Highlands Homes for Sale

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  /33

  $301,000

  Open Sat 12PM - 2PM $17K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,878 Sq Ft

  702 Glasgow Ct, Winter Springs, FL 32708

  Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  702 Glasgow Ct, Winter Springs, FL 32708
• Explore Highlands

• 

  

  

  /73

  $374,900

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,721 Sq Ft

  622 Anhinga Rd, Winter Springs, FL 32708

  $374,900 NEW TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026,

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  622 Anhinga Rd, Winter Springs, FL 32708
• 

  

  

  /24

  $185,000

  $5K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 945 Sq Ft

  343 San Miguel St Unit 343, Winter Springs, FL 32708

  Welcome to this freshly painted 2-bedroom, 2-bathroom condominium located in the desirable Deer Song community in Winter Springs. Offering a low-maintenance lifestyle in a convenient Central Florida location, this residence is a great fit for a first-time buyer, downsizer, seasonal resident, or investor looking for a well-positioned property with everyday comfort and community appeal. Inside, the

  

  Michael Rogers

  INNOVATIVE REALTY, LLC

  343 San Miguel St Unit 343, Winter Springs, FL 32708
• 

  

  

  /27

  $319,900

  $10K PRICE DROP

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

  1715 Sunset Dr, Longwood, FL 32750

  Virtually Staged. Welcome to this inviting single-story home in Longwood, offering a bright layout, spacious rooms, and a large yard surrounded by mature trees. The HVAC was replaced in 2020 and the water heater was replaced in 2021, adding practical updates for peace of mind. From the moment you arrive, the fresh exterior, extended driveway, and peaceful setting create a sense of privacy and

  

  Carlos German

  EXP REALTY LLC

  1715 Sunset Dr, Longwood, FL 32750
• 

  

  

  /15

  $230,000

  Pre-Foreclosure

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

  118 Deer Song Dr, Winter Springs, FL 32708

  Opportunity knocks in Winter Springs! If you've been waiting for an affordable way to own in a desirable Central Florida community, this is it This 3-bedroom, 2-bath home offers 1,105 square feet with a very functional layout. This makes it an excellent opportunity for homeowners ready to build equity or investors looking for their next project. The biggest expense has already been taken care of

  James Evans CENTURY 21 ALTON CLARK

  118 Deer Song Dr, Winter Springs, FL 32708
• 

  

  /3

  $135,500

  • 2 Beds
  • 2 Baths

  63 Majorca 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

  63 Majorca Dr, Winter Springs, FL 32708
• 

  

  /14

  $365,500

  • 3 Beds
  • 2 Baths
  • 1,368 Sq Ft

  101 S Flamingo Ave, Winter Springs, FL 32708

  Sweet 3 bed, 2 bath, 1368 sq ft, home on a corner lot in the heart of Winter Springs. Recently remodeled! Fresh Paint, New Kitchen, SS appliances, Tile flooring throughout, Dining area, Living and Family Room, inside laundry room. Big, open, wrap-around porch in back is pre-plumbed & trussed for possible expansion of Primary Bedroom. Fenced in backyard, with mature oaks and landscaping. Single

  Adrien Love HAMILTON REALTY

  101 S Flamingo Ave, Winter Springs, FL 32708
• 

  

  /21

  $100,000

  • 2 Beds
  • 2 Baths
  • 1,440 Sq Ft

  106 La Vista, Winter Springs, FL 32708

  This home still looks like new. Beautifully done, custom ordered by original owner. It is a must to see. Open front porch, screened in area attached to carport. En Suite bathroom with sitting room in master bedroom. Hacienda is loaded with amenities-Pickle Ball Court, Doggy Park, Putt Putt Courses, BBQ Grills for outside grilling and much more- Major roads close. Only 45 minutes to the beaches or

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  106 La Vista, Winter Springs, FL 32708
• 

  

  /33

  $475,000

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,857 Sq Ft

  629 Ryan Ct, Winter Springs, FL 32708

  Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an

  Lisa D Orazio SOTERA LIVING

  629 Ryan Ct, Winter Springs, FL 32708
• 

  

  /16

  $360,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  3711 N Ronald Reagan Blvd, Longwood, FL 32750

  Prime Investment Opportunity – 3711 N Ronald Reagan Blvd, Longwood, FL 32750! This versatile .65-acre property (including an adjacent parcel) offers outstanding potential for residential use, commercial redevelopment, or a developer seeking to build or operate a business in a rapidly growing Central Florida location. Featuring a solid 960 sqft block-construction building (built 1969) with a

