Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What DeLand is known for
DeLand is the home of Stetson University and a brick-lined historic downtown on Woodland Boulevard full of murals, sculpture and locally owned restaurants. It sits near several freshwater springs on the St. Johns River side of Volusia County. It is also a well-known skydiving town, with Skydive DeLand operating at the city airport since 1982.
New York businessman Henry A. DeLand founded the town in 1876 and promised settlers he would buy back their land if they were unhappy. He and Dr. John H. Griffith opened DeLand Academy on November 5, 1883, and it became Stetson University in 1889 with support from hat maker John B. Stetson. When the 1894-95 freezes wiped out the orange groves, DeLand kept his promise and lost his fortune doing it. DeLand mixes college students, longtime families, retirees and commuters who ride SunRail into Orlando. Daily life centers on a walkable downtown with coffee, craft beer, theater and weekend festivals under big oak trees.
Where to live
The commercial core along Woodland Boulevard from Rich Avenue to Euclid Avenue, with 65+ contributing buildings from 1885 to 1945. Shops, restaurants and the Athens Theatre sit a short walk from older homes on the surrounding streets. (source)
Residential blocks along the West Michigan Avenue corridor north and west of downtown. Homes date from the 1880s to the 1940s in Victorian, Queen Anne, Colonial Revival and Craftsman styles, plus early Florida Cracker wood-frame houses. The 1886 Henry A. DeLand House Museum and the Stetson Mansion are here. (source)
A National Register historic district listed in 1992, bounded by University, Florida, New York and Orange Avenues. It holds 375 historic buildings, mostly older single-family homes on tree-lined streets close to downtown. (source)
A master-planned community made up of five subdivisions: Cresswind at Victoria Gardens, Victoria Commons, Victoria Hills, Victoria Oaks and Victoria Trails. Victoria Hills has a Ron Garl-designed golf course. Cresswind is an active-lifestyle section with a clubhouse, fitness center, resort-style pool, tennis and pickleball. (source)
A historically African-American neighborhood on the southwest side of DeLand, named for a spring near South Clara Avenue and Vermont Street. Many of its homes were built between 1900 and the early 1950s. The city and county created a Community Redevelopment Agency for the area in 2004. (source)
Local favorites
Locally sourced seafood and vegetables plus game dishes like elk bolognese, braised lamb shank and New Zealand venison chops. A 2026 DiRoNA Award recipient with a Wine Spectator Award of Excellence. (source)
Downtown's go-to for gyros, moussaka, pastitsio and dolmades. (source)
Wine, sangria and more than 50 tapas-style dishes, with chipotle salmon and a weekend brunch with huevos rancheros. (source)
Creative artisanal pizzas and contemporary Italian plates with strong gluten-free and vegan options, plus a covered patio. (source)
Scratch-made breakfast, then sandwiches, wraps and salads for lunch and dinner, tucked into Artisan Alley. (source)
Cubano sandwiches, churrasco, arroz con pollo and Cuban coladas, with live music on some nights. (source)
A fresh seafood market and restaurant in one, with daily specials and homemade cakes. Owned by Margo and Nick Costa. (source)
You make your own pancakes at the table, a nod to the historic sugar mill that once ran on the spring's power. (source)
After hours
Downtown craft brewery started by two home brewers, known for Gypsy Hiker IPA and Vacation Wheat. Hosts yoga and trivia nights and opens onto Artisan Alley. (source)
Wine bar that calls itself DeLand's Living Room since 2003, with more than 40 wines by the glass, craft beer and seasonal small plates. (source)
Specialty coffee roaster serving downtown since 2014, with espresso, pour-overs, nitro cold brew, breakfast and an outdoor deck. (source)
Craft beer and sports bar in the downtown historic district with 27 TVs, a full kitchen and outdoor seating. (source)
Downtown cooking school with hands-on classes from pasta making to global cuisines, plus private events and kids' camps. (source)
Shopping
Three-story, 7,000-square-foot vintage mall in a 1920s building with 35+ vendors selling mid-century pieces, records, vintage clothing and upcycled furniture. (source)
Cooperative shop with 70+ local crafters selling handmade jewelry, home decor, seasonal gifts and local art. (source)
Downtown women's boutique with denim, dresses, shoes, Kendra Scott jewelry and a kids' collection. (source)
Friday night farmers and makers market from 6 to 9 p.m., rain or shine, with produce, local art and handmade goods in 100-year-old brick buildings. (source)
Outdoors
City park with a one-mile walking trail, duck pond, picnic pavilions, playground, basketball courts and a skate and bike park. Home of the DeLand Outdoor Art Festival. (source)
A 72-degree spring with swimming, paddling, eco and heritage boat tours, trails and an old-growth bald cypress. People have visited the spring for more than 6,000 years. (source)
A 1,650-acre island on the St. Johns River reached only by boat or the free park ferry, with paddling, fishing, hiking, cabins and camping. (source)
Hundreds of manatees shelter in the spring run from mid-November through March. Also offers the 4.5-mile Pine Island Trail, kayak rentals and St. Johns River cruises. Day-use visitors need advance reservations starting July 15, 2026. (source)
A 21,574-acre refuge established in 1964 for migratory waterfowl and wading birds, with 15 miles of trails for hiking, biking and some horseback riding. (source)
Undeveloped barrier island beaches, dunes, Mosquito Lagoon and ancient Timucua shell mounds. The Apollo Beach entrance is south of New Smyrna Beach. (source)
Things to do
John B. Stetson's 1886 Gilded Age home, the first in Florida built with Edison electricity. Historic tours run February through May and Christmas tours run November through mid-January. (source)
Historic 1922 theater in the heart of downtown with a full season of musicals, tribute concerts, films and youth workshops. (source)
Rotating art exhibitions, lectures and workshops at its downtown gallery on Woodland Boulevard. (source)
Volunteer-run military museum in a WWII-era building at the city airport, with a TBF Avenger, F-14 Tomcat and exhibits on NAS DeLand (1942-1946). Open Wednesdays and Saturdays, free. (source)
Year-round dropzone at DeLand Municipal Airport since 1982, offering tandem jumps, Accelerated Freefall training and operations for experienced skydivers. (source)
On the calendar
More than 200 beers to sample on West Georgia Avenue downtown. The 17th annual festival was held January 17, 2026. (source)
Free two-day show at Earl Brown Park with about 135 fine artists and crafters, live folk, bluegrass and blues, and a youth art division. 2026 was the 61st year. (source)
Free downtown festival on West Indiana Avenue with native plant vendors, expert talks and gardening for birds, butterflies and wildlife. (source)
Downtown street festival with hundreds of vendors selling handmade woodwork, jewelry and more. (source)
Juried fine arts festival that turns Woodland Boulevard into an open-air gallery with 160+ artists, live music, food and kids' activities. Free entry. (source)
Schools
Citrus Grove Elementary, Edith I. Starke Elementary, Freedom Elementary, George W. Marks Elementary, Blue Lake Elementary, Woodward Avenue Elementary
DeLand Middle School, Southwestern Middle School
DeLand High School
St. Peter Catholic School, St. Barnabas Episcopal School, Stetson Baptist Christian School, First Presbyterian Church School
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
I-4, US 17/92, SR 44 (New York Avenue) and SR 15A. SunRail commuter rail has served DeLand Station at 2491 Old New York Avenue since August 12, 2024, with weekday trains south to Sanford, Orlando and Osceola County.
Orlando Sanford International (SFB), about 30 minutes. Daytona Beach International (DAB), about 35 minutes. Orlando International (MCO), about 1 hour.
Ryan C. Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Researched and verified 2026-09-28. Businesses change; call ahead.