17,391

Winter Springs, FL Homes

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  • /24

    $185,000

    $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 945 Sq Ft

    343 San Miguel St Unit 343, Winter Springs, FL 32708

    Welcome to this freshly painted 2-bedroom, 2-bathroom condominium located in the desirable Deer Song community in Winter Springs. Offering a low-maintenance lifestyle in a convenient Central Florida location, this residence is a great fit for a first-time buyer, downsizer, seasonal resident, or investor looking for a well-positioned property with everyday comfort and community appeal. Inside, the

    Agent Photo

    Michael Rogers

    INNOVATIVE REALTY, LLC

    343 San Miguel St Unit 343, Winter Springs, FL 32708
  • /15

    $2,775 Per Month

    • 4 Beds
    • 2 Baths
    • 1,977 Sq Ft
    • House for Rent

    814 Big Buck Cir, Winter Springs, FL 32708

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2919.90. That covers your base rent, $2775.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    814 Big Buck Cir, Winter Springs, FL 32708
  • /2

    $615,000

    Sold Jul 16, 2025

    338 Wooded Vine Dr, Winter Springs, FL 32708

    • 4 Beds
    • 2 Baths
    • 1,916 Sq Ft
    • Built 2019

    Last Sold Summary

    • 2% Below List Price
    • $321/SF
    • 24 Days On Market

    Current Estimated Value $614,951

    Last Listing Agent Valentina Vakhova LA ROSA REALTY KISSIMMEE

    338 Wooded Vine Dr, Winter Springs, FL 32708
    • /2

      Est $523,528

      Not Listed For Sale

      842 Bentley Green Cir, Winter Springs, FL 32708

      • 3 Beds
      • 2 Baths
      • 2,046 Sq Ft
      • Built 1991
      842 Bentley Green Cir, Winter Springs, FL 32708

      Last Sold Summary

      • 9 Days On Market

  • /35

    $285,000

    • 4 Beds
    • 1.5 Baths
    • 1,212 Sq Ft

    101 Melton Dr, Winter Springs, FL 32708

    Charming 4-Bedroom Home in the Heart of Winter Springs! Welcome to this well-positioned 4-bedroom, 1.5-bath home offering comfort, functionality, and a spacious lot in an established Winter Springs neighborhood. Situated on nearly a quarter acre, this property provides plenty of outdoor space for entertaining, gardening, pets, or future enhancements. Inside, you'll find a practical floor plan

    Agent Photo

    Ariel Vargas

    EXP REALTY LLC

    101 Melton Dr, Winter Springs, FL 32708
  • /14

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft
    • House for Rent

    47 Macgregor Rd, Winter Springs, FL 32708

    Property Id: 2705198A beautiful 3 bedrooms, 2 bath single-family-home in a family-oriented neighborhood in Winter Springs. Excellent neighborhood for a family with school going kids. The house is ideal for a family with young kids and/or responsible students. The house is in very good shape. Relatively newly painted interior and exterior. The schools are the best in Central Florida

    47 Macgregor Rd, Winter Springs, FL 32708
  • /2

    $170,000

    Sold Jul 25, 2025

    240 Moree Loop Unit 5, Winter Springs, FL 32708

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • Built 1978

    Last Sold Summary

    • $143/SF
    • 0 Days On Market

    Current Estimated Value $172,616

    Last Listing Agent Richard Sherrod Jr EXP REALTY LLC

    240 Moree Loop Unit 5, Winter Springs, FL 32708
    • /2

      Est $340,042

      Not Listed For Sale

      561 Pinebranch Cir, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,564 Sq Ft
      • Built 2005
      561 Pinebranch Cir, Winter Springs, FL 32708

      Last Sold Summary

      • 12 Days On Market

  • /29

    $215,900

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,134 Sq Ft

    71 Bombay Ave, Winter Springs, FL 32708

    Set in the heart of Winter Springs, 71 Bombay Ave offers the kind of opportunity buyers are always looking for: an established location, a functional footprint, and the chance to create a home that reflects their own style. This property is ready for its next chapter, making it an ideal choice for those who appreciate potential, value, and the ability to personalize a space over time. Life here

