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Highlands Homes for Sale

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  • /45

    $499,900

    Open Sat 11AM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 2,222 Sq Ft

    472 Dewars Ct, Winter Springs, FL 32708

    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

    Agent Photo

    David Coker

    KELLER WILLIAMS WINTER PARK

    (321) 608-4087

    472 Dewars Ct, Winter Springs, FL 32708
  • /33

    $313,700

    $4K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,878 Sq Ft

    702 Glasgow Ct, Winter Springs, FL 32708

    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

    Agent Photo

    Carrie Shawfield

    SHAWFIELD REALTY GROUP

    (321) 638-5391

    702 Glasgow Ct, Winter Springs, FL 32708
  • /73

    $384,900

    $35K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,721 Sq Ft

    622 Anhinga Rd, Winter Springs, FL 32708

    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

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 450-8473

    622 Anhinga Rd, Winter Springs, FL 32708
  • /30

    $279,990

    $6K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,091 Sq Ft

    314 San Gabriel St, Winter Springs, FL 32708

    **BUYER INCENTIVE AVAILABLE!! Preferred Lender is offering a COMPLIMENTARY TEMPORARY RATE BUY DOWN for qualified buyers on new loan locks completed on or before 6/30/26!!** 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

    Agent Photo

    Linda Bain

    WEICHERT REALTORS HALLMARK PRO

    (321) 467-7851

    314 San Gabriel St, Winter Springs, FL 32708
  • /29

    $225,900

    • 2 Beds
    • 2 Baths
    • 1,134 Sq Ft

    71 Bombay Ave, Winter Springs, FL 32708

    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

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    Heather Unger, PA

    ACME REAL ESTATE FLORIDA LLC

    (321) 394-9487

    71 Bombay Ave, Winter Springs, FL 32708
  • /35

    $285,000

    • 4 Beds
    • 1.5 Baths
    • 1,212 Sq Ft

    101 Melton Dr, Winter Springs, FL 32708

    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

    Agent Photo

    Ariel Vargas

    EXP REALTY LLC

    (321) 205-9958

    101 Melton Dr, Winter Springs, FL 32708
  • /27

    $235,000

    $15K PRICE DROP
    • 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
  • /33

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,857 Sq Ft

    629 Ryan Ct, Winter Springs, FL 32708

    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

    Lisa D Orazio SOTERA LIVING

    629 Ryan Ct, Winter Springs, FL 32708
  • /2

    $132,500

    • 2 Beds
    • 2 Baths

    8 La Vista Dr, Winter Springs, FL 32708

    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

    Todd Vagts Hacienda Village

    8 La Vista Dr, Winter Springs, FL 32708
  • /2

    $135,500

    • 2 Beds
    • 2 Baths

    77 Majorca Dr, Winter Springs, FL 32708

    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

    Todd Vagts Hacienda Village

    77 Majorca Dr, Winter Springs, FL 32708
  • /54

    $28,700

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,358 Sq Ft

    272 Ponce de Leon Dr, Winter Springs, FL 32708

    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!

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    272 Ponce de Leon Dr, Winter Springs, FL 32708
  • /40

    $264,900

    Open Sat 2PM - 4PM
    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft

    724 Lakeside Dr, Winter Springs, FL 32708

    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 neighborhoods.As you step

    Eric Campbell LPT REALTY, LLC

    724 Lakeside Dr, Winter Springs, FL 32708
  • /35

    $285,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,089 Sq Ft

    276 San Gabriel St, Winter Springs, FL 32708

    Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity for anyone looking for a move-in-ready property in Winter Springs. With its newly updated kitchen, Modern faucet, granite countertops, and indoor laundry. High ceilings at living room, the home feels both modern and spacious. The community offers excellent amenities, including a gated pool and tennis

    Mariam Sherkawy KELLER WILLIAMS WINTER PARK

    276 San Gabriel St, Winter Springs, FL 32708
  • /54

    $35,000

    $41K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 672 Sq Ft

    80 Majorca Dr, Winter Springs, FL 32708

    Just bring a toothbrush- This home has all new everything. It was completely remodeled in 2021/2022. 1 bedroom with a den in front (could be used as a second bedroom). New A/C unit to keep you nice & cool! Handicap accessible with a ramp. There is a gas line to the home. There is a gas tankless hot water heater. All new windows with exception of the kitchen bay window. The roof is new with

