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Highlands Condos for Sale

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  • 429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
    429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
    429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
    /34

    $199,900

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft

    429 Sheoah Blvd Unit 12, Winter Springs, FL 32708

    Located in The Highlands, a planned environmental community, this condo offers more than just a home - it's a true Florida lifestyle. Surrounded by winding nature trails and a peaceful creekside path, you'll enjoy a friendly neighborhood setting with regular community events and an abundance of activities. Spend your free time at the junior-sized Olympic pool, play pickleball or basketball with

    Chris Creegan CREEGAN GROUP

    429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
  • 60 Moree Loop Unit 45, Winter Springs, FL 32708
    60 Moree Loop Unit 45, Winter Springs, FL 32708
    60 Moree Loop Unit 45, Winter Springs, FL 32708
    /13

    $189,900

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft

    60 Moree Loop Unit 45, Winter Springs, FL 32708

    Uncover a Hidden Gem in Central Florida! Welcome to this charming FIRST FLOOR, single story, 3-bedroom, 2 bath condo nestled in the Highlands community, renowned for its exceptional recreational offerings. The kitchen boasts light-colored cabinets and in unit washer / dryer. Spacious open-concept living and dining areas seamlessly connect to a large screened patio, perfect for relaxation or

    Matt Merdian MERDIAN REALTY LLC

    60 Moree Loop Unit 45, Winter Springs, FL 32708
  • 419 Sheoah Blvd Unit 27, Winter Springs, FL 32708
    419 Sheoah Blvd Unit 27, Winter Springs, FL 32708
    419 Sheoah Blvd Unit 27, Winter Springs, FL 32708
    /20

    $175,000

    • 2 Beds
    • 2 Baths
    • 955 Sq Ft

    419 Sheoah Blvd Unit 27, Winter Springs, FL 32708

    Welcome to this FULLY RENOVATED first floor condo in the premier Baytree Village, nestled within The Highlands community of Winter Springs! Surrounded by towering oaks, pines and cypress trees – some more than a thousand years old – this home offers a rare blend of modern living and natural beauty. Step inside where you will find LUXURY VINYL PLANK flooring throughout, FRESH PAINT, and a SPLIT

    Jennifer Wemert WEMERT GROUP REALTY LLC

    419 Sheoah Blvd Unit 27, Winter Springs, FL 32708
  • 40 Moree Loop Unit 11, Winter Springs, FL 32708
    40 Moree Loop Unit 11, Winter Springs, FL 32708
    40 Moree Loop Unit 11, Winter Springs, FL 32708
    /26

    $210,000

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

    40 Moree Loop Unit 11, Winter Springs, FL 32708

    Discover a Hidden Gem in the Heart of Central Florida!Welcome to this amazing two-story, 3-bedroom, 2.5-bath condo located in the sought-after Highlands community—rated as one of the area’s best recreational neighborhoods! Step inside to an updated kitchen with granite countertops, light cabinetry, and sleek dark appliances. The spacious open-concept living/dining area flows effortlessly to a

    Jessica Brown MARK SPAIN REAL ESTATE

    40 Moree Loop Unit 11, Winter Springs, FL 32708
  • 429 Sheoah Blvd Unit 8, Winter Springs, FL 32708
    429 Sheoah Blvd Unit 8, Winter Springs, FL 32708
    429 Sheoah Blvd Unit 8, Winter Springs, FL 32708
    /32

    $248,500

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft

    429 Sheoah Blvd Unit 8, Winter Springs, FL 32708

    Discover Your Dream Home! Welcome to this stunning 3-bedroom, 2-bathroom condo, nestled on the serene 2nd floor. Recently updated to enhance your living experience, this residence boasts fresh interior paint and brand-new floor throughout, ensuring a move-in ready condition that invites comfort and style. The spacious living room and dining area merge seamlessly, featuring a charming wet

    Elizabeth Dowell UPZEL REALTY LLC

    429 Sheoah Blvd Unit 8, Winter Springs, FL 32708
Florida Seminole County Winter Springs Highlands

Condos for Sale in Highlands, Winter Springs

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.
Learn more about living in Highlands

Home Trends in Highlands, FL

On average, homes in Highlands, Winter Springs sell after 97 days on the market compared to the national average of 70 days. The median sale price for homes in Highlands, Winter Springs over the last 12 months is $377,015, down 13% from the median home sale price over the previous 12 months.

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
23
Last 12 months Home Sales
108
Months of Supply
2.60
Median List Price
$416,290
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-13%
How to Buy a Home How to Finance a Home How to Sell a Home

In Highlands, there are currently 5 condos for sale, providing a range of options for prospective buyers. With condos ranging from $175,000 to $248,500, there's something for every budget. As of August, 2025 the median home price in Highlands, Winter Springs is $416,290, while the average sale price is $419,742, providing insight into local market trends. On average, condos spend 97 days on the market before being sold. Whether you're considering condominiums, apartments for sale, or modern condos, there are options available to suit your needs. Explore the variety of condos for sale in Highlands, Winter Springs, and find the perfect place to call home.

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