Highlands Homes

• 

  

  

  /49

  $365,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,490 Sq Ft

  602 Nighthawk Cir, Winter Springs, FL 32708

  BEAUTIFUL HOME IN WINTER SPRINGS! Located in the sought-after neighborhood of THE HIGHLANDS, this MOVE-IN READY home offers a great OPEN CONCEPT with the living room offering a wood-burning FIREPLACE and a dining room with BAY WINDOWS. The kitchen has an EAT-IN BAR and access to a small screened patio with ceramic flooring. The spacious PRIMARY BEDROOM offers PRIVATE ACCESS TO THE

  Alexandra Repetto REPETTO REALTY GROUP LLC

  602 Nighthawk Cir, Winter Springs, FL 32708
• 

  

  

  /20

  $2,095 per month

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Renovated 3-Bed Home with Modern Upgrades ...

  220 W Panama Rd, Winter Springs, FL 32708

  Welcome to this renovated home, now available in the desirable location of Winter Springs, FL. This property boasts three spacious bedrooms and two full bathrooms, offering ample space for your needs. The home features new laminated wood flooring throughout, adding a touch of elegance and durability. The kitchen is a chef's dream with new white cabinets, stainless steel appliances, and plenty of

  220 W Panama Rd, Winter Springs, FL 32708
• 

  

  /2

  $275,000 Sold Aug 27, 2025

  • 1,461 Sq Ft
  • $188/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1972

  609 David St, Winter Springs, FL 32708

  Location Location- 4 bedroom 2 bath - $290,000. Your new home awaits in this charming Winter Springs community. The property features open layout with a dining and kitchen combo. The kitchen is a blank canvas. Bring your tools to customize and potentially increase the property value. Situated in a convenient location, this home provides easy access to local amenities and attractions. Don't

  Steven Koleno BEYCOME OF FLORIDA LLC

  609 David St, Winter Springs, FL 32708
• 

  

  

  /5

  Not Listed For Sale

  0 Florida Ave, Winter Springs, FL 32708

  0 Florida Ave, Winter Springs, FL 32708
• 

  

  

  /51

  $360,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,946 Sq Ft

  212 S Moss Rd, Winter Springs, FL 32708

  Welcome to this beautifully updated Winter Springs home with no HOA!Inside, you’ll find new luxury vinyl plank flooring throughout, fresh interior and exterior paint, and a spacious layout with a bonus room and abundant closet space. The recently upgraded kitchen is a chef’s dream, featuring a gas range for cooking and plenty of room to gather with family and friends. Major updates also

  Danielle Pensala KELLER WILLIAMS HERITAGE REALTY

  212 S Moss Rd, Winter Springs, FL 32708
• 

  

  /26

  $1,400 per month

  • 2 Beds
  • 1.5 Baths
  • 910 Sq Ft
  • Condo for Rent

  127 Lori Anne Ln Unit 127, Winter Springs, FL 32708

  Nice Move-in ready TWO Bedroom/ 1.5 Bath condo style unit. Located in the north side of Winter Springs, near Moss Road. This unit has ALL tile flooring, new microwave, completely repainted on the inside and Kitchen has Large Eat-in area, plus Granite counter tops... There is Assigned Parking, and the unit is on the first level. Call today to get pre-qualified and schedule a viewing

  Bobby Keen KEEN REALTY GROUP, INC.

  127 Lori Anne Ln Unit 127, Winter Springs, FL 32708
• 

  /2

  $365,000 Sold Aug 26, 2025

  • 1,576 Sq Ft
  • $232/SF
  • 5 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1974

  416 S Hawthorn Cir, Winter Springs, FL 32708

  This FULLY RENOVATED home boasts stunning curb appeal and modern upgrades throughout. From the moment you arrive, you'll be delighted by the beautifully landscaped front yard and welcoming entryway. Situated on a large lot with a fully fenced, oversized backyard, featuring a newly resurfaced pool to enjoy on hot Summer days!This home offers a great floorplan with a neutral, light color

  Lisa Demarco Rubel KELLER WILLIAMS ADVANTAGE REALTY

  416 S Hawthorn Cir, Winter Springs, FL 32708
• 

  

  /15

  Est $168,175 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 831 Sq Ft

  420 San Gabriel St Unit 56, Winter Springs, FL 32708

  420 San Gabriel St Unit 56, Winter Springs, FL 32708
• 

  

  /23

  $275,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,166 Sq Ft

  718 Wildwood Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Discover the perfect blend of privacy, low-maintenance living, and style in this freestanding 2-bedroom, 2-bath townhome in the desirable Wildwood community of Winter Springs. With no shared walls and a single-family feel, this home features vaulted ceilings, open living and dining areas, and abundant natural light throughout. The primary suite is

