Highlands Homes for Sale

• 

  

  

  /49

  $18,000

  • 2 Beds
  • 2 Baths
  • 1,266 Sq Ft

  396 El Camino Real Cir, Winter Springs, FL 32708

  Home has a few bruises-Great Price! You will love Hacienda. A lot of amenities-2 pools, pickelball,Putt,Doggy Park. Always some activity going on. Major Highway close by about 45 minutes to beaches & Parks. Restaurants, shopping, doctors, Police & Fire Dept within minutes. Base Monthly rent $1025.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  396 El Camino Real Cir, Winter Springs, FL 32708
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  /2

  $137,500

  • 2 Beds
  • 2 Baths

  67 Majorca Dr, Winter Springs, FL 32708

  2026 Jacobsen home - Coming Soon!

  Todd Vagts Hacienda Village

  67 Majorca Dr, Winter Springs, FL 32708
• 

  

  

  /14

  $64,800

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  Discover your perfect Florida retreat in this beautifully updated 2-bedroom, 2-bath home located in a desirable 55+ community in Winter Springs. Featuring luxury plank flooring, a remodeled kitchen, and a semi-furnished, move-in-ready interior with all appliances included. The 5-year-old roof adds peace of mind, while resort-style amenities offer an active, social lifestyle just steps from your

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  338 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  

  /42

  $34,900

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  265 Ponce de Leon Dr, Winter Springs, FL 32708

  LOVELY HOME WITH BEAUTIFUL WOOD FLOORING. Close to Moss Road-Easy Access! Comfortable Home. Enclosed Porch area! 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

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  265 Ponce de Leon Dr, Winter Springs, FL 32708
• 

  

  /2

  $137,500

  • 2 Beds
  • 2 Baths

  264 Ponce de Leon Dr, Winter Springs, FL 32708

  2026 Jacobsen Home - Coming Soon!

  Todd Vagts Hacienda Village

  264 Ponce de Leon Dr, Winter Springs, FL 32708
• 

  

  /40

  $625,000

  • 4 Beds
  • 3.5 Baths
  • 2,486 Sq Ft

  125 E Trade Winds Rd, Winter Springs, FL 32708

  Opportunity knocks in the heart of Winter Springs — with NO HOA and room to live freely.Nestled on a private, full one-acre lot, this 4-bedroom, 2.5-bath pool home offers 2,486 square feet of living space, soaring ceilings, and the kind of solid construction you simply don’t find anymore.Set back from the road, the property provides a peaceful, estate-like feel while still being close to

  Christopher Soucy REALTY ONE GROUP MVP

  125 E Trade Winds Rd, Winter Springs, FL 32708
• 

  

  /23

  $39,999

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  463 Ponce de Leon Cir, Winter Springs, FL 32708

  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 Springs, and all of Central Florida.

  Bella Siracusa SUNBELT HOME SALES INC

  463 Ponce de Leon Cir, Winter Springs, FL 32708
• 

  

  /37

  $308,900

  • 3 Beds
  • 1 Bath
  • 1,058 Sq Ft

  111 N Fairfax Ave, Winter Springs, FL 32708

  Welcome home to this beautifully updated 3 bedroom, 1 bath home located in a well established neighborhood in Winter Springs with no HOA restrictions. This home offers comfort, style, and convenience in one inviting space. Conveniently located near schools, parks, shopping centers, and with quick access to I4 and 417, this home puts everything you need within reach.From the moment you step

  Carla Cabrera MODERN WORLD REALTY LLC

  111 N Fairfax Ave, Winter Springs, FL 32708
• 

  

  /15

  $172,900

  • 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
• 

  

  /28

  $348,000

  • 4 Beds
  • 3 Baths
  • 1,270 Sq Ft

  31 S Edgemon Ave, Winter Springs, FL 32708

  This charming home offers a spacious floor plan with a unique twist— the garage has been converted into a private studio with its own entrance, perfect for guests, a home office, extra living space or residual income. Inside, you'll find comfortable living areas, cozy bedrooms, and a kitchen ready for your culinary adventures. Enjoy the convenience of being close to local amenities, parks, and

  Florentino Beltran KELLER WILLIAMS ADVANTAGE 2 REALTY

  31 S Edgemon Ave, Winter Springs, FL 32708
• 

  

  /35

  $299,990

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  150 N Edgemon Ave, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Motivated Seller!! Winter Springs single-family home on nearly 1⁄4 acre with A-rated schools,NO HOA, Eligible for FHA/VA financing; suitable for first-time buyers, and energy-efficient upgrades. Major improvements include NEW ROOF (2025), PAID-OFF SOLAR PANELS (installed Nov 2020) for lower monthly utility costs, NEW WINDOWS (2022), GAS WATER HEATER

  Kathern Cox-Uvalle EMPIRE NETWORK REALTY

  150 N Edgemon Ave, Winter Springs, FL 32708
• 

  

  /27

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  705 Crestwood Way, Winter Springs, FL 32708

