27

Winter Springs, FL Homes for Sale under $100,000

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  • /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
  • /47

    $44,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    219 El Camino, Winter Springs, FL 32708

    HACIENDA 55+ COMPLETELY REMODELEDBrand New Inside - Completely redone, Beautiful new floors, repainted inside and out, New Front Door, Screened-in Porch redone, nice size storage room. Hacienda Village is a Legacy Community - 55+.Monthly rent $1025 Base

    Frank Filippelli SOUTHERN REALTY ENTERPRISES

    219 El Camino, Winter Springs, FL 32708
  • /54

    $35,000

    • 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
  • /53

    $39,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    442 Dorado Dr, Winter Springs, FL 32708

    Hacienda Village a 55+ Community has been updated-Pickel Ball Courts, 2 Pools one heated, Putt Putt, Doggy Park, Tiki Huts, Grills, always something going on. Hacienda Village has easy access to all major highways with beaches and Parks only 45 minutes away. Fire and Police Dept close by, Restaurants, Medical, Shopping and more in the area.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    442 Dorado Dr, Winter Springs, FL 32708
  • /5

    $90,000

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    624 Bonita Rd, Winter Springs, FL 32708

    Foreclosure Auction Ends December 04, 2025 at 11:00 AM EST. Comfortable 3-bedroom, 2-bath home with an open design, updated finishes, and a relaxing patio in a quiet residential area. Sold As-is. Explore more details and submit your bid through Federa Home App.

    Jamie Boone Federa

    624 Bonita Rd, 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
  • /60

    $38,000

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

    47 La Vista Dr, Winter Springs, FL 32708

    HACIENDA VILLAGE 55+ 3 bedroom/2 bath with spacious floor plan, extra room with separate A/C/Heat- cute little tiled porch floor. Newer front windows, 2 storage sheds. Hacienda Village is a Legacy Community. Amenities include: Pickle Ball, Small Putt, Putt golf course, doggy park; tiki Huts, some with grills, 2 pools. Recreation Hall (Rec Hall has full kitchen; exercise room, pool tables and

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    47 La Vista Dr, 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
  • /89

    $93,500

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft

    411 La Vista Dr, Winter Springs, FL 32708

    HACIENDA VILLAGE 55+ - 1536 DOUBLE WIDE 3 BEDROOMS 2 BATHS SPLIT PLAN WITH A LOT OF UPGRADES. FAMILY ROOM, SCREENED IN AREA, LOTS & LOTS OF STORAGE, WATER PURIFIER, AND A NICE SIZE LOT TO ENJOY. NEIGHBORHOOD IS CLOSE TO ALL MAJOR HIGHWAYS, SHOPPING, DOCTORS AND RESTAURANTS. WE HAVE ALL THE LATEST AND GREATEST AMENITIES. HACIENDA VILLAGE IS A LEGACY COMMUNITY. MONTHLY RENT $1025

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    411 La Vista Dr, Winter Springs, FL 32708
  • /34

    $49,900

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft

    382 La Vista Dr, Winter Springs, FL 32708

    NEWLY RENOVATED- 2 BEDROOM/2 BATH- 1 MONTH FREE LOT RENT!!! Totally Renovated home with new drywall, paint, & baseboards. Bathrooms have been beautifully renovated with new vanities, showers, and fixtures. Flooring and sub flooring has been installed with waterproof vinyl laminate. All new stainless-steel appliances. The A/C is a 3-new A/C mini split installed, 1 in each bedroom and 1 in the main

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    382 La Vista Dr, Winter Springs, FL 32708
  • /43

    $14,000

    • 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
  • /47

    $31,900

    • 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 $1025.00.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    242 Aztec Dr, Winter Springs, FL 32708
  • /54

    $45,000

    • 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
  • /64

    $39,900

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

    82 Bonita Cir, Winter Springs, FL 32708

    A lot of room and storage-newer plumbing underneath. "as is" use your imagination in this home. Conveniently with recreation Hall across the street with a heated pool. Community is located near major highways-45 minutes beaches & parks. Located nearby are restaurants, medical shops as well as police and fire department. Monthly base rent is $1025.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    82 Bonita Cir, Winter Springs, FL 32708
  • /11

