Dunedin, Pinellas County
Highland Woods, Dunedin, FL Real Estate
Family-friendly Dunedin neighborhood with tree-lined streets and convenient access to downtown.
About Highland Woods
Highland Woods is a residential neighborhood located in central Dunedin, Pinellas County, Florida. The community features single-family homes and townhomes set among mature oak and pine trees, characteristic of Dunedin's natural landscape. Residents enjoy proximity to downtown Dunedin's shops, restaurants, and cultural venues along Main Street, as well as nearby parks and the Dunedin Library. The neighborhood's tree-canopy and quiet streets appeal to families and professionals seeking a smaller-town feel within the Tampa Bay metro area. Located within easy driving distance of Honeymoon Island State Park and the Gulf of Mexico beaches, Highland Woods offers a balance of suburban living and coastal access.
Highland Woods on the map
Approximate location of Highland Woods. This map is centered on the area and does not show an exact boundary.
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No official boundary is published for Highland Woods yet. We show the center point instead of drawing a line we cannot verify.
Living in Highland Woods
Daily life in Highland Woods centers on Dunedin's walkable, arts-focused downtown core. Residents routinely visit Main Street for coffee, dining, and galleries, or access the Dunedin Nature Preserve for trails and wildlife viewing. The neighborhood is family-oriented, with good access to local schools and parks. Proximity to the Intracoastal Waterway and beach communities makes weekend trips to Honeymoon Island or Clearwater Beach routine. The area attracts retirees, young professionals, and established families valuing Dunedin's small-town character over sprawl.
Why buyers choose Highland Woods
- Daily life in Highland Woods centers on Dunedin's walkable, arts-focused downtown core. Residents routinely visit Main Street for coffee, dining, and galleries, or access the Dunedin Nature Preserve for trails and wildlife viewing. The neighborhood is family-oriented, with good access to local schools and parks. Proximity to the Intracoastal Waterway and beach communities makes weekend trips to Honeymoon Island or Clearwater Beach routine. The area attracts retirees, young professionals, and established families valuing Dunedin's small-town character over sprawl.
Highland Woods market snapshot
Highland Woods appeals to buyers seeking established Dunedin neighborhoods with character and convenience. The market typically attracts downsizers from larger homes, families prioritizing walkable access to schools and downtown amenities, and buyers drawn to Pinellas County's year-round climate and beach proximity. Home styles range from mid-century single-family residences to newer townhomes, reflecting Dunedin's mixed-era housing stock. Demand remains steady among those seeking alternatives to newer subdivisions while staying close to Gulf Coast recreation and employment centers.
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Highland Woods real estate FAQ
- What's it like living in Highland Woods compared to other Dunedin neighborhoods?
- Highland Woods offers quiet, tree-shaded streets with a residential feel while staying central to Dunedin's walkable downtown. Unlike newer subdivisions like Dunedin Commons or the waterfront-focused character of Dunedin Cove, Highland Woods balances neighborhood privacy with convenient access to Main Street shops, parks, and schools. The established tree canopy and mixed housing types make it popular with families and retirees.
- Can I walk to restaurants and shops from Highland Woods?
- Yes, downtown Dunedin Main Street is accessible by car in minutes and by foot from parts of the neighborhood. Dunedin's downtown offers independent restaurants, coffee shops, galleries, and retail within the historic core. The neighborhood also has nearby convenience stores and services, though a car is helpful for regular errands outside the immediate area.
- How far is Highland Woods from the beach?
- Honeymoon Island State Park and Gulf-facing beaches are roughly 10–15 minutes by car from Highland Woods. Clearwater Beach and other Pinellas County beaches are similarly close, making weekend beach trips and water recreation very accessible for residents.
- What kinds of homes are in Highland Woods?
- The neighborhood features a mix of single-family homes, many built in the mid-20th century on tree-lined lots, alongside some newer townhomes. Home styles vary, reflecting Dunedin's established residential character. Lot sizes and home ages differ throughout, so prospective buyers should tour specific listings to find their preferred style and condition.
Licensed Agents in Highland Woods
Keller Williams REALTORS® who cover Highland Woods. Tap any card to see their full profile.
4 licensed agents cover Highland Woods.
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Will ToliverTeam Pepka - KW Suncoast - View profile →
Ron PepkaBroker AssociateTeam Pepka - KW Suncoast - View profile →
Katie FergusonAgent ConsultantTeam Pepka - KW Suncoast - View profile →
Hailie RatermanTeam Pepka - KW Suncoast
