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

Imagine coming home to a space where comfort, privacy, and peace of mind come together effortlessly. Welcome to 4467 Brook Hollow Cir, the beautifully maintained and updated 3-bedroom, 2.5-bath townhome, offering 1,344 sq ft, invites you to slow down and truly enjoy everyday living. The ceramic tile flooring throughout the first floor creates a bright and welcoming atmosphere.At upstairs, new

Miriam Hernandez Gonzalez LA ROSA REALTY ORLANDO LLC

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

Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third

Hanoi Burgos COLDWELL BANKER REALTY

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

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 move-in ready, and all appliances stay, so you can

Alie Gattis MAINFRAME REAL ESTATE

Outstanding 2 BD 1.5 BT! Open-concept, two-story home with a lot of natural light Move-in Ready. New AC (4 Years New) & Newer Appliances. Great Schools! Community Pool. 2 parking Spaces. Walk to Trotwood & Trail. Hurry! Won't last!

Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

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

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

Very motivated sellers! Condo in Tuskawilla’s Tuscany Place •Discover comfort and convenience in Winter Springs’ Tuskawilla neighborhood. Tuscany Place is a gated community with a private pool, near Trotwood Park, Cross Seminole Trail, and top-rated schools. •Double Balcony (length of condo) •Corner unit with pool view •Updated kitchen w/stainless steel appliances •New water heater (2023) •New

Kelly Boulton WORTH CLARK REALTY

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. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo offering the perfect blend of style, comfort, and convenience in the heart of Seminole County. Inside, you’ll find quartz countertops throughout, stainless steel appliances, and stylish brick-lay tile flooring that adds character and a modern touch to the main living areas. The

Dominick Florio RE/MAX TOWN & COUNTRY REALTY

Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a

Tamara Martin INFINITY REAL ESTATE GROUP

**One or more photo(s) has been virtually staged**.Move-In Ready Home – Fully Updated Inside and Out! Simply bring your personal belongings — this 3-bedroom, 2-bathroom home is ready for immediate occupancy. Freshly painted throughout, it features many upgrades and improvements, including roof (2021), water heater (2020), indoor A/C unit (2018), and outdoor A/C unit (2025). The remodeled kitchen

Olga Carballea Diaz CHARLES RUTENBERG REALTY ORLANDO

PRICE REDUCTION: Welcome to your dream home in the highly sought-after Deer Song Community of Winter Springs! This charming 3-bedroom, 2-bath corner single family home is packed with upgrades, including a brand new hot water heater (installed 2/23/2026), a newer roof (2021) and re-plumb (2021), state-of-the-art appliances (2021-2022), a top-of-the-line air conditioning system (2022), a water

Linda Bain WEICHERT REALTORS HALLMARK PRO

Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a 2020 A/C system, a full

Jeff Singletary KELLER WILLIAMS HERITAGE REALTY

Beautiful 2 bedroom 2 bathroom townhome within The Highlands Community. 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 direct access to the 2nd bathroom. All appliances purchased New in 2022 and are included with sale. New

Paul Buscemi FLORIDA HOME TEAM REALTY LLC

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 home to this maintained 3-bedroom, 2-bathroom ground-floor condominium offering 1,425 square feet of comfortable, low-maintenance living in a desirable gated community in the heart of Tuscawilla — perfect for investors or those seeking a primary residence. Step inside to an inviting open floor plan highlighted by tile flooring throughout the main living areas, creating a seamless space

Veronica Figueroa EXP REALTY LLC

Welcome to this beautiful townhome in the heart of desirable Winter Springs! This townhome sits on a quiet street an established community. Roof was replaced in 2023! Featuring a split floor plan, vaulted ceilings, and a large primary suite with walk-in closet, the layout provides comfort and flexibility. The screened-in lanai overlooks backyard with a community walk, perfect for relaxing or

Shadi Tamimi SET HOMES REALTY LLC