27

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

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  • /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
  • /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 $703.00 per month ( No additional

    Todd Newby NEWBY REALTY INC

    314 Pawnee Trail, Winter Springs, FL 32708
  • /48

    $42,400

    • 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /50

    $39,900

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

    445 Dorado Dr, Winter Springs, FL 32708

    3 Bedroom, 2 bath spacious 1440 Living Area-Screen enclosed porch- Inside utility room/ wet bar. A really great layout, middle bath has a tub/shower combo. Master Bath has been redone with an enclosed shower. This home has been beautifully maintained throughout the years. A Must See-Priced to sell-Not to Mention-A beautiful lot! Base rent $1025.00

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    445 Dorado 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
  • /19

    $30,000

    • 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
  • /56

    $49,900

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

    365 Casa Grande Ct, Winter Springs, FL 32708

    Home has an open feeling-nice layout, nice side screened-in porch with open patio. Beautiful corner lot! Area close to major highways, shopping, doctors, restaurants, police, fire station, etc. Hacienda Village is a Legacy Community, 55+. Base Lot rent is $1025. This Community offers lots of amenities -something to do all of the time. "YOU WON'T BE BORED!"

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    365 Casa Grande Ct, Winter Springs, FL 32708
  • /34

    $57,900

    • 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

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    382 La Vista Dr, Winter Springs, FL 32708
  • /57

    $45,000

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

    180 La Vista Dr, Winter Springs, FL 32708

    New Roof, New electrical, subflooring put in in 2024. Home has been well maintained, original family owners. Very Spacious. Lot of storage areas. 3 Bedrooms, 2 bath. appliances sold "as is". Hacienda Village, A Legacy Community 55+ Basic monthly lot rent $1025. This park offers many amenities, 2 pools (Family Pool-Recreation Hall, heated pool) Clun House, mini golf. You won't be bored,

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    180 La Vista Dr, Winter Springs, FL 32708
  • /13

    $99,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    306 Pawnee Trail, Winter Springs, FL 32708

    Move-in ready to a well sought after Community. Home has many new renovations. Relaxing in the screen porch with a view of the pond and its birdlife is inviting. Land Lease is $703.00 per month(No additional Taxes or Fees) Lease also includes Septic Maintenance and use of amenities.

    Todd Newby NEWBY REALTY INC

    306 Pawnee Trail, 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
  • /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
  • /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
  • /46

    $44,900

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

    320 Casa Grande Ct, Winter Springs, FL 32708

    Home has been completely redone roof, electric, plumbing, vapor barrier, waterproof, bath, flooring, new window. has been repainted inside & out. Only room left is the kitchen and it is in good shape. Tiled screened in porch, partial brick driveway-painted driveway. You name it, it has been done! Just bring your toothbrush. Hacienda is a Legacy 55+ Community, Monthly rent is $1025.00 with great

    Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

    320 Casa Grande Ct, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /3

    $5,000

    • 2 Beds
    • 2.5 Baths
    • 1,282 Sq Ft

    3805 Black Spruce Ln, Winter Springs, FL 32708

    Foreclosure Auction Ends December 04, 2025 at 11:00 AM EST. Charming 2-bedroom, 2.5-bath townhome featuring modern interiors, a private patio, and access to community amenities in a peaceful neighborhood. The list price is the opening bid for the online auction. Sold As-is.

    Jamie Boone Jaime L Boone LLC

    3805 Black Spruce Ln, Winter Springs, FL 32708

Home Trends in Winter Springs, FL

Housing Trends

Median Sale Price
$415,431
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$414,229
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$147,500
Average Price Per Sq Ft
$246
Number of Homes for Sale
129
Last 12 months Home Sales
630
Months of Supply
2.50
Median List Price
$430,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-4%
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