  Christopher Lyons AGILE GROUP REALTY

  3711 N Ronald Reagan Blvd, Longwood, FL 32750
• 

  /2

  $132,500

  • 2 Beds
  • 2 Baths

  8 La Vista Dr, Winter Springs, FL 32708

  This brand-new 2026 "The Solara" model offers a perfect blend of style and functionality, featuring recessed lighting, luxury plank flooring, and a beautiful decorative glass entry door. The modern kitchen is equipped with stainless steel appliances and a spacious island, ideal for cooking and entertaining. The home also includes a walk-in closet for added storage and a shed with

  Todd Vagts Hacienda Village

  8 La Vista Dr, Winter Springs, FL 32708
• 

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  77 Majorca Dr, Winter Springs, FL 32708

  Brand-new 2026 Home - The Riviera - 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

  77 Majorca Dr, Winter Springs, FL 32708
• 

  

  /30

  $54,900

  322 Casa Grande Ct, Winter Springs, FL 32708

  HOME HAS A DOUBLE ROOF, BATHROOMS HAVE BEEN REMODELED, SUB-FLOORING HAS BEEN REDONE 3/4 PLYWOOD WITH NEW FLOORING ON TOP, THE HOME HAS BEEN REPAINTED INSIDE, NEW COUNTER TOPS IN KITCHEN AND BATHROOMS. ALL NEW A/C DUCT WORK UNDER THE HOUSE WAS REDONE, A/C SERVICED AND BLOWER WAS REPLACED. Age-Restricted (55+) Community. Hacienda Village, Winter Springs, FL 32708

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  322 Casa Grande Ct, Winter Springs, FL 32708
• 

  

  /54

  $28,700

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,358 Sq Ft

  272 Ponce de Leon Dr, Winter Springs, FL 32708

  HACIENDA VILLAGE 55+ WELL MAINTAINED HOME! PERFECT FLOOR PLAN. INSIDE UTILITY CENTRAL AIR SYSTEM - FULL SYSTEM 2 HTD AREA 2 BEDROOMS - SPACIOUS MASTE SUITE WITH DRESSING, KITCHEN HAS AN ISLAND TOP COOKING. BEAUTIFUL BACKYARD AND SCREENED INSIDE PORCH. HACIENDA VILLAGE IS A LEGACY COMMUNITY - WITH NEW AMENITIES. MONTHLY Base RENT $1075. COME SEE US TODAY!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

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

  

  /35

  $279,000

  $11K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,089 Sq Ft

  276 San Gabriel St, Winter Springs, FL 32708

  Price Improvements. This 3-bedroom, 2-bathroom home in Deersong-2 is a fantastic opportunity for anyone looking for a move-in-ready property in Winter Springs. With its newly updated kitchen, Modern faucet, granite countertops, and indoor laundry. High ceilings at living room, the home feels both modern and spacious. The community offers excellent amenities, including a gated pool and tennis

  Mariam Sherkawy KELLER WILLIAMS WINTER PARK

  276 San Gabriel St, Winter Springs, FL 32708
• 

  

  /10

  $17,500

  • 2 Beds
  • 1 Bath

  172 Costa Cir, Winter Springs, FL 32708

  This home is a 2-bed, 1-bath with laminate flooring in the main areas and carpet in the bedrooms, has new windows and doors installed, along with kitchen cabinets with a soft-close feature.

  Todd Vagts Hacienda Village

  172 Costa Cir, Winter Springs, FL 32708
• 

  

  /43

  $269,000

  $11K PRICE DROP

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

  446 Club Dr, Winter Springs, FL 32708

  Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third

  Hanoi Burgos COLDWELL BANKER REALTY

  446 Club Dr, Winter Springs, FL 32708
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  /61

  $1,049,000

  $350K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,464 Sq Ft

  120 E Bahama Rd, Winter Springs, FL 32708

  Mid-Century Modern Paradise!! A Beautiful, well-designed home with spectacular architecture offering privacy, space, and long-term versatility on a rare 2.22-acre lot with RV/Toy parking—delivering exceptional value in this area. A separate in-law or guest suite features its own exterior entrance and full bathroom, ideal for multigenerational living, a private office, studio, or extended stays.

