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Highlands Townhomes for Sale

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  • /32

    $310,500

    • 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,

    Agent Photo

    Martha Grasty

    RE/MAX ASSURED

    (321) 496-7412

    737 Tanglewood Rd, Winter Springs, FL 32708
  • /6

    $246,000

    • 2 Beds
    • 1.5 Baths
    • 896 Sq Ft

    122 Kristi Ann Ct, Winter Springs, FL 32708

    Stunning fully remodeled townhome featuring top-quality finishes and modern design throughout! Enjoy a bright open floor plan with wide-plank flooring, a chef’s kitchen with quartz countertops, custom cabinetry, and premium stainless appliances. All bathrooms have been beautifully updated with designer fixtures and tile. Recent upgrades include new HVAC, windows, and more. Conveniently located

    Vered Thacker DALTON WADE INC

    122 Kristi Ann Ct, Winter Springs, FL 32708
  • /25

    $245,000

    • 3 Beds
    • 1.5 Baths
    • 1,130 Sq Ft

    411 Green Spring Cir, Winter Springs, FL 32708

    Opportunity knocks in the Vineyards of Mount Greenwood! This 3-bedroom, 1.5-bath townhome in Winter Springs is full of potential and ready for a buyer with vision. The main floor features a spacious living and dining area, kitchen, convenient half bath, and extra storage under the stairs. Sliding glass doors lead to a covered and screened rear porch with an additional storage closet—ideal for

    Sarita Cabrera WATSON REALTY CORP

    411 Green Spring Cir, Winter Springs, FL 32708
  • /31

    $235,000

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

    30 Moree Loop Unit 39, Winter Springs, FL 32708

    Fall in love with this 3 bed, 2.5 bath townhome-style condo in one of Winter Springs’ most sought-after communities! Featuring a remodeled kitchen, luxury vinyl plank floors, updated baths with new vanities, new tile shower, and fresh paint, this home is stylish and low-maintenance. Roof replaced in 2021, new fencing, and newer water heater mean peace of mind for years to come!Inside,

    Casey Irwin PARK VIEW REALTY INC

    30 Moree Loop Unit 39, Winter Springs, FL 32708
  • /50

    $298,990

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

    718 Lakeside Dr, Winter Springs, FL 32708

    Welcome to 718 LAKESIDE Drive in the heart of Winter Springs! This beautifully move in ready 2-bedroom, 2-bath Home perfectly blends style, comfort, and convenience. As you step inside, you are greeted by a BRIGHT OPEN LIVING SPACE with VAULTED CEILINGS, UPDATED FIXTURE, STYLIST NEWER LAMINATE FLOORING, and a COZY FIREPLACE that instantly makes the home feel warm and inviting. The spacious

    Mariana Cisneros PREMIUM PROPERTIES R.E SERVICE

    718 Lakeside Dr, Winter Springs, FL 32708
  • /27

    $250,000

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft

    498 Club Dr, Winter Springs, FL 32708

    Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    498 Club Dr, Winter Springs, FL 32708
  • /45

    $284,900

    • 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
  • /39

    $322,497

    • 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
  • /63

    $347,000

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft

    452 Harbor Winds Ct, Winter Springs, FL 32708

    PRICE REDUCED!!!Discover this stunning 3-bedroom, 2.5-bathroom townhome with 1,914 square feet of well-designed living space. Situated in a gated community, this home offers both luxury and convenience, including a 2-car garage and access to a sparkling community pool.Enjoy the serene views of the wooded area from your private screened porch, the perfect spot for morning coffee or evening

    Roxanna Cabrera LA ROSA REALTY PREMIER LLC

    452 Harbor Winds Ct, 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
$320,000
Median Single Family Sale Price
$337,000
Median Townhouse Sale Price
$500,000
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$147,500
Average Price Per Sq Ft
$229
Number of Homes for Sale
37
Last 12 months Home Sales
165
Months of Supply
2.70
Median List Price
$325,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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