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Winter Springs, FL Homes for Sale under $400,000

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  • /53

    $399,000

    • 3 Beds
    • 2.5 Baths
    • 1,721 Sq Ft

    622 Anhinga Rd, Winter Springs, FL 32708

    Price confirmed at $399,000 based on the completed 4-Point Inspection, which confirms the clay tile roof has approximately 13 years of remaining useful life—creating a strong opportunity for buyers to take advantage of the current value. The roof, HVAC (2017–2018), electrical panels, plumbing, and water heater (2022) were all reviewed in the 4-Point Inspection completed on 01/12/2026, with all

    Agent Photo

    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 450-3189

    622 Anhinga Rd, Winter Springs, FL 32708
  • /12

    $399,007 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,678 Sq Ft

    1268 Crab Apple Ln, Winter Springs, FL 32708

    The Catalina I is a harmonious blend of style, functionality, and comfort, offering a lifestyle that caters to your every need. As you step inside you are greeted by an open-concept design that seamlessly integrates the gathering room, dining room, and kitchen, creating an inviting space for both everyday living and entertaining. This townhome features 3 bedrooms, providing flexible living

    Mattamy Homes Builder
    1268 Crab Apple Ln, Winter Springs, FL 32708
  • /18

    $381,733 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    1276 Crab Apple Ln, Winter Springs, FL 32708

    As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a

    Mattamy Homes Builder
    1276 Crab Apple Ln, Winter Springs, FL 32708
  • /19

    $374,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    Aurora Plan at Hickory Grove, Winter Springs, FL 32708

    As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a

    Mattamy Homes Builder
    1458 Blumberg Blvd Unit 36446067, Winter Springs, FL 32708
  • /25

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,983 Sq Ft

    221 Albert St, Winter Springs, FL 32708

    This 4-bedroom, 2-bath home offers 1,983 sq. ft. of living space with an open layout connecting the family room, dining, and kitchen areas. The kitchen features a skylight and a peninsula that opens seamlessly to the family room, while a Florida room connects directly from the kitchen and leads out to the backyard deck with a 12x12 hardtop gazebo that conveys. Both bathrooms also have skylights,

    David Zambrano REDFIN CORPORATION

    221 Albert St, Winter Springs, FL 32708
  • /18

    $383,091 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    1264 Crab Apple Ln, Winter Springs, FL 32708

    As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a

    Mattamy Homes Builder
    1264 Crab Apple Ln, Winter Springs, FL 32708
  • /12

    $397,093 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,678 Sq Ft

    1272 Crab Apple Ln, Winter Springs, FL 32708

    The Catalina I is a harmonious blend of style, functionality, and comfort, offering a lifestyle that caters to your every need. As you step inside you are greeted by an open-concept design that seamlessly integrates the gathering room, dining room, and kitchen, creating an inviting space for both everyday living and entertaining. This townhome features 3 bedrooms, providing flexible living

    Mattamy Homes Builder
    1272 Crab Apple Ln, Winter Springs, FL 32708
  • /13

    $389,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,678 Sq Ft

    Catalina Plan at Hickory Grove, Winter Springs, FL 32708

    The Catalina I is a harmonious blend of style, functionality, and comfort, offering a lifestyle that caters to your every need. As you step inside you are greeted by an open-concept design that seamlessly integrates the gathering room, dining room, and kitchen, creating an inviting space for both everyday living and entertaining. This townhome features 3 bedrooms, providing flexible living

    Mattamy Homes Builder
    1458 Blumberg Blvd Unit 36468370, Winter Springs, FL 32708
  • /44

    $340,000

    • 2 Beds
    • 2.5 Baths
    • 1,558 Sq Ft

    650 Pinebranch Cir, Winter Springs, FL 32708

    Amazing move-in-ready townhouse in the private, GATED community of Barclay Reserve. This two-story, 2 bedroom 2.5 bath townhome with 1 car garage has Ceramic tile floors in the lower level & BRAND NEW carpet in the upper level bedrooms hallway. This spacious kitchen has wood cabinets, A fully equipped kitchen with all appliances, a breakfast bar, & a large pantry. Enjoy the open floor plan,

    Sascha Davis EXP REALTY LLC

    650 Pinebranch Cir, Winter Springs, FL 32708
  • /25

    $325,000

    • 3 Beds
    • 2.5 Baths
    • 1,468 Sq Ft

    116 Philadelphia Way, Winter Springs, FL 32708

    Well-appointed 3-bedroom, 2.5-bath townhome for sale in a gated community, offering a great combination of functionality, privacy, and location. Designed for comfortable living, this home includes energy-efficient double-pane windows that enhance interior comfort and help reduce outside noise. The primary suite features a spacious walk-in closet with natural light, creating a bright and welcoming

    Isabel Sirizzotti SUNNY 365 REALTY GROUP

    116 Philadelphia Way, Winter Springs, FL 32708
  • /3

    $400,000

    • Land
    • 2.72 Acres
    • $147,059 per Acre

    835 E State Road 434, Winter Springs, FL 32708

    The lot has been completely cleared and is ready to be developed.