    $9,000

    • 2 Beds
    • 1 Bath

    139 Columbus Cir Unit 139, Winter Springs, FL 32708

    Your Perfect Florida Retreat Discover the perfect balance of comfort and convenience in this charming home. Featuring 2 bedrooms and a versatile bonus flex room, there is plenty of space for guests or creative projects. The oversized indoor laundry room makes chores a breeze, while the private screened patio offers a peaceful sanctuary to enjoy your morning coffee. Whether you're looking for a

    Gabriel Dumeng AMAZING MOBILE HOMES LLC

    139 Columbus Cir Unit 139, Winter Springs, FL 32708
  • /47

    $12,000

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

    468 Ponce de Leon Cir, Winter Springs, FL 32708

    Perfect Location-circle-corner lot. Owner says "make an Offer!" priced to sell. Hacienda Village a 55+ Community has been updated-Pickel Ball Courts, 2 Pools one heated, Putt Putt, Doggy Park, Tiki Huts, Grills, always something going on. Hacienda Village has easy access to all major highways with beaches and Parks only 45 minutes away. Fire and Police Dept close by, Restaurants,

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    468 Ponce de Leon Cir, Winter Springs, FL 32708
  • /13

    $97,500

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft

    314 Pawnee Trail, Winter Springs, FL 32708

    This Home has an excellent view from its all window front. Enjoy the pond and wildlife . Spacious Living Room, Family Room and Kitchen, Screen room adjacent to dining area makes it nice for outside relaxing or entertaining. Home has some unique features such as the wood accent walls in Living Room and Dining area. Private backyard a plus as well. Land lease is $755.00 per month ( No additional

    Todd Newby NEWBY REALTY INC

    314 Pawnee Trail, Winter Springs, FL 32708
  • /49

    $18,000

    • 2 Beds
    • 2 Baths
    • 1,266 Sq Ft

    396 El Camino Real Cir, Winter Springs, FL 32708

    Home has a few bruises-Great Price! You will love Hacienda. A lot of amenities-2 pools, pickelball,Putt,Doggy Park. Always some activity going on. Major Highway close by about 45 minutes to beaches & Parks. Restaurants, shopping, doctors, Police & Fire Dept within minutes. Base Monthly rent $1025.00.

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    396 El Camino Real Cir, 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
  • /42

    $34,900

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

    265 Ponce de Leon Dr, Winter Springs, FL 32708

    LOVELY HOME WITH BEAUTIFUL WOOD FLOORING. Close to Moss Road-Easy Access! Comfortable Home. Enclosed Porch area! Hacienda Village a 55+ Community has been updated-Pickel Ball Courts, 2 Pools one heated, Putt Putt, Doggy Park, Tiki Huts, Grills, always something going on. Hacienda Village has easy access to all major highways with beaches and Parks only 45 minutes away. Fire and Police Dept close

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    265 Ponce de Leon Dr, Winter Springs, FL 32708
  • /23

    $32,000

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    463 Ponce de Leon Cir, Winter Springs, FL 32708

    SELLER CONSIDERING ALL OFFERS! 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

    Bella Siracusa SUNBELT HOME SALES INC

    463 Ponce de Leon Cir, Winter Springs, FL 32708
  • /13

    $29,900

    • 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
  • /2

    $5,000

    • 3 Beds
    • 2 Baths
    • 1,357 Sq Ft

    509 S Edgemon Ave, Winter Springs, FL 32708

    Foreclosure Auction Ends February 17, 2026 at 11:00 AM EST. Comfortable 3-bedroom, 2-bath home offering a functional layout and inviting living spaces. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa Home App.

    Jamie Boone Jamie L Boone LLC

    509 S Edgemon Ave, 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
  • /47

    $44,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    219 El Camino Real Cir, Winter Springs, FL 32708

    Brand New Inside - Completely redone, Beautiful new floors, repainted inside and out, New Front Door, Screened-in Porch redone, nice size storage room. Hacienda Village is a Legacy Community - 55+.Monthly rent $1025 Base

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    219 El Camino Real Cir, Winter Springs, FL 32708

Home Trends in Winter Springs, FL

Housing Trends

Median Sale Price
$416,599
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$409,995
Median 2 Bedroom Sale Price
$173,500
Median 1 Bedroom Sale Price
$147,500
Average Price Per Sq Ft
$245
Number of Homes for Sale
125
Last 12 months Home Sales
620
Months of Supply
2.40
Median List Price
$429,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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