14

Woodland Drives Homes for Sale

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  • /23

    $284,500

    • 1,462 Sq Ft

    502 E Jennings St Unit 2, Tallahassee, FL 32301

    WONDERFUL INVESTMENT OPPORTUNITY NEAR MYERS PARK* THIS CUTE MULTI-FAMILY PROPERTY FEATURES TWO UNITS WITH 2 BEDROOMS AND 1 BATH EACH* EXTERIOR PHOTOS ONLY DUE TO TENANT OCCUPANCY.

    Agent Photo

    Sarah Eden

    Eden & Company

    (850) 779-0224

    502 E Jennings St Unit 2, Tallahassee, FL 32301
  • /37

    $575,900

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

    1003 Maple Dr, Tallahassee, FL 32301

    Motivated Seller!! 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 and a second story

    Taylor Rosier Florida Management Associates,

    1003 Maple Dr, Tallahassee, FL 32301
  • /34

    $412,500 Open Sun 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 2,314 Sq Ft

    1120 Sarasota Dr, Tallahassee, FL 32301

    Get it before someone else does at the OPEN HOUSE SUN 9/7, 2-4! 2024 roof, newer kitchen with stainless steel appliances and granite countertops, fresh interior 2025 paint, original oak hardwood floors refinished in 2025, new 2025 LVP replaced the last of the carpet, brick on all 4 sides, and more. Updates where it counts! Multiple large living and dining areas, including what had been an art

    Allyson Foster Armor Realty, Inc

    1120 Sarasota Dr, Tallahassee, FL 32301
  • /39

    $429,000

    • 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

    $597,500 Open Sun 2PM - 4PM

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

    1017 Cherokee Dr, Tallahassee, FL 32301

    OPEN HOUSE SUNDAY 2-4 SEPTEMBER 7, 2025 - Masterfully re designed, no expense spared in this mid century modern two level home, 4 or 5 bedroom, three full baths. Full living area upstairs, and downstairs. Room for multi generational living. Office accommodations downstairs with outside entrance, or perfect for efficiency apartment or in-law suite with it's own outside entrance. Beautifully

    Sandy Brown Magnolia Properties&Investment

    1017 Cherokee Dr, Tallahassee, FL 32301
  • /34

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,320 Sq Ft

    1046 Holland Dr, Tallahassee, FL 32301

    Charming Myers Park Home in Prime Downtown Location! The recent home inspection, WDO, radon, and survey have already been completed; all that’s left is for your buyer to move in. Motivated seller! Located in the heart of one of Tallahassee’s most established neighborhoods, this 3-bedroom, 2-bathroom gem has been freshly painted inside and out and is ready for its next chapter. Major updates

    E. Gray Nichols Hill Spooner & Elliott Inc

    1046 Holland Dr, Tallahassee, FL 32301
  • /56

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,261 Sq Ft

    1138 S Magnolia Dr, Tallahassee, FL 32301

    Just like new construction! Totally renovated home in popular Indianhead acres. Completely remodeled from 2024 tornado. All new inside walls, kitchen, baths, flooring, wiring, roof, water heater - everything!! Fantastic open living room with cathedral ceiling and wood beams. Enjoy the enormous back yard from the super cute screened porch room. Light and bright, this home is ideal for those

    Cindy Cooper Coldwell Banker Hartung

    1138 S Magnolia Dr, Tallahassee, FL 32301
  • /49

    $205,000

    • 3 Beds
    • 1 Bath
    • 1,070 Sq Ft

    405 Perkins St, Tallahassee, FL 32301

    Myers Park-adjacent charmer with canopied front and back yard // Gorgeous original hardwood floors and tasteful basket-eave vintage bathroom tile // 2021 roof, 2019 water heater...most appliances replaced in last three years // Hurricane hallway with nook storage // Surprisingly large laundry room and separate interior storage room // Dining and living rooms are separate, but open to another //

    Christie Perkins Coldwell Banker Hartung

    405 Perkins St, Tallahassee, FL 32301
  • /42

    $600,000

    • 2,150 Sq Ft

    637 E Seaboard St Unit 1, Tallahassee, FL 32301

    Step into this 2025-built southern-modern duplex where refined design meets low-maintenance ease. From the quartz countertops and stainless steel appliances to durable cement-fiber siding and a metal roof, every finish was chosen to last — giving you upscale living without the upkeep. Located in the soulful neighborhood of Smokey Hollow — just steps from Cascades Park, downtown, and Myers Park —

    Phillip Kelly Passage Real Estate

    637 E Seaboard St Unit 1, Tallahassee, FL 32301
  • /44

    $799,900 Open Sun 2PM - 4PM

    • 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
  • /55

    $990,000

    • 6 Beds
    • 6 Baths
    • 4,648 Sq Ft

    1117 Myers Park Dr, Tallahassee, FL 32301

    *Showings can start August 6th. Step into timeless charm with this stunning historic home located in the heart of Myers Park. Situated on approximately 1.15 acres of fully fenced property, this rare gem offers privacy, space, and elegance. Inside, you’ll find five spacious bedrooms and five bathrooms, providing ample room for comfortable living. The beautifully remodeled kitchen features custom

    Daniela Farris Xcellence Realty

    1117 Myers Park Dr, Tallahassee, FL 32301
  • /37

    $379,000

    • 1,750 Sq Ft

    1454 S Gadsden St, Tallahassee, FL 32301

    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

    1454 S Gadsden St, 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
  • /28

    $1,200,000

    • 5,706 Sq Ft

    316 E Pershing St Unit 316-328, Tallahassee, FL 32301

    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

    316 E Pershing St Unit 316-328, 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.

Frequently Asked Questions

Is Woodland Drives a good place to live?
Woodland Drives is a good place to live. Woodland Drives is considered very car-dependent and somewhat bikeable with some transit options. Woodland Drives is a suburban neighborhood. Woodland Drives has 6 parks for recreational activities. It is fairly sparse in population with 3.0 people per acre and a median age of 35. The average household income is $91,010 which is below the national average. College graduates make up 68.9% of residents. A majority of residents in Woodland Drives are renters, with 51.6% of residents renting and 48.4% of residents owning their home. A local real estate agent serving Woodland Drives can help you decide if this neighborhood is the right one for you. Learn more on our Woodland Drives neighborhood guide.
How much do you need to make to afford a house in Woodland Drives?
The median home price in Woodland Drives is $394,494. If you put a 20% down payment of $78,900 and had a 30-year fixed mortgage with an interest rate of 6.5%, your estimated principal and interest payment would be $1,990 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $85K a year to afford the median home price in Woodland Drives. The average household income in Woodland Drives is $91K.
What are the best public schools in Woodland Drives?
The best public schools that serve Woodland Drives are:
What are the best private schools in Woodland Drives?
The best private schools that serve Woodland Drives are:
What are the most popular zip codes in Woodland Drives, Tallahassee, FL?
The most popular zip codes in Woodland Drives, Tallahassee, FL include 32301, 32308, 32310, 32304 and 32303.
What are the most popular neighborhoods near Woodland Drives, Tallahassee, FL?
The most popular neighborhoods near Woodland Drives, Tallahassee, FL are Downtown Tallahassee, FAMU, South City, Hilaman and Magnolia.

Home Trends in Woodland Drives, FL

Housing Trends

Median Sale Price
$379,250
Median Single Family Sale Price
$380,000
Average Price Per Sq Ft
$198
Number of Homes for Sale
10
Last 12 months Home Sales
26
Months of Supply
4.60
Median List Price
$394,494
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
26%
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