    Keith Moore HOMEVEST REALTY

    835 E State Road 434, Winter Springs, FL 32708
  • /18

    $374,900

    • 4 Beds
    • 2 Baths
    • 1,312 Sq Ft

    113 Lido Rd, Winter Springs, FL 32708

    Welcome home to this 4 bedroom 2 bath in the heart of Winter Springs! Walk thru the front door to be wowed with LVP flooring and a spacious living space with large windows letting in natural light. The eat-in space in the kitchen features French doors leading out into the oversized backyard perfect for a summer game of baseball or even a firepit for those cool FL nights. Kitchen has updated real

    Nicole Anderson HD REALTY LLC

    113 Lido Rd, Winter Springs, FL 32708
  • /42

    $369,900

    • 3 Beds
    • 2.5 Baths
    • 1,914 Sq Ft

    451 Harbor Winds Ct, Winter Springs, FL 32708

    Well maintained! Move-in Ready! Fabulous 2-story, 3 bedroom, 2 full bath and a half bath townhouse with attached 2-car garage in the exclusive gated community of Harbor Winds. Upgrades include: New Roof (2023); New Gutters (2023); New A/C System (2023); New Water Heater (2023); New Stainless Steel Appliances (2023) to include Refrigerator, Range, Dish Washer and Microwave. Inside, the perfectly

    Anderson (Luis) Zamora OLYMPUS EXECUTIVE REALTY INC

    451 Harbor Winds Ct, Winter Springs, FL 32708
  • /19

    $318,900

    • 2 Beds
    • 2.5 Baths
    • 1,558 Sq Ft

    554 Pinebranch Cir, Winter Springs, FL 32708

    Short Sale. Short Sale and new price approved by the bank! Welcome to Barclay Reserve, a private and gated community in Winter Springs! This beautifully maintained townhome is located in the highly sought-after “A” rated Seminole County school district. Inside, you’ll find gorgeous laminate flooring throughout the main living areas, with ceramic tile in the wet areas for easy care. The open floor

    Lucilma Roman LLC LA ROSA REALTY CW PROPERTIES L

    554 Pinebranch Cir, Winter Springs, FL 32708
  • /25

    $320,000

    • 2 Beds
    • 2 Baths
    • 1,044 Sq Ft

    222 W Panama Rd, Winter Springs, FL 32708

    Well-maintained 3-bedroom, 2-bath home located in sought-after Winter Springs. This property offers a fully fenced backyard with a private pool, providing excellent privacy and space for outdoor entertaining. Situated in a quiet, established neighborhood with no HOA restrictions. Conveniently located near local parks, shopping centers, dining, and major highways for easy commuting. Zoned for

    Melissa Maldonado CENTURY 21 MCBRIDE REALTY GROUP

    222 W Panama Rd, Winter Springs, FL 32708
  • /36

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,522 Sq Ft

    625 Nighthawk Cir, Winter Springs, FL 32708

    This charming 3 bedroom, 2 bathroom single family home boasts a beautiful open plan. The kitchen has been recently remodeled and includes solid counter tops and back splatch. The appliances are all within a couple years old and barely used. The tile roof is 2 years old. The water heater is brand new. The entire property has been recently painted and the carpeting is brand new. The primary

    Warren Gagne NEXTHOME NEIGHBORHOOD REALTY

    625 Nighthawk Cir, Winter Springs, FL 32708
  • /33

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,602 Sq Ft

    563 Pinebranch Cir, Winter Springs, FL 32708

    PRICE REDUCED FOR FASTER SALE!!! EXCELLENT PRICE FOR THIS AMAZING WATERfRONT TOWNHOUSE! Welcome Home!!! This beautiful & Spacious townhome in Winter Springs offers 3 ample bedrooms and 2 and a Half baths, brand new floors throughout the 1st floor, as well as brand new interior painting.The primary suite includes a large walk-in closet, double sinks, & a combination of tub & Shower. Enjoy the

    Vicky Valdez LA ROSA REALTY LLC

    563 Pinebranch Cir, Winter Springs, FL 32708
  • /24

    $359,700

    • 3 Beds
    • 3 Baths
    • 1,104 Sq Ft

    310 Panama Cir, Winter Springs, FL 32708

    BEAUTIFUL HOME! TOTALLY UPGRADED 3 BEDROOMS 2 BATHS!! & IN-LAW SUITE 1 BEDROOM 1 BATHROOM AND LAUNDRY. Priced to Sell! This home is not like no other home in this area, Nice Kitchen Cabinets and Granite counter tops, modern tile floors, Stain Steel appliances, Refrigerator, Range & microwave. This home is clean, immaculate and a pleasure to show.