    Agent Photo

    Heather Unger, PA

    ACME REAL ESTATE FLORIDA LLC

    71 Bombay Ave, Winter Springs, FL 32708
  • /16

    $2,590 Per Month

    • 4 Beds
    • 2 Baths
    • 1,607 Sq Ft
    • House for Rent

    116 S Moss Rd, Winter Springs, FL 32708

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    116 S Moss Rd, Winter Springs, FL 32708
  • /2

    $150,000

    Sold May 22, 2026

    704 Glasgow Ct, Winter Springs, FL 32708

    • 1 Bed
    • 1 Bath
    • 896 Sq Ft
    • Built 1974

    Last Sold Summary

    • 2% Below List Price
    • $167/SF
    • 6 Days On Market

    Current Estimated Value $151,242

    Last Listing Agent Todd Schroth EXP REALTY LLC

    704 Glasgow Ct, Winter Springs, FL 32708
    • /2

      Est $407,589

      Not Listed For Sale

      939 Glen Abbey Cir, Winter Springs, FL 32708

      • 3 Beds
      • 3 Baths
      • 1,667 Sq Ft
      • Built 2001
      939 Glen Abbey Cir, Winter Springs, FL 32708

      Last Sold Summary

      • 23 Days On Market

  • /26

    $624,000

    • 4 Beds
    • 2.5 Baths
    • 3,334 Sq Ft

    1204 Swan St, Winter Springs, FL 32708

    Rare opportunity in the heart of Winter Springs! Situated on an expansive 0.72-acre lot with NO HOA, this unique 4-bedroom, 2.5-bath pool home offers endless potential for the buyer seeking space, privacy, and the chance to create something truly special. The property features a recently resurfaced pool, a fully fenced backyard, and an incredible outdoor setting designed for entertaining and

    Agent Photo

    Chandler Williams

    EXIT REALTY PREMIER LEGACY

    1204 Swan St, Winter Springs, FL 32708
  • /16

    $2,310 Per Month

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • House for Rent

    209 Banyan Ct, Winter Springs, FL 32708

    Welcome to 209 Banyan Court, a comfortable 3-bedroom, 2-bathroom home offering 1,305 square feet of inviting living space. Step inside to find a bright living area that flows effortlessly into the kitchen, which features a full suite of stainless steel appliances, ample cabinetry, and lovely countertops. For added convenience, the home includes dedicated washer and dryer hookups, while a

    209 Banyan Ct, Winter Springs, FL 32708
  • /2

    $253,000

    Sold Apr 10, 2026

    565 Green Spring Cir, Winter Springs, FL 32708

    • 2 Beds
    • 1.5 Baths
    • 1,363 Sq Ft
    • Built 1990

    Last Sold Summary

    • 1% Above List Price
    • $186/SF
    • 19 Days On Market

    Current Estimated Value $253,747

    Last Listing Agent Sharyon Neilen COLDWELL BANKER REALTY

    565 Green Spring Cir, Winter Springs, FL 32708
    • /2

      Est $503,103

      Not Listed For Sale

      150 Tarpon Cir, Winter Springs, FL 32708

      • 3 Beds
      • 2 Baths
      • 1,963 Sq Ft
      • Built 1978
      150 Tarpon Cir, Winter Springs, FL 32708

      Last Sold Summary

      • 19 Days On Market

  • /19

    $379,990

    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
  • /2

    $3,185 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,206 Sq Ft
    • Townhouse for Rent

    1408 Winter Wharf Ln, Winter Springs, FL 32708

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    1408 Winter Wharf Ln, Winter Springs, FL 32708
  • /2

