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Highlands Homes for Sale with View

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  • /38

    $399,999 Open Sun 1PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,762 Sq Ft

    340 Inglenook Cir Unit 1, Winter Springs, FL 32708

    Buyer changed there mind! New Price!!! Welcome to 340 Inglenook Cir, a beautifully maintained pool home in the heart of Winter Springs offering the perfect blend of comfort, privacy, and Florida lifestyle living. This 3-bedroom, 2-bath residence features a light-filled, open layout designed for both everyday living and effortless entertaining. At the heart of the home, spacious living areas flow

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (689) 399-2598

    340 Inglenook Cir Unit 1, Winter Springs, FL 32708
  • /25

    $195,000 Open Sat 1PM - 4PM

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

    30 Moree Loop Unit 37, Winter Springs, FL 32708

    New to market. Seller offering $5,000 toward buyer closing costs and concessions! This newly remodeled unit is a two-bedroom, 2.5 bath with converted office/flex room in the wonderful community of Bay Tree. Bay Tree is part of a diverse set of communities in the community of Highlands, offering an array of amenities including tennis, lake, community park, gazebos, playground, community pool, and

    Brett Womack PREMIER SOTHEBYS INT'L REALTY

    30 Moree Loop Unit 37, Winter Springs, FL 32708
  • /29

    $185,000

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

    60 Sheoah Blvd Unit 38A, Winter Springs, FL 32708

    **Seller may consider buyer concessions if made in an offer**Welcome to this BEAUTIFULLY UPDATED 2-bedroom, 1.5-bath condo in The Highlands of Winter Springs, offering the feel of a townhome with NO REAR NEIGHBORS and peaceful green space views. Thoughtfully maintained and MOVE-IN READY, this home combines comfort, style, and a desirable location. A SCREENED FRONT PORCH welcomes you in—perfect

    Jennifer Wemert WEMERT GROUP REALTY LLC

    60 Sheoah Blvd Unit 38A, Winter Springs, FL 32708
  • /52

    $285,000

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

    476 Club Dr, Winter Springs, FL 32708

    Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a 2020 A/C system, a full

    Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

    476 Club Dr, Winter Springs, FL 32708
  • /32

    $229,500

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

    502 Club Dr, Winter Springs, FL 32708

    Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a

    Tamara Martin INFINITY REAL ESTATE GROUP

    502 Club Dr, Winter Springs, FL 32708
  • /24

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,366 Sq Ft

    712 Linden Dr, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to this well-maintained 3-bedroom, 2-bathroom block townhome offering 1,366 square feet of comfortable living space in the desirable Wildwood community of Winter Springs. Tucked along a quiet tree-lined street. Inside, the home features an open and inviting layout highlighted by vaulted ceilings, neutral tones, and vinyl flooring that create

    Kaleb Shaw SHAW SIGNATURE RE

    712 Linden Dr, Winter Springs, FL 32708
  • /24

    $374,900

    • 3 Beds
    • 2.5 Baths
    • 1,771 Sq Ft

    618 Nighthawk Cir, Winter Springs, FL 32708

    Move in Ready home in Greenspointe section of The Highlands. This Light & Bright Home has No Rear Neighbors and a Nice View of the open space out back. New Tile Roof 2017, New A/C. Primary Bathroom has a Large Step-In Shower/Tub. The community offers a variety of amenities including a Olympic Size Community Pool, Tennis & Pickleball Courts, Audibon Park, Nature Trails and a Clubhouse. Highly

    Paul Buscemi FLORIDA HOME TEAM REALTY LLC

    618 Nighthawk Cir, Winter Springs, FL 32708
  • /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
  • /40

    $279,900

    • 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
  • /47

    $1,299,900

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

    120 E Bahama Rd, Winter Springs, FL 32708

    This property offers a rare opportunity to own a home with true flexibility, privacy, and long-term value—perfect for today’s evolving lifestyles. Designed with flexibility in mind, this home features a private in-law or guest suite with its own separate exterior entrance and full bathroom, creating an ideal setup for multigenerational living, visiting guests, or a private home office. The in-law

    Alma Merrill EXP REALTY LLC

    120 E Bahama Rd, Winter Springs, FL 32708
  • /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
  • /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
  • /24

    $352,000

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    310 Panama Cir, Winter Springs, FL 32708

    BEAUTIFUL HOME! TOTALLY UPGRADED 3 BEDROOMS 2 BATHS!! & IN-LAW SUITE 1 BEDROOM 1 BATHROOM AND LAUNDRY. Priced to Sell! This home is not like no other home in this area, Nice Kitchen Cabinets and Granite counter tops, modern tile floors, Stain Steel appliances, Refrigerator, Range & microwave. This home is clean, immaculate and a pleasure to show.

    Everardo Santos ESG INVESTMENT ENTERPRISE INC

    310 Panama Cir, Winter Springs, FL 32708
  • /34

    $315,500

    • 4 Beds
    • 2 Baths
    • 1,356 Sq Ft

    114 Sundance Ct, Winter Springs, FL 32708

    Discover comfort and convenience at 114 Sundance Ct, a 4-bedroom home in the cul-de-sac community of The Seasons in Winter Springs. Backing to conservation for added privacy, this home features vaulted ceilings, an open layout, tile flooring in the main living areas, laminate flooring in the bedrooms, and fresh interior paint. The split-bedroom design offers a functional layout, while the kitchen

    Nora Rios WEICHERT REALTORS HALLMARK PRO

    114 Sundance Ct, Winter Springs, FL 32708
  • /37

    $450,000

    • 5 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
  • /27

    $235,000

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

    498 Club Dr, Winter Springs, FL 32708

    Welcome to Cypress Club, a townhome community located in The Highlands within Winter Springs. Two bedrooms/two bath home is two stories offering split bedrooms. The living room/dining room combo provides high lofty ceilings with celestial windows providing natural sunlight to the home. Sliding glass doors open to a screen enclosed patio to the rear of the property that overlooks Winter Springs

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    498 Club Dr, Winter Springs, FL 32708
  • /44

    $847,500 Pre-Foreclosure

    • 6 Beds
    • 4 Baths
    • 3,100 Sq Ft

    135 W Trade Winds Rd, Winter Springs, FL 32708

    As you arrive, you’re greeted by a circular driveway and the peace, privacy, and wide-open feel of over an acre of land. Step inside to a thoughtfully designed layout that flows with ease. To the right, a staircase leads to three spacious bedrooms, a full bathroom, and the primary suite featuring its own private bath. To the left, a cozy living room offers the perfect setting to relax and unwind.

    Joshua Crittendon EXP REALTY LLC

    135 W Trade Winds Rd, Winter Springs, FL 32708
  • /26

    $275,000 Pre-Foreclosure

    • 3 Beds
    • 2 Baths

    331 San Gabriel St, Winter Springs, FL 32708

    IN WINTER SPRINGS, FL Welcome to this beautifully refreshed 3-bedroom, 2-bathroom home located in the desirable Deersong community of Tuscawilla. This move-in-ready residence offers a perfect blend of efficiency and style, featuring a fully owned solar panel system on the roof that provides significant monthly energy savings. The interior has been tastefully updated with fresh paint throughout

    Judy Palladino Compass Florida, LLC

    331 San Gabriel St, Winter Springs, FL 32708

Home Trends in Highlands, FL

Housing Trends

Median Sale Price
$309,000
Median Single Family Sale Price
$330,000
Median Townhouse Sale Price
$500,000
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$125,000
Average Price Per Sq Ft
$230
Number of Homes for Sale
45
Last 12 months Home Sales
149
Months of Supply
3.60
Median List Price
$324,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-6%
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