  Joseph Schultz, PLLC LPT REALTY, LLC

  718 Wildwood Dr, Winter Springs, FL 32708
• 

  

  /11

  $2,075 per month

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • House for Rent

  213 Sweetgum Ct, Winter Springs, FL 32708

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2219.90. That covers your base rent, $2075.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  213 Sweetgum Ct, Winter Springs, FL 32708
• 

  /2

  $340,000 Sold Aug 18, 2025

  • 1,204 Sq Ft
  • $282/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  620 Fruitwood Ave, Winter Springs, FL 32708

  Tucked away in a PEACEFUL and established Winter Springs neighborhood, this lovingly maintained 3-bedroom, 2-bath home offers the ideal balance of comfort, thoughtful updates, and everyday functionality—all with NO HOA and a welcoming community known for its friendly neighbors. Recent exterior UPGRADES include NEW gutters and landscaping (2024) and a NEW ROOF (2022), offering peace of mind and

  Jennifer Wemert WEMERT GROUP REALTY LLC

  620 Fruitwood Ave, Winter Springs, FL 32708
• 

  

  /24

  Est $430,653 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  625 Seven Oaks Blvd, Winter Springs, FL 32708

  625 Seven Oaks Blvd, Winter Springs, FL 32708
• 

  

  /32

  $282,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,182 Sq Ft

  466 Club Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Beautiful Single-Level Townhome in Winter Springs!This charming single-level townhome seamlessly blends comfort, style, and a prime location. Thoughtfully crafted for those who appreciate practicality without compromising on elegance, every detail has been carefully considered to create a warm, functional living experience.The home features a

  Diana Gutierrez Venegas LPT REALTY, LLC

  466 Club Dr, Winter Springs, FL 32708
• 

  

  /16

  $1,350 per month

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft
  • Townhouse for Rent

  156 Lori Anne Ln, Winter Springs, FL 32708

  Charming Updated End-Unit Townhome – Winter Springs, FLNow available for rent! This beautifully maintained 2-bedroom, 1.5-bath end-unit townhome in Winter Springs offers no HOA and a convenient location near the Casselberry border. You’ll have quick access to 434, 17-92, shopping, dining, and top-rated Seminole County schools.Situated on a corner lot, the home provides extra

  Richard Cunningham CHARLES RUTENBERG REALTY ORLANDO

  156 Lori Anne Ln, Winter Springs, FL 32708
• 

  /2

  $359,000 Sold Aug 12, 2025

  • 1,596 Sq Ft
  • $225/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  739 Mimosa Ct, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. This elegant home is nestled in the desirable Foxmoor neighborhood, located in the heart of Winter Springs. It sits in a peaceful cul-de-sac, perfect for those who cherish tranquility and community.Upon entry, you'll be greeted by vaulted ceilings and a light, bright interior with a large living room and dining space. The interior of the

  Robin Cook WEST WING REAL ESTATE COMPANY

  739 Mimosa Ct, Winter Springs, FL 32708
• 

  /2

  Est $356,478 Not Listed For Sale

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

  1638 Grand Rue Dr, Casselberry, FL 32707

  1638 Grand Rue Dr, Casselberry, FL 32707
• 

  

  /25

  $379,000 Pending

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

  704 Lancewood Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. Don’t miss your opportunity to buy this beautiful FOUR bed POOL home with a detached BONUS OFFICE! This home is perfect for entertaining family and friends. Enjoy the beautiful WELL-LIT VAULTED ceilings. CERAMIC TILE and LAMINATE flooring throughout. The kitchen features tiled BACKSPLASH and STAINLESS STEEL appliances. In the owner’s suite you’ll have

  Amanda Haines PREFERRED REAL ESTATE BROKERS II

  704 Lancewood Dr, Winter Springs, FL 32708
• 

  

  /16

  $2,320 per month

  • 4 Beds
  • 2 Baths
  • 2,014 Sq Ft
  • House for Rent

  20 N 2nd St, Winter Springs, FL 32708

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month’s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  20 N 2nd St, Winter Springs, FL 32708
• 

  /2

  $335,000 Sold Aug 12, 2025

  • 1,386 Sq Ft
  • $242/SF
  • 62 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2007

  432 Harbor Winds Ct, Winter Springs, FL 32708

  THE WINTER SPRINGS RETREAT // Welcome to this charming ONE STORY, end-unit in the quaint gated community of Harbor Winds in Winter Springs! ***NEW ROOF PUT ON IN 2023! *** Roof Assessment fully paid off!*** This townhome offers a serene conservation view with the added privacy of no rear neighbors, along with a convenient 2-car garage and a side entry that provides a glimpse of the

  Kristina Mollo ALL REAL ESTATE & INVESTMENTS

  432 Harbor Winds Ct, Winter Springs, FL 32708
• 

  

