Winter Springs, FL Homes for Sale under $300,000

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  /28

  $259,900

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  585 Shadow Glenn Place, Winter Springs, FL 32708

  Welcome home to this move in ready 3 bedroom, 2 bathroom end unit townhome nestled in the heart of Winter Springs! With 1,350 sq ft of well utilized living space, this charming residence offers the perfect blend of comfort and convenience — ideal for first-time buyers looking to plant roots in one of Seminole County's most sought-after communities.As an end unit, enjoy added privacy, extra

  Rodrigo Marsal LIFESTYLE INTERNATIONAL REALTY

  585 Shadow Glenn Place, Winter Springs, FL 32708
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• 

  

  /2

  $135,500

  • 2 Beds
  • 2 Baths

  102 La Vista Dr, Winter Springs, FL 32708

  This brand-new 2026 Jacobsen home offers 2 bedrooms and 2 bathrooms, with quality finishes throughout. Highlights include a kitchen island, stainless steel appliances and walk-in closets!

  Todd Vagts Hacienda Village

  102 La Vista Dr, Winter Springs, FL 32708
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  /38

  $179,500

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft

  50 Sheoah Blvd Unit 33, Winter Springs, FL 32708

  WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy,

  Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

  50 Sheoah Blvd Unit 33, Winter Springs, FL 32708
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  /41

  $199,000

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

  429 Sheoah Blvd Unit 9, Winter Springs, FL 32708

  Welcome to this beautifully maintained 3-bedroom, 2-bath condominium nestled in the highly desirable Highlands community of Winter Springs. Offering the perfect blend of comfort, style, and convenience, this move-in-ready home features an updated kitchen with granite countertops, stainless steel appliances, and ample cabinetry. The spacious floor plan is complemented by updated bathrooms,

  Freddy Escobar LPT REALTY, LLC

  429 Sheoah Blvd Unit 9, Winter Springs, FL 32708
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  /24

  $182,000

  $11K PRICE DROP

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

  240 Moree Loop Unit 3, Winter Springs, FL 32708

  Virtually Staged. Welcome to Baytree Village in the heart of Winter Springs—where beautifully landscaped grounds and a welcoming atmosphere create the perfect place to call home. This MOVE-IN READY second-floor condo offers 3 bedrooms, 2 full baths, and added privacy, all in a prime location close to top-rated schools, parks, shopping, dining, and major roadways for an easy commute.Step

  Christine Landrau MARK SPAIN REAL ESTATE

  240 Moree Loop Unit 3, Winter Springs, FL 32708
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  /25

  $82,500

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

  411 La Vista Dr, Winter Springs, FL 32708

  THE HOME THAT KEEPS GOING... AND GOING! Looking for space, flexibility, storage, and character all in one home? This rare Hacienda Village gem offers approximately 15 functional living spaces designed for comfortable everyday living, entertaining, hobbies, working from home, and so much more! This spacious split-floor-plan home features 3 spacious bedrooms, multiple living and dining areas, a

  Gabriel Dumeng AMAZING MOBILE HOMES LLC

  411 La Vista Dr, Winter Springs, FL 32708
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  /13

  $237,000

  $26K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,148 Sq Ft

  120 N Fairfax Ave, Winter Springs, FL 32708

  Charming ranch-style home brimming with potential and ready for your personal touch! Ideally situated in a convenient location, this property offers easy access to nearby schools, shopping centers, public transportation, and everyday essentials. Inside, you’ll find a practical layout featuring 2 comfortable bedrooms and 1 full bathroom, along with durable terrazzo and tile flooring

  Chris Creegan CREEGAN GROUP

  120 N Fairfax Ave, Winter Springs, FL 32708
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  /31

  $299,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,726 Sq Ft

  600 Northern Way Unit 1804, Winter Springs, FL 32708

  Welcome to Tuscany Place in the heart of sought after Tuscawilla! This well-maintained townhouse style condo offers a spacious floor plan with abundant natural light, generous living and dining areas, and a well-appointed kitchen perfect for everyday living and entertaining. Enjoy spacious bedrooms, ample storage and an outdoor patio ideal for relaxing after a long day. Located in a gated

