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Highlands Homes for Rent

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    $1,153 - $3,490 per month

    The Avenues at Winter Springs

    1 - 3 Beds

    1 Laurel Oaks Dr, Winter Springs, FL 32708

    The Avenues at Winter Springs offer a tranquil living experience in Winter Springs, FL, blending comfort, convenience, and affordability. Nestled in a serene residential area, residents enjoy peaceful surroundings while remaining conveniently close to Interstate 4 and the vibrant Uptown Altamonte Springs area. With easy access to shopping, dining, and entertainment options, residents can explore

    1 Laurel Oaks Dr, Winter Springs, FL 32708
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    $2,000 per month

    • 2 Beds
    • 2 Baths
    • 909 Sq Ft
    • House for Rent

    500 Evergreen Ave, Winter Springs, FL 32708

    ONE OF A KID 2 BEDROMMS, 2 BATHS REMODELED SINGLE FAMILY HOME LOCATE IN THE HEART OF WINTER SPRIGS... HOME HAS 2 FULL REMODELED BATHROOMS, NEW CERAMIC FLOOR, NEW CABINETS & COUNTERTOPS, NEW FULL SET OF APPLIANCES INCLUDING WASHER AND DRYER...LOCATED IN A LARGE FENCED CORNER LOT, READY FOR THE RIGHT TENANTS... CONTACT US NOW BEFORE IS GONE

    Hilton Soto HJ BEST PROPERTIES LLC

    500 Evergreen Ave, Winter Springs, FL 32708
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    $1,100 - $1,600 per month

    Mosswood

    Studio - 2 Beds

    101 Mosswood Cir, Winter Springs, FL 32708

    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

    101 Mosswood Cir, Winter Springs, FL 32708
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    $2,150 per month

    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft
    • Townhouse for Rent

    670 Macduff Ln Unit A, Winter Springs, FL 32708

    Spacious, updated townhouse style half-duplex with 2 car garage and yard in the highly desirable Highlands Community! Open floor plan with high ceilings & fireplace. Ample front and back yards! Updates include fresh interior neutral paint & LPV floors throughout, granite counters and updated vanities. Located across the street from one of the community parks! Community features multiple parks,

    Jennifer King KELLER WILLIAMS HERITAGE REALTY

    670 Macduff Ln Unit A, Winter Springs, FL 32708
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    $1,596 - $1,912 per month

    Seville on the Green

    1 - 3 Beds

    300 Sheoah Blvd, Winter Springs, FL 32708

    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

    300 Sheoah Blvd, Winter Springs, FL 32708
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    $1,400 per month

    • 2 Beds
    • 1.5 Baths
    • 910 Sq Ft
    • Condo for Rent

    127 Lori Anne Ln Unit 127, Winter Springs, FL 32708

    Nice Move-in ready TWO Bedroom/ 1.5 Bath condo style unit. Located in the north side of Winter Springs, near Moss Road. This unit has ALL tile flooring, new microwave, completely repainted on the inside and Kitchen has Large Eat-in area, plus Granite counter tops... There is Assigned Parking, and the unit is on the first level. Call today to get pre-qualified and schedule a viewing

    Bobby Keen KEEN REALTY GROUP, INC.

    127 Lori Anne Ln Unit 127, Winter Springs, FL 32708
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    $1,174 - $1,799 per month

    Moss Park

    1 - 4 Beds

    170 N Gardenridge Ct, Winter Springs, FL 32708

    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

    170 N Gardenridge Ct, Winter Springs, FL 32708
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    $1,350 per month

    • 2 Beds
    • 1.5 Baths
    • 990 Sq Ft
    • Townhouse for Rent

    156 Lori Anne Ln, Winter Springs, FL 32708

    Charming Updated End-Unit Townhome – Winter Springs, FLNow available for rent! This beautifully maintained 2-bedroom, 1.5-bath end-unit townhome in Winter Springs offers no HOA and a convenient location near the Casselberry border. You’ll have quick access to 434, 17-92, shopping, dining, and top-rated Seminole County schools.Situated on a corner lot, the home provides extra

    Richard Cunningham CHARLES RUTENBERG REALTY ORLANDO

    156 Lori Anne Ln, Winter Springs, FL 32708
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    $2,825 per month

    • 4 Beds
    • 3 Baths
    • 2,933 Sq Ft
    • House for Rent

    109 Lisa Loop, Winter Springs, FL 32708

    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 $2969.90. That covers your base rent, $2825.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    109 Lisa Loop, Winter Springs, FL 32708
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    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • Condo for Rent