  Alma Merrill EXP REALTY LLC

  120 E Bahama Rd, Winter Springs, FL 32708
• 

  

  /33

  $215,000

  $24K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,002 Sq Ft

  506 Club Dr, Winter Springs, FL 32708

  Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. The HOA just installed

  Kathleen Harrison CALL IT CLOSED INTL REALTY

  506 Club Dr, Winter Springs, FL 32708
• 

  

  /25

  $210,000

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  30 Moree Loop Unit 39, Winter Springs, FL 32708

  Welcome to your move-in ready 3-bedroom, 2.5-bath townhome-style condo located in the desirable Highlands of Winter Springs community known for its beautiful tree-lined streets, scenic walking trails, and resort-style amenities. This stylish home offers approximately 1,400 square feet of updated living space designed for comfort and low-maintenance living. Inside, you’ll find a fully remodeled

  Casey Irwin PARK VIEW REALTY INC

  30 Moree Loop Unit 39, Winter Springs, FL 32708
• 

  

  /35

  $249,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,089 Sq Ft

  270 San Gabriel St, Winter Springs, FL 32708

  Quick Closing Available. Welcome to 270 San Gabriel Street in Winter Springs—now offered at an updated price and ready for its next owner. This well-maintained, single-story home features vaulted ceilings and a bright, open layout that creates a comfortable and inviting living space. With neutral finishes and ceramic tile flooring throughout, the home is truly move-in ready. All appliances are

  Alie Gattis MAINFRAME REAL ESTATE

  270 San Gabriel St, Winter Springs, FL 32708
• 

  

  /23

  $199,900

  $45K PRICE DROP

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

  411 Green Spring Cir, Winter Springs, FL 32708

  Short Sale. INVESTOR ALERT. This 3-bedroom, 1.5-bath townhome in Winter Springs is offered as a short sale and presents an exceptional opportunity for investors, renovators, or buyers ready to create their own vision. Featuring a spacious living and dining area, functional kitchen, convenient half bath downstairs, and additional storage beneath the staircase, the layout offers a strong foundation

  Sarita Cabrera WATSON REALTY CORP

  411 Green Spring Cir, Winter Springs, FL 32708
• 

  

  /24

  $399,000

  $21K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,218 Sq Ft

  203 Sweetgum Ct, Winter Springs, FL 32708

  This meticulously maintained home offers an impressive combination of recent upgrades, thoughtful features, and exceptional outdoor living. The curb appeal is enhanced by professional landscape lighting, while 10-foot access gates on both sides of the property provide convenience and flexibility. A three-zone irrigation system helps maintain the beautifully landscaped grounds year-round.The

  Joseph Connolly CENTURY 21 ALTON CLARK

  203 Sweetgum Ct, Winter Springs, FL 32708
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  /49

  $39,900

  $5K PRICE DROP

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

  210 El Camino Real Cir, Winter Springs, FL 32708

  Bought A New Home in Hacienda, Letting this perfect one go-Private backyard; newer windows, All ducts redone-Electric up to date-Hacienda centrally located about 45 minutes to the beaches & parks, Hacienda has a lot of amenities-2 pools, pickle ball, doggy park. Close to fire and police station, restaurants, shopping. Monthly base rate is $1075.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

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

  

  /3

  $110,000

  • Land
  • 12,632 Sq Ft
  • $379,310 per Acre

  Unlisted Address

  Incredible opportunity to build your dream home on this fantastic vacant land! Great location,situated near Highway 17-92, and SR 434, this property has many conveniences only a few minutesaway from popular spots like Winter Springs town center, Target, Publix, Lowes, Home Depot, and thebeautiful Lake Concord Park. Enjoy life in a well established neighborhood with quick access

  R Webb REALTY PROFESSIONALS USA LLC

  Unlisted Address
• 

  

  /24

  $355,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,769 Sq Ft

  710 Briarwood Dr, Winter Springs, FL 32708

  Virtually Staged. BRAND-NEW 2026 HVAC • VACANT Beautifully updated 4-bedroom, 2-bath home in Winter Springs featuring a spacious layout, modern upgrades, and a fresh, clean feel throughout. Inside, you’ll find fresh interior paint, updated lighting and ceiling fans, new baseboards and trim, and custom shelving in the living room. The home features multiple living spaces, well-sized bedrooms, and

  Steven Koleno BEYCOME OF FLORIDA LLC

  710 Briarwood Dr, Winter Springs, FL 32708
• 

  

  /54

  $18,000

  $7K PRICE DROP

  • 2 Beds
  • 2 Baths

  364 Casa Grande Dr, Winter Springs, FL 32708

  Priced to Sell - Make Offer - Screened in Porch, Good Size Shed, 2 Bedrooms, 2 Baths, Located in Phase III, Golf Cart Path Close. Hacienda Village has a lot of amenities, 2 pools (1 heated), Pickleball, Putt Putt, Doggy Park. Hacienda is located near major highways within 45 minutes of beaches & parks - Check us out! Base Monthly rent is $1075.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  364 Casa Grande Dr, Winter Springs, FL 32708
• 