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    80 Majorca Dr, Winter Springs, FL 32708
  • /58

    $820,000

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,252 Sq Ft

    330 Hayes Rd, Winter Springs, FL 32708

    Located on 2 acres with R-1AA zoning, this property offers space, flexibility, and privacy while still being conveniently close to everyday essentials. Ideal for those looking to keep horses, store equipment, or run a home-based business.The home features a bright, open layout with high ceilings, abundant natural light, and updated windows with plantation shutters. The remodeled kitchen

    Glendys Lorenzo Martinez NONA LEGACY POWERED BY LA ROSA

    330 Hayes Rd, Winter Springs, FL 32708
  • /40

    $269,000

    $11K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    446 Club Dr, Winter Springs, FL 32708

    Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third

    Hanoi Burgos COLDWELL BANKER REALTY

    446 Club Dr, Winter Springs, FL 32708
  • /46

    $1,199,000

    $200K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 4,464 Sq Ft

    120 E Bahama Rd, Winter Springs, FL 32708

    Mid-Century Modern Paradise!! A Beautiful, well-designed home with spectacular architecture offering privacy, space, and long-term versatility on a rare 2.22-acre lot with RV/Toy parking—delivering exceptional value in this area. A separate in-law or guest suite features its own exterior entrance and full bathroom, ideal for multigenerational living, a private office, studio, or extended stays.

    Alma Merrill EXP REALTY LLC

    120 E Bahama Rd, Winter Springs, FL 32708
  • /33

    $232,000

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,002 Sq Ft

    506 Club Dr, Winter Springs, FL 32708

    Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. Residents enjoy amenities

    Kathleen Harrison CALL IT CLOSED INTL REALTY

    506 Club Dr, Winter Springs, FL 32708
  • /53

    $39,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    442 Dorado Dr, Winter Springs, FL 32708

    Hacienda Village a 55+ Community has been updated-Pickel Ball Courts, 2 Pools one heated, Putt Putt, Doggy Park, Tiki Huts, Grills, always something going on. Hacienda Village has easy access to all major highways with beaches and Parks only 45 minutes away. Fire and Police Dept close by, Restaurants, Medical, Shopping and more in the area.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    442 Dorado Dr, Winter Springs, FL 32708
  • /24

    $300,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,366 Sq Ft

    712 Linden Dr, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to this well-maintained 3-bedroom, 2-bathroom block townhome offering 1,366 square feet of comfortable living space in the desirable Wildwood community of Winter Springs. Tucked along a quiet tree-lined street. Inside, the home features an open and inviting layout highlighted by vaulted ceilings, neutral tones, and vinyl flooring that create

    Kaleb Shaw SHAW SIGNATURE RE

    712 Linden Dr, Winter Springs, FL 32708
  • /25

    $210,000

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,400 Sq Ft

    30 Moree Loop Unit 39, Winter Springs, FL 32708

    Welcome to your move-in ready 3-bedroom, 2.5-bath townhome-style condo located in the desirable Highlands of Winter Springs community known for its beautiful tree-lined streets, scenic walking trails, and resort-style amenities. This stylish home offers approximately 1,400 square feet of updated living space designed for comfort and low-maintenance living. Inside, you’ll find a fully remodeled

    Casey Irwin PARK VIEW REALTY INC

    30 Moree Loop Unit 39, Winter Springs, FL 32708
  • /35

    $259,000

    $21K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,089 Sq Ft

    270 San Gabriel St, Winter Springs, FL 32708

    Price Improvement to $259,000 * Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly

    Alie Gattis MAINFRAME REAL ESTATE

    270 San Gabriel St, Winter Springs, FL 32708
  • /50

    $59,900

    $20K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    168 Costa Cir, Winter Springs, FL 32708