    429 Sheoah Blvd Unit 12, Winter Springs, FL 32708

    This spacious 3-bedroom, 2-bath home offers 1,187 sq. ft. of comfortable living in the heart of Winter Springs. Located in a well-maintained community with HOA, this property combines convenience and lifestyle.Enjoy access to a refreshing community pool and beautifully maintained common areas. The home features an inviting layout with ample natural light, making it perfect for both

    Jason Hamilton THE REALTY MEDICS

    429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
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    $2,095 per month

    • 3 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Renovated 3-Bed Home with Modern Upgrades ...

    220 W Panama Rd, Winter Springs, FL 32708

    Welcome to this renovated home, now available in the desirable location of Winter Springs, FL. This property boasts three spacious bedrooms and two full bathrooms, offering ample space for your needs. The home features new laminated wood flooring throughout, adding a touch of elegance and durability. The kitchen is a chef's dream with new white cabinets, stainless steel appliances, and plenty of

    220 W Panama Rd, Winter Springs, FL 32708
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    $1,349 per month

    • 2 Beds
    • 2 Baths
    • 938 Sq Ft
    • Condo for Rent

    117 Cory Ln, Winter Springs, FL 32708

    *Move in now and enjoy your 1st month FREE with a 12-month lease* Welcome home! This fantastic 2-bedroom, 2-bath home is available for immediate move in! Located conveniently in the desirable community of Winter Springs, this property features a comfortable layout with well apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features

    Steve Simpson 407 PROPERTIES

    117 Cory Ln, Winter Springs, FL 32708
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    $2,075 per month

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft
    • House for Rent

    213 Sweetgum Ct, Winter Springs, FL 32708

    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 $2219.90. That covers your base rent, $2075.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    213 Sweetgum Ct, Winter Springs, FL 32708
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    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Townhouse for Rent

    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 features an

    Lee Sloan KELLER WILLIAMS ADVANTAGE REALTY

    424 Club Dr, Winter Springs, FL 32708
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    $2,320 per month

    • 4 Beds
    • 2 Baths
    • 2,014 Sq Ft
    • House for Rent

    20 N 2nd St, Winter Springs, FL 32708

    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 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    20 N 2nd St, Winter Springs, FL 32708
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    $2,499 per month

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    640 Macduff Ln Unit A, Winter Springs, FL 32708

    Step into the inviting warmth of this charming 3-bedroom, 2-bathroom rental home at 640 Macduff Lane, Winter Springs, FL 32708. The spacious living area offers a perfect blend of comfort and style, while the fully equipped kitchen inspires culinary creativity. Enjoy peaceful moments in the delightful backyard or relax on the screened-in porch, all with the added convenience of a two-car garage.

    Steve Simpson 407 PROPERTIES

    640 Macduff Ln Unit A, Winter Springs, FL 32708
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    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,060 Sq Ft
    • House for Rent

    110 Elderwood St, Winter Springs, FL 32708

    **BEAUTIFUL POOL** This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee

    110 Elderwood St, Winter Springs, FL 32708
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    $2,089 per month

    • 3 Beds
    • 2 Baths
    • 1,008 Sq Ft
    • House for Rent

    762 S Edgemon Ave, Winter Springs, FL 32708

    Take a look at this lovely home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage, fenced backyard, back screen porch and approximately 1,008 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user)

    Cathy Behe TAH FLORIDA LLC

    762 S Edgemon Ave, Winter Springs, FL 32708
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    $1,790 per month

    • 2 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Townhouse for Rent

    130 Kristi Ann Ct, Winter Springs, FL 32708

    Welcome home to this 2 bed, 1.5 bath townhouse in the heart of Winter Springs. You will be just minutes away from the Winter Springs Town Center, Great Seminole County Schools, Coffee Shops, Premium Gyms, Center Winds Park, and multiple conveniences nearby. The living room and patio offer ample space for relaxation and entertainment. Each bedroom is designed for functionality, with ceiling fans

    130 Kristi Ann Ct, Winter Springs, FL 32708
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    $1,900 per month

    • 4 Beds
    • 2.5 Baths
    • 1,405 Sq Ft
    • House for Rent

    201 Bennett St, Winter Springs, FL 32708

    Four bedroom house in Winter Springs. Close to everything. Nice fenced in back yard.

