$314,477Average Value$226Average Price per Sq Ft57Homes 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 64 days on the market compared to the national average of 58 days. The median sale price for homes in Highlands, Winter Springs over the last 12 months is $305,000, down 7% from the median home sale price over the previous 12 months.
Beautifully maintained 2-bedroom, 2-bath single-family home located in the desirable Deersong community of Winter Springs! Built in 1994 and offering 1,105 heated square feet, this move-in-ready home features numerous major updates for peace of mind. Recent improvements include interior paint (2025), waterproof laminate flooring in the living room and both bedrooms (2025), a full-home repipe
One or more photo(s) has been virtually staged. Welcome to 724 Lakeside Dr, nestled in the highly sought-after Wildwood community. This beautifully maintained 2-bedroom, 2-bathroom home offers 1,168 square feet of comfortable living space and presents an excellent opportunity for first-time homebuyers, downsizers, or anyone seeking a move-in-ready home in one of Winter Springs' most established
Welcome to 504 Green Spring Circle, a beautifully maintained 2 bedroom 2.5 bath townhome nestled in the heart of Winter Springs, where comfort, charm, and everyday functionality come together effortlessly. Inside, the UPDATED KITCHEN features modern finishes, GRANITE countertops, ample prep space, and room for a dine-in table. The home has been thoughtfully maintained, offering peace of mind 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
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, providing
Seller offering $2,500.00 toward Buyers Closing costs with an acceptable offer. Welcome to your dream home, perfectly positioned for easy commuting in Central Florida. This 3 bedroom, 2 full baths, split bedroom plan and screen enclosed side porch home boasts upgrades that make it shine brighter than most — capturing attention with these enhancements: Water Heater (Installed 03/2026), Roof
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
Set in the heart of Winter Springs, 71 Bombay Ave offers the kind of opportunity buyers are always looking for: an established location, a functional footprint, and the chance to create a home that reflects their own style. This property is ready for its next chapter, making it an ideal choice for those who appreciate potential, value, and the ability to personalize a space over time. Life here
Charming 4-Bedroom Home in the Heart of Winter Springs! Welcome to this well-positioned 4-bedroom, 1.5-bath home offering comfort, functionality, and a spacious lot in an established Winter Springs neighborhood. Situated on nearly a quarter acre, this property provides plenty of outdoor space for entertaining, gardening, pets, or future enhancements. Inside, you'll find a practical floor plan
BEST QUADPLEX IN THE NEIGHBORHOOD — PRIME LOCATION DIRECTLY ACROSS FROM Torcaso Park!Exceptional investment opportunity in a high-demand rental area with strong income potential and low maintenance. This well-kept quadplex features key upgrades, stable tenants, and excellent upside in rents.Major improvements include a roof replacement in 2018 and three of four exterior A/C units replaced
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
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
This brand-new 2026 "The Solara" model offers a perfect blend of style and functionality, featuring recessed lighting, luxury plank flooring, and a beautiful decorative glass entry door. The modern kitchen is equipped with stainless steel appliances and a spacious island, ideal for cooking and entertaining. The home also includes a walk-in closet for added storage and a shed with
Brand-new 2026 Home - The Riviera - 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
Dreams Do Come True CABLE INCLUDED!! All new Stainless Steel style Appliances and this Gem is ready for you! Welcome home to this stunning 3-bedroom, 2-bath First-floor condo offering nearly 1,200 sq ft of wide-open living space designed for effortless entertaining and everyday comfort. From the moment you step inside, you’ll appreciate the no-wasted-space floorplan, stylish tile flooring, Open
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
Experience the perfect blend of modern style and functional living in this impressive 1,161 sq ft residence, designed for a seamless single-story layout. The inviting interior features a bright, open-concept layout with stylish wood-look flooring and soaring vaulted ceilings, where the spacious living area flows directly into a contemporary kitchen fully equipped with a complete suite of
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 $2669.90. That covers your base rent, $2525.00 + 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,
Property Id: 2567526Here is a professional, conversion-focused TurboTenant description tailored to the specific details of the property at 213 S Moss Rd. It uses clear spacing and bullet points for high readability on mobile devices, with absolutely no emojis.Charming 2-Bedroom Rental in the Heart of Winter SpringsWelcome to 213 S Moss Road, a well-designed 2-bedroom property offering the
Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.
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,
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 $2639.90. That covers your base rent, $2495.00 + 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 lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and
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