Highlands Homes for Sale

• 

  

  

  /26

  $230,000

  $45K PRICE DROP Pre-Foreclosure

  • 3 Beds
  • 2 Baths

  331 San Gabriel St, Winter Springs, FL 32708

  IN WINTER SPRINGS, FL Welcome to this beautifully refreshed 3-bedroom, 2-bathroom home located in the desirable Deersong community of Tuscawilla. This move-in-ready residence offers a perfect blend of efficiency and style, featuring a fully owned solar panel system on the roof that provides significant monthly energy savings. The interior has been tastefully updated with fresh paint throughout

  Judy Palladino Compass Florida, LLC.

  331 San Gabriel St, Winter Springs, FL 32708
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /3

  $132,500

  • 2 Beds
  • 2 Baths

  67 Majorca Dr, Winter Springs, FL 32708

  Brand-new 2026 Home - The Solara - 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

  67 Majorca Dr, Winter Springs, FL 32708
• 

  

  

  /29

  $140,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 710 Sq Ft

  220 Moree Loop Unit 2, Winter Springs, FL 32708

  Virtually Staged. Price improvement for the perfect starter home, investment opportunity or downsizing. Excellent condition! Not every condo feels like HOME the moment you walk in—but this one does. EXCELLENT CONDITION! Tucked beneath the canopy of mature oaks in The Highlands of Winter Springs, this beautifully UPDATED FIRST FLOOR ONE BEDROOM/ONE BATH condominium offers the perfect blend of

  Patricia Woodhouse RE/MAX CENTRAL REALTY

  220 Moree Loop Unit 2, Winter Springs, FL 32708
• 

  

  

  /18

  $354,900

  $12K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft

  221 Sherry Ave, Winter Springs, FL 32708

  Beautiful fully renovated property featuring 4 spacious bedrooms, 2 modern bathrooms, and an additional room perfect for an office or play room. The home has been completely updated, including a new roof and new windows, providing improved energy efficiency and peace of mind. Open layout with excellent natural light and modern finishes throughout. Move-in ready, ideal for a family home or

  Rodrigo Chavez LA ROSA REALTY ORLANDO LLC

  221 Sherry Ave, Winter Springs, FL 32708
• 

  

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  102 La Vista Dr, Winter Springs, FL 32708

  This brand-new 2026 Jacobsen home offers 2 bedrooms and 2 bathrooms, with quality finishes throughout. Highlights include a kitchen island, stainless steel appliances and walk-in closets!

  Todd Vagts Hacienda Village

  102 La Vista Dr, Winter Springs, FL 32708
• 

  

  /41

  $199,000

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft

  429 Sheoah Blvd Unit 9, Winter Springs, FL 32708

  Welcome to this beautifully maintained 3-bedroom, 2-bath condominium nestled in the highly desirable Highlands community of Winter Springs. Offering the perfect blend of comfort, style, and convenience, this move-in-ready home features an updated kitchen with granite countertops, stainless steel appliances, and ample cabinetry. The spacious floor plan is complemented by updated bathrooms,

  Freddy Escobar LPT REALTY, LLC

  429 Sheoah Blvd Unit 9, Winter Springs, FL 32708
• 

  

  /30

  $365,500

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft

  240 N Devon Ave, Winter Springs, FL 32708

  Welcome to 240 N Devon Avenue, a fully updated three-bedroom, two-bath home in the heart of Winter Springs, where the renovation has been done for you and the only thing left to do is move in. Inside, the open-concept main living area is anchored by a stunning stone fireplace with built-in shelving and crown molding throughout. The kitchen has been beautifully upgraded with custom wood cabinetry,

  Lindsey Hudson REAL BROKER, LLC

  240 N Devon Ave, Winter Springs, FL 32708
• 

  

  /24

  $182,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft

  240 Moree Loop Unit 3, Winter Springs, FL 32708

  Virtually Staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute.Step

  Christine Landrau MARK SPAIN REAL ESTATE

  240 Moree Loop Unit 3, Winter Springs, FL 32708
• 

  

  /25

  $79,700

  $3K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  411 La Vista Dr, Winter Springs, FL 32708

  THE HOME THAT KEEPS GOING... AND GOING! Looking for space, flexibility, storage, and character all in one home? This rare Hacienda Village gem offers approximately 15 functional living spaces designed for comfortable everyday living, entertaining, hobbies, working from home, and so much more! This spacious split-floor-plan home features 3 spacious bedrooms, multiple living and dining areas, a

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  411 La Vista Dr, Winter Springs, FL 32708
• 

  

  /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
• 

  

