17,328

Winter Springs, FL Homes

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  • /5

    $465,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,928 Sq Ft

    797 Night Owl Ln, Winter Springs, FL 32708

    Welcome home to Oak Forest in the heart of Winter Springs! This well maintained 4 bedroom 2 bath POOL home is ready for new owners. Bring your own style. Split floor plan, large lving room, open kitchen and bonus family room with wood burning fire place. Roof 2020, Water heater 2025. Backs up to conservation, no rear neighbors. Conveniently located close to shopping, dining, major roadways and A+

    Cara Seguin KELLER WILLIAMS ADVANTAGE REALTY

    797 Night Owl Ln, Winter Springs, FL 32708
  • /14

    $2,200 Per Month

    • 3 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • House for Rent

    1243 Las Cruces Dr, Winter Springs, FL 32708

    Welcome to 1243 Las Cruces Drive! This inviting 3-bedroom, 2-bathroom rental offers comfortable living with a nice backyard, perfect for relaxing, entertaining, or enjoying time outdoors. Zoned for A-rated Seminole County schools, this home is an excellent choice for a growing family. Conveniently located near major highways, dining, shopping, and just minutes from Oviedo and Winter Park, you’ll

    Alexandra Araque KELLER WILLIAMS LEGACY REALTY

    1243 Las Cruces Dr, Winter Springs, FL 32708
  • /2

    $630,000

    Sold Dec 02, 2025

    875 Bentley Green Cir, Winter Springs, FL 32708

    • 4 Beds
    • 3 Baths
    • 2,616 Sq Ft
    • Built 1993

    Last Sold Summary

    • 14% Below List Price
    • $241/SF
    • 114 Days On Market

    Current Estimated Value $644,876

    Last Listing Agent Kristin Vogt PLLC KGV REALTY GROUP

    875 Bentley Green Cir, Winter Springs, FL 32708
    • /34

      Est $287,716

      Not Listed For Sale

      600 Northern Way Unit 902, Winter Springs, FL 32708

      • 3 Beds
      • 3 Baths
      • 1,447 Sq Ft
      • Built 2016
      600 Northern Way Unit 902, Winter Springs, FL 32708

      Last Sold Summary

      • 72 Days On Market

      Last Listing Agent Liz Amor Pagan WATSON REALTY CORP

  • /2

    $930,000

    • 4 Beds
    • 3 Baths
    • 2,272 Sq Ft

    864 Bentley Green Cir, Winter Springs, FL 32708

    Welcome to 864 Bentley Green Circle, a move-in ready luxury sanctuary situated on a quiet cul-de-sac lot in Winter Springs. Offering 4 bedrooms, 3 full bathrooms, and over 2,200 square feet of meticulously updated living space, this home seamlessly blends sophisticated interior accents with private, resort-style outdoor living.Arrive via a grand circular drive centered around a professionally

    Patrick Calathes REAL BROKER, LLC

    864 Bentley Green Cir, Winter Springs, FL 32708
  • /16

    $2,575 Per Month

    • 4 Beds
    • 2 Baths
    • 1,677 Sq Ft
    • 4 Bedroom Pet-Friendly Home in Winter Springs, FL with Main Street Renewal

    1077 Chokecherry Dr, Winter Springs, FL 32708

    Beautiful, pet-friendly home coming soon! Apply now — available date is tentative and move-in will be scheduled within 5–10 days of the home being ready. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $55 per adult. Security Deposit: one month's rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo),

    1077 Chokecherry Dr, Winter Springs, FL 32708
  • /2

    $425,000

    Sold Nov 24, 2025

    1189 Orange Ave, Winter Springs, FL 32708

    • 4 Beds
    • 3.5 Baths
    • 2,288 Sq Ft
    • Built 2015

    Last Sold Summary

    • 1% Below List Price
    • $186/SF
    • 30 Days On Market

    Current Estimated Value $425,128

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    1189 Orange Ave, Winter Springs, FL 32708
    • /18

