Highlands Homes for Sale

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  /47

  $29,900

  • 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
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• 

  

  

  /54

  $40,000

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

  125 Las Almas Ln, Winter Springs, FL 32708

  Very Modern-open-Newer Windows, New Rood 2021, Newer Appliances, Replumbed. A beautiful setting. Hacienda Village is a Legacy 55+ Community with newer Amenities, Pickle Ball, Putt Putt, Doggie Park, 2 pools, one which is heated. Always something going on- Never a dull moment. Base mo. rent is $1075. (Pictures coming soon) Great buy for this large home!!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  125 Las Almas Ln, Winter Springs, FL 32708
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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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  /64

  $37,900

  • 3 Beds
  • 3 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 Jacobsen Home 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 decorative

  Todd Vagts Hacienda Village

  2 La Vista Dr, Winter Springs, FL 32708
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  /47

  $12,000

  • 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
• 

  

  /3

  $137,500

  • 2 Beds
  • 2 Baths

  67 Majorca Dr, Winter Springs, FL 32708

  Brand-new 2026 Jacobsen Home 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 decorative

  Todd Vagts Hacienda Village

  67 Majorca Dr, Winter Springs, FL 32708
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  /14

  $64,800

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  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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  /16

  $169,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  130 Columbus Cir, Winter Springs, FL 32708

  Looking for your dream home? This stunning 3-bedroom, 2-bathroom property is ready for you! From the moment you arrive, you'll appreciate the curb appeal, with a generous 3-car driveway and a 1-car garage. Step inside and discover an open-concept living space with vaulted ceilings, modern light fixtures, and a walk-in food pantry for all your storage needs. The kitchen is a chef's delight,

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  130 Columbus Cir, Winter Springs, FL 32708
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  /16

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  229 Bennett St, Winter Springs, FL 32708

  This spacious 4-bedroom, 2-bathroom home offers a comfortable living experience with 1164 sq. ft. of space. The kitchen is equipped with stainless steel appliances, including a refrigerator, microwave, range oven, and dishwasher. The property also features window coverings, a ceiling fan, a bathtub, and an attached garage. Located conveniently close to restaurants, grocery stores, schools, and

  Chantel Gutierrez-Davis RISE 24 REAL ESTATE LLC

  229 Bennett St, Winter Springs, FL 32708
• 

  

  /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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  /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
• 

  

  /15

  $169,900

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708

  Prime First-Floor Living in Prestigious Highlands of Winter Springs! Discover the ultimate in convenient living with this exceptional first-floor 2 bedroom, 2 bathroom condo in the highly sought-after Highlands community. Located in top-rated Seminole County School District, this ground-level gem eliminates the hassle of stairs while offering effortless accessibility for residents and guests

  Matt Merdian MERDIAN REALTY LLC

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708
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  /30

  $279,990

  • 3 Beds
  • 2 Baths
  • 1,091 Sq Ft

  314 San Gabriel St, Winter Springs, FL 32708

  PRICE REDUCTION: Welcome to your dream home in the highly sought-after Deer Song Community of Winter Springs! This charming 3-bedroom, 2-bath corner single family home is packed with upgrades, including a brand new hot water heater (installed 2/23/2026), a newer roof (2021) and re-plumb (2021), state-of-the-art appliances (2021-2022), a top-of-the-line air conditioning system (2022), a water

  Linda Bain WEICHERT REALTORS HALLMARK PRO

  314 San Gabriel St, Winter Springs, FL 32708
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  /23

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  403 Murphy Rd, Winter Springs, FL 32708

  Welcome home to this beautiful 3 bedrooms, 2 bathrooms house with a pool. Come and enjoy the large pool, modern and updated kitchen with granite countertop and stainless-steel appliances. The spacious interior along with the bonus room will give your family enough space to grow. In the last 4 years the roof, air conditioning unit and water heater have all been replaced. The solar panels will

  Celeste Baez FLORIDA REALTY INVESTMENTS

  403 Murphy Rd, Winter Springs, FL 32708
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  /13

  $29,900

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  31 La Vista Dr, Winter Springs, FL 32708

  A must-see home that has been totally renovated with new luxury vinyl flooring, Kitchen has quartz counter tops and all new stainless-steel appliances. New baseboards freshly painted throughout. New A/C ductwork. Master bathroom has been totally remodeled. a GREAT 55+ COMMUNITY offering lots of amenities. Restaurants & major roads nearby. Vacant & ready for a new owner!!!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  31 La Vista Dr, Winter Springs, FL 32708
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  /68