    BEAUTIFUL RENOVATED HOME with ALL NEW APPLIANCES including a surface gas stove, new hot water heater & HVAC. Beautiful 4 panel doors, vinyl flooring throughout.All new vapor barrier and installation underneath. New homes will be put in next door and this home has beautiful landscaping all around. This is a must see home! Shopping,Restaurants, major highways nearby. Fire Department, hospital,

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    168 Costa Cir, Winter Springs, FL 32708
  • /45

    $770,000

    $78K PRICE DROP Pre-Foreclosure
    • 6 Beds
    • 4 Baths
    • 3,100 Sq Ft

    135 W Trade Winds Rd, Winter Springs, FL 32708

    Discover this stunning home nestled on over an acre in the highly sought-after Ranch Lands, where you can enjoy the freedom of no HOA—offering ample space and proximity to Orlando, shopping, theme parks, beaches, and both Orlando and Sanford airports; pull into the oversized roundabout driveway and step into a bright living room, with access to the kitchen or a right turn to the second level

    Joshua Crittendon EXP REALTY LLC

    135 W Trade Winds Rd, Winter Springs, FL 32708
  • /49

    $45,000

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft

    210 El Camino Real Cir, Winter Springs, FL 32708

    Bought A New Home in Hacienda, Letting this perfect one go-Private backyard; newer windows, All ducts redone-Electric up to date-Hacienda centrally located about 45 minutes to the beaches & parks, Hacienda has a lot of amenities-2 pools, pickle ball, doggy park. Close to fire and police station, restaurants, shopping. Monthly base rate is $1075.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    210 El Camino Real Cir, Winter Springs, FL 32708
  • /32

    $49,900

    $8K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft

    382 La Vista Dr, Winter Springs, FL 32708

    NEWLY RENOVATED- 2 BEDROOM/2 BATH- 1 MONTH FREE LOT RENT!!! Totally Renovated home with new drywall, paint, & baseboards. Bathrooms have been beautifully renovated with new vanities, showers, and fixtures. Flooring and sub flooring has been installed with waterproof vinyl laminate. All new stainless-steel appliances. The A/C is a 3-new A/C mini split installed, 1 in each bedroom and 1 in the main

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    382 La Vista Dr, Winter Springs, FL 32708
  • /28

    $284,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 974 Sq Ft

    337 Kirkcaldy Dr, Winter Springs, FL 32708

    Warm and inviting home located in the highly sought-after Highland Village community of Winter Springs—where residents love to live and rarely want to leave. This 2-bedroom, 2-bath home features an open floor plan, abundant natural light, and no carpet throughout. The spacious living and dining areas open a comfortable layout, perfect for everyday living or entertaining. The primary bedroom is

    Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO

    337 Kirkcaldy Dr, Winter Springs, FL 32708
  • /24

    $365,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,769 Sq Ft

    710 Briarwood Dr, Winter Springs, FL 32708

    MOVE-IN READY WITH NEW ROOF & HVAC SYSTEM TO BE COMPLETED PRIOR TO CLOSING. Beautifully updated 4-bedroom, 2-bath home in Winter Springs featuring a spacious layout, modern upgrades, and a fresh, clean feel throughout. Inside, you’ll find fresh interior paint, updated lighting and ceiling fans, new baseboards and trim, and custom shelving in the living room. The home features multiple living

    Steven Koleno BEYCOME OF FLORIDA LLC

    710 Briarwood Dr, Winter Springs, FL 32708
  • /54

    $18,000

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths

    364 Casa Grande Dr, Winter Springs, FL 32708

    Priced to Sell - Make Offer - Screened in Porch, Good Size Shed, 2 Bedrooms, 2 Baths, Located in Phase III, Golf Cart Path Close. Hacienda Village has a lot of amenities, 2 pools (1 heated), Pickleball, Putt Putt, Doggy Park. Hacienda is located near major highways within 45 minutes of beaches & parks - Check us out! Base Monthly rent is $1075.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    364 Casa Grande Dr, Winter Springs, FL 32708
  • /30