  /38

  Est $362,831 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft

  1630 Grand Rue Dr, Casselberry, FL 32707

  1630 Grand Rue Dr, Casselberry, FL 32707
• 

  

  /57

  $625,000

  • 6 Beds
  • 4 Baths
  • 1,123 Sq Ft

  212 Perth Ct Unit B, Winter Springs, FL 32708

  Exceptional investment opportunity in the sought-after Highlands community of Winter Springs! This well-maintained duplex offers two spacious 3-bedroom, 2-bath units, each featuring a 2-car garage, fenced backyard, and thoughtfully designed floor plan. Both sides are professionally leased, generating a combined $3,600/month in gross income, with tenants responsible for their own utilities —

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  212 Perth Ct Unit B, Winter Springs, FL 32708
• 

  

  /35

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Condo for Rent

  429 Sheoah Blvd Unit 12, Winter Springs, FL 32708

  This spacious 3-bedroom, 2-bath home offers 1,187 sq. ft. of comfortable living in the heart of Winter Springs. Located in a well-maintained community with HOA, this property combines convenience and lifestyle.Enjoy access to a refreshing community pool and beautifully maintained common areas. The home features an inviting layout with ample natural light, making it perfect for both

  Jason Hamilton THE REALTY MEDICS

  429 Sheoah Blvd Unit 12, Winter Springs, FL 32708
• 

  /2

  $339,000 Sold Aug 12, 2025

  • 1,305 Sq Ft
  • $260/SF
  • 70 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  408 S Edgemon Ave, Winter Springs, FL 32708

  Fantastic property with NO HOA! New Roof in 2022! This 2 Car Garage Home has over ~$35K of recent renovations! Such renovations include: Granite Countertops, HVAC, Water Heater, Luxury Vinyl Flooring, Paint, Window Screens, Blinds, Sliding Glass Door, GE Refrigerator, GE Range, GE Hood, GE Dishwasher, Garbage disposal, Marble Vanity, and much more! Zoned for Seminole County schools! Property

  Allen Steigman STEIGMAN REALTY LLC

  408 S Edgemon Ave, Winter Springs, FL 32708
• 

  

  /28

  Est $171,725 Not Listed For Sale

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

  407 Sheoah Blvd Unit 13, Winter Springs, FL 32708

  407 Sheoah Blvd Unit 13, Winter Springs, FL 32708
• 

  

  /36

  $47,000

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft

  346 Casa Grande Dr, Winter Springs, FL 32708

  Welcome to 346 Casa Grande Dr, a charming mobile home located in Winter Springs, FL. This cozy home was built in 1980 and offers a comfortable living space for its residents. With 2 bathrooms and a total finished area of 828 sq.ft., this property is perfect for a small family or couple looking for a low-maintenance home.The lot size of this property is 3,267 sq.ft., providing a decent amount of

  Zachary Greenberg COASTAL REAL ESTATE PROFESSIONALS LLC

  346 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  /17

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,060 Sq Ft
  • House for Rent

  110 Elderwood St, Winter Springs, FL 32708

  **BEAUTIFUL POOL** This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee

  110 Elderwood St, Winter Springs, FL 32708
• 

  /2

  $285,000 Sold Aug 08, 2025

  • 1,544 Sq Ft
  • $185/SF
  • 12 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  201 Sweetgum Ct, Winter Springs, FL 32708

  Welcome to this 4-bedroom, 2-bathroom single-family home nestled in a quiet cul-de-sac in desirable Winter Springs, offering privacy, potential, and NO HOA! Sitting on an oversized 0.30-acre lot, this property features no rear neighbors and only one side neighbor, with the other side bordering a beautifully maintained city-preserved green space.With a new roof (2021), water heater (2022),

  Brianna Perez Montalvo EXP REALTY LLC

  201 Sweetgum Ct, Winter Springs, FL 32708
• 

  /2

  Est $441,148 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,972 Sq Ft

  1848 Marley Place, Longwood, FL 32750

  1848 Marley Place, Longwood, FL 32750
• 

  

  /39

  $310,000

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  Unlisted Address

  This cozy bungalow-style home has plenty to offer aside from a quiet location with great proximity to parks, shopping and restaurants. The home features New Roof (May 2023); Goodman AC (2023); New interior/exterior neutral paint and carpet. This 3/2 split floorplan gives you plenty of space plus vaulted ceilings and plenty of natural light flow throughout the home. Open kitchen is light and

  Vincent Scarlatos CORCORAN PREMIER REALTY

  Unlisted Address
• 

  

  /11

  $1,349 per month

  • 2 Beds
  • 2 Baths
  • 938 Sq Ft
  • Condo for Rent

  117 Cory Ln, Winter Springs, FL 32708

  *Move in now and enjoy your 1st month FREE with a 12-month lease* Welcome home! This fantastic 2-bedroom, 2-bath home is available for immediate move in! Located conveniently in the desirable community of Winter Springs, this property features a comfortable layout with well apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features

  Steve Simpson 407 PROPERTIES

  117 Cory Ln, Winter Springs, FL 32708
• 

  /2

  $240,000 Sold Aug 06, 2025

  • 1,056 Sq Ft
  • $227/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  619 Locust Ct, Winter Springs, FL 32708

  Needs TLC. See realtor remarks for showing instructions.