    Everardo Santos ESG INVESTMENT ENTERPRISE INC

    310 Panama Cir, Winter Springs, FL 32708
  • /37

    $304,900

    • 3 Beds
    • 1 Bath
    • 1,058 Sq Ft

    111 N Fairfax Ave, Winter Springs, FL 32708

    Welcome home to this beautifully updated 3 bedroom, 1 bath home located in a well established neighborhood in Winter Springs with no HOA restrictions. This home offers comfort, style, and convenience in one inviting space. Conveniently located near schools, parks, shopping centers, and with quick access to I4 and 417, this home puts everything you need within reach.From the moment you step

    Carla Cabrera MODERN WORLD REALTY LLC

    111 N Fairfax Ave, Winter Springs, FL 32708
  • /58

    $399,900

    • 3 Beds
    • 2 Baths
    • 1,368 Sq Ft

    717 Wilson Rd, Winter Springs, FL 32708

    ADORABLE home located in DESIRABLE TUSCAWILLA Wedgewood Tennis Villas known for its' CHARMING TREE-LINED STREETS!! Walk to clubhouse, tennis games, and fitness center! BEAUTIFUL CURB APPEAL! Home is OPEN, LIGHT, BRIGHT, and SPACIOUS!! With BRICK FIREPLACE and VOLUME CEILINGS!! NEWER laminate wood FLOORING throughout living and bedroom area installed 2018! Kitchen features LIGHT MAPLE WOOD

    Cameron Hasan FLORIDA USA REALTY

    717 Wilson Rd, Winter Springs, FL 32708
  • /39

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,377 Sq Ft

    600 Northern Way Unit 1403, Winter Springs, FL 32708

    A Beautiful, Well-Appointed Condo in Tuscany Place Condominiums ~ Upon Entering this Beautiful Unit You will find High Ceilings and Upscale Wood Laminate Flooring throughout the first floor ~ The Owner's Suite is on the First Floor with Large Closets with Built-in Shelving. The Kitchen has Wood Cabinetry with High-end Features, Back Splash, Granite Counters, Stainless Appliances, Under Cabinet

    Elizabeth Larsen JULIE B REALTY, INC

    600 Northern Way Unit 1403, Winter Springs, FL 32708
  • /28

    $348,000

    • 4 Beds
    • 3 Baths
    • 1,270 Sq Ft

    31 S Edgemon Ave, Winter Springs, FL 32708

    This charming home offers a spacious floor plan with a unique twist— the garage has been converted into a private studio with its own entrance, perfect for guests, a home office, extra living space or residual income. Inside, you'll find comfortable living areas, cozy bedrooms, and a kitchen ready for your culinary adventures. Enjoy the convenience of being close to local amenities, parks, and

    Florentino Beltran KELLER WILLIAMS ADVANTAGE 2 REALTY

    31 S Edgemon Ave, Winter Springs, FL 32708
  • /27

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    705 Crestwood Way, Winter Springs, FL 32708

    Welcome to this delightful one-story home in Wildwood, perfectly set on a spacious corner lot! Offering 3 bedrooms and 2 baths, this inviting home features a bright, cheerful living room ideal for family gatherings. The kitchen offers with wood cabinetry, granite countertops, a stylish tile backsplash, and durable ceramic tile flooring. The primary bedroom provides a comfortable retreat with its

    Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

    705 Crestwood Way, Winter Springs, FL 32708
  • /53

    $305,900

    • 3 Beds
    • 2 Baths
    • 1,101 Sq Ft

    515 Seasons Ct, Winter Springs, FL 32708

    **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

    515 Seasons Ct, Winter Springs, FL 32708
  • /24

    $310,000

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

    600 Northern Way Unit 906, Winter Springs, FL 32708

    Turnkey townhouse is in excellent shape and ready for immediate move-in. Exceptional open floor plan with flexibility for multi-generation living. This beautiful home has three en-suites with one of the bedrooms on the ground level, so it’s perfect for a mother-in-law suite. Large sized rooms, updated bathrooms, and all the features you are looking for. The kitchen has stainless steel appliances,

    John Vincent JR REALTY GROUP LLC

    600 Northern Way Unit 906, Winter Springs, FL 32708
  • /12

    $399,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 1,678 Sq Ft

    1328 Crab Apple Ln, Winter Springs, FL 32708

    With a spacious open concept ground floor, the Catalina II has plenty of room for entertaining. This floorplan features 4 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The owners suite features an ensuite owner's bath and a walk-in closet. This chef-worthy kitchen features stainless steel appliances, a walk-in pantry, and a breakfast bar.