    $545,000

    • 5 Beds
    • 3 Baths
    • 2,852 Sq Ft

    811 Maple Leaf Loop, Winter Springs, FL 32708

    Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen includes a functional island, and the primary bathroom provides double sinks for practical use, a walk in closet and convenience of a separate tub and shower. Beyond the interior, exterior grounds feature a covered patio and a fenced in backyard. Discover modern comfort and practical living in this updated

    Karen Albright OPENDOOR BROKERAGE LLC

    811 Maple Leaf Loop, Winter Springs, FL 32708
  • /28

    $354,900

    • 3 Beds
    • 2.5 Baths
    • 1,498 Sq Ft

    1562 Grand Rue Dr, Casselberry, FL 32707

    Welcome to this like-new 2022 Craftsman-style END-UNIT townhome in the heart of highly desirable Seminole County! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern design, energy efficiency, and low-maintenance living. As an end unit, the home is filled with abundant natural light and offers additional privacy along with extra green space to enjoy—without the

    Simon Colak USCO CAPITAL GROUP

    1562 Grand Rue Dr, Casselberry, FL 32707
  • /38

    $228,800

    • 3 Beds
    • 2 Baths
    • 1,326 Sq Ft

    618 Locust Ct, Winter Springs, FL 32708

    The seller is currently in a multiple offer scenario related to the Buyer/Property Address listed aboveand you are receiving this message as a result of a request for the Buyer's highest and best offer. Should the Buyer choose to participate in submitting their highest and best offer, the deadline to doso is 6/10/2026 11:59:00 PM Mountain Time.***SEE ATTACHMENTS...Awesome opportunity

    dave kellam REAL ESTATE PROFESSIONALS SE

    618 Locust Ct, Winter Springs, FL 32708
  • /50

    $29,900

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft

    128 Las Almas Ln, Winter Springs, FL 32708

    SURPRISE!- A large enclosed bonus room not included in the square footage! Double carport area. Home has been renovated! A lot of bang for the buck! Close to recreation Hall and heated pool. Hacienda has a lot to offer, it is centrally located, close to major highway-45 minutes to beaches, 9 parks. Fire & Police Dept. 5 minutes away. Restaurants, shopping medical near. Never a dull moment with

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    128 Las Almas Ln, Winter Springs, FL 32708
  • /26

    $48,998

    $6K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,032 Sq Ft

    288 La Vista Dr, Winter Springs, FL 32708

    This move-in-ready home has been beautifully updated from top to bottom, featuring a metal roof, new flooring throughout, new drywall, updated walls, remodeled bathrooms, a brand-new kitchen, and newer appliances. As you enter the home, you are welcomed by a spacious enclosed Florida room, perfect for relaxing and enjoying Florida sunsets in a private and comfortable setting. The open-concept

    Corali Fuentes Four Star Homes, Inc.

    288 La Vista Dr, Winter Springs, FL 32708
  • /47

    $24,900

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 966 Sq Ft

    242 Aztec Dr, Winter Springs, FL 32708

    Bank Owned-repainted-2-bedroom, 2 bath newer HVAC about 2023. Hacienda Village has recently been renovated with an added pickle ball court, putt putt, Doggy Park, Tiki Huts, Barbecue's, and More. Hacienda is located near major highways with only about 45 minutes to Beaches & Parks, Restaurants, Shopping, Doctors, Fire & Police Departments close by. Monthly base rent is $1075.00.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    242 Aztec Dr, Winter Springs, FL 32708
  • /37

    $250,000

    • 2 Beds
    • 2.5 Baths
    • 1,363 Sq Ft

    504 Green Spring Cir, Winter Springs, FL 32708

    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

    Riki Cantelli EXP REALTY LLC

    504 Green Spring Cir, Winter Springs, FL 32708
  • /50

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,178 Sq Ft

    335 Kirkcaldy Dr, Winter Springs, FL 32708

    Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new

    Irina Carp MILLENIUM REALTY GROUP

    335 Kirkcaldy Dr, Winter Springs, FL 32708
  • /43

    $489,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,309 Sq Ft

    131 Lisa Loop, Winter Springs, FL 32708

    Check out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly sought-after Seminole County school district! Discover comfort and space in this corner lot home in The Oaks at the Highlands Subdivision. This well-designed home offers more than 2,300 square feet of living space with a functional layout that features the primary suite on the first floor along with a flex

