs inside the City of Longwood?

No. The Springs has a Longwood mailing address but is in unincorporated Seminole County. The same is true of Sweetwater Oaks and much of the Markham Woods corridor.

Which schools serve Longwood?

Most Longwood-area homes are in Seminole County and served by Seminole County Public Schools, and Lyman High School is in Longwood. Attendance zones change and don’t follow city or ZIP lines, so verify any address with SCPS.

Do Longwood neighborhoods have HOAs?

Some do and some don’t. The Springs and Sweetwater Oaks both have associations. Read the documents and the budget before your inspection period ends.

Is there acreage in Longwood?

Yes, mainly along the Markham Woods Road corridor, where county rules keep density low.

How is a Longwood home valued if it has acreage?

Acreage and non-acreage homes are priced from different comparable sales. Lot size, usable land, zoning and location along corridors like Markham Woods Road all matter. Request a free home value report for your address.

Do you help buyers searching between Longwood and closer-in areas?

Yes. I work with buyers from about $500K to $50M across Longwood, Lake Mary, Maitland, Winter Park and Baldwin Park and can compare tradeoffs street by street.

Call or text 407-620-7785, or get a free home value report.

Compare nearby areas

Longwood buyers often weigh it against Lake Mary to the north. Closer to Orlando, Maitland, Winter Park and Baldwin Park trade acreage for older streets, lakes and a shorter drive downtown.

Thinking about buying or selling in Longwood?

Send me the address and I’ll show you what’s actually selling nearby.

Will LaValle, REALTOR® · RE/MAX 200 Realty · 1155 Louisiana Ave., Suite 110, Winter Park, FL 32789 · 407-620-7785 · will@irlhomes.com · FL license #3389936