Highlands Homes for Sale

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  /43

  $489,000

  • 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
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  /2

  $135,500

  • 2 Beds
  • 2 Baths

  154 Hacienda Dr, 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, Winter Springs, FL 32708
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  /27

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,105 Sq Ft

  130 Deer Song Dr, Winter Springs, FL 32708

  Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to own one of the most beautifully updated homes in the community! Positioned on a desirable corner lot with ample parking, this fully renovated 3-bedroom, 2-bathroom home stands out as a rare find offering both style and convenience. From the moment you step inside, you’ll notice the thoughtful upgrades

  Yosseff Roman KELLER WILLIAMS ADVANTAGE III

  130 Deer Song Dr, Winter Springs, FL 32708
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  /64

  $32,900

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

  82 Bonita Cir, Winter Springs, FL 32708

  A lot of room and storage-newer plumbing underneath. "as is" use your imagination in this home. Conveniently with recreation Hall across the street with a heated pool. Community is located near major highways-45 minutes beaches & parks. Located nearby are restaurants, medical shops as well as police and fire department. Monthly base rent is $1075.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  82 Bonita Cir, Winter Springs, FL 32708
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  /3

  $132,500

  • 2 Beds
  • 2 Baths

  2 La Vista 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

  2 La Vista Dr, Winter Springs, FL 32708
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  /26

  $275,000 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
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  /47

  $8,000

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

  468 Ponce de Leon Cir, Winter Springs, FL 32708

  Perfect Location-circle-corner lot. Owner says "make an Offer!" priced to sell. 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,

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  468 Ponce de Leon Cir, Winter Springs, FL 32708
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  /3

  $137,500

  • 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
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  /52

  $18,000

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  460 Ponce de Leon Cir, Winter Springs, FL 32708

  GREAT BUY!!-Located in a Cul de sac, lovely front porch-Just sit and relax. A/C is 7 years old. Electric fireplace. Roof is only 3 years old. Located close to the clubhouse with pool.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  460 Ponce de Leon Cir, Winter Springs, FL 32708
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  /14

  $59,900

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  Price is negotiable. Flooring: Redwood Oak waterproof plank flooring throughout. Roof: Roof approximately 3 years old, including laundry area and porch. Community & Lifestyle: Enjoy a peaceful, pet-friendly, resort-style community featuring two swimming pools (one heated), two clubhouses with banquet room, library, and fitness center, tennis courts, golf, RV storage, and scenic walking paths.

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  338 Casa Grande Dr, Winter Springs, FL 32708
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  /24

  $193,000

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

  240 Moree Loop Unit 3, Winter Springs, FL 32708

  One or more photo(s) has been 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

  Christine Landrau MARK SPAIN REAL ESTATE

  240 Moree Loop Unit 3, Winter Springs, FL 32708
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  /23

  $32,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  463 Ponce de Leon Cir, Winter Springs, FL 32708

  SELLER CONSIDERING ALL OFFERS! Welcome to this cozy and inviting 2-bedroom, 1-bathroom home located in the highly desirable 55+ community of Hacienda Village in Winter Springs, Florida. This peaceful, well-maintained community offers an ideal combination of comfort, convenience, and Florida living. With quick access to the 417, you can easily reach the beaches, theme parks, downtown Winter

  Bella Siracusa SUNBELT HOME SALES INC

  463 Ponce de Leon Cir, Winter Springs, FL 32708
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  /22

  $82,500

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

  411 La Vista Dr, Winter Springs, FL 32708

  Beautiful and spacious home in Hacienda Village featuring a split floor plan with plenty of flexible living space and storage throughout. This well-maintained home offers a welcoming living room, dining area with built-in cabinetry, a bright kitchen, generously sized bedrooms, and a private primary suite with ensuite bath and walk-in closet. You'll also love the enclosed Florida room with

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  411 La Vista Dr, Winter Springs, FL 32708
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  /28

  $229,000

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

  429 Sheoah Blvd Unit 12, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo offering the perfect blend of style, comfort, and convenience in the heart of Seminole County. Inside, you’ll find quartz countertops throughout, stainless steel appliances, and stylish brick-lay tile flooring that adds character and a modern touch to the main living areas. The

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
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  /13

  $263,000

  • 2 Beds
  • 1 Bath
  • 1,148 Sq Ft

  120 N Fairfax Ave, Winter Springs, FL 32708

  Charming ranch-style home brimming with potential and ready for your personal touch! Ideally situated in a convenient location, this property offers easy access to nearby schools, shopping centers, public transportation, and everyday essentials. Inside, you’ll find a practical layout featuring 2 comfortable bedrooms and 1 full bathroom, along with durable terrazzo and tile flooring

  Chris Creegan CREEGAN GROUP

  120 N Fairfax Ave, Winter Springs, FL 32708
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  /32

  $229,500

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

  502 Club Dr, Winter Springs, FL 32708

  Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a

  Tamara Martin INFINITY REAL ESTATE GROUP

  502 Club Dr, Winter Springs, FL 32708
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  /53

  $299,900

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

  515 Seasons Ct, Winter Springs, FL 32708

  **One or more photo(s) has been virtually staged**.Move-In Ready Home – Fully Updated Inside and Out! Simply bring your personal belongings — this 3-bedroom, 2-bathroom home is ready for immediate occupancy. Freshly painted throughout, it features many upgrades and improvements, including roof (2021), water heater (2020), indoor A/C unit (2018), and outdoor A/C unit (2025). The remodeled kitchen

