8

Woodland Drives Houses for Sale

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  • /39

    $599,900

    • 5 Beds
    • 3 Baths
    • 2,960 Sq Ft

    1003 Maple Dr, Tallahassee, FL 32301

    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,

    1003 Maple Dr, Tallahassee, FL 32301
  • /68

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,948 Sq Ft

    2025 Chuli, Tallahassee, FL 32301

    Open House: Sunday Aug 3rd, 2-4 pm! Welcome home to one of Tallahassee’s most beloved neighborhoods! Nestled on .45 acres, this 1948 square foot, 3-bedroom, 2-bath home offers a rare blend of updates and charm, comfort and natural beauty. The large windows in the main living area bring in so much light and make a beautiful place to enjoy bird-watching! Step outside and discover what makes this

    Joyce Gardner Armor Realty, Inc

    2025 Chuli, Tallahassee, FL 32301
  • /42

    $649,900

    • 4 Beds
    • 2 Baths
    • 4,294 Sq Ft

    1614 S Meridian St, Tallahassee, FL 32301

    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

    1614 S Meridian St, Tallahassee, FL 32301
  • /44

    $849,900

    • 4 Beds
    • 3 Baths
    • 2,893 Sq Ft

    909 Circle Dr, Tallahassee, FL 32301

    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

    909 Circle Dr, Tallahassee, FL 32301
  • /42

    $349,000

    • 5 Beds
    • 2 Baths
    • 3,012 Sq Ft

    1700 S Meridian St, Tallahassee, FL 32301

    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

    1700 S Meridian St, Tallahassee, FL 32301
  • /36

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    2115 Old Fort Dr, Tallahassee, FL 32301

    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

    2115 Old Fort Dr, Tallahassee, FL 32301
  • /39

    $449,000

    • 4 Beds
    • 3 Baths
    • 2,250 Sq Ft

    1024 Cherokee Dr, Tallahassee, FL 32301

    **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

    1024 Cherokee Dr, Tallahassee, FL 32301
  • /36

    $660,000

    • 4 Beds
    • 3 Baths
    • 2,948 Sq Ft

    1017 Cherokee Dr, Tallahassee, FL 32301

    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

    1017 Cherokee Dr, Tallahassee, FL 32301

Why Live in Woodland Drives

Woodland Drives in Tallahassee offers a serene environment with its towering loblollies and sprawling live oaks, while being conveniently close to downtown attractions. The neighborhood features multiple parks and nature trails, and is a short bicycle ride to Cascades Park. Homes here, built mostly between the 1940s and 1960s, showcase diverse architecture, including brick ranchers, Classical styles, New Traditional builds, and Cape Cod-style homes. The historic Myers Park district within Woodland Drives includes bungalows and cottages from the 1920s. The Capital City Country Club, a central feature, is ranked as the best golf course in Tallahassee and offers public play, a tennis complex, an Olympic-size swimming pool, and dining at the Champions Bar and Grill. Myers Park provides additional recreational options with tennis courts, a playground, a hiking trail, and a baseball field. Local schools include Hartsfield Elementary, Cobb Middle, Fairview Middle, and Rickards High School, which has an International Baccalaureate program. Monroe Street, the neighborhood’s western boundary, offers shopping and dining, including Tallahassee’s first craft brewery, Proof Brewing Company. Apalachee Parkway features a variety of retailers and restaurants, such as Sahara Café, and entertainment at The Moon nightclub. Woodland Drives combines quiet charm with city amenities, making it a desirable place to live.

Home Trends in Woodland Drives, FL

Housing Trends

Median Sale Price
$780,000
Median Single Family Sale Price
$495,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
2
Last 12 months Home Sales
15
Months of Supply
1.60
Median List Price
$639,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
61%
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