      Not Listed For Sale

      1286 Tarflower Dr, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,476 Sq Ft
      1286 Tarflower Dr, Winter Springs, FL 32708

      Last Sold Summary

      • 103 Days On Market

  • /28

    $406,990

    New Construction Pending
    • 3 Beds
    • 2.5 Baths
    • 1,476 Sq Ft

    225 Spindle Palm Cove, Winter Springs, FL 32708

    Under Construction. Final opportunity! Don't miss your chance to make this beautiful property yours! 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

    Elizabeth Manchester MATTAMY REAL ESTATE SERVICES

    225 Spindle Palm Cove, Winter Springs, FL 32708
  • /22

    $1,625 Per Month

    • 2 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Townhouse for Rent

    130 Rhoden Ln, Winter Springs, FL 32708

    This 2/1.5 corner-unit townhome features carpet in both bedrooms and NEW laminate flooring in the downstairs living room and kitchen. (Pictures coming soon)The living room has a fireplace. The screened-in patio has a laundry closet. Torasco Park is just across the street with SPLASH PARK, a basketball court, a soccer field, a playground, and an exercise trail. Keller Williams residents are

    Kelly Popchock KELLER WILLIAMS REALTY AT THE PARKS

    130 Rhoden Ln, Winter Springs, FL 32708
  • /18

    $444,940

    Sold Jun 15, 2026

    161 Bear Springs Dr, Winter Springs, FL 32708

    • 3 Beds
    • 2.5 Baths
    • 1,704 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 8% Below List Price
    • $261/SF
    • 13 Days On Market

    Current Estimated Value $479,066

    Mattamy Homes Hickory Grove

    161 Bear Springs Dr, Winter Springs, FL 32708
    • /12

      Not Listed For Sale

      1282 Tarflower Dr, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,678 Sq Ft
      1282 Tarflower Dr, Winter Springs, FL 32708

      Last Sold Summary

      • 135 Days On Market

  • /52

    $497,000

    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft

    1610 Fox Glen Ct, Winter Springs, FL 32708

    Welcome to this beautiful 4-bedroom home in the heart of Tuscawilla! This well-appointed home offers a comfortable and versatile floor plan with a primary bedroom conveniently located on the main floor. Upstairs, you'll find three additional bedrooms and a spacious loft-perfect for a reading area, sitting room, home office or additional living space. Relax and enjoy the peaceful private garden

    Lawrence Jasper TUSCAWILLA REALTY, INC

    1610 Fox Glen Ct, Winter Springs, FL 32708
  • /11

    $1,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,247 Sq Ft
    • House for Rent

    202 Perth Ct, Winter Springs, FL 32708

    Lovely renovated 3 bedroom, 2 bath duplex in a quiet cul-de-sac in beautiful Winter Springs. Large spacious living room, galley kitchen with Stainless Steel appliances, granite countertops with backsplash and new white cabinets. Tiled throughout the home and ceiling fans installed in every bedroom. Central Air and Heat. Freshly painted, clean and ready for move in. Private courtyard off the

    202 Perth Ct, Winter Springs, FL 32708
  • /2

    $473,000

    Sold May 15, 2026

    348 Michael Blake Blvd, Winter Springs, FL 32708

    • 3 Beds
    • 2.5 Baths
    • 1,988 Sq Ft
    • Built 2013

    Last Sold Summary

    • 5% Below List Price
    • $238/SF
    • 59 Days On Market

    Current Estimated Value $471,923

    Last Listing Agent Shahram Sondi SHAHRAM SONDI + CO.