    Mike Northam NORTHAM REALTY, LLC

    201 Bennett St, Winter Springs, FL 32708
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    $2,300 per month

    • 3 Beds
    • 2 Baths
    • 1,161 Sq Ft
    • House for Rent

    526 Seasons Ct, Winter Springs, FL 32708

    Property Id: 2121780Welcome 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,

    526 Seasons Ct, Winter Springs, FL 32708
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    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,695 Sq Ft
    • House for Rent

    510 Spoonbill Ct, Winter Springs, FL 32708

    Elevate your lifestyle at Greenspointe! This sought-after Winter Springs community offers an abundance of amenities designed for relaxation and recreation: a clubhouse with gathering spaces, sparkling pool, tennis courts, parks, playground, beach volleyball, scenic walking trails, picnic pavilions, and open green spaces.For your convenience FLOOR PLAN WAS ADDED. Step inside and you’ll

    Liliana Lamadrid Sierra LA ROSA REALTY CW PROPERTIES L

    510 Spoonbill Ct, Winter Springs, FL 32708
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    $2,145 per month

    • 3 Beds
    • 2 Baths
    • 1,146 Sq Ft
    • House for Rent

    218 Perth Ct, Winter Springs, FL 32708

    Totally Renovated 3BR/2BA Duplex in Winter Springs Quiet Cul-de-Sac!Welcome to this beautifully updated 3-bedroom, 2-bathroom duplex offering 1,146 sq ft of modern living in the highly desirable Winter Springs community. Nestled in a peaceful cul-de-sac, this home blends style, comfort, and convenience.Property Highlights (Unit B):- Completely renovated interior with brand new

    218 Perth Ct, Winter Springs, FL 32708
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    $1,449 per month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Townhouse for Rent

    250 Moree Loop Unit 6, Winter Springs, FL 32708

    Available for move-in 9/17. Close to shopping and restaurants and A+ schools. This townhome has 2 bedrooms and 1.5 bathrooms. This beautiful home has ceramic tile flooring throughout the downstairs with a living room/dining room/kitchen combination and a half bath downstairs. The large kitchen has a breakfast bar and floor-to-ceiling window that offers great morning natural light. Both bedrooms

    Steve Simpson 407 PROPERTIES

    250 Moree Loop Unit 6, Winter Springs, FL 32708
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    $2,450 per month

    • 3 Beds
    • 2 Baths
    • 1,693 Sq Ft
    • House for Rent

    767 S Edgemon Ave, Winter Springs, FL 32708

    Welcome to the beautiful and peaceful city of Winter Springs. This 3/2 home sits on a large, corner lot with a very spacious fenced-in backyard. Inside, you can enjoy a split floor plan that divides the living room/dining room with a separate family room. A remodeled kitchen features granite countertops, stainless steel appliances, and tile flooring and backsplash. A new and fresh coat of paint

    Peter Dang ALLIANCE RENTAL HOMES

    767 S Edgemon Ave, Winter Springs, FL 32708
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    $2,450 per month

    • 3 Beds
    • 2 Baths
    • 1,401 Sq Ft
    • House for Rent

    302 Bridie Ct, Winter Springs, FL 32708

    3 Bedroom, 2 1/2 Bath Single Family Home For Rent in Winter Springs, FL 32708. Range, Refrigerator, D/W, Disposal, Central Heat and A/C.

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    302 Bridie Ct, Winter Springs, FL 32708
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    $1,970 per month

    • 3 Beds
    • 2 Baths
    • 1,098 Sq Ft
    • House for Rent

    135 Cortez Ct, Winter Springs, FL 32708

    Tucked away on a quiet cul-de-sac in the desirable Winter Springs area, this well-maintained home offers comfort, space, and a fantastic location — perfect for families or anyone seeking a peaceful lifestyle close to everything.Features include:Bright and welcoming interior with neutral paint tonesSpacious screened-in porch, ideal for relaxing or entertainingFully fenced backyard

    Vivian Lippi LIPPI REALTY LLC

    135 Cortez Ct, Winter Springs, FL 32708
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    $2,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • House for Rent

    633 White Ibis Ct, Winter Springs, FL 32708

    Located in the highly desirable city of Winter Springs, this gorgeous updated one story 3 bedroom, 2 bath home is calling your name! Two car garage! Upon entry, you are greeted with a beautiful living room upgraded foyer lighting, To the left you have your master suite with large master bathroom which includes private water closet, stand-up shower, brand new tub, brand new double vanities with

