Highlands Homes for Sale

• 

  

  

  /16

  $329,000

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  472 Harbor Winds Ct, Winter Springs, FL 32708

  Delightful 2 story townhouse - backs up to pond. New appliances, Granite counters, New Carpet - MOVE-IN READY.

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  472 Harbor Winds Ct, Winter Springs, FL 32708
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /49

  $350,000

  • 2 Beds
  • 2 Baths
  • 1,502 Sq Ft

  321 Kirkcaldy Dr, Winter Springs, FL 32708

  Great Opportunity in Winter Springs! This single family home has 2 bedrooms, 2 bathrooms, and a large upstairs bonus room - great for an office (or used as another bedroom!). Upon entry you'll be impressed with the high vaulted ceilings and wide open view to the living and dining room. The Primary Bedroom is well sized, and the bathroom features a large walk-in closet, dual sinks, and a shower

  Emily Halpern COLDWELL BANKER REALTY

  321 Kirkcaldy Dr, Winter Springs, FL 32708
• 

  

  

  /35

  $199,900

  $33K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  497 Club Dr, Winter Springs, FL 32708

  Great investment property!...Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! **Freshly Painted with light and neutral colors throughout! Vaulted ceiling in the very spacious/huge... family/great room with a wood burning fireplace! Split bedroom floorplan, with one bedroom downstairs. Brand new ceiling fan

  Edyta Olejnik WATSON REALTY CORP

  497 Club Dr, Winter Springs, FL 32708
• 

  

  

  /31

  $14,700

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  308 Casa Grande Ct, Winter Springs, FL 32708

  2 bEDROOM 2 BATH- A LOT OF THE MAIN WORK DONE! ALL NEW DUCTING,PLUMBING IS GOOD, ELECTRIC GOOD, CARPETING PULLED UP, SUB FLOORING DONE. KITCHEN SOME CABINETS HAVE PULL OUTS. NEW ALL YOU HAVE TO DO IS PUT YOUR OWN PERSONAL TOUCH. THIS IS ONE OF THE MOST POPULAR FLOOR PLANS. YHIS DOES HAVE A SPRINKLER SYSTEM(AS IS) HACIENDA VILLAGE IS FULL OF AMENITIES-2 POOLS, PICKLE Ball. centrally located-base

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  308 Casa Grande Ct, Winter Springs, FL 32708
• 

  

  

  /36

  $179,900

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  70 Moree Loop Unit 61, Winter Springs, FL 32708

  Virtually Staged. If you’ve been dreaming of a MOVE-IN READY home where you can enjoy scenic parks, peaceful walking trails, and beautiful green spaces, welcome to Baytree 9, one of the charming communities within the Highlands of Winter Springs. This WELL-MAINTAINED two-story, 2-bedroom, 11⁄2-bath condo offers the perfect blend of comfort, convenience, and carefree Florida living.Ideally

  Susan Schneider COLDWELL BANKER REALTY

  70 Moree Loop Unit 61, Winter Springs, FL 32708
• 

  

  /28

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft

  1735 Timocuan Way, Longwood, FL 32750

  Rare 3.39-Acre Income-Producing Estate in Sought-After Seminole CountyDiscover an exceptional opportunity where wide-open freedom meets unbeatable value on this 3.39-acre property in one of Central Florida's most desirable locations. Built in 1982, this versatile estate seamlessly blends modern comfort with rural charm — providing a lifestyle that's increasingly hard to find.Turnkey

  Sukumar Haldar AVANTI WAY REALTY LLC

  1735 Timocuan Way, Longwood, FL 32750
• 

  

  /33

  $267,500

  $18K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  476 Club Dr, Winter Springs, FL 32708

  Virtually Staged. Welcome to 476 Club Drive, a beautifully maintained 3-bedroom, 2-bath townhome in the highly sought-after Cypress Club section of The Highlands in Winter Springs. NEW ROOF 2026, NEW WATER HEATER 2026, 2020 A/C, FULL-HOME REPIPE 2016, and WHOLE-HOME WATER SOFTENER 2016! This spacious home offers a flexible floor plan, peaceful wooded views, and an impressive list of

  Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

  476 Club Dr, Winter Springs, FL 32708
• 

  

  /56

  $284,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,101 Sq Ft

  412 Horizon Dr, Winter Springs, FL 32708

  Welcome to 412 Horizon Drive, a well maintained home in the heart of Winter Springs with the updates already taken care of. Inside, you’ll find a welcoming kitchen with granite countertops, stylish cabinetry, stainless steel appliances, and ceramic tile and wood laminate flooring throughout. The primary bathroom is a standout, featuring a barn door entry, large tiled shower, rainfall shower

  Christopher Groomes KELLER WILLIAMS ADVANTAGE REALTY

  412 Horizon Dr, Winter Springs, FL 32708
• 

  

  /20

  $249,000

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

  498 Green Spring Cir, Winter Springs, FL 32708

  Welcome to 498 Green Spring Circle in the desirable Mount Greenwood community of Winter Springs! This beautifully maintained 2 bedroom, 1.5 bath end-unit townhome offers peaceful pond views, low-maintenance living, and access to top-rated Seminole County schools.Step inside to an open and inviting floor plan featuring ceramic tile flooring throughout the main living areas and fresh

