Woodland Drives Homes for Sale

Charming Historic District Home! Nestled in Tallahassee’s coveted historic district, 1003 Maple Dr blends timeless character with a taste of southern feel. This inviting home features a 2022 roof, 2024 updated energy-efficient windows, fresh paint to the back deck and a weather-responsive irrigation system to keep the lush landscaping thriving with ease. Step in the back to a detached shed that

Taylor Rosier Florida Management Associates,

Brand-new southern-modern duplex in historic Smokey Hollow—crafted with high-end finishes and exceptional detail. Built in 2025, each unit features quartz countertops, stainless steel appliances, and durable cement fiber siding with a metal roof. This isn’t your typical builder-grade project. Located just minutes from downtown Tallahassee and within walking distance to Cascades Park and Myers

Phillip Kelly Passage Real Estate

Rare Myers Park Historical Registry Gem on 1.27 Acres! Discover a unique opportunity to own a spacious and versatile property in the coveted Myers Park neighborhood. This historic home offers 4 bedrooms and 2 bathrooms, plus a ground-floor in-law suite (ADU) with its own kitchen & bathroom—perfect for multi-generational living or rental income ~Additionally, there's a separate home office with a

Mariela Bartens Coldwell Banker Hartung

Great Investment Opportunity! Live in 1 side and rent the other. Low maintenance duplex, 2 bedroom 1 bath on each side. Very well maintained. Original hardwood floors that are fantastic shape. Oversized 2 car garage under the home that has great storage and room for 2 cars. Each unit has washer and dryer that are on the back screen in porches. Floor plan is large living room with arched entry

Stacie Spears Dixon The Naumann Group Real Estate

Step into your own private oasis just five minutes from downtown Tallahassee! This stunning in-town estate sits on an entire city block and offers luxury, privacy, and convenience. The beautifully maintained 3BR/3BA home features hardwood floors throughout, a spacious living room with a bay window and cozy wood-burning fireplace (also wired for electric), as well as a separate dining room with

Hettie Spooner Hill Spooner & Elliott Inc

Charming & Spacious Myers Park Home – Walk to Everything! Discover this beautifully preserved vintage gem in the heart of Myers Park—just a short stroll to vibrant bars, scenic parks, and popular restaurants. This large 5-bedroom, 2-bath home blends timeless charm with modern convenience. Original hardwood floors in excellent condition throughout main living areas. Abundant natural light fills

Stacie Spears Dixon The Naumann Group Real Estate

Welcome to 2115 Old Fort Drive, located in beautiful Woodland Drives, one of Tallahassee oldest established neighborhoods. This wonderful home is tucked away from the street, giving a sense of seclusion and privacy. Once you step inside this mid-century ranch, the natural light from the oversized windows will saturate the space - truly spectacular. The vintage features of this 1959 home have been

Jim Butler Coldwell Banker Hartung

**Motivated Seller**Assumable 2.75% VA Loan** This newly updated, 1947 brick home in Woodland Drives is situated on a sprawling 1.12-acre lot. Offering a blend of classic charm and modern convenience, this property is truly one-of-a-kind. This home features two large primary bedrooms with attached bathrooms, plenty of closet space, large laundry/pantry room, and so much more. New paint inside

Ashley Jordan HomeSweetHome PM & Sales

Attention all investors this is an awesome investment opportunity perfectly situated just steps away from a beautiful city park. This is an income producing property all units are occupied with strong rental history. Don't miss out on this opportunity to own a stabilized asset in a high demand area.

Katesa Wood Empire Properties

Must See Opportunity Zone property! 9 units with proven rental history- 3 Triplexes consisting of (8) 2/1 units and (1) 1/1 unit. 4 units were renovated in 2022, 2 units renovated in 2024. 2 newer Roofs. Lots of upgrades to property. All tenants on yearly leases. All units rented and gross rent of $9650.00 per month. Perfect addition to a rental portfolio. Must see!

Lee Hall Capital City Real Estate Group

A true Mid Century Modern 4 bedroom 3 bath home in charming Woodland Drives. Remodeled and crafted to perfection with a chef's kitchen, stainless appliances. Open living/ dining room overlooking screened Lani and spa. Natural wood tones and polished oak hardwood flooring , to include tile downstairs.2 Updated bathrooms up and one down. Fourth bedroom and bath downstairs with separate outside

Sandy Brown Magnolia Properties&Investment