22

Highlands Houses for Sale

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  • /58

    $365,000

    • 3 Beds
    • 2 Baths
    • 1,387 Sq Ft

    45 S Edgemon Ave, Winter Springs, FL 32708

    LOCATION LOCATION LOCATION This charming fully renovated home offers 3-bedroom, 2-bathroom home featuring 1,387 sqft of stylish living space. This property boasts brand-new cabinets, elegant quartz countertops, Brand new stainless steel appliances, cozy fireplace, and sleek laminate flooring throughout. Brand new roof. Enjoy outdoor living at its best with an in-ground pool perfect for

    Agent Photo

    John Gomez

    EXP REALTY LLC

    (321) 385-8619

    45 S Edgemon Ave, Winter Springs, FL 32708
  • /25

    $399,900

    • 4 Beds
    • 2 Baths
    • 1,983 Sq Ft

    221 Albert St, Winter Springs, FL 32708

    This 4-bedroom, 2-bath home offers 1,983 sq. ft. of living space with an open layout connecting the family room, dining, and kitchen areas. The kitchen features a skylight and a peninsula that opens seamlessly to the family room, while a Florida room connects directly from the kitchen and leads out to the backyard deck with a 12x12 hardtop gazebo that conveys. Both bathrooms also have skylights,

    David Zambrano REDFIN CORPORATION

    221 Albert St, Winter Springs, FL 32708
  • /45

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,652 Sq Ft

    746 N Gretna Ct, Winter Springs, FL 32708

    Welcome to Your Dream Home in The Highlands of Winter Springs!This beautifully maintained residence offers everything you've been waiting for — and more! Featuring a desirable split-bedroom floor plan, this home boasts upgraded appliances, a brand-new HVAC system, and a bright, inviting family room perfect for gatherings or quiet evenings in.Enjoy Florida living at its best with a

    John Muccigrosso RE/MAX 200 REALTY

    746 N Gretna Ct, Winter Springs, FL 32708
  • /51

    $399,999

    • 4 Beds
    • 3 Baths
    • 2,008 Sq Ft

    878 Elgin Dr, Winter Springs, FL 32708

    MOTIVATED SELLER/ AS IS CONTRACT- Step into comfort and flexibility at 878 Elgin Dr in Winter Springs! This spacious home offers a rare layout with two master bedrooms, three full bathrooms, and plenty of room for everyone. Whether you’re looking for space to grow, host guests, or live with extended family — this one fits the bill. You’ll love the solar panels, fenced backyard, and security

    Yasesky Abreu LPT REALTY, LLC

    878 Elgin Dr, Winter Springs, FL 32708
  • /36

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    625 Nighthawk Cir, Winter Springs, FL 32708

    This charming 3 bedroom, 2 bathroom single family home boasts a beautiful open plan. The kitchen has been recently remodeled and includes solid counter tops and back splatch. The appliances are all within a couple years old and barely used. The tile roof is 2 years old. The water heater is brand new. The entire property has been recently painted and the carpeting is brand new. The primary

    Warren Gagne NEXTHOME NEIGHBORHOOD REALTY

    625 Nighthawk Cir, Winter Springs, FL 32708
  • /49

    $365,000

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

    602 Nighthawk Cir, Winter Springs, FL 32708

    BEAUTIFUL HOME IN WINTER SPRINGS! ***SELLER OFFERING $5,000 TOWARDS BUYER'S CLOSING COSTS/RATE BUY DOWN*** 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

    Alexandra Repetto REPETTO REALTY GROUP LLC

    602 Nighthawk Cir, Winter Springs, FL 32708
  • /29

    $429,900

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    213 Almaden Ct, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to the quiet subdivision of Mount Greenwood. This beautiful 3-bedroom, 2-bathroom homefeatures a sparkling crystal-clear pool enclosed in a large screen lanai and fenced backyard perfectfor relaxation and entertaining. The modern open floorplan offers stylish laminate flooring in theliving areas, plush new carpeting in the

    Christine Landrau MARK SPAIN REAL ESTATE

    213 Almaden Ct, Winter Springs, FL 32708
  • /50

    $315,000

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

    515 Seasons Ct, Winter Springs, FL 32708

    Welcome to this beautifully remodeled 3-bedroom, 2-bathroom home located in the sought-after area of Winter Springs, known for its top-rated schools.Inside, you’ll find a modern open layout starting with a spacious living room that flows seamlessly to the private patio. To the right, the brand-new kitchen and dining area combo feature new wood cabinets, quartz countertops, and brand new