  $93,500

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

  411 La Vista Dr, Winter Springs, FL 32708

  Hacienda Village 55+-Double Wide 1536 sq. ft. 3 bedrooms, 2 bath, split plan with a lot of upgrades. Family Room, screened in area, lots of storage-water purifier, nice size lot to enjoy. Neighborhood is close to all major highways, shopping, doctors, restaurants. All the latest and greatest amenities. Hacienda Village is a legacy Community. Monthly rent is $1025.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES

  411 La Vista Dr, Winter Springs, FL 32708
• 

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  38 La Vista Dr, Winter Springs, FL 32708

  Brand-new 2026 Jacobsen Home 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 decorative

  Todd Vagts Hacienda Village

  38 La Vista Dr, Winter Springs, FL 32708
• 

  

  /17

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1211 Phillip St, Winter Springs, FL 32708

  PRICE REDUCED!!! 3 BEDROOM 2 BATH BLOCK HOME REMODELED IN 2023, REPLACED CABINETS, ROOF AND A/C. FEATURES AN ENCLOSED PATIO, SEPARATE LAUNDRYROOM, WELL WITH A FILTRATION SYSTEM, LARGE LOT, AND A GARAGE CONVERSION THAT PROVIDES A 4TH BEDROOM, BUT CAN EASILY BE CONVERTED BACK TO A GARAGE. PLENTY OF STORAGE SPACE IN THE LAUNDRY ROOM AND A LARGE SHED IN THE BACK. NICE CALM NEIGHBORHOOD, NEAR

  Marina Munoz OUTLET REALTY

  1211 Phillip St, Winter Springs, FL 32708
• 

  

  /20

  $230,500

  • 2 Beds
  • 1.5 Baths
  • 1,130 Sq Ft

  543 Green Spring Cir, Winter Springs, FL 32708

  This charming townhome is a rare find! Meticulously maintained by a single owner, this 2-bedroom, 1.5-bathroom gem offers the perfect blend of comfort and peace of mind in a quiet, established community. Step inside to a bright, airy floor plan that feels like home the moment you enter. Beyond the aesthetics, this property boasts major "big-ticket" upgrades, ensuring a low-maintenance lifestyle

  Tracy Phillips COLDWELL BANKER REALTY

  543 Green Spring Cir, Winter Springs, FL 32708
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  /57

  $120,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  18 La Vista Cir, Winter Springs, FL 32708

  2018 Clayton Built 3-bedroom 2 bath Home- Private backyard, quiet end of street. Lots of space-Great kitchen all modern appliances-Location, Location close to all highways. Near restaurants, shopping, medical. Community soon will have new things to do. 55+Community. Hacienda Village a Legacy Community-Monthly rent $1075.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  18 La Vista Cir, Winter Springs, FL 32708
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  /42

  $331,000

  • 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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  /28

  $335,000

  • 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
• 

  

  /55

  $185,000

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

  429 Sheoah Blvd Unit 1, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Stunning upgraded corner-unit with extra privacy and garden views! Enjoy wood-look flooring, an open kitchen with granite countertops, stainless steel appliances, bar area plus a wet bar with built-in wine cooler, perfect for entertaining. Plantation shutters throughout the living room, tinted windows, and a newer tankless electric water heater add

  Marielle Parra COMPASS FLORIDA LLC

  429 Sheoah Blvd Unit 1, Winter Springs, FL 32708
• 

  

  /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
• 

  

  /33

  $449,997

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

  872 Falkirk Dr, Winter Springs, FL 32708

  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 3 bedrooms and 2 bathrooms with a bright open floor plan

  Elizabeth Rodriguez CAISSA REALTY INVESTMENT INC

  872 Falkirk Dr, Winter Springs, FL 32708
• 

  

  /25

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,265 Sq Ft

  744 N Gretna Ct, Winter Springs, FL 32708

  Small but cozy, 3-bedroom house. Detached and very large backyard. Perfect for investors interested in fixing and flipping Or for rental. Currently is being rented to students.

  Gregory Sullivan BY OWNER.COM

  744 N Gretna Ct, Winter Springs, FL 32708
• 

  

  /47

  $39,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  293 Casa Grande Dr, Winter Springs, FL 32708

  Beautiful Home all Remodeled-New HVAC, all new ductwork, freshly painted-Move in Ready! New Kitchen-corner Lot, No Flood Zone, Phase III. Clubhouse , Recreation Hall, 2 Pools (one heated), Pickle Ball Court, Putt, Putt, Doggy Park and more. Close to all major Highways, close to Restaurants, Shopping, Parks & Beaches (45 minutes away) lot of activities-You won't be bored. Mo. Base Lot Rent $1025.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  293 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  /47

  $44,900

  • 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
• 

  

  /29

  $324,500

  • 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 - 70, Page 2 of 2