    Nathan Bailey BAILEY CAMPBELL PROPERTIES

    131 Lisa Loop, Winter Springs, FL 32708
  • /33

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,161 Sq Ft

    108 Sundance Ct, Winter Springs, FL 32708

    Welcome home to this beautifully remodeled gem tucked away on a quiet cul-de-sac in desirable Winter Springs! From the moment you walk in, you’ll fall in love with the bright, open-concept layout designed for easy living and effortless entertaining. With 1,161 sq ft under air, every inch of this home has been thoughtfully updated and filled with charm.The stunning fully remodeled kitchen is

    Matias Gomez JEMINI REALTY CORP

    108 Sundance Ct, Winter Springs, FL 32708
  • /2

    $135,500

    • 2 Beds
    • 2 Baths

    154 Hacienda Dr Unit 154, Winter Springs, FL 32708

    This brand-new 2026 model home offers modern comfort and style throughout, featuring recessed lighting, elegant crown molding, and durable luxury plank flooring. The thoughtfully designed layout includes spacious walk-in closets and a versatile den-perfect for a home office or study space. The kitchen is equipped with sleek stainless steel appliances, and the property also includes a shed with

    Todd Vagts Hacienda Village

    154 Hacienda Dr Unit 154, Winter Springs, FL 32708

Showing Results 1 - 40, Page 1 of 3

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

Is Highlands a good place to live?
Highlands is a good place to live. Highlands is considered car-dependent and bikeable with minimal transit options. Highlands has 9 parks for recreational activities. It is fairly sparse in population with 5.0 people per acre and a median age of 40. The average household income is $72,590 which is below the national average. College graduates make up 29.8% of residents. A majority of residents in Highlands are home owners, with 39% of residents renting and 61% of residents owning their home. A local real estate agent serving Highlands can help you decide if this neighborhood is the right one for you. Learn more on our Highlands neighborhood guide.
Is Highlands, FL a safe neighborhood?
Highlands, FL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.
How much do you need to make to afford a house in Highlands?
The median home price in Highlands is $319,450. If you put a 20% down payment of $63,900 and had a 30-year fixed mortgage with an interest rate of 6.52%, your estimated principal and interest payment would be $1,620 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K a year to afford the median home price in Highlands. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Highlands is $73K.
What are the best public schools in Highlands?
The best public schools that serve Highlands are:
  • Seminole High School has an A- Niche grade, a student teacher ratio of 21:1 and an average review score of 3.9.
  • Lake Mary High School has an A- Niche grade, a student teacher ratio of 21:1 and an average review score of 3.9.
  • Winter Springs High School has an A- Niche grade, a student teacher ratio of 19:1 and an average review score of 3.6.
What are the best private schools in Highlands?
The best private schools that serve Highlands are:
What are the most popular zip codes in Highlands, Winter Springs, FL?
The most popular zip codes in Highlands, Winter Springs, FL include 32708, 32707, 32750, 32746 and 32773.
What are the most popular neighborhoods near Highlands, Winter Springs, FL?
The most popular neighborhoods near Highlands, Winter Springs, FL are Longwood Lakes, Greenwood Lakes, Alaqua, Lake Howell and Spring Valley.
Are home prices dropping in Highlands?
Yes, home prices in Highlands are down 8% in the last 12 months.

Highlands Home Prices vs. Nearby Winter Springs, FL Neighborhoods

Highlands Central Park Conway Willow Run
Median Home Price
$319,450
$329,999
$361,500
$319,999
Median Sale Price
$300,000
-9% YoY
$325,000
+10% YoY
$360,000
-4% YoY
$292,500
-11% YoY
Median Single Family Price
$322,450
$326,200
$430,000
$315,000
Median Townhouse Price
$354,900
$220,000
$302,500
$269,900
Median Condo Price
$172,000
$202,500
$158,000
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Total Active Listings
53
21
143
21
Market Conditions
5 Months
Balanced Market
2 Months
Seller's Market
5 Months
Balanced Market
3 Months
Seller's Market
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