    Olga Carballea Diaz CHARLES RUTENBERG REALTY ORLANDO

    515 Seasons Ct, Winter Springs, FL 32708
  • /32

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,336 Sq Ft

    121 N Fairfax Ave, Winter Springs, FL 32708

    Beautiful 3 bedrooms 2 baths home in Winter Springs, Florida. Sit out on your front porch and enjoy the lake/park view. Beautiful, paved driveway can hold 2 cars. Relax in the backyard within big area. This home is minutes from all shopping, Interstate 4 and the 417-toll road. Close to the police station for added security. The back yard has turf grass. Kitchen was remolded new counter and

    Ruben Cabrera AVILA & ASSOCIATES REALTY

    121 N Fairfax Ave, Winter Springs, FL 32708
  • /37

    $525,000

    • 4 Beds
    • 2.5 Baths
    • 2,092 Sq Ft

    431 S Hawthorn Cir, Winter Springs, FL 32708

    **Single-Family Home with Detached ADU & Pool**Tucked away in a quiet cul-de-sac, this over 2,000 sq. ft. home with a detached Accessory Dwelling Unit (ADU) is a rare find in the highly desirable, non-HOA community of North Orlando Terrace! NEWER ROOF (2022), as well as a massive remodel in 2023 that consisted of NEW kitchen, bathrooms, plumbing, electrical panel, interior/exterior paint,

    Elliot Shugan THE SHUGAN GROUP INC

    431 S Hawthorn Cir, Winter Springs, FL 32708
  • /68

    $349,900

    • 4 Beds
    • 2 Baths
    • 1,604 Sq Ft

    221 N Devon Ave, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to a stunning oasis in the heart of Winter Springs, where style meets convenience. This beautifully maintained 4-bedroom, 2-bathroom pool home has been updated to provide a bright and open floor plan, featuring durable laminate and ceramic tile flooring.This home features elegant Level 3 granite countertops in both the kitchen and

    Sara Nicholas, PA CHARLES RUTENBERG REALTY ORLANDO

    221 N Devon Ave, Winter Springs, FL 32708
  • /39

    $299,000

    • 3 Beds
    • 1 Bath
    • 945 Sq Ft

    150 N Cortez Ave, Winter Springs, FL 32708

    PRICE DROP-Move-In Ready! Beautifully Remodeled 3-Bedroom Home with No HOAWelcome to this charming and fully remodeled 3-bedroom, 1-bath home located in the heart of Winter Springs! Centrally situated near top-rated schools, shopping, dining, and just minutes from scenic bike and walking trails, this home offers the perfect blend of convenience and comfort. Enjoy quick access to I-4 and the

    Robert McGrew, PA FLAT FEE REAL ESTATE SERVICES LLC

    150 N Cortez Ave, Winter Springs, FL 32708
  • /34

    $310,000

    • 4 Beds
    • 2 Baths
    • 1,322 Sq Ft

    551 Laurel Ct Unit 3, Winter Springs, FL 32708

    Priced well below recent appraisal! Investor special in the sought-after Highlands of Winter Springs! This home is in a desirable community of Winter Springs. Sitting on a large cul-de-sac lot, this property needs some TLC, but offers strong flip or rental potential. Features a split floor plan, open living/dining area, and access to community amenities including pool, tennis, and walking

    Miraya Lane KELLER WILLIAMS ADVANTAGE III

    551 Laurel Ct Unit 3, Winter Springs, FL 32708
  • /36

    $495,000

    • 3 Beds
    • 2.5 Baths
    • 2,185 Sq Ft

    821 Sheoah Cir, Winter Springs, FL 32708

    Exceptional two-story home in the sought-after Highlands of Winter Springs, a community surrounded by scenic nature trails and lush green spaces. Located within walking distance to top-rated Seminole County schools, with shopping, dining, and major roadways just minutes away. Situated on a premium conservation lot with no rear neighbors, this 3-bedroom, 2.5-bath residence offers nearly 2,200 sq.

