$314,681Average Value$224Average Price per Sq Ft52Homes For Sale
Mix of country sights and urban comforts
Part of a nationally recognized school district and surrounded by nature, Highlands offers home buyers rural scenery with all the comforts of the city. Residents are a short distance from lush natural parks that host community events, as well as shopping centers and local businesses.
Beautifil nature trails in Spring Hammock Preserve near Highlands.
Winn Dixie at Sun Lake Plaza near Highlands.
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Mid-century ranch-style houses and contemporary townhomes
The Highlands Homeowner's Association includes more than 1,400 area homes, encompassing a range of single-family houses, condos and townhomes. Homes range from 1,000 to 2,000 square feet, mixing the spacious floorplans of ranch-style homes with the stucco exteriors and covered outdoor spaces typical of Spanish-revival-style houses. "There's a nice mix of established and new builds here," says Krystal King, a local Realtor at eXp Realty with over $11 million in sales. Most homes were built in the mid-to-late 20th century, with some more recent construction taking place in the communities condos and townhomes. Residents enjoy backyards looking out onto mature trees and wide streets with sidewalks connecting neighbors and providing routes for joggers and cyclists. The HOA amenities include four tennis courts, a junior-sized Olympic swimming pool, a playground, a lakeside park, nature trails and an outdoor grill area. Houses range in price from $200,000 to $449,000 and come with a monthly HOA fee of less than $30.
A ranch-style homes, featuring stucco exteriors and small court yard entrances in the Highlands community.
Condos in the Highland community.
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High marks from Seminole County Public Schools
Highlands is part of Seminole County Public Schools, widely recognized as a Premier National School District. Students begin their academic careers at Highlands Elementary, which features an overall B-plus rating and ranks above the state average for test scores and student progress according to Niche. Kids can also participate in various extracurriculars, including HLN News Crew and Leadership Academy. Students move on to intermediate and secondary institutions such as Indian Trails Middle and Winter Springs High School. Both schools have an overall A-minus rating according to Niche. The high school's rigorous fine arts program teaches everything from 3D design to TV production and theater. Most notably, the Winter Springs High School Chorus has earned the title of Honor Choir with Disney's Candlelight Processional. The high school also offers nearly two dozen athletic options, including water polo and lacrosse.
Welcome to Indian Trails Middle School in Flordia.
Winter Springs High School is a public school in Winter Springs, FL.
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Lush parks and water sports around Lake Jessup
Take the boardwalk in Spring Hammock Preserve and explore more than 1,500 acres of bald cypress trees, including some of the oldest trees in the world. Local athletes can head to Soldiers' Creek Park, hit home runs on the championship baseball field, youth and women's softball fields and batting cages, or take a ride along the mountain bike trail. This park also features an entry point for the Cross Seminole Trail, which spans over 20 miles and features pedestrian bridges connecting long-distance runners and cyclists to downtown Orlando. Kids will enjoy Torcaso Park, which has a nautical-themed playground and splash pad. Anglers reel in largemouth bass and catfish from the waters of Lake Jessup.
Soldier's Creek Park's batting cages near Highlands.
Cross Seminole Trail Sign at Soldier's Creek Park near Highlands.
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Local restaurants and shopping around Highlands
Patrons beneath the sombrero-lined walls at Chilangos, an authentic Mexican restaurant serving homemade guacamole and deep-fried jalapeno poppers. Sweet treats and hot beverages are available at Argentinian Bakery and Café, a small counter-service spot famous for its gooey empanadas and sweet bread. Victorio's is a casual yet authentic Italian eatery known for its homemade, hand-rolled Italian meatballs. The Winter Springs Town Center is a modern, outdoor shopping complex. Grab groceries at the Publix Super Market, pick up healthy food at The Daily Dose and then come back for nightlife at the Spill Wine and Craft Beer Bar. A broader selection of shopping options can be found at the nearby Altamonte Mall and Oviedo Mall.
3oz. homemade Italian Meatballs baked with Mozzarella atVictorios II Italian Restaurant & Pizzeria in Highlands.
Enjoy a wine tasting at Spill Wine Bar, just minutes from Highlands.
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Quick routes to Downtown Orlando
Locals can bike around the neighborhood however cars and trucks are the main modes of transportation around Highlands. Public buses and the nearby SunRail transport commuters to Downtown Orlando, 15 miles to the south.
The Lynx bus system provides transportation throughout Highlands and Central Florida.
Hop aboard SunRail, minutes from Highlands, for your transportation needs.
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Cultral festivals and musical performances
The Central Florida Scottish Highland Games is the town's most popular event, featuring attractions like boulder boogie, bagpipe performances, and border collie demonstrations. During the Hometown Harvest Festival and Central Winds Music Festival, fresh produce vendors and live music performances populate Central Winds Park.
Central Winds Park is the hub for athletes to show off their skills.
Central Winds Park in Winter Springs blooms with the rhythm of nature and lively gatherings.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Highlands neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Highlands
US
Homicide
3
4
Sexual Assault
3
4
Assault with Weapon
3
4
Robbery
4
4
Burglary
4
4
Motor Vehicle Theft
4
4
Larceny
4
4
Crime Score
3
4
Source: WhatIsMyCrimeRisk.com
Highlands Demographics and Home Trends
On average, homes in Highlands, Winter Springs sell after 62 days on the market compared to the national average of 56 days. The median sale price for homes in Highlands, Winter Springs over the last 12 months is $300,000, down 8% from the median home sale price over the previous 12 months.