  /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

  $210,000

  $23K PRICE DROP

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

  497 Club Dr, Winter Springs, FL 32708

  Move in Ready!...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 in upstairs

  Edyta Olejnik WATSON REALTY CORP

  497 Club Dr, Winter Springs, FL 32708
• 

  

  /26

  $359,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,616 Sq Ft

  717 Lancewood Dr, Winter Springs, FL 32708

  MOVE-IN READY HOME on an amazing 0.3-acre corner lot! In the heart of Seminole County's Winter Springs lies your future home. This warm, cozy yet spacious home with an oversized primary bedroom and wood-burning fireplace will make you fall in love. The dining area flows into the kitchen and then into the family room, overlooking a sweeping backyard that's perfect for indoor-outdoor living. Fresh

  Bridd BONE KELLER WILLIAMS SUBURBAN TAMPA

  717 Lancewood Dr, Winter Springs, FL 32708
• 

  

  /31

  $24,500

  $10K 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
• 

  

  /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
• 

  

  /37

  $275,000

  $10K PRICE DROP

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

  476 Club Dr, Winter Springs, FL 32708

  Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a new roof 2026, new water

  Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

  476 Club Dr, Winter Springs, FL 32708
• 

  

  /20

  $249,000

  Open Sun 1PM - 3PM

  • 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 interior

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  498 Green Spring Cir, Winter Springs, FL 32708
• 

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  38 La Vista Dr, Winter Springs, FL 32708

  Brand-new 2026 Home - The Laguna - 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

  38 La Vista Dr, Winter Springs, FL 32708
• 

  

  /26

  $357,000

  $4K 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
• 

  

  /33

  $300,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,075 Sq Ft

  65 S Devon Ave, Winter Springs, FL 32708

  Discover the charm and convenience of life in Winter Springs at 65 S Devon Avenue — a move-in-ready 3 bedroom, 2 bath block-construction home with a fantastic yard and no HOA. Perfect for first-time buyers, downsizers, or anyone looking for an affordable single-family home in a top-rated school district. Step inside to a bright, welcoming layout filled with natural light and comfortable living

  Tina Bircher RE/MAX PRIME PROPERTIES

  65 S Devon Ave, Winter Springs, FL 32708
• 

  

  /25

  $219,500

  $36K 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) 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. Guest/2nd bedroom on the first floor with

  Paul Buscemi FLORIDA HOME TEAM REALTY LLC

  499 Club Dr, Winter Springs, FL 32708
• 

  

  /12

  $30,000

  • 1 Bed
  • 1 Bath

  80 Majorca Dr, Winter Springs, FL 32708

  Renovated Home! New on-demand water heater and newer AC unit. Home is ready for its new owner, all furniture is included and new appliances. Home features 1 bedroom plus an office that can be used as a 2nd bedroom!

  Todd Vagts Hacienda Village

  80 Majorca 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
• 

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  73 Majorca Dr, Winter Springs, FL 32708

  This brand-new 2026 "The Laguna" model combines modern design with everyday functionality, featuring recessed lighting, luxury plank flooring, and a stylish dining room chandelier. The kitchen is a standout with stainless steel appliances, a spacious island, and smooth glide drawers for added convenience. The home also offers a walk-in closet, providing ample storage and comfort

  Todd Vagts Hacienda Village

  73 Majorca Dr, Winter Springs, FL 32708
• 

  

  /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
• 

  

  /33

  $424,997

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  872 Falkirk Dr, Winter Springs, FL 32708

  PRICE IMPROVED + SELLER CONTRIBUTES TO CLOSING COSTS!, BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Updated Pool Home in Winter Springs | Seminole County | Move-In ReadyWelcome to this beautifully maintained 3-bedroom, 2-bath home featuring a private screened pool in an established Winter Springs neighborhood. The updated kitchen and updated bathroom deliver a fresh, modern feel,

  Elizabeth Rodriguez CAISSA REALTY INVESTMENT INC

  872 Falkirk 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

  $283,500

  $7K 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
• 

  

  /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
• 

  

  /25

  $211,000

  $29K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,180 Sq Ft

  510 Green Spring Cir, Winter Springs, FL 32708

  Explore 510 Green Spring Cir, a residence recently enhanced with fresh interior paint and partial flooring replacement throughout. The kitchen includes an accent backsplash, complementing the recent updates for a refreshed interior feel. This property blends modern updates and practical style, ready for you to enjoy. Included 100-Day Home Warranty with buyer activation

  Karen Albright OPENDOOR BROKERAGE LLC

  510 Green Spring Cir, Winter Springs, FL 32708
• 

  

  /25

  $380,000

  $10K 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

  $39,500

  $6K 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

  $289,000

  $36K 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 - 74, Page 2 of 2