  Welcome to this delightful one-story home in Wildwood, perfectly set on a spacious corner lot! Offering 3 bedrooms and 2 baths, this inviting home features a bright, cheerful living room ideal for family gatherings. The kitchen offers with wood cabinetry, granite countertops, a stylish tile backsplash, and durable ceramic tile flooring. The primary bedroom provides a comfortable retreat with its

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  705 Crestwood Way, Winter Springs, FL 32708
• 

  

  /53

  $305,900

  • 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
• 

  

  /30

  $281,500 Open Sat 11AM - 2PM

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

  314 San Gabriel St, Winter Springs, FL 32708

  Welcome home to this charming 3 bedroom, 2 Bath home in the heart of Winter Springs, in centrally located Deer Song Community. This home features: Corner unit, open floor plan, high ceilings, NEW ROOF 2021, RE-PLUMBED 2021, NEW APPLIANCES 2021-2022, NEW AIR CONDITIONING SYSTEM 2022, NEW WATER SOFTENER SYSTEM 2022 AND NEW LUXURY VINYL FLOORING IN BEDROOMS 2022. Home has been well maintained and

  Linda Bain WEICHERT REALTORS HALLMARK PRO

  314 San Gabriel St, Winter Springs, FL 32708
• 

  

  /13

  $35,900

  • 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
• 

  

  /24

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  10 N Devon Ave, Winter Springs, FL 32708

  This solid block home is ready for its next chapter-- full of character and possibility! This diamond in the rough is offering a rare opportunity to restore and reimagine a true Florida classic. Featuring terrazzo floors, an oversized Florida room, and a spacious screened-in porch overlooking an in-ground pool creating a space for a private retreat. This home needs love but the potential is

  Christine Monday CHARLES RUTENBERG REALTY ORLANDO

  10 N Devon Ave, 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

  $259,900

  • 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
• 

  

  /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 $1025.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  18 La Vista Cir, Winter Springs, FL 32708
• 

  

  /40

  $331,000

  • 3 Beds
  • 1 Bath
  • 1,188 Sq Ft

  140 N Fairfax Ave, Winter Springs, FL 32708

  Welcome to 140 N. Fairfax Ave — a beautifully completely updated Winter Springs home that blends classic Florida charm with modern style. This extensively remodeled 3-bedroom, 1-bath residence sits on a generous 8,900 sq ft lot and offers an ideal layout for first-time buyers, downsizers, or investors seeking a true turnkey property in highly desirable Seminole County.Inside, you’ll

  Shawn McCormick ERA GRIZZARD REAL ESTATE

  140 N Fairfax Ave, Winter Springs, FL 32708
• 

  

  /42

  $485,950

  • 3 Beds
  • 2 Baths
  • 2,022 Sq Ft

  811 Gatehouse Dr, Winter Springs, FL 32708

  2025 Roof Installed! A rare gem in a sought-after location, this stunning single-story ranch home sits on a nearly 1/3 acre homesite, nestled at the end of a peaceful cul-de-sac. This is your chance to own a slice of paradise in one of Winter Springs’ most desirable neighborhoods! Designed for both entertaining and everyday living, this home blends function and luxury seamlessly. As you enter,

  Cleve Loveland LOVELAND PROPERTIES

  811 Gatehouse Dr, Winter Springs, FL 32708
• 

  

  /57

  $200,000

  • 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

  $110,000

  • 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
• 

  

  /21

  $275,000

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  51 N Cortez Ave, Winter Springs, FL 32708

  Welcome to 51 N. Cortez Ave in Winter Springs—a thoughtfully updated 2-bedroom, 1-bath home that’s ideal for a first-time buyer or anyone looking to own without the hassle. Inside, you’ll find a clean, refreshed interior that’s move-in ready from day one. Outside, the fully fenced yard offers space to relax, garden, or let pets roam, while the detached shed provides extra storage for tools,

  Julie Cvercko PRIME REAL ESTATE, INC.

  51 N Cortez Ave, 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
• 

  

  /30

  $425,000

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

  717 Lancewood Dr, Winter Springs, FL 32708

  MOVE-IN READY HOME on an amazing CORNER LOT! In the heart of Seminole County’s Winter Springs lies your next model home or cash-flowing business. This warm, cozy yet spacious home with an OVERSIZED PRIMARY BEDROOM and wood-burning FIREPLACE, will make you fall in love! It boasts privacy, potential, and NO HOA! Sitting on a HUGE 0.30-acre lot, the backyard is suitable for a garden, a retreat, or

  Dana Thomas REALTY ONE GROUP MVP

  717 Lancewood Dr, 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 $1025 Base

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  219 El Camino Real Cir, Winter Springs, FL 32708
• 

  

  /26

  $359,000

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft

  219 Bennett St, Winter Springs, FL 32708

  Nestled in the charming community of Winter Springs, this home has been meticulously cared for by its owner. The master bedroom is a true retreat, featuring a large walk-in closet and abundant skylights that flood the room with natural light. The master bathroom exudes luxury, featuring a hot tub, glass shower, and marble finishes, providing a spa-like experience at home. The family room,

  Fook Snipper PARK PLACE REAL ESTATE

  219 Bennett St, Winter Springs, FL 32708

Showing Results 41 - 69, Page 2 of 2