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Studio to 2 Bedroom Homes for Sale in Highlands

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  • /50

    $289,000

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

    718 Lakeside Dr, Winter Springs, FL 32708

    Experience comfort and effortless living in this beautifully maintained Winter Springs home with LOW HOA fees and COMPLETE PRIVACY- NO SHARE WALLS. The open living area impresses with VAULTED CEILINGS, UPGRADED LAMINATE FLOORINGS, STYLIST FIXTURES, AND CHARMING FIREPLACE. The well-designed kitchen offers generous storage, while the serene primary suite features double closets and an ENSUITE BATH.

    Mariana Cisneros PREMIUM PROPERTIES R.E SERVICE

    718 Lakeside Dr, Winter Springs, FL 32708
  • /27

    $250,000

    • 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
  • /19

    $20,000

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

    153 Hacienda Dr, Winter Springs, FL 32708

    Remodeled 2 bedroom/2bath beautiful condition with updated features. Porch with vaulted ceiling & a finished look with wall A/C. Newer windows, Great working kitchen. Oversized storage shed. Room for a flower garden or other plants of your choice. Hacienda Village is a Legacy Community with base rent of $1025. Located close to major Highways, shopping restaurants. Close to Fire stations, Police &

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    153 Hacienda Dr, Winter Springs, FL 32708
  • /57

    $49,900

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

    87 Bonita Cir, Winter Springs, FL 32708

    Beautiful home - Updated in 2022. Open and very unique. Nice Screened in Porch, Situated at the end of a Cul-de-sac. Hacienda is a legacy community 55+ - A lot of Amenities- 2 pools, pickleball court, putt-putt, doggy park and more

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    87 Bonita Cir, Winter Springs, FL 32708
  • /54

    $48,500

    • 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 RENT $1025 .COME SEE US TODAY!

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    272 Ponce de Leon Dr, Winter Springs, FL 32708
  • /25

    $169,900 Open Sat 11AM - 2PM

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

    40 Sheoah Blvd Unit 27, Winter Springs, FL 32708

    Experience the perfect blend of comfort, convenience, and community with this beautifully maintained 2/2, 1187 sqft, first-floor condo located in the highly desirable Highlands neighborhood in Winter Springs. Set within the top-rated Seminole County School District, this ground-level residence offers true ease of living—no stairs, no hassle, just effortless accessibility from the moment you

    Travis Cepregi KELLER WILLIAMS WINTER PARK

    40 Sheoah Blvd Unit 27, Winter Springs, FL 32708
  • /54

    $39,999

    • 1 Bed
    • 1.5 Baths
    • 672 Sq Ft

    80 Majorca Dr, Winter Springs, FL 32708

    Just bring a toothbrush- This home has all new everything. It was completely remodeled in 2021/2022. 1 bedroom with a den in front (could be used as a second bedroom). New A/C unit to keep you nice & cool! Handicap accessible with a ramp. There is a gas line to the home. There is a gas tankless hot water heater. All new windows with exception of the kitchen bay window. The roof is new with

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    80 Majorca Dr, Winter Springs, FL 32708
  • /2

    $12,500

    • 2 Beds
    • 2 Baths

    322 Casa Grande Ct, Winter Springs, FL 32708

    2 bedroom, 2 bath needs everything, real fixer upper located in a cul-de-sac great location in Hacienda Village.

    Todd Vagts Hacienda Village

    322 Casa Grande Ct, Winter Springs, FL 32708
  • /33

    $239,000

    • 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. Residents enjoy amenities

    Kathleen Harrison CALL IT CLOSED INTL REALTY

    506 Club Dr, Winter Springs, FL 32708
  • /8

    $16,000

    • 2 Beds
    • 2 Baths

    433 Dorado Dr, Winter Springs, FL 32708

    This home is a handyman special, with large sunroom, carport storage area with washer and dryer hookups, join the great community of Hacienda Village that features 2 swimming pools and several other amenities, pet friendly residential community.

    Todd Vagts Hacienda Village

    433 Dorado Dr, Winter Springs, FL 32708
  • /48

    $39,900

    • 2 Beds
    • 2 Baths
    • 864 Sq Ft

    346 Casa Grande Dr, Winter Springs, FL 32708

    Beautiful well-kept home-Peaceful backyard, screened in porch, carport with storage shed & laundry facilities. Freshly painted inside. Location: Major Roads nearby about 45 minutes to Beaches & Parks. There are lots of amenities including 2 pools, (1 heated), Pickel ball, Putt Putt, Doggy Park and more. Plenty of activities for all. Base rent is 1025. ( average rent is $1200 which includes a

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    346 Casa Grande Dr, Winter Springs, FL 32708
  • /55