  

  /30

  $540,000

  $5K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,852 Sq Ft

  811 Maple Leaf Loop, Winter Springs, FL 32708

  Explore 811 Maple Leaf Loop, recently enhanced with fresh interior paint. The kitchen includes a functional island, and the primary bathroom provides double sinks for practical use, a walk in closet and convenience of a separate tub and shower. Beyond the interior, exterior grounds feature a covered patio and a fenced in backyard. Discover modern comfort and practical living in this updated

  Karen Albright OPENDOOR BROKERAGE LLC

  811 Maple Leaf Loop, Winter Springs, FL 32708
• 

  

  /28

  $344,900

  $10K PRICE DROP

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

  1562 Grand Rue Dr, Casselberry, FL 32707

  Welcome to this like-new 2022 Craftsman-style END-UNIT townhome in the heart of highly desirable Seminole County! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of modern design, energy efficiency, and low-maintenance living. As an end unit, the home is filled with abundant natural light and offers additional privacy along with extra green space to enjoy—without the

  Simon Colak USCO CAPITAL GROUP

  1562 Grand Rue Dr, Casselberry, FL 32707
• 

  

  /50

  $29,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  128 Las Almas Ln, Winter Springs, FL 32708

  SURPRISE!- A large enclosed bonus room not included in the square footage! Double carport area. Home has been renovated! A lot of bang for the buck! Close to recreation Hall and heated pool. Hacienda has a lot to offer, it is centrally located, close to major highway-45 minutes to beaches, 9 parks. Fire & Police Dept. 5 minutes away. Restaurants, shopping medical near. Never a dull moment with

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  128 Las Almas Ln, Winter Springs, FL 32708
• 

  

  /26

  $39,000

  $16K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  288 La Vista Dr, Winter Springs, FL 32708

  This move-in-ready home has been beautifully updated from top to bottom, featuring a metal roof, new flooring throughout, new drywall, updated walls, remodeled bathrooms, a brand-new kitchen, and newer appliances. As you enter the home, you are welcomed by a spacious enclosed Florida room, perfect for relaxing and enjoying Florida sunsets in a private and comfortable setting. The open-concept

  Maria Orozco Four Star Homes, Inc.

  288 La Vista Dr, Winter Springs, FL 32708
• 

  

  /41

  $19,900

  $12K PRICE DROP

  • 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
• 

  

  /37

  $235,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,363 Sq Ft

  504 Green Spring Cir, Winter Springs, FL 32708

  Welcome to 504 Green Spring Circle, a beautifully maintained 2 bedroom 2.5 bath townhome nestled in the heart of Winter Springs, where comfort, charm, and everyday functionality come together effortlessly. BRAND NEW HVAC JULY 2026, AIR DUCTS 2026, ROOF 2020!! Inside, the UPDATED KITCHEN features modern finishes, GRANITE countertops, ample prep space, and room for a dine-in table. The home has

  Riki Cantelli EXP REALTY LLC

  504 Green Spring Cir, Winter Springs, FL 32708
• 

  

  /50

  $329,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft

  335 Kirkcaldy Dr, Winter Springs, FL 32708

  Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new

  Irina Carp MILLENIUM REALTY GROUP

  335 Kirkcaldy Dr, Winter Springs, FL 32708
• 

  

  /43

  $489,000

  $10K PRICE DROP

  • 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
• 

  

  /33

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,161 Sq Ft

  108 Sundance Ct, Winter Springs, FL 32708

  Welcome home to this beautifully remodeled gem tucked away on a quiet cul-de-sac in desirable Winter Springs! From the moment you walk in, you’ll fall in love with the bright, open-concept layout designed for easy living and effortless entertaining. With 1,161 sq ft under air, every inch of this home has been thoughtfully updated and filled with charm.The stunning fully remodeled kitchen is

  Matias Gomez JEMINI REALTY CORP

  108 Sundance Ct, Winter Springs, FL 32708
• 

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  154 Hacienda Dr Unit 154, 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 Unit 154, Winter Springs, FL 32708
• 

  

  /39

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,497 Sq Ft

  655 Nighthawk Cir, Winter Springs, FL 32708

  Welcome home to this impeccably maintained 2-bedroom, 2-bath home in the highly desirable area of Winter Springs, Florida! From the moment you step inside, you'll appreciate the open floor plan, soaring vaulted ceilings, and spacious living area centered around a stunning wood-burning fireplace—creating the perfect setting for both relaxing evenings and entertaining guests. The heart of the home

