$314,338Average Value$229Average Price per Sq Ft44Homes 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 57 days on the market compared to the national average of 54 days. The median sale price for homes in Highlands, Winter Springs over the last 12 months is $303,500, down 8% from the median home sale price over the previous 12 months.
Welcome to 710 Briarwood Drive in highly desirable Winter Springs! This beautifully maintained 4-bedroom, 2-bath home offers 1,769 square feet of comfortable living space, perfectly positioned on a quiet cul-de-sac with a private backyard setting. Inside, you’ll find Luxury vinyl and tile flooring throughout — no carpet — creating a clean, cohesive look and easy maintenance. The bright white
PRICE REDUCTION: Welcome to your dream home in the highly sought-after Deer Song Community of Winter Springs! This charming 3-bedroom, 2-bath corner single family home is packed with upgrades, including a brand new hot water heater (installed 2/23/2026), a newer roof (2021) and re-plumb (2021), state-of-the-art appliances (2021-2022), a top-of-the-line air conditioning system (2022), a water
Experience the perfect blend of location and low-maintenance living at 471 Harbor Winds Court. Located in a secure, gated Winter Springs community, this move-in ready home offers ultimate peace of mind with a NEW ROOF (2024). The functional interior features a rare and highly desired Large Primary Suite on the Main Floor, complete with dual closets for abundant storage. The open, inviting layout
4-Point Inspection completed 01/12/2026 is available in the MLS. The clay tile roof has approximately 13 years of remaining useful life. HVAC (2017–2018), electrical panels, plumbing, and water heater (2022) were all reviewed and marked satisfactory. An insurance quote is available upon request. This well-maintained two-story home offers 1,721 sq ft of living space with a bright, open layout,
Welcome home to this charming 3-bedroom, 2-bathroom home, which offers 1,032 square feet of beautifully updated living space. This property features a newly painted interior and a fully remodeled eat-in kitchen equipped with brand-new stainless steel appliances, shaker cabinets with modern hardware, a trendy backsplash, and granite countertops. The home is designed with a functional split-floor
Welcome to the Seven Oaks Community, where this lakefront pool home offers the perfect blend of luxury, comfort, and Florida lifestyle! Nestled on a spacious lot with peaceful views of Boat Lake, this beautifully maintained home is designed for everyday living and creating unforgettable memories. When you arrive, you will be impressed by the mature landscaping and curb appeal. Step inside to find
***Buyer's Financing fell through***Looking for a 4-bed home in Winter Springs with Seminole County schools, wooded views, and easy access to parks, trails, and shops? Welcome to 114 Sundance Ct, a move-in ready gem with real lifestyle value. Set in the quiet cul-de-sac community of The Seasons, this home offers a blend of comfort, convenience, and nature. The open floor plan features vaulted
Experience comfort and effortless living in this beautifully maintained Winter Springs home with LOW HOA fees and COMPLETE PRIVACY- NO SHARE WALLS. The open living area impresses with VAULTED CEILINGS, UPGRADED LAMINATE FLOORINGS, STYLIST FIXTURES, AND CHARMING FIREPLACE. The well-designed kitchen offers generous storage, while the serene primary suite features double closets and an ENSUITE BATH.
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
Own this well-maintained 2 bedroom, 1 1/2 bath townhome for less than rent in Winter Springs! Excellent opportunity for both owner-occupants and investors.Spacious, open floor plan with covered & screened patio overlooking peaceful water and conservation views. The main living areas are designed for practical everyday living and entertaining.Upstairs features two generously sized bedrooms
Welcome to this charming 3-bedroom, 2-bath home nestled on a spacious cul-de-sac lot in the heart of Winter Springs. Offering added privacy and room to spread out, the oversized homesite provides a peaceful setting while still being close to everything you need. Inside, you’ll find a warm and inviting interior with tile and wood flooring throughout, complemented by neutral tones that make it easy
One or more photo(s) has been virtually staged. You will LOVE living in Baytree, a towhome styled condominium community in the desirable Highlands of Winter Springs! This home has been well loved and owned by the same owner for many years and is ready for YOU to make it YOURS. Offering a great floor plan and lots of space with a screen enclosed back porch and covered entry. Two large bedrooms on
Brand-new 2026 Jacobsen Home 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 decorative
HACIENDA VILLAGE 55+ WELL MAINTAINED HOME! PERFECT FLOOR PLAN. INSIDE UTILITY CENTRAL AIR SYSTEM - FULL SYSTEM 2 HTD AREA 2 BEDROOMS - SPACIOUS MASTE SUITE WITH DRESSING, KITCHEN HAS AN ISLAND TOP COOKING. BEAUTIFUL BACKYARD AND SCREENED INSIDE PORCH. HACIENDA VILLAGE IS A LEGACY COMMUNITY - WITH NEW AMENITIES. MONTHLY Base RENT $1075. COME SEE US TODAY!