  Sandra Moshir BHHS FLORIDA REALTY

  600 Northern Way Unit 1804, Winter Springs, FL 32708
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  /26

  $218,000

  Open Sun 10AM - 12PM $15K PRICE DROP

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

  497 Club Dr, Winter Springs, FL 32708

  Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! Light and neutral colors throughout, freshly painted approximately two years ago! *Vaulted ceiling in the spacious family/great room with a wood burning fireplace! Tile flooring in the living areas and laminate in the bedrooms. Split bedroom floorplan, with

  Edyta Olejnik WATSON REALTY CORP

  497 Club Dr, Winter Springs, FL 32708
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  /31

  $34,500

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

  308 Casa Grande Ct, Winter Springs, FL 32708

  2 bEDROOM 2 BATH- A LOT OF THE MAIN WORK DONE! ALL NEW DUCTING,PLUMBING IS GOOD, ELECTRIC GOOD, CARPETING PULLED UP, SUB FLOORING DONE. KITCHEN SOME CABINETS HAVE PULL OUTS. NEW ALL YOU HAVE TO DO IS PUT YOUR OWN PERSONAL TOUCH. THIS IS ONE OF THE MOST POPULAR FLOOR PLANS. YHIS DOES HAVE A SPRINKLER SYSTEM(AS IS) HACIENDA VILLAGE IS FULL OF AMENITIES-2 POOLS, PICKLE Ball. centrally located-base

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  308 Casa Grande Ct, Winter Springs, FL 32708
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  /29

  $290,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,609 Sq Ft

  600 Northern Way Unit 906, Winter Springs, FL 32708

  Turnkey townhouse in Tuscany Place is totally move-in ready. The townhouse style is limited to only a few homes in the new phase of this wonderful, gated community. Built in 2016 and much newer than many competing condos/townhomes. All 3 bedrooms have their own private full bathrooms. The first-floor bedroom with en-suite bath is great for guests, home office, or multigenerational living. Brand

  John Vincent JR REALTY GROUP LLC

  600 Northern Way Unit 906, Winter Springs, FL 32708
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  /25

  $170,000

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

  70 Moree Loop Unit 63, Winter Springs, FL 32708

  Two story condominium in Winter Springs. The two bedroom, 1 and 1/2 bath unit is located in the Highlands Community. Tile and laminate flooring, fresh paint, spacious layout, kitchen has a pass thru window to the dining area. Combo living/dining with sliding glass doors which offers natural sunlight and opens to an exterior patio. Two bedrooms, master full bath and laundry utility on the second

  Joyce Gary PAINE-ANDERSON PROPERTIES, INC

  70 Moree Loop Unit 63, Winter Springs, FL 32708
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  /59

  $255,000

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

  725 Lakeside Dr, Winter Springs, FL 32708

  Enjoy easy living in this beautifully maintained townhome. Ideally located in the sought-after Wildwood community in Winter Springs. This home features 2 bedrooms and 2 bathrooms, freshly painted interior and new blinds in the living room. Tile floors throughout make cleaning a breeze. Enjoy sitting out on the screened in lanai with your favorite beverage. The spacious primary suite serves as a

  Irene Hayden GLOBAL PROPERTIES SALES & MGMT

  725 Lakeside Dr, Winter Springs, FL 32708
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  /20

  $249,000

  Open Sat 10AM - 12PM

  • 2 Beds
  • 1.5 Baths
  • 1,363 Sq Ft

  498 Green Spring Cir, Winter Springs, FL 32708

  Welcome to 498 Green Spring Circle in the desirable Mount Greenwood community of Winter Springs! This beautifully maintained 2 bedroom, 1.5 bath end-unit townhome offers peaceful pond views, low-maintenance living, and access to top-rated Seminole County schools. Step inside to an open and inviting floor plan featuring ceramic tile flooring throughout the main living areas and fresh interior

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  498 Green Spring Cir, Winter Springs, FL 32708
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  /2

  $135,500

  • 2 Beds
  • 2 Baths

  38 La Vista Dr, Winter Springs, FL 32708

  Brand-new 2026 Home - The Laguna - offering modern design and quality craftsmanship throughout. This beautifully appointed residence features recessed lighting, elegant crown molding, and luxury plank flooring that flows seamlessly through the home. The stylish kitchen is equipped with stainless steel appliances, creating a sleek and functional space for everyday living and entertaining. A