    $49,900

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

    367 Casa Grande Ct, Winter Springs, FL 32708

    Hacienda Village 2 bedroom/ 2 bath well maintained home. 1358 Sq ft of heated area. Very spacious home! Great Layout. Nice Size Storage Living Room, Dining Rm, family rm, Breakfast Bar in Kitchen, Large screened in porch. On a circle-Great Lot in Phase III. Hacienda Village, A Legacy Community 55+ Monthly Lot Rent $1025. New/Newer Amenities. Close to major Highways, Shopping, Medical,

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    367 Casa Grande Ct, Winter Springs, FL 32708
  • /15

    $35,900

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft

    100 Hacienda Dr, Winter Springs, FL 32708

    This home boasts a spacious alley-style kitchen equipped with all appliances, including a built-in microwave, and features a cozy breakfast nook or sitting area. The expansive living room offers endless possibilities for furniture arrangements and includes a large window that welcomes the natural Florida sunlight. The dining area is ample enough to accommodate a generous table for gatherings or

    Allan Trager Four Star Homes, Inc.

    100 Hacienda Dr, Winter Springs, FL 32708
  • /50

    $79,900

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

    168 Costa Cir, Winter Springs, FL 32708

    BEAUTIFUL RENOVATED HOME with ALL NEW APPLIANCES including a surface gas stove, new hot water heater & HVAC. Beautiful 4 panel doors, vinyl flooring throughout.All new vapor barrier and installation underneath. New homes will be put in next door and this home has beautiful landscaping all around. This is a must see home! Shopping,Restaurants, major highways nearby. Fire Department, hospital,

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    168 Costa Cir, Winter Springs, FL 32708
  • /43

    $25,000

    • 2 Beds
    • 1 Bath
    • 720 Sq Ft

    39 La Vista Dr, Winter Springs, FL 32708

    Really cute single wide, 2 bedroom/1 bath. Living area is very open-Just plain cozy. Side screened in porch-So Cute!! Beautiful treed private backyard. Hacienda Village, near all major highways. 45 minutes to the beaches & parks, Hospital, Police, Fire Departments are close, also shopping and restaurants. The amenities include 2 pools, 1 that is heated. Pickel ball, putt Putt, Doggie Park & much

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    39 La Vista Dr, Winter Springs, FL 32708
  • /54

    $49,900

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

    125 Las Almas Ln, Winter Springs, FL 32708

    Very Modern-open-Newer Windows, New Rood 2021, Newer Appliances, Replumbed. A beautiful setting. Hacienda Village is a Legacy 55+ Community with newer Amenities, Pickle Ball, Putt Putt, Doggie Park, 2 pools, one which is heated. Always something going on- Never a dull moment. Base mo. rent is $1025. (Pictures coming soon) Great buy for this large home!!

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    125 Las Almas Ln, 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
  • /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
  • /15

    $174,900

    • 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

    Matt Merdian MERDIAN REALTY LLC

    10 Sheoah Blvd Unit 5, Winter Springs, FL 32708
  • /41

    $225,000

    • 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 backyard—ideal

    Matt Magee LPT REALTY LLC

    505 Moree Loop, Winter Springs, FL 32708
  • /13

    $37,900

    • 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
  • /22

    $245,000

    • 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. This 2-bedroom, 2-bath Winter Springs home offers a functional layout with endless potential. Featuring vaulted ceilings, lots of natural light, stylish new laminate flooring, inside laundry, and outdoor storage. Conveniently located near top-rated Seminole County schools, Central Winds Park, the Winter Springs Town Center, plus major highways. Roof

    Christine Schneider RE/MAX TOWN & COUNTRY REALTY

    294 San Gabriel St, Winter Springs, FL 32708
  • /51

    $39,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    86 Bonita Cir, Winter Springs, FL 32708

    Beautiful well maintained 2 bedroom 2 bath Home, ready to move in Great Enclosed Porch. Ideal location, home is located across from the Recreational Hall with Pool and Mail room. Rec Hall has a meeting room, kitchen, pool table, exercise Room, kitchen Tiki Huts outside, Pickle Ball, Doggie Park & More. Hacienda Village is close to major highways, restaurants, doctors & more. Monthly base lot

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    86 Bonita Cir, 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

Home Trends in Highlands, FL

Housing Trends

Median Sale Price
$315,000
Median Single Family Sale Price
$330,000
Median Townhouse Sale Price
$500,000
Median 2 Bedroom Sale Price
$174,950
Median 1 Bedroom Sale Price
$140,000
Average Price Per Sq Ft
$229
Number of Homes for Sale
37
Last 12 months Home Sales
167
Months of Supply
2.70
Median List Price
$325,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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