    $329,900

    Sold Apr 23, 2026

    5 Gumtree Ct, Winter Springs, FL 32708

    • 4 Beds
    • 2 Baths
    • 1,485 Sq Ft
    • Built 1974

    Last Sold Summary

    • $222/SF
    • 4 Days On Market

    Current Estimated Value $332,451

    Last Listing Agent Dean Erlandson LIVE FLORIDA NOW LLC

    5 Gumtree Ct, Winter Springs, FL 32708
    • /17

      Est $393,744

      Not Listed For Sale

      564 Jesup Springs Ln, Winter Springs, FL 32708

      • 3 Beds
      • 2 Baths
      • 1,668 Sq Ft
      • Built 2016
      564 Jesup Springs Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 8 Days On Market

  • /40

    $825,000

    $25K PRICE DROP Pending
    • 5 Beds
    • 3.5 Baths
    • 3,118 Sq Ft

    1160 Citrus Oaks Run, Winter Springs, FL 32708

    Under contract-accepting backup offers. Exceptional luxury living awaits in this beautifully reimagined 5-bedroom, 3.5-bath residence located within an exclusive gated community. Offering over 3,100 square feet of refined living space, this impressive home showcases luxury finishes and thoughtful upgrades throughout, including elegant travertine flooring, rich oil-rubbed plank floors, and a

    Michael Julian JULIAN PROPERTIES, INC.

    1160 Citrus Oaks Run, Winter Springs, FL 32708
  • /19

    $2,490 Per Month

    • 3 Beds
    • 2 Baths
    • 2,025 Sq Ft
    • House for Rent

    1172 La Mesa Ave, Winter Springs, FL 32708

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2634.90. That covers your base rent, $2490.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    1172 La Mesa Ave, Winter Springs, FL 32708
  • /2

    $351,000

    Sold Nov 21, 2025

    1054 W Pebble Beach Cir, Winter Springs, FL 32708

    • 2 Beds
    • 2 Baths
    • 1,420 Sq Ft
    • Built 1980

    Last Sold Summary

    • 17% Below List Price
    • $247/SF
    • 75 Days On Market

    Current Estimated Value $355,793

    Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

    1054 W Pebble Beach Cir, Winter Springs, FL 32708
    • /2

      Est $379,066

      Not Listed For Sale

      368 Innisbrook Ln, Winter Springs, FL 32708

      • 3 Beds
      • 3.5 Baths
      • 1,844 Sq Ft
      • Built 2013
      368 Innisbrook Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 78 Days On Market

  • /68

    $2,625,000

    New Construction Open Sun 10:30AM - 12:30PM $275K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 6,132 Sq Ft

    1447 Bird Rd, Winter Springs, FL 32708

    Discover the pinnacle of secluded luxury in this brand-new, 8,000 SF estate, nestled in picturesque Winter Springs. From the moment you arrive, the custom glass French entry doors hint at the artistry within. Stepping into the grand foyer, you are greeted by statement marble and mosaic flooring that sets a tone of elegance, a design narrative that flows seamlessly throughout the home. Designed

    Robert Kirkwood MAVREALTY

    1447 Bird Rd, Winter Springs, FL 32708
  • /16

    $2,150 Per Month

    • 3 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • House for Rent

    109 N Alderwood St, Winter Springs, FL 32708

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    109 N Alderwood St, Winter Springs, FL 32708
  • /2

    $639,900

    Sold Jun 11, 2026

    1109 Duncan Dr, Winter Springs, FL 32708

    • 4 Beds
    • 2 Baths
    • 2,118 Sq Ft
    • Built 1980

    Last Sold Summary

    • $302/SF
    • 3 Days On Market

    Current Estimated Value $559,540

    Last Listing Agent Doug Woehr COLDWELL BANKER REALTY

    1109 Duncan Dr, Winter Springs, FL 32708
    • /2

      Est $382,862

      Not Listed For Sale

      384 Innisbrook Ln, Winter Springs, FL 32708

      • 3 Beds
      • 3.5 Baths
      • 1,844 Sq Ft
      • Built 2013
      384 Innisbrook Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 192 Days On Market