  Todd Vagts Hacienda Village

  38 La Vista Dr, Winter Springs, FL 32708
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  /25

  $235,000

  $20K PRICE DROP

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

  499 Club Dr, Winter Springs, FL 32708

  Beautiful 2 bedroom 2 bathroom townhome (Not a condo which means more financing choices for you as a buyer) within The Highlands Community. Brand New Roof on this townhome. The 20ft high ceiling in the Great Room gives this home a very open design with lots of natural light. Sliding doors lead out to a screened porch with separate locked storage space. Guest/2nd bedroom on the first floor with

  Paul Buscemi FLORIDA HOME TEAM REALTY LLC

  499 Club Dr, Winter Springs, FL 32708
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  /2

  $135,500

  • 2 Beds
  • 2 Baths

  73 Majorca Dr, Winter Springs, FL 32708

  This brand-new 2026 "The Laguna" model combines modern design with everyday functionality, featuring recessed lighting, luxury plank flooring, and a stylish dining room chandelier. The kitchen is a standout with stainless steel appliances, a spacious island, and smooth glide drawers for added convenience. The home also offers a walk-in closet, providing ample storage and comfort

  Todd Vagts Hacienda Village

  73 Majorca Dr, Winter Springs, FL 32708
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  /13

  $129,000

  $21K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  306 Pawnee Trail, Winter Springs, FL 32708

  Move-in ready to a well sought after All Age Community. Home has many new renovations including a new roof. Relaxing in the screen porch with a view of the pond and its birdlife is inviting. Land Lease is $755.00 per month (no additional fees or taxes) Lease also includes Septic Maintenance and use of amenities.

  Todd Newby NEWBY REALTY INC

  306 Pawnee Trail, Winter Springs, FL 32708
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  /49

  $59,900

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

  374 Casa Grande Ct, Winter Springs, FL 32708

  2 Bedroom 2 Bath 1152 Heated Area does not include porch. 1980 Built, well maintained. It's absolutely beautiful Phase III. Golf Cart path near, RV storage ($25.per month). Hacienda Village is centrally located -45 minutes to beaches & parks. Close to restaurants, shopping, police and fire departments. Hacienda offers many amenities including 2 pools (1 heated)Pickelball courts, Doggy Park, Putt

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  374 Casa Grande Ct, Winter Springs, FL 32708
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  /50

  $89,900

  $20K PRICE DROP

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

  65 Majorca Dr, Winter Springs, FL 32708

  Located close to an entrance, "solar Panels" paid for. Open, Modern 2 Entrances, Shows Well, Crown Molding-SUPER KITCHEN is a must see! GREAT LOCATION, close to major roads, Doctors, Fire Dept. Restaurants, Shopping & more! Updated Amenities-2 Pools, Pickle Ball, Putt Putt Golf, Doggy Park & More, Never a dull moment, always something to do! Base Mo. lor rent is $1025.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  65 Majorca Dr, Winter Springs, FL 32708
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  /47

  $70,000

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

  162 Costa Cir, Winter Springs, FL 32708

  SIZE TOTAL 1392 INCLUDING ENCLOSED PORCH. FLOORS, WALLS, APPLIANCES & MORE ALL UPDATED. SITUATED IN A QUIED CUL-DE-SAC. HACIENDA IS CENTRALLY LOCATED - 45 MINUTES TO BEACH & PARKS. CLOSE TO RESTAURANTS, SHOPPING DOCTORS, POLICE & FIRE DEPARTMENT. A LOT OF AMMENITIES IN PARK PLUS ACTIVITIES. DROP BY & YOU'LL LOVE IT!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  162 Costa Cir, Winter Springs, FL 32708
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  /25

  $285,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,326 Sq Ft

  299 Woodgreen Ln, Winter Springs, FL 32708

  Welcome to this BEAUTIFULLY UPDATED 3-bedroom, 2.5-bath townhome in the PEACEFUL Mount Greenwood community of Winter Springs, where modern upgrades and a thoughtfully designed layout create a truly inviting place to call home. As a CORNER UNIT, this residence enjoys added privacy along with a serene setting, including POND VIEWS just beyond the rear fence, best appreciated from the upstairs

  Jennifer Wemert WEMERT GROUP REALTY LLC

  299 Woodgreen Ln, Winter Springs, FL 32708
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  /10

  $59,900

  • 2 Beds
  • 2 Baths

  338 Casa Grande Dr, Winter Springs, FL 32708

  Thoughtfully renovated with modern finishes, this home features elegant waterproof flooring, a stylish kitchen, and a bright comfortable living space, designed for easy living!