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 bar area
Beautiful 3-bedroom, 2-bath home located in the desirable Seasons at Mt. Greenwood community in Winter Springs. Offering 1,161 sq. ft. of living space, this well-maintained home features a freshly painted interior, granite countertops, rich cherrywood cabinetry, recessed lighting, and vaulted ceilings with a skylight that fills the great room with natural light. Enjoy relaxing on the spacious
One or more photo(s) has been virtually staged. **Limited Time Offer - 1/2 Off Second’s Month Rent! Beautiful property updated and ready for immediate occupancy! This stunning residence features a bright and open floor plan with soaring ceilings and modern luxury vinyl flooring throughout. The modern updated kitchen boasts new grey shaker soft-close cabinets, a dual stainless steel sink, and
Move-in ready and easy to rent! This 3BR/2.5BA townhome in gated Harbor Winds in Winter Springs offers a fast approval process — no HOA application required.Bright open layout, kitchen with 42” cabinets, granite counters, and stainless steel appliances. Private entrance and screened lanai. Upstairs features wood floors throughout and a spacious primary suite with tray ceiling, jetted tub, and
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
A RARE FIND! Fantastic Florida ranch-style home available for lease in The Arbors of Mt. Greenwood with NEW ROOF. Move in tomorrow as this property is ready NOW! This meticulously maintained 3 bed 2 bath home with split floor plan has 1,500 sq ft of living space, a spacious screened lanai backing up to conservation area, and is situated snug in the hamlet of Winter Springs. This property is zoned
Welcome to Mosswood Apartments! At Mosswood, you'll find comfortable apartments with washer/dryer connections & extra storage. We're located just north of Orlando in Winter Springs, FL. Come home to our quiet residential setting & lake views that have easy access to I-417 and public transportation. Our single-story, villa-style East Winter Springs apartments feature private entrances and patios
**TWO WEEKS FREE-MOVE IN QUICKLY -within two weeks** Move in today and take advantage of our Two Weeks FREE Rent Special! Secure your new home now and enjoy instant savings. Valid for a limited time only – don’t miss out! Welcome to 209 S Moss Rd — a comfortable home featuring two spacious bedrooms, two and a half bathrooms. Conveniently located near schools, shopping, and major highways, this
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
Well maintained 4 Bedroom/2 bath home includes a large bonus office/den. New Kitchen, Gas HVAC system, washer and dryer included. Large fenced rear yard on corner lot. Covered patio perfect for entertaining. Pets must be Owner approved (Dog $400 non-refundable pet deposit) Cat $200 non-refundable pet deposit. Spacious family home.
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
Welcome home to this move-in ready 2 bedroom, 1.5 bath ground level condo located in a quiet quadplex just northeast of Downtown Orlando. With 909 square feet of comfortable living space, this home offers a practical layout that feels both cozy and functional. You’ll appreciate the in-unit washer and dryer hookups for added convenience, along with the ease of ground-floor access. The kitchen and
Spacious & Modern 4 Bed 2 Bath Home in Winter Springs – Huge Fenced Yard & Garage - Newly Renovated - Move-In Ready April 1 Requirements: -560 credit score minimum - Minimum Security Deposit = $2450 (may be more depending on generated credit score in application)-Maximum of 2 pets -No aggressive dog breeds Welcome to your next home at 119 N Alderwood St in
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