  • /13

    $394,990

    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
  • /16

    $2,350 Per Month

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

    1445 Bird Rd, Winter Springs, FL 32708

    This property is available. Please inquire on this site to schedule a showing. Welcome to the first-floor rental at your dream home located at 1445 Bird Road, Winter Springs, FL 32708. This stunning property offers a blend of elegance and modern comfort, set on a spacious lot with lush surroundings. As you enter through the gated driveway, you're greeted by a grand two-story residence

    Unit

    1445 Bird Rd, Winter Springs, FL 32708
  • /2

    $920,000

    Sold Feb 10, 2026

    704 Forest View Ct, Winter Springs, FL 32708

    • 5 Beds
    • 3 Baths
    • 3,068 Sq Ft
    • Built 2023

    Last Sold Summary

    • 16% Below List Price
    • $300/SF
    • 201 Days On Market

    Current Estimated Value $944,258

    Last Listing Agent Walter Givens LPT REALTY, LLC

    704 Forest View Ct, Winter Springs, FL 32708
    • /63

      Est $374,395

      Not Listed For Sale

      365 Old Farm Ln, Winter Springs, FL 32708

      • 3 Beds
      • 3 Baths
      • 1,732 Sq Ft
      • Built 2013
      365 Old Farm Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 25 Days On Market

  • /54

    $499,000

    Open Sun 1PM - 3PM $40K PRICE INCREASE
    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft

    934 Torrey Pine Dr, Winter Springs, FL 32708

    Virtually Staged. Beautifully remodeled golf course home in the highly desirable Tuscawilla community! This move-in ready residence has been extensively updated with a fresh modern design throughout, including all new flooring, new interior paint, new granite countertops, custom designer backsplash, stainless steel appliances, and an updated interior lighting package. The spacious primary suite

    James Clark CENTURY 21 ALTON CLARK

    934 Torrey Pine Dr, Winter Springs, FL 32708
  • /14

    $3,640 Per Month

    • 3 Beds
    • 2 Baths
    • 1,641 Sq Ft
    • House for Rent

    1000 Dinero Dr, Winter Springs, FL 32708

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    1000 Dinero Dr, Winter Springs, FL 32708
  • /2

    $199,900

    Sold Jul 22, 2025

    429 Sheoah Blvd Unit 3, Winter Springs, FL 32708

    • 2 Beds
    • 2 Baths
    • 1,343 Sq Ft
    • Built 1978

    Last Sold Summary

    • $149/SF
    • 32 Days On Market

    Current Estimated Value $198,197

    Last Listing Agent Marielle Parra COMPASS FLORIDA LLC

    429 Sheoah Blvd Unit 3, Winter Springs, FL 32708
    • /2

      Est $411,249

      Not Listed For Sale

      1157 Orange Ave, Winter Springs, FL 32708

      • 3 Beds
      • 3.5 Baths
      • 2,104 Sq Ft
      • Built 2015
      1157 Orange Ave, Winter Springs, FL 32708

      Last Sold Summary

      • 61 Days On Market

  • /14

    $409,990

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

    Catalina II Plan at Hickory Grove, 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
    1458 Blumberg Blvd Unit 36446933, Winter Springs, FL 32708
  • /12

    $2,499 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,859 Sq Ft
    • House for Rent

    320 Cello Cir, Winter Springs, FL 32708

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2643.90. That covers your base rent, $2499.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    320 Cello Cir, Winter Springs, FL 32708
  • /2

    $420,000

    Sold Apr 22, 2026

    1706 Fox Glen Ct, Winter Springs, FL 32708

    • 3 Beds
    • 2 Baths
    • 1,656 Sq Ft
    • Built 2001

    Last Sold Summary

    • 4% Below List Price
    • $254/SF
    • 23 Days On Market

    Current Estimated Value $422,325

    Last Listing Agent Harry Kazarian STRONG FOUNDATION REALTY LLC

    1706 Fox Glen Ct, Winter Springs, FL 32708
    • /2

      Est $370,817

      Not Listed For Sale

      548 Jesup Springs Ln, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,545 Sq Ft
      • Built 2016
      548 Jesup Springs Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 8 Days On Market

Showing Results 41 - 80, Page 2 of 18

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