    Mattamy Homes Builder
    1328 Crab Apple Ln, Winter Springs, FL 32708
  • /17

    $335,000

    • 3 Beds
    • 2 Baths
    • 1,026 Sq Ft

    1211 Phillip St, Winter Springs, FL 32708

    PRICE REDUCED!!! 3 BEDROOM 2 BATH BLOCK HOME REMODELED IN 2023, REPLACED CABINETS, ROOF AND A/C. FEATURES AN ENCLOSED PATIO, SEPARATE LAUNDRYROOM, WELL WITH A FILTRATION SYSTEM, LARGE LOT, AND A GARAGE CONVERSION THAT PROVIDES A 4TH BEDROOM, BUT CAN EASILY BE CONVERTED BACK TO A GARAGE. PLENTY OF STORAGE SPACE IN THE LAUNDRY ROOM AND A LARGE SHED IN THE BACK. NICE CALM NEIGHBORHOOD, NEAR

    Marina Munoz OUTLET REALTY

    1211 Phillip St, Winter Springs, FL 32708
  • /40

    $331,000

    • 3 Beds
    • 1 Bath
    • 1,188 Sq Ft

    140 N Fairfax Ave, Winter Springs, FL 32708

    Welcome to 140 N. Fairfax Ave — a beautifully completely updated Winter Springs home that blends classic Florida charm with modern style. This extensively remodeled 3-bedroom, 1-bath residence sits on a generous 8,900 sq ft lot and offers an ideal layout for first-time buyers, downsizers, or investors seeking a true turnkey property in highly desirable Seminole County.Inside, you’ll

    Shawn McCormick ERA GRIZZARD REAL ESTATE

    140 N Fairfax Ave, Winter Springs, FL 32708
  • /22

    $319,999

    • 3 Beds
    • 2.5 Baths
    • 1,468 Sq Ft

    476 Tradition Ln, Winter Springs, FL 32708

    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

    476 Tradition Ln, Winter Springs, FL 32708
  • /25

    $385,000

    • 3 Beds
    • 2 Baths
    • 1,265 Sq Ft

    744 N Gretna Ct, Winter Springs, FL 32708

    Small but cozy, 3-bedroom house. Detached and very large backyard. Perfect for investors interested in fixing and flipping Or for rental. Currently is being rented to students.

    Gregory Sullivan BY OWNER.COM

    744 N Gretna Ct, Winter Springs, FL 32708
  • /12

    $361,000

    • 3 Beds
    • 2 Baths
    • 1,551 Sq Ft

    1171 San Blas Cove, Winter Springs, FL 32708

    Welcome to 1171 San Blas Cove, a charming single-family home nestled in the heart of Winter Springs, FL. Built in 1984, this well-maintained property offers a perfect blend of comfort and convenience for its residents. Boasting a spacious interior with a total finished area of 1,551 square feet, this home provides ample space for relaxation and entertainment.This cozy residence features 2

    Moe Mossa SAVVY AVENUE, LLC

    1171 San Blas Cove, Winter Springs, FL 32708
  • /26

    $339,000

    • 3 Beds
    • 2.5 Baths
    • 1,602 Sq Ft

    540 Pinebranch Cir, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to this beautifully maintained townhome in the gated community of Barkley Reserve, perfectly situated in the heart of Winter Springs. This spacious 3-bedroom, 2.5-bath home offers an inviting open layout, a large living area filled with natural light, and a well-appointed kitchen with plenty of cabinet space. One of the biggest highlights of

    Joshua Lopez EXP REALTY LLC

    540 Pinebranch Cir, Winter Springs, FL 32708
  • /59

    $378,000

    • 3 Beds
    • 2.5 Baths
    • 1,435 Sq Ft

    449 Gee Hammock Ln, Winter Springs, FL 32708

    Welcome to your dream home at 449 Gee Hammock Lane, nestled in the tranquil and highly sought-after neighborhood of Jesups Landing. This stunning home boasts Stainless Steel appliances, Granite countertops, 42" Cabinets, Tiled kitchen backsplash, Pendant lighting, Walk-in pantry, Breakfast bar, and charming built-in storage shelves. This home offers a split floor-plan, giving you the option to

    Angela Magac THE PROPERTY STOP LLC

    449 Gee Hammock Ln, Winter Springs, FL 32708
  • /22

    $369,900

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

    984 Legacy Winds Way, Casselberry, FL 32707

    Short Sale. GREAT OPPORTUNITY! Located in desirable Legacy Winds, this townhome offers the perfect blend of modern design, comfort, and convenience. Featuring 3 bedrooms and 2.5 baths, this TH welcomes you with an open and airy floor plan designed for everyday living and easy entertaining. The open kitchen is the heart of the home, complete with stainless steel appliances, a spacious center

    Doug Woehr COLDWELL BANKER RESIDENTIAL RE

    984 Legacy Winds Way, Casselberry, FL 32707

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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