  Makena Clark EXIT REALTY PREMIER LEGACY

  619 Locust Ct, Winter Springs, FL 32708
• 

  

  /58

  Not Listed For Sale

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

  423 Sheoah Blvd Unit 15TH, Winter Springs, FL 32708

  423 Sheoah Blvd Unit 15TH, Winter Springs, FL 32708
• 

  

  /41

  $249,900 Open Sat 9AM - 11PM

  • 2 Beds
  • 2.5 Baths
  • 1,434 Sq Ft

  505 Moree Loop, Winter Springs, FL 32708

  Welcome to this charming 2-bedroom, 2 1/2-bath home located in the heart of Winter Springs! This beautifully maintained residence offers an open and functional layout, perfect for both everyday living and entertaining. The bright kitchen features ample cabinet space and a breakfast bar that overlooks the spacious living and dining areas.Step outside to a large wood deck and fenced

  Matt Magee LPT REALTY LLC

  505 Moree Loop, Winter Springs, FL 32708
• 

  

  /11

  $1,790 per month

  • 2 Beds
  • 1.5 Baths
  • 896 Sq Ft
  • Townhouse for Rent

  130 Kristi Ann Ct, Winter Springs, FL 32708

  Welcome home to this 2 bed, 1.5 bath townhouse in the heart of Winter Springs. You will be just minutes away from the Winter Springs Town Center, Great Seminole County Schools, Coffee Shops, Premium Gyms, Center Winds Park, and multiple conveniences nearby. The living room and patio offer ample space for relaxation and entertainment. Each bedroom is designed for functionality, with ceiling fans

  130 Kristi Ann Ct, Winter Springs, FL 32708
• 

  /2

  $260,000 Sold Aug 06, 2025

  • 1,540 Sq Ft
  • $169/SF
  • 20 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1973

  229 Bitterwood St, Winter Springs, FL 32708

  Charming 4-Bedroom Home in Prime Winter Springs Location – No HOA!Nestled in one of Winter Springs' most desirable neighborhoods, this delightful 4-bedroom, 2-bathroom home offers a perfect blend of comfort and convenience. With a spacious layout and thoughtful features, it's an ideal choice for families or anyone seeking a serene lifestyle.The open-concept living area seamlessly

  Justen Abudaif LPT REALTY, LLC

  229 Bitterwood St, Winter Springs, FL 32708
• 

  

  /52

  Est $341,983 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,626 Sq Ft

  514 George St, Winter Springs, FL 32708

  514 George St, Winter Springs, FL 32708
• 

  

  /15

  $189,500

  • 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

  Matt Merdian MERDIAN REALTY LLC

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708
• 

  

  /39

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Townhouse for Rent

  424 Club Dr, Winter Springs, FL 32708

  Welcome to this well-maintained 3-bedroom, 2-bath home located in the desirable Cypress Club community of Winter Springs. Nestled in a peaceful neighborhood, this inviting residence offers comfortable living with access to a host of amenities that make every day feel like a getaway. Enjoy spacious living areas, a functional layout, and thoughtful updates throughout. The primary suite features an

  Lee Sloan KELLER WILLIAMS ADVANTAGE REALTY

  424 Club Dr, Winter Springs, FL 32708
• 

  /2

  $337,000 Sold Jul 31, 2025

  • 1,131 Sq Ft
  • $298/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  610 Huntly Ln, Winter Springs, FL 32708

  Welcome to your beautifully updated home in the highly desirable Highlands community of Winter Springs! This charming 3-bedroom, 2-bath home is truly move-in ready, with thoughtful upgrades throughout. Step inside to discover 9-inch porcelain tile floors, elegant 6-inch craftsman-style baseboards, and recessed LED lighting with a nightlight function that creates a warm ambiance. The brand-new

  Alicia Kerns KORR REALTY CORP

  610 Huntly Ln, Winter Springs, FL 32708
• 

  

  /10

  Est $277,275 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  1232 Lake Lucerne Cir, Winter Springs, FL 32708

  1232 Lake Lucerne Cir, Winter Springs, FL 32708

Showing Results 41 - 80, Page 2 of 18