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Highlands Townhomes for Sale

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  • /27

    $336,000 Open Sat 1:30PM - 4:30PM

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    479 Harbor Winds Ct, Winter Springs, FL 32708

    Beautiful Townhome in Gated Harbor Winds – Prime Location & Resort-Style Amenities! Don’t miss this opportunity to own a beautifully maintained 3-bedroom, 2.5-bathroom townhome located in the highly desirable gated community of Harbor Winds in Winter Springs. This spacious 1,680 sq. ft. home offers an open, airy floor plan designed for both comfort and functionality. The primary suite is

    Ryan Rogers EXP REALTY LLC

    479 Harbor Winds Ct, Winter Springs, FL 32708
  • /32

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft

    737 Tanglewood Rd, Winter Springs, FL 32708

    Welcome to your new home! This charming 3-bedroom, 2-bathroom home also features a versatile flex room—perfect as a 4th bedroom or home office. The open layout and vaulted ceilings create a spacious, airy feel throughout, while the inviting sunken living room, complete with a cozy wood-burning fireplace, is perfect for relaxing on cool evenings. The custom-designed kitchen is a true highlight,

    Martha Grasty RE/MAX ASSURED

    737 Tanglewood Rd, Winter Springs, FL 32708
  • /45

    $285,000

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    424 Club Dr, Winter Springs, FL 32708

    Welcome to this well-maintained 3-bedroom, 2-bath home located in the desirable Cypress Club community of Winter Springs. Nestled in a peaceful neighborhood, this inviting residence offers comfortable living with access to a host of amenities that make every day feel like a getaway.Enjoy spacious living areas, a functional layout, and thoughtful updates throughout. The primary suite

    Lee Sloan KELLER WILLIAMS ADVANTAGE REALTY

    424 Club Dr, Winter Springs, FL 32708
  • /59

    $378,000

    • 3 Beds
    • 3 Baths
    • 2,176 Sq Ft

    506 Harbor Winds Ct, Winter Springs, FL 32708

    Well maintained 2-story, 3 bedroom, 3 full bath, end unit townhouse with attached 2-car garage, in the exclusive gated community of Harbor Winds. You can enjoy peace and relaxation as this unit backs up to a serene pond view. Inside, the kitchen includes a cozy breakfast nook, granite counters, custom cabinetry, huge closet pantry and breakfast bar. The kitchen looks out to the living room area

    Anderson (Luis) Zamora OLYMPUS EXECUTIVE REALTY INC

    506 Harbor Winds Ct, Winter Springs, FL 32708
  • /23

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,166 Sq Ft

    718 Wildwood Dr, Winter Springs, FL 32708

    Discover the perfect blend of privacy, low-maintenance living, and style in this freestanding 2-bedroom, 2-bath townhome in the desirable Wildwood community of Winter Springs. With no shared walls and a single-family feel, this home features vaulted ceilings, open living and dining areas, and abundant natural light throughout. The primary suite is generously sized with an en-suite bath and ample

    Joseph Schultz, PLLC LPT REALTY, LLC

    718 Wildwood Dr, Winter Springs, FL 32708
  • /39

    $322,499

    • 4 Beds
    • 2.5 Baths
    • 1,878 Sq Ft

    702 Glasgow Ct, Winter Springs, FL 32708

    Two fenced in spaces for your dog ! Master bedroom DOWNSTAIRS Updated Townhome in Sought-After Pebble Creek at The Highlands4 Beds | 2.5 Baths | Gas Double Oven | Inside Utility | Appliances Included | HOA-Maintained ExteriorWelcome to 702 Glasgow Court—your peaceful retreat tucked away in the heart of Winter Springs. Located in the charming Pebble Creek enclave of The Highlands,

    Amy Phillips CALL IT CLOSED INTL REALTY

    702 Glasgow Ct, Winter Springs, FL 32708
  • /22

    $270,000

    • 3 Beds
    • 2 Baths
    • 1,182 Sq Ft

    426 Club Dr, Winter Springs, FL 32708

    Beautifully located townhome, single story, end unit. Three bedrooms/two bath home has new luxury vinyl flooring throughout. Large windows to carry in natural sunlight, sliding glass doors that overlook the large screen enclosure which provides views that overlook the tropical common areas of the community. Located within The Highlands, Cypress Club HOA offers the community its own private

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    426 Club Dr, Winter Springs, FL 32708
  • /26

    $215,000

    • 2 Beds
    • 1.5 Baths
    • 898 Sq Ft

    113 Kristi Ann Ct, Winter Springs, FL 32708

    PRICE IMPROVEMENT ON!!!!!!!!!!!! this beautifully updated 2 bedroom, 2 bath townhouse in the heart of Winter Springs. Perfect for those seeking convenience, and modern comfort with a touch of elegance, this home offers a stylish and low-maintenance living experience. Freshly painted throughout, tile floors in the main living areas, Close to shopping, dining, schools, and major

    Kenia Palacios KELLER WILLIAMS REALTY AT THE LAKES

    113 Kristi Ann Ct, Winter Springs, FL 32708
  • /33

    $302,000

    • 3 Beds
    • 2 Baths
    • 1,470 Sq Ft

    701 Castlewood Dr, Winter Springs, FL 32708

    Welcome to 701 Castlewood, Winter Springs, Florida! This charming 3-bedroom, 2-bath home is nestled in a highly sought-after community known for its abundant amenities and prime location. The property boasts a newly replaced roof (2020), ensuring peace of mind and long-term durability.As you step inside, you'll be greeted by a bright and airy living space, perfect for both relaxation and

    Torey Eisenman BENCHMARK REAL ESTATE GRP INC

    701 Castlewood Dr, Winter Springs, FL 32708

Why Live in Highlands

Highlands in Winter Springs, Florida, is a neighborhood known for its lush natural scenery and access to urban amenities. The area is part of the Seminole County Public Schools, a Premier National School District, with highly rated institutions like Indian Trails Middle and Winter Springs High School. The neighborhood features a mix of single-family homes, condos, and townhomes, with styles ranging from ranch-style to Spanish-revival, built primarily in the mid-to-late 20th century. The Highlands Homeowner's Association provides amenities such as tennis courts, a junior-sized Olympic swimming pool, a playground, a lakeside park, nature trails, and an outdoor grill area. Residents enjoy proximity to several parks, including Spring Hammock Preserve with its ancient bald cypress trees and Soldiers' Creek Park, which offers championship baseball fields and access to the Cross Seminole Trail. Torcaso Park provides a nautical-themed playground and splash pad for children, while anglers can fish in Lake Jessup. Dining options include Chilangos for Mexican cuisine, Argentinian Bakery and Café for sweet treats, and Victorio's for Italian fare. The Winter Springs Town Center offers shopping and nightlife, with additional retail options at nearby Altamonte Mall and Oviedo Mall. Highlands is safer than the national average, making it a practical choice for families. While biking is popular, most residents rely on cars and trucks, with public buses and SunRail providing transportation to Downtown Orlando, 15 miles away. The neighborhood hosts events like the Central Florida Scottish Highland Games and the Hometown Harvest Festival, adding to its community appeal.

Home Trends in Highlands, FL

Housing Trends

Median Sale Price
$377,015
Median Single Family Sale Price
$375,990
Median Townhouse Sale Price
$418,100
Median 2 Bedroom Sale Price
$450,000
Average Price Per Sq Ft
$215
Number of Homes for Sale
22
Last 12 months Home Sales
108
Months of Supply
2.40
Median List Price
$416,290
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-13%
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