    348 Michael Blake Blvd, Winter Springs, FL 32708
    • /12

      Not Listed For Sale

      1318 Tarflower Dr, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,678 Sq Ft
      1318 Tarflower Dr, Winter Springs, FL 32708

      Last Sold Summary

      • 137 Days On Market

  • /41

    $749,000

    $26K PRICE DROP Pending
    • 5 Beds
    • 3 Baths
    • 3,164 Sq Ft

    1209 Deer Run Dr, Winter Springs, FL 32708

    Beautiful 5 bedroom, 3 full bath home, in highly sought after Tuscawilla golf community, on a large lot with desirable side entry 2-car garage. The home boast neutral paint and flooring décor, abundant natural light with views of the lake. The primary bedroom sits on one side of the house and has an adjoining room that can be used as an office or gym area. The remodeled kitchen is a chef’s dream,

    Tommy Fransen, Jr EXIT REAL ESTATE RESULTS

    1209 Deer Run Dr, Winter Springs, FL 32708
  • /6

    $1,395 Per Month

    • 2 Beds
    • 1.5 Baths
    • 930 Sq Ft
    • Townhouse for Rent

    Unlisted Address

    "2 Weeks Free"Spacious 2-Bedroom, 1.5-Bath Townhome in a Prime Location! Conveniently located near major highways, shopping, dining, and schools, this well-maintained townhome offers both comfort and convenience. The home features two spacious bedrooms, 1.5 bathrooms, a bright and open great room, a functional kitchen, a private patio perfect for relaxing, and a dedicated parking space. Enjoy

    maria vega THE EXPERTS TEAM REALTY INC

    Unlisted Address
  • /37

    $385,000

    Sold Sep 04, 2026

    787 Evert Ct, Winter Springs, FL 32708

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1984

    Last Sold Summary

    • 3% Above List Price
    • $247/SF
    • 7 Days On Market

    Current Estimated Value $389,714

    Last Listing Agent Nick Gustafson FLORIDA REALTY INVESTMENTS

    787 Evert Ct, Winter Springs, FL 32708
    • /2

      Est $437,077

      Not Listed For Sale

      1299 Tarflower Dr, Winter Springs, FL 32708

      • 4 Beds
      • 2.5 Baths
      • 1,678 Sq Ft
      • Built 2024
      1299 Tarflower Dr, Winter Springs, FL 32708

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES

  • /25

    $850,000

    Under Contract
    • 8 Beds
    • 8 Baths
    • 3,636 Sq Ft

    46 N Fairfax Ave, Winter Springs, FL 32708

    Under contract-accepting backup offers. Fully leased multi family investment property in the heart of Winter Springs. This 2 story gem has 4 units, each are the same with 2 bedrooms and 1.5 bathrooms with washer and dryer inside units. All appliances were updated, units have been well maintained and updated in the last 12+ months. Ample parking for each unit, tenant pays all utilities and all

    Brandon McCarter RE/MAX PRIME PROPERTIES

    46 N Fairfax Ave, Winter Springs, FL 32708
  • /20

    $1,900 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Townhouse for Rent

    477 Green Spring Cir, Winter Springs, FL 32708

    Available NOW! Welcome home to this updated 3-bedroom, 1.5-bath end-unit townhome in Mount Greenwood of Winter Springs. Freshly renovated and move-in ready, this home features all-new interior paint, updated light fixtures, brand-new modern vanities with LED mirrors in both bathrooms, new carpet on the stairs, wood-look tile flooring throughout the main living areas, and laminate flooring

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

    $350,000

    Sold May 29, 2026

    1275 Marley Ln, Winter Springs, FL 32708

    • 3 Beds
    • 2.5 Baths
    • 1,425 Sq Ft
    • Built 2015

    Last Sold Summary

    • 4% Below List Price
    • $246/SF
    • 51 Days On Market

    Current Estimated Value $350,565

    Last Listing Agent David Weiss COLDWELL BANKER REALTY

    1275 Marley Ln, Winter Springs, FL 32708
    • /2

      Est $233,230

      Not Listed For Sale

      613 Casa Park Court B Ct N Unit B, Winter Springs, FL 32708

      • 2 Beds
      • 2.5 Baths
      • 1,156 Sq Ft
      • Built 1984
      613 Casa Park Court B Ct N Unit B, Winter Springs, FL 32708