    Yousong Liu SUNSHINE GROUP USA, INC

    633 White Ibis Ct, Winter Springs, FL 32708
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    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Townhouse for Rent

    474 Club Dr, Winter Springs, FL 32708

    Lovely 3 bedroom, 2 bathroom townhome located in the peaceful and well-maintained Cypress Club community in Winter Springs, Florida. This home features a split-bedroom layout with two bedrooms and a full bathroom upstairs, complete with a garden tub and separate shower, and one bedroom with a full bathroom downstairs ideal for guests, extended family, or a home office setup. The living and dining

    Oscar Fonseca JEMCO REALTY & PROPERTY MANAGEMENT

    474 Club Dr, Winter Springs, FL 32708
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    $1,495 per month

    • 2 Beds
    • 2 Baths
    • 972 Sq Ft
    • Condo for Rent

    10 Sheoah Blvd Unit 7, Winter Springs, FL 32708

    Spacious and bright 2 bedroom 2 bathroom condo for rent at The Highlands in Winter Springs. Just repainted throughout entire interior. Large family room with a small dining area. The two bedrooms on a split floor plan. The large master bedroom has sliding doors that lead to patio. The second, smaller, bedroom has its set of sliding doors leading to the screened-in porch and it's own bathroom.

    Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

    10 Sheoah Blvd Unit 7, Winter Springs, FL 32708
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    $2,100 per month

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • House for Rent

    705 Woodlawn Dr, Winter Springs, FL 32708

    Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout is perfect for comfortable living that you can enjoy with your pets too; we’re proud to be pet friendly. Our homes are built using high-quality, eco-friendly materials with neutral paint colors, updated fixtures, and energy-efficient appliances. Enjoy the

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    705 Woodlawn Dr, Winter Springs, FL 32708
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    $2,200 per month

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft
    • Townhouse for Rent

    452 Harbor Winds Ct, Winter Springs, FL 32708

    Welcome to 452 Harbor Winds Ct in the heart of Winter Springs! This spacious and well-maintained 3-bedroom, 2.5-bath townhome offers the perfect blend of comfort, style, and convenience. Step inside to an open-concept floor plan featuring a generous family room, dedicated dining area, and a cozy breakfast nook-ideal for both everyday living and entertaining. The kitchen flows seamlessly into the

    Roxanna Cabrera La Rosa Realty

    452 Harbor Winds Ct, Winter Springs, FL 32708
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    $1,295 per month

    • 2 Beds
    • 1.5 Baths
    • 900 Sq Ft
    • Townhouse for Rent

    181 Garden Dr, Winter Springs, FL 32708

    181 Garden Dr. Winter Springs - Two story townhouse with two bedroom 1 1/2 bath, all bedrooms upstairs. Large back & Front yard. Minutes away from 17-92 and SR 417.

    Courtney Davis ABSOLUTE REALTY GROUP, LLC

    181 Garden Dr, Winter Springs, FL 32708
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    $1,795 per month

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • House for Rent

    506 San Gabriel Ct, Winter Springs, FL 32708

    Move In Special! Receive $250 OFF your first month of rent if approved and moving in by February 23rd!Welcome home to 506 San Gabriel Court, a charming 3 bedroom, 2 bath home featuring 1,187 square feet of living space. As you enter the home, you are welcomed into the main living area, featuring vaulted ceilings and plenty of natural light through the numerous windows and sliding glass

    Justin Recca INNOVATIVE REALTY, LLC

    506 San Gabriel Ct, Winter Springs, FL 32708
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    $1,695 per month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • Townhouse for Rent

    208 Perth Ct Unit B, Winter Springs, FL 32708

    Highlights: 2 Car Garage | Spacious Backyard | Serene Patio | Community Pool | Nature Trails | BBQ Area Grills | Tennis Court | Community Playground | Picnic Area |Discover the vibrant charm of Winter Springs, nestled by the serene Lake Jesup and offering upscale living, diverse dining options, and a rich cultural scene. With pristine parks, top-notch schools, and annual festivities like

    Amy Johnston BELMONT REALTY

    208 Perth Ct Unit B, 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.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Highlands?
The most popular neighborhoods for renters near Highlands are Longwood Lakes, Greenwood Lakes, Alaqua, Lake Howell and Dreamworld.
What are the most popular zip codes for renters near Highlands?
The most popular zip codes for renters near Highlands are 32708, 32750, 32707, 32746 and 32773.
How to Rent a Home