    Sean Calegan CFRP REALTY LLC

    821 Sheoah Cir, Winter Springs, FL 32708
  • /23

    $339,900

    • 3 Beds
    • 2 Baths
    • 1,168 Sq Ft

    409 Murphy Rd, Winter Springs, FL 32708

    In the heart of Winter Springs lies your next model home or your next short-term cash-flowing business!! This warm, cozy yet spacious home will make you fall in love from the start and that's not just the homestyle screened in front porch w/ rocking chairs! Step inside & discover a wide-open layout w/ spacious bedrooms, gleaming wood-look flooring, & abundant natural light. The primary suite

    Brandon Ford TOWER TEAM REALTY, LLC

    409 Murphy Rd, Winter Springs, FL 32708
  • /23

    $337,500

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft

    391 Panama Cir, Winter Springs, FL 32708

    Welcome to 391 Panama Circle:This move-in ready 3 bedroom, 2 bath residence features fresh interior paint and brand new carpet and luxury vinyl laminate throughout, offering a clean and inviting atmosphere. Enjoy Florida living on the screened-in porch overlooking a private, fully fenced backyard perfect for relaxing or entertaining. Additional highlights include a spacious 2-car

    Summer Hornburg BELMONT REALTY

    391 Panama Cir, Winter Springs, FL 32708
  • /42

    $295,900

    • 4 Beds
    • 1 Bath
    • 1,120 Sq Ft

    206 Charles St, Winter Springs, FL 32708

    Price Reduced! VIEW WALKTROUGH VIDEO! Charming Bungalow that lives quite large. Discover your dream home nestled in the heart of Winter Springs, on one floor, perfect for all family types. All new neutral FRESH INTERIOR PAINT! Split plan. Great eat in kitchen and floorplan that overlooks the backyard! This enchanting single-family residence boasts four cozy bedrooms, offering a flexible split

    Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

    206 Charles St, Winter Springs, FL 32708
  • /31

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,318 Sq Ft

    207 Bitterwood St, Winter Springs, FL 32708

    Welcome to 207 Bitterwood St – A Pool Home Gem in the Heart of Winter Springs! Tucked into a quiet, established neighborhood with NO HOA, this move-in-ready 3-bedroom, 2-bath home sits on a generous 9,104 sq ft lot and offers the perfect blend of space, comfort, and convenience. Step inside to find an open, flexible floor plan with neutral tile flooring throughout, spacious living and dining

    Milton Figueroa EMPIRE NETWORK REALTY

    207 Bitterwood St, Winter Springs, FL 32708
  • /7

    $315,000

    • 4 Beds
    • 2.5 Baths
    • 1,405 Sq Ft

    Unlisted Address

    The house is on a corner lot with a nice fenced in back yard. The big work has all been done - the roof was replaced in 2020, and the HVAC was replaced in 2023. The house has a formal Living Room, Dining Room, a Family Room in addition to the 4 bedrooms, and a private fenced in back yard. Make this beautiful property your new home!

    Mike Northam NORTHAM REALTY, LLC

    Unlisted Address
  • /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
  • /22

    $260,000

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

    294 San Gabriel St, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Charming 2-bedroom, 2-bath, Move-In-Ready home featuring an open living and dining area with vaulted ceilings, stylish new laminate flooring, outside storage room, plus the convenience of an inside laundry. With a few finishing touches, this property can truly shine making it a smart investment or a perfect place to call your own. Roof 2018, Water

    Christine Schneider RE/MAX TOWN & COUNTRY REALTY

    294 San Gabriel St, Winter Springs, FL 32708
  • /42

    $494,000

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

    811 Gatehouse Dr, Winter Springs, FL 32708

    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, you are greeted by

    Cleve Loveland LOVELAND PROPERTIES

    811 Gatehouse Dr, Winter Springs, FL 32708

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.

Home Trends in Highlands, FL

Housing Trends

Median Sale Price
$320,000
Median Single Family Sale Price
$335,000
Median Townhouse Sale Price
$500,000
Median 2 Bedroom Sale Price
$182,250
Median 1 Bedroom Sale Price
$147,500
Average Price Per Sq Ft
$228
Number of Homes for Sale
36
Last 12 months Home Sales
163
Months of Supply
2.70
Median List Price
$325,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-5%
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