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

Ground Floor Condo in a Gated Community! 2024 Condo Roof, 2020 A/C, 2026 Water Heater & Garbage Disposal! This 3 bedroom, 2 bathroom unit has a split plan bedroom arrangement, an eat-in kitchen with pull out cabinet drawers, custom geometric accent walls, hall & laundry custom closets, no carpets, 2 covered lanai areas for outdoor living, and covered front entry to protect from the rain. Tuscany

Sheri Malin REDFIN CORPORATION

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

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

Discover Your Dream Home! Welcome to this stunning 3-bedroom, 2-bathroom condo, nestled on the serene 2nd floor. Recently updated to enhance your living experience, this residence boasts fresh interior paint and brand-new floor throughout, ensuring a move-in ready condition that invites comfort and style. The spacious living room and dining area merge seamlessly, featuring a charming wet bar area

Elizabeth Dowell UPZEL REALTY LLC

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

Welcome to your move-in ready 3-bedroom, 2.5-bath townhome-style condo located in the desirable Highlands of Winter Springs community known for its beautiful tree-lined streets, scenic walking trails, and resort-style amenities. This stylish home offers approximately 1,400 square feet of updated living space designed for comfort and low-maintenance living. Inside, you’ll find a fully remodeled

Casey Irwin PARK VIEW REALTY INC

Price Improvement and Available for Quick Closing! Welcome to 270 San Gabriel Street in Winter Springs, Florida — this home perfectly blends comfort, style, and the easygoing "Florida" lifestyle. A well-cared-for, single-story residence featuring vaulted ceilings and an open great-room plan that creates a bright, spacious feel throughout. The home’s neutral décor and ceramic tile flooring make it

Alie Gattis MAINFRAME REAL ESTATE

One or more photo(s) has been virtually staged. AS-IS Opportunity in the Vineyards of Mount Greenwood! This 3-bedroom, 1.5-bath townhome in Winter Springs is a true handyman’s special ideal for investors and first-time buyers looking to build equity. Inside, you’ll find a spacious living and dining area, kitchen, half bath, and extra storage under the stairs, while sliding glass doors open to a

Sarita Cabrera WATSON REALTY CORP

Welcome to this beautifully maintained 2 bedroom, 2 bathroom townhome located in the Golfside Villas community. Situated on a corner lot, this home offers added privacy and a peaceful setting with tranquil wooded views in the back. A charming private courtyard welcomes you before entering the home. Inside, you’ll find high ceilings that enhance the light and open feel, along with new flooring in

Carla Cabrera MODERN WORLD REALTY LLC

Warm and inviting home located in the highly sought-after Highland Village community of Winter Springs—where residents love to live and rarely want to leave. This 2-bedroom, 2-bath home features an open floor plan, abundant natural light, and no carpet throughout. The spacious living and dining areas open a comfortable layout, perfect for everyday living or entertaining. The primary bedroom is

Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO

Located in the highly sought-after Casa Park Villas community. This unit has been completely rehabbed down to the studs. New drywall, electrical, plumbing, AC and ductwork, doors, trim, flooring, kitchen and bathrooms and much more. Dual primary suites that offers two spacious suites, each equipped with its own private full bathroom, offering ideal privacy for roommates or guests. Unbeatable

Tamara Kerr PA SAND DOLLAR REALTY GROUP INC

Welcome home to 4431 Brook Hollow Circle, where clean design meets comfortable living. This light-filled residence offers an open, airy layoutthat feels both spacious and welcoming, with neutral finishes that create a fresh, move-in-ready atmosphere. The living and dining areas flowseamlessly, making everyday living and entertaining effortless. One of the home’s standout features is the

Nicolas Merino EXP REALTY LLC

Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a

Robert Bretz, PA EXP REALTY LLC

One or more photo(s) has been virtually staged. This beautifully updated 2 large bedroom and 2 1/2 bath townhouse is move-in ready! New carpet and luxury vinyl floor coverings, as well as brand new appliances: dishwasher, range, hood, microwave just installed in 2026. Newer AC and refrigerator ( 2 yrs.) complete this well-maintained townhouse overlooking the back patio and pond. The home boasts

Iris Bolt Malishewsky ABSOLUTE REALTY GROUP, LLC

One or more photo(s) has been virtually staged. *FLASH SALE* Motivated Seller!! Winter Springs single-family home on nearly 1⁄4 acre with A-rated schools,NO HOA, Eligible for FHA/VA financing; suitable for first-time buyers, and energy-efficient upgrades. Major improvements include NEW ROOF (2025), PAID-OFF SOLAR PANELS (installed Nov 2020) for lower monthly utility costs, NEW WINDOWS (2022), GAS

Kathern Cox-Uvalle EMPIRE NETWORK REALTY

Welcome home to this charming 3 bedroom, 2 Bath home in the heart of Winter Springs, in centrally located Deer Song Community. This home features: Corner unit, open floor plan, high ceilings, NEW ROOF 2021, RE-PLUMBED 2021, NEW APPLIANCES 2021-2022, NEW AIR CONDITIONING SYSTEM 2022, NEW WATER SOFTENER SYSTEM 2022 AND NEW LUXURY VINYL FLOORING IN BEDROOMS 2022. Home has been well maintained and

Linda Bain WEICHERT REALTORS HALLMARK PRO

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

Welcome to 51 N. Cortez Ave in Winter Springs—a thoughtfully updated 2-bedroom, 1-bath home that’s ideal for a first-time buyer or anyone looking to own without the hassle. Inside, you’ll find a clean, refreshed interior that’s move-in ready from day one. Outside, the fully fenced yard offers space to relax, garden, or let pets roam, while the detached shed provides extra storage for tools,

Julie Cvercko PRIME REAL ESTATE, INC.