      Last Sold Summary

      • 32 Days On Market

      Last Listing Agent Anthony Ballerino COLDWELL BANKER REALTY

  • /31

    $1,150,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 3,876 Sq Ft

    738 Bear Creek Cir, Winter Springs, FL 32708

    Under contract-accepting backup offers. Virtually Staged. This remarkable, tenderly loved estate home is situated on over an acre in Tuscawilla’s most coveted neighborhood, Bear Creek Estates. Homes in this gated upscale neighborhood are rarely available to purchase! With nearly 4000 square feet of thoughtfully designed living space, the home combines dramatic architecture, generous proportions,

    Colleen Kahl RE/MAX TOWN & COUNTRY REALTY

    738 Bear Creek Cir, Winter Springs, FL 32708
  • /24

    $1,700 Per Month

    • 3 Beds
    • 2 Baths
    • 1,187 Sq Ft
    • Condo for Rent

    280 Moree Loop Unit 2, Winter Springs, FL 32708

    This charming two-bedroom, two-bath first-floor condo in Winter Springs has been beautifully remodeled with an open floor plan. The unit features tile and laminate flooring, wood cabinets, and stone countertops, subway backsplash, complemented by double sliding glass doors that lead from the living area to a screened porch overlooking the community’s lush, tree-lined common spaces. With new

    Joyce Gary PAINE-ANDERSON PROPERTIES, INC

    280 Moree Loop Unit 2, Winter Springs, FL 32708
  • /2

    $470,000

    Sold Apr 29, 2026

    1029 Antelope Trail, Winter Springs, FL 32708

    • 4 Beds
    • 2 Baths
    • 1,939 Sq Ft
    • Built 1977

    Last Sold Summary

    • 8% Below List Price
    • $242/SF
    • 138 Days On Market

    Current Estimated Value $471,591

    Last Listing Agent Rick Cole KELLER WILLIAMS WINTER PARK

    1029 Antelope Trail, Winter Springs, FL 32708
    • /2

      Est $363,793

      Not Listed For Sale

      1255 Marley Ln, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,435 Sq Ft
      • Built 2015
      1255 Marley Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 41 Days On Market

      Last Listing Agent Eddie Cooper MAINFRAME REAL ESTATE

  • /73

    $2,299,000

    $100K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 3,657 Sq Ft

    4910 E Lake Dr, Winter Springs, FL 32708

    A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private

    Kris Kennedy COMPASS FLORIDA LLC

    4910 E Lake Dr, Winter Springs, FL 32708
  • /86

    $5,500 Per Month

    • 6 Beds
    • 4.5 Baths
    • 4,403 Sq Ft
    • House for Rent

    420 Park Lake Dr, Winter Springs, FL 32708

    Welcome to your dream rental home in the desirable Winter Springs area!, You can enjoy the perfect combination of comfort, space, privacy, and convenience in this beautiful home located in a gated community with a pool.This amazing property offers not only a spacious main house but also a separate apartment located above the garage, creating endless possibilities perfect for a private

    420 Park Lake Dr, Winter Springs, FL 32708
  • /2

    $300,000

    Sold Oct 28, 2025

    207 Bitterwood St, Winter Springs, FL 32708

    • 3 Beds
    • 2 Baths
    • 1,318 Sq Ft
    • Built 1973

    Last Sold Summary

    • 17% Below List Price
    • $228/SF
    • 66 Days On Market

    Current Estimated Value $322,491

    Last Listing Agent Milton Figueroa FIGLOFT INC

    207 Bitterwood St, Winter Springs, FL 32708
    • /2

      Est $405,225

      Not Listed For Sale

      1011 Cedar Bay Ln, Winter Springs, FL 32708

      • 4 Beds
      • 3.5 Baths
      • 1,938 Sq Ft
      • Built 2016
      1011 Cedar Bay Ln, Winter Springs, FL 32708

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

  • /22

    $385,000

    $45K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,450 Sq Ft

    724 Barrington Cir, Winter Springs, FL 32708

    Under contract-accepting backup offers. Very well maintained home in Tuscawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners. Replace all appliance, the roof was replaced last year, house been re-plombe, have access to the neighborhood clubhouse and Community pool, HOA takes care