  Olga Carballea Diaz CHARLES RUTENBERG REALTY ORLANDO

  515 Seasons Ct, Winter Springs, FL 32708
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  /52

  $275,000

  • 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 2020 A/C system, a full

  Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

  476 Club Dr, Winter Springs, FL 32708
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  /26

  $375,000

  • 2 Beds
  • 2 Baths
  • 1,477 Sq Ft

  448 Macgregor Rd, Winter Springs, FL 32708

  Explore 448 MacGregor Rd, a individual residence with a straightforward design and integrated features. The interior includes a fireplace, and the primary bedroom features a walk in closet; the primary bathroom provides double sinks and a Jacuzzi. The exterior includes a covered patio and a fenced in backyard, providing an enclosed outdoor area. This property contains practical elements for daily

  Karen Albright OPENDOOR BROKERAGE LLC

  448 Macgregor Rd, Winter Springs, FL 32708
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  /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
• 

  

  /20

  $247,500

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

  499 Club Dr, Winter Springs, FL 32708

  Beautiful 2 bedroom 2 bathroom townhome within The Highlands Community. 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 direct access to the 2nd bathroom. All appliances purchased New in 2022 and are included with sale. New

  Paul Buscemi FLORIDA HOME TEAM REALTY LLC

  499 Club Dr, Winter Springs, FL 32708
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  /67

  $300,000

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

  736 Summerland Dr, Winter Springs, FL 32708

  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 throughout.Offers

  Jose Hernandez LA ROSA REALTY CW PROPERTIES L

  736 Summerland Dr, Winter Springs, FL 32708
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  /42

  $325,000

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  140 N Fairfax Ave, Winter Springs, FL 32708

  Fully Renovated Winter Springs Home with No HOA – Move-In Ready in Seminole County Welcome to 140 N. Fairfax Avenue in Winter Springs, Florida, a beautifully renovated home that blends classic Florida charm with modern upgrades in one of Seminole County’s most desirable and convenient locations. This extensively updated 3-bedroom, 1-bath home sits on a generous 8,900-square-foot lot and offers a

  Shawn McCormick ERA GRIZZARD REAL ESTATE

  140 N Fairfax Ave, Winter Springs, FL 32708
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  /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
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  /28

  $330,000

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

  471 Harbor Winds Ct, Winter Springs, FL 32708

  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

  Terrica Francois KELLER WILLIAMS ADVANTAGE III

  471 Harbor Winds Ct, Winter Springs, FL 32708
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  /50

  $89,900

  • 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
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  /33

  $448,997

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

  872 Falkirk Dr, Winter Springs, FL 32708

  BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Beautifully maintained home located in one of the most desirable areas of Winter Springs, offering the perfect blend of comfort, convenience, and outdoor living. Surrounded by scenic walking and biking trails throughout the neighborhood, this home delivers a peaceful setting while staying close to everything you need. This property features

  Elizabeth Rodriguez CAISSA REALTY INVESTMENT INC

  872 Falkirk Dr, Winter Springs, FL 32708
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  /48

  $725,000

  • 4 Beds
  • 2 Baths
  • 2,158 Sq Ft

  130 E Bahama Rd, Winter Springs, FL 32708

  Don’t miss the opportunity to see this exceptional property! Located in the desirable Ranchlands neighborhood of Winter Springs, this exceptional property sits on over 1.5 acres of land, offering both space and privacy. A large circular driveway provides easy access and ample parking. This well-maintained home features 4 bedrooms, 2 bathrooms, and over 2,100 square feet of living space, with a

  Zac Hernandez EMPIRE NETWORK REALTY

  130 E Bahama Rd, Winter Springs, FL 32708
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  /47

  $39,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  219 El Camino Real Cir, Winter Springs, FL 32708

  Brand New Inside - Completely redone, Beautiful new floors, repainted inside and out, New Front Door, Screened-in Porch redone, nice size storage room. Hacienda Village is a Legacy Community - 55+.Monthly rent $1075. Base

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  219 El Camino Real Cir, Winter Springs, FL 32708
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  /14

  $137,000

  • 3 Beds
  • 2 Baths

  154 Hacienda Dr, Winter Springs, FL 32708

  Spacious and well-appointed, this 1,920 sq. ft. home offers 3 bedrooms and 2 bathrooms, featuring both a great room and a family room for flexible living and entertaining. The home includes a 13x18 layout area and a one-car garage measuring 14x21. All appliances are Samsung, complemented by a brand-new Hotpoint washer and dryer, plus an additional refrigerator in the utility room for extra

  Todd Vagts Hacienda Village

  154 Hacienda Dr, Winter Springs, FL 32708
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  /29

  $315,000

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

  421 Horizon Dr, Winter Springs, FL 32708

  Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This beautifully maintained one story home offers 3 bedrooms, 2 bathrooms, and 1,069 square feet of thoughtfully updated living space. Major improvements provide peace of mind, including a 50 year Rhino shingle roof installed in 2019, a 3.5 ton 14 SEER A C unit with heat pump and updated ductwork, a new electric

  Peter Luu REAL BROKER, LLC

  421 Horizon Dr, Winter Springs, FL 32708

Showing Results 41 - 71, Page 2 of 2