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  498 Green Spring Cir, Winter Springs, FL 32708
• 

  

  /26

  $354,000

  $7K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft

  830 Dunbar Terrace, Winter Springs, FL 32708

  Welcome to 830 Dunbar Ter, a residence arranged for everyday comfort and practical living. The interior features a fireplace, serving as a central point, while the kitchen contains an accent backsplash that provides a subtle design element. Exterior amenities include a substantial deck that connects directly to a fully fenced in backyard, suitable for various outdoor activities. Move right into

  Karen Albright OPENDOOR BROKERAGE LLC

  830 Dunbar Terrace, Winter Springs, FL 32708
• 

  

  /25

  $210,000

  $45K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  499 Club Dr, Winter Springs, FL 32708

  Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices for you as a buyer) located in the desirable Cypress Club within the Highlands Community. Brand New Roof on this townhome. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space.

  Paul Buscemi FLORIDA HOME TEAM REALTY LLC

  499 Club Dr, Winter Springs, FL 32708
• 

  

  /14

  $297,000

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft

  207 Birch Terrace, Winter Springs, FL 32708

  3 BEDROOM 2 BATH HOME LOCATED ON CUL DE SAC STREET. WOOD CABINETS, SOLID SURFACE COUNTERS IN KITCHEN. SPLIT BEDROOM PLAN. FENCED REAR YARD. NEW ROOF IN 2025. A LITTLE TLC MAKES THIS A GREAT HOME. GREAT HOME FOR OWNER OCCUPANT OR INVESTOR.

  Bernard Reilly REILLY REALTY & MGMT.

  207 Birch Terrace, Winter Springs, FL 32708
• 

  

  /18

  $210,000

  • 2 Beds
  • 1.5 Baths
  • 898 Sq Ft

  113 Kristi Ann Ct, Winter Springs, FL 32708

  Virtually Staged. Charming Winter Springs Townhouse – Perfect for Buyers or Investors! Welcome to 113 Kristi Ann Court, a beautifully maintained 2BR/1.5BA townhouse in the highly sought-after Winter Springs area. Offering 898 sq ft of thoughtfully designed living space, this home features a bright, open living area and a well-appointed kitchen optimized for everyday comfort. Step outside to your

  Jose Perez COLDWELL BANKER REALTY

  113 Kristi Ann Ct, Winter Springs, FL 32708
• 

  /2

  $22,500

  • 2 Beds
  • 2 Baths

  7 La Vista Dr, Winter Springs, FL 32708

  A new opportunity is coming soon at Hacienda Village! This home is currently being refreshed and will soon be ready for its market debut. Additional details and photos will be added as they become available, so check back periodically to see more. Beyond the home itself, there is plenty to enjoy at Hacienda Village. The setting beyond the home is equally easy to enjoy. Hacienda Village offers an

  Todd Vagts Hacienda Village

  7 La Vista Dr, Winter Springs, FL 32708
• 

  

  /13

  $135,500

  • 2 Beds
  • 2 Baths

  73 Majorca Dr, Winter Springs, FL 32708

  Welcome Home to The Laguna - Brand-New for 2026 Step into modern comfort and effortless style with ""The Laguna"", a beautifully designed brand-new 2026 home featuring thoughtful upgrades and quality craftsmanship throughout. From the moment you enter through the decorative glass front door, you'll appreciate the bright, polished interior featuring recessed lighting, elegant crown molding, and

  Todd Vagts Hacienda Village

  73 Majorca Dr, Winter Springs, FL 32708
• 

  

  /35

  $342,999

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

  1610 Grand Rue Dr, Casselberry, FL 32707

  Welcome home to this beautifully maintained 2022 end-unit townhome in the desirable Legacy Place community! Offering 3 bedrooms, 2.5 bathrooms, a versatile loft, and a private patio, this move-in-ready home showcases true pride of ownership while delivering exceptional value. Step inside to a bright, open-concept floor plan filled with natural light from energy-efficient double-pane tinted

  CARLA RHODES COLDWELL BANKER REALTY

  1610 Grand Rue Dr, Casselberry, FL 32707
• 

  

  /49

  $59,900

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

  374 Casa Grande Ct, Winter Springs, FL 32708

  2 Bedroom 2 Bath 1152 Heated Area does not include porch. 1980 Built, well maintained. It's absolutely beautiful Phase III. Golf Cart path near, RV storage ($25.per month). Hacienda Village is centrally located -45 minutes to beaches & parks. Close to restaurants, shopping, police and fire departments. Hacienda offers many amenities including 2 pools (1 heated)Pickelball courts, Doggy Park, Putt

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  374 Casa Grande Ct, Winter Springs, FL 32708
• 

  