    Ramon Ortiz Cruz DIAMOND 2000 REALTY, INC

    724 Barrington Cir, Winter Springs, FL 32708
  • /11

    $1,900 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,275 Sq Ft
    • Townhouse for Rent

    164 Constitution Way, Winter Springs, FL 32708

    Immaculate 2 bed, 2 1/2 bath townhome with double master plan and a 1 car garage located in gated Heritage Park in Winter Springs. Unit features New Paint, New Vanity downstairs, New Light Fixtures, Tile in the wet areas. Lux Vinyl downstairs, New Microwave, an expansive Kitchen with large pantry, and and open floorplan. Schedule your viewing today, you will be impressed!

    Christy Fauquher PERFECT FIT PROPERTIES

    164 Constitution Way, Winter Springs, FL 32708
  • /2

    $255,000

    Sold May 21, 2026

    4467 Brook Hollow Cir, Winter Springs, FL 32708

    • 3 Beds
    • 2.5 Baths
    • 1,344 Sq Ft
    • Built 1991

    Last Sold Summary

    • 15% Below List Price
    • $190/SF
    • 72 Days On Market

    Current Estimated Value $255,819

    Last Listing Agent Miriam Hernandez Gonzalez LA ROSA REALTY ORLANDO LLC

    4467 Brook Hollow Cir, Winter Springs, FL 32708
    • /2

      Est $400,857

      Not Listed For Sale

      1287 Tarflower Dr, Winter Springs, FL 32708

      • 3 Beds
      • 2.5 Baths
      • 1,476 Sq Ft
      • Built 2024
      1287 Tarflower Dr, Winter Springs, FL 32708

      Last Sold Summary

      • 71 Days On Market

      Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES

  • /2

    $17,500

    • 2 Beds
    • 1 Bath

    172 Costa Cir, Winter Springs, FL 32708

    Coming Soon! This home at Hacienda Village is currently being refreshed and prepared for its next owner. Additional home details and photos will soon be available. Check back periodically for a full look inside. In the meantime, get to know Hacienda Village and the lifestyle that comes with calling it home. Just outside your door, the community experience continues. Enjoy an active lifestyle at

    Todd Vagts Hacienda Village

    172 Costa Cir, Winter Springs, FL 32708
  • /25

    $2,350 Per Month

    • 3 Beds
    • 2 Baths
    • 1,947 Sq Ft
    • House for Rent

    834 Seneca Meadows Rd, Winter Springs, FL 32708

    Winter Springs Rental Home located in the Gated Community of ParkStone. This award-winning community offers a Community Pool, Volleyball, Tennis Courts, Walking Trails, and a Fishing Dock. Minutes from the 417, Winter Springs Town Center and Central Winds Park. This 3 Bedroom, 2 Bath home features a Formal Living room and Dining room, Kitchen/Family Combo, Vaulted Ceilings, 2 Car Garage,

    834 Seneca Meadows Rd, Winter Springs, FL 32708
  • /2

    $649,000

    Sold Apr 10, 2026

    102 Avery Lake Dr, Winter Springs, FL 32708

    • 4 Beds
    • 3 Baths
    • 2,713 Sq Ft
    • Built 2002

    Last Sold Summary

    • $239/SF
    • 2 Days On Market

    Current Estimated Value $645,507

    Last Listing Agent Bobby Keen KEEN REALTY GROUP, INC.

    102 Avery Lake Dr, Winter Springs, FL 32708
    • /2

      Est $1,417,543

      Not Listed For Sale

      1035 Northern Way Unit 171, Winter Springs, FL 32708

      • 7 Beds
      • 6 Baths
      • 7,239 Sq Ft
      • Built 1983
      1035 Northern Way Unit 171, Winter Springs, FL 32708

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Scott Minor CHARLES RUTENBERG REALTY ORLANDO

Showing Results 161 - 200, Page 5 of 18

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