  Todd Vagts Hacienda Village

  338 Casa Grande Dr, Winter Springs, FL 32708
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  /36

  $230,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft

  4490 Brook Hollow Cir, Winter Springs, FL 32708

  Welcome to 4490 Brook Hollow, a beautifully maintained property nestled in a quiet and desirable Florida community. This home offers the perfect blend of comfort, functionality, and Florida lifestyle living.Step inside to find a light-filled interior with an open and inviting floor plan, ideal for both everyday living and entertaining. The spacious living areas flow seamlessly into a

  Nicolas Merino EXP REALTY LLC

  4490 Brook Hollow Cir, Winter Springs, FL 32708
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  /25

  $221,000

  $19K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,180 Sq Ft

  510 Green Spring Cir, Winter Springs, FL 32708

  Explore 510 Green Spring Cir, a residence recently enhanced with fresh interior paint and partial flooring replacement throughout. The kitchen includes an accent backsplash, complementing the recent updates for a refreshed interior feel. This property blends modern updates and practical style, ready for you to enjoy. Included 100-Day Home Warranty with buyer activation

  Karen Albright OPENDOOR BROKERAGE LLC

  510 Green Spring Cir, Winter Springs, FL 32708
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  /28

  $45,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  284 La Vista Dr, Winter Springs, FL 32708

  This clean and move-in ready 2 bedroom, 2 bath home is located in a quiet and well maintained senior community, offering comfort, convenience, and a relaxed lifestyle. Featuring a spacious floor plan with large bedrooms, a bright living room, dedicated dining area, and an oversized kitchen with plenty of cabinet space, this home is perfect for everyday living and entertaining. Recent updates

  Corali Fuentes Four Star Homes, Inc.

  284 La Vista Dr, Winter Springs, FL 32708
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  /18

  $120,000

  • 3 Beds
  • 2 Baths

  154 Hacienda Dr Unit 378, Winter Springs, FL 32708

  Spacious and well-appointed, this 1,920 sq. ft. home offers 3 bedrooms and 2 bathrooms, featuring both a great room and a family room for flexible living and entertaining. The home includes a 13x18 layout area and a one-car garage measuring 14x21. All appliances are Samsung, complemented by a brand-new Hotpoint washer and dryer, plus an additional refrigerator in the utility room for extra

  Todd Vagts Hacienda Village

  154 Hacienda Dr Unit 378, Winter Springs, FL 32708
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  /15

  $145,000

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft

  1084 Cheyenne Trail, Winter Springs, FL 32708

  Large Immaculate 1584 sq.ft. remodeled home and roomy out buildings Has so many extras to make this home a must see. The tiled screen porch and deck with back covered area offers so much welcoming relaxation space. Interior is loaded with upgradeds. Park maintains Septic System and Lot rent is $755.00 per month

  Todd Newby NEWBY REALTY INC

  1084 Cheyenne Trail, Winter Springs, FL 32708
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  /29

  $294,900

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,069 Sq Ft

  421 Horizon Dr, Winter Springs, FL 32708

  Welcome to 421 Horizon Drive in Winter Springs, located in The Seasons community. This move-in ready home checks all the big boxes upfront: a 50-year Rhino shingle roof (2019), a 3.5-ton 14 SEER AC unit with heat pump and updated ductwork, a new electric panel, and a 2019 water heater. Beautifully maintained and thoughtfully updated throughout, this one-story home offers 3 bedrooms, 2 bathrooms,

  Peter Luu REAL BROKER, LLC

  421 Horizon Dr, Winter Springs, FL 32708
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  /26

  $299,000

  New Construction $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  781 Bayou Dr, Casselberry, FL 32707

  One or more photo(s) has been virtually staged. Brand New 2026! This home sits in a desirable location in Casselberry Florida. Living near Lake Kathryn Park in Casselberry, Florida, offers a balanced lifestyle that combines quiet residential charm with modern recreational amenities. Commuter Friendly to Downtown Orlando, 5 minutes to I-4, convenient shopping, Altamonte Mall and "the Greater

  Aimee Anselmi LLC KELLER WILLIAMS HERITAGE REALTY

  781 Bayou Dr, Casselberry, FL 32707

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