  Bill Mauer RE/MAX INNOVATION

  655 Nighthawk Cir, Winter Springs, FL 32708
• 

  

  /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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2

Why Live in Highlands

Highlands in Winter Springs, Florida, is a neighborhood known for its lush natural scenery and access to urban amenities. The area is part of the Seminole County Public Schools, a Premier National School District, with highly rated institutions like Indian Trails Middle and Winter Springs High School. The neighborhood features a mix of single-family homes, condos, and townhomes, with styles ranging from ranch-style to Spanish-revival, built primarily in the mid-to-late 20th century. The Highlands Homeowner's Association provides amenities such as tennis courts, a junior-sized Olympic swimming pool, a playground, a lakeside park, nature trails, and an outdoor grill area. Residents enjoy proximity to several parks, including Spring Hammock Preserve with its ancient bald cypress trees and Soldiers' Creek Park, which offers championship baseball fields and access to the Cross Seminole Trail. Torcaso Park provides a nautical-themed playground and splash pad for children, while anglers can fish in Lake Jessup. Dining options include Chilangos for Mexican cuisine, Argentinian Bakery and Café for sweet treats, and Victorio's for Italian fare. The Winter Springs Town Center offers shopping and nightlife, with additional retail options at nearby Altamonte Mall and Oviedo Mall. Highlands is safer than the national average, making it a practical choice for families. While biking is popular, most residents rely on cars and trucks, with public buses and SunRail providing transportation to Downtown Orlando, 15 miles away. The neighborhood hosts events like the Central Florida Scottish Highland Games and the Hometown Harvest Festival, adding to its community appeal.

Learn more about living in Highlands

Highlands Home Prices vs. Nearby Winter Springs, FL Neighborhoods

	Highlands	Greenwood Lakes	Lake Mary	Altamonte Springs
Median Home Price	$320,000	$385,000	$406,250	$269,000
Median Sale Price	$302,500 -7% YoY	$365,000 -3% YoY	$392,000 +2% YoY	$300,000 -4% YoY
Median Single Family Price	$325,000	$400,000	$400,000	$429,000
Median Townhouse Price	$454,950	$405,000	$390,000	$399,000
Median Condo Price	$175,000	$154,250	$197,500	$163,500
Total Active Listings	49	31	111	138
Market Conditions	4 Months of Supply Balanced Market	3 Months of Supply Seller's Market	3 Months of Supply Seller's Market	6 Months of Supply Balanced Market

Frequently Asked Questions

Is Highlands a good place to live?

Highlands is a good place to live. Highlands is considered car-dependent and bikeable with minimal transit options. Highlands has 9 parks for recreational activities. It is fairly sparse in population with 5.0 people per acre and a median age of 40. The average household income is $72,590 which is below the national average. College graduates make up 29.8% of residents. A majority of residents in Highlands are home owners, with 39% of residents renting and 61% of residents owning their home. A local real estate agent serving Highlands can help you decide if this neighborhood is the right one for you. Learn more on our Highlands neighborhood guide.

Is Highlands, FL a safe neighborhood?

Highlands, FL is safer than the average neighborhood in the United States. It received a crime score of 3 out of 10.

How much do you need to make to afford a house in Highlands?

The median home price in Highlands is $320,000. If you put a 20% down payment of $64,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $1,630 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $70K a year to afford the median home price in Highlands. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Highlands is $73K.

What are the best public schools in Highlands?

The best public schools that serve Highlands are:

• Seminole High School has an A- Niche grade, a student teacher ratio of 20:1 and an average review score of 3.9.
• Lake Mary High School has an A- Niche grade, a student teacher ratio of 21:1 and an average review score of 3.9.
• Winter Springs High School has an A- Niche grade, a student teacher ratio of 20:1 and an average review score of 3.6.

What are the best private schools in Highlands?

The best private schools that serve Highlands are:

• The Geneva School has an A+ Niche grade, a student teacher ratio of 9:1 and an average review score of 4.4.
• Oak Arbor Christian School has a student teacher ratio of 50:1.
• Revival Fire Christian Academy has a student teacher ratio of 10:1.

What are the most popular zip codes in Highlands, Winter Springs, FL?

The most popular zip codes in Highlands, Winter Springs, FL include 32708, 32707, 32750, 32746 and 32773.

What are the most popular neighborhoods near Highlands, Winter Springs, FL?

The most popular neighborhoods near Highlands, Winter Springs, FL are Longwood Lakes, Greenwood Lakes, Alaqua, Lake Howell and Spring Valley.

Are home prices dropping in Highlands?

Yes, home prices in Highlands are down 7% in the last 12 months.