$374,900 NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026,
Welcome to 472 Dewars Court, a beautifully maintained 4-bedroom, 2.5-bath pool home offering over 2,200 square feet of living space in one of Winter Springs' most desirable communities. Tucked away at the end of a quiet cul-de-sac, this exceptional property provides the perfect combination of privacy, comfort, and convenience with a serene wooded backdrop and no rear neighbors. Inside, you'll
This clean and move-in ready 2 bedroom, 2 bath home is located in a quiet and well maintained senior community, offering comfort, convenience, and a relaxed lifestyle. Featuring a spacious floor plan with large bedrooms, a bright living room, dedicated dining area, and an oversized kitchen with plenty of cabinet space, this home is perfect for everyday living and entertaining. Recent updates
Welcome to this freshly painted 2-bedroom, 2-bathroom condominium located in the desirable Deer Song community in Winter Springs. Offering a low-maintenance lifestyle in a convenient Central Florida location, this residence is a great fit for a first-time buyer, downsizer, seasonal resident, or investor looking for a well-positioned property with everyday comfort and community appeal. Inside, the
Virtually Staged. Welcome to this inviting single-story home in Longwood, offering a bright layout, spacious rooms, and a large yard surrounded by mature trees. The HVAC was replaced in 2020 and the water heater was replaced in 2021, adding practical updates for peace of mind. From the moment you arrive, the fresh exterior, extended driveway, and peaceful setting create a sense of privacy and
Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and
Opportunity knocks in Winter Springs! If you've been waiting for an affordable way to own in a desirable Central Florida community, this is it This 3-bedroom, 2-bath home offers 1,105 square feet with a very functional layout. This makes it an excellent opportunity for homeowners ready to build equity or investors looking for their next project. The biggest expense has already been taken care of
Brand-new 2026 Home - The Laguna - offering modern design and quality craftsmanship throughout. This beautifully appointed residence features recessed lighting, elegant crown molding, and luxury plank flooring that flows seamlessly through the home. The stylish kitchen is equipped with stainless steel appliances, creating a sleek and functional space for everyday living and entertaining. A
Sweet 3 bed, 2 bath, 1368 sq ft, home on a corner lot in the heart of Winter Springs. Recently remodeled! Fresh Paint, New Kitchen, SS appliances, Tile flooring throughout, Dining area, Living and Family Room, inside laundry room. Big, open, wrap-around porch in back is pre-plumbed & trussed for possible expansion of Primary Bedroom. Fenced in backyard, with mature oaks and landscaping. Single
This home still looks like new. Beautifully done, custom ordered by original owner. It is a must to see. Open front porch, screened in area attached to carport. En Suite bathroom with sitting room in master bedroom. Hacienda is loaded with amenities-Pickle Ball Court, Doggy Park, Putt Putt Courses, BBQ Grills for outside grilling and much more- Major roads close. Only 45 minutes to the beaches or
Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. New shingle roofing installed within the past months. Freshly painted and new luxury vinyl flooring throughout the unit. 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
Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an
Prime Investment Opportunity – 3711 N Ronald Reagan Blvd, Longwood, FL 32750! This versatile .65-acre property (including an adjacent parcel) offers outstanding potential for residential use, commercial redevelopment, or a developer seeking to build or operate a business in a rapidly growing Central Florida location. Featuring a solid 960 sqft block-construction building (built 1969) with a
Housing Choice Voucher applicants are welcome. Welcome to this move-in ready 3-bedroom, 2.5-bathroom home located in the highly desirable Greenspointe community of Winter Springs. Offering 1,721 square feet of living space, this home features one of the area's most desirable floor plans with the primary suite conveniently located on the first floor and a spacious loft upstairs that can serve as a
Experience resort-style living at The Avenues at Winter Springs! Our pet-friendly community offers spacious 1, 2, and 3-bedroom apartment homes with modern finishes and everyday conveniences.Enjoy amenities like a resort-style pool with sundeck, 24-hour fitness and wellness center, tennis court, playground, and leash-free pet park. Stay connected with 400 Mbps internet, and take advantage
Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature
Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located
SPLIT THE PAYMENT! Reserve your new home by paying 50% of your security deposit now, with the remaining balance due before move-in.Welcome to 209 Banyan Court, a comfortable 3-bedroom, 2-bathroom home offering 1,305 square feet of inviting living space. Step inside to find a bright living area that flows effortlessly into the kitchen, which features a full suite of stainless steel
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2454.90. That covers your base rent, $2310.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve
Property Id: 2121780 Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the heart of Winter Springs, FL. Built in 1998 and freshly renovated, this home features brand new luxury vinyl plank flooring, modern kitchen cabinets topped with quartz countertops, a new refrigerator, updated bathroom vanities, and fresh interior and exterior paint. Enjoy a bright, open
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2339.90. That covers your base rent, $2195.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2189.90. That covers your base rent, $2045.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,
Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,
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