  /50

  $89,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft

  65 Majorca Dr, Winter Springs, FL 32708

  Located close to an entrance, "solar Panels" paid for. Open, Modern 2 Entrances, Shows Well, Crown Molding-SUPER KITCHEN is a must see! GREAT LOCATION, close to major roads, Doctors, Fire Dept. Restaurants, Shopping & more! Updated Amenities-2 Pools, Pickle Ball, Putt Putt Golf, Doggy Park & More, Never a dull moment, always something to do! Base Mo. lor rent is $1025.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  65 Majorca Dr, Winter Springs, FL 32708
• 

  

  /47

  $70,000

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

  162 Costa Cir, Winter Springs, FL 32708

  SIZE TOTAL 1392 INCLUDING ENCLOSED PORCH. FLOORS, WALLS, APPLIANCES & MORE ALL UPDATED. SITUATED IN A QUIED CUL-DE-SAC. HACIENDA IS CENTRALLY LOCATED - 45 MINUTES TO BEACH & PARKS. CLOSE TO RESTAURANTS, SHOPPING DOCTORS, POLICE & FIRE DEPARTMENT. A LOT OF AMMENITIES IN PARK PLUS ACTIVITIES. DROP BY & YOU'LL LOVE IT!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  162 Costa Cir, Winter Springs, FL 32708
• 

  

  /25

  $275,000

  $15K PRICE DROP

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

  299 Woodgreen Ln, Winter Springs, FL 32708

  Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Greenwood community of Winter Springs, where modern upgrades and a thoughtfully designed layout create a truly inviting place to call home. As a CORNER UNIT, this residence enjoys added privacy along with a serene setting, including POND VIEWS just beyond the rear fence, best appreciated from the upstairs

  Jennifer Wemert WEMERT GROUP REALTY LLC

  299 Woodgreen Ln, Winter Springs, FL 32708
• 

  

  /52

  $178,900

  • 2 Beds
  • 2 Baths
  • 945 Sq Ft

  311 San Miguel St Unit 311, Winter Springs, FL 32708

  Virtually Staged. Enjoy life in this beautiful, recently renovated 2 bedroom, 2 bathroom patio home located in the beautiful Indian River community in Winter Springs. Welcome to a low maintenance lifestyle with the Condo Assn maintaining the lawn, sparkling community pool and clubhouse, tennis courts. This Central Florida location, near roads 434, 419 and 17/92, provides convenient access to the

  Michael Ussery COLDWELL BANKER COAST REALTY

  311 San Miguel St Unit 311, Winter Springs, FL 32708
• 

  

  /10

  $59,900

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  Thoughtfully renovated with modern finishes, this home features elegant waterproof flooring, a stylish kitchen, and a bright comfortable living space, designed for easy living!

  Todd Vagts Hacienda Village

  338 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  /46

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft

  203 Cottonwood Dr, Winter Springs, FL 32708

  ADORABLE and MOVE-IN READY! Whether you're a FIRST-TIME HOMEBUYER or looking to "RIGHT-SIZE" into a more manageable home without sacrificing comfort. This charming 3-Bedroom, 2-Bath WATER-FRONT HOME will meet your needs and more. Paddleboard or canoe on the Water out back! Step inside to discover a bright and inviting open floor plan featuring soaring vaulted ceilings, abundant natural light, and

  Johnna Brizendine COLDWELL BANKER REALTY

  203 Cottonwood Dr, Winter Springs, FL 32708
• 

  

  /56

  $295,900

  $3K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,298 Sq Ft

  736 Summerland Dr, Winter Springs, FL 32708

  SINGLE FAMILY HOME. Stunningly Renovated Gem in Winter Springs. Looking for the perfect blend of modern comfort and community living? Look no further! This spectacular, Renovated home in the desirable Wildwood community is ready for its new owners. Brand New Solar Panel System, Green energy. Paid off. This almost 1,300 sq. ft. residence has been thoughtfully updated with high-end finishes

  Jose Hernandez LA ROSA REALTY CW PROPERTIES L

  736 Summerland Dr, Winter Springs, FL 32708
• 

  

  /25

  $359,000

  $31K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,425 Sq Ft

  142 Bayberry Ct, Winter Springs, FL 32708

  PRICE IMPROVEMENT: This 4 bedroom 2 bath home located on a quiet cul de sac is perfect for Family Living. Upgraded kitchen features pass through window to the large rear screened patio. Open floorplan is perfect for entertaining. The original garage has been converted to a large space offering additional square footage to be utilized as a bedroom, game room, home office, theatre or a gym. Fenced

  Roxanne Rose ROSE PROPERTY MANAGEMENT INC

  142 Bayberry Ct, Winter Springs, FL 32708
• 

  

  /28

  $35,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  284 La Vista Dr, Winter Springs, FL 32708

  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

  Corali Fuentes Four Star Homes, Inc.

  284 La Vista Dr, Winter Springs, FL 32708
• 

  

  /29

  $285,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,069 Sq Ft

  421 Horizon Dr, Winter Springs, FL 32708

  MOTIVATED SELLERS!!! Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3

  Peter Luu REAL BROKER, LLC

  421 Horizon Dr, Winter Springs, FL 32708

Showing Results 41 - 67, Page 2 of 2