Winter Springs, FL Homes

• 

  

  

  /55

  $709,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,429 Sq Ft

  650 Cayuga Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Price Improvement - Sellers Motivated! Welcome home to this stunning 4-bedroom, 3-full bath pool home located in the highly sought-after Chelsea Woods community of Tuscawilla! Situated on an oversized corner lot, this property offers a fully fenced backyard framed by majestic shade trees, providing exceptional

  

  Jamie Ampel

  ALL SELLERS & BUYERS REALTY INC

  (321) 341-2960

  650 Cayuga Dr, Winter Springs, FL 32708
• Selling your home? Sell it faster and for more with a Homes.com Boost.

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• 

  

  

  /20

  $2,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,558 Sq Ft
  • House for Rent

  1154 W Winged Foot Cir, Winter Springs, FL 32708

  3 Bed 2 Bath house rental opportunity in the charming district of Winter Springs, Florida. This spacious property offers comfortable living with convenient access to nearby shopping and recreational options, including Trotwood Park, perfect for outdoor enthusiasts of all ages.Don’t miss your chance to live in this welcoming community—schedule a viewing today and take the first step toward

  (321) 496-7603

  1154 W Winged Foot Cir, Winter Springs, FL 32708
• 

  

  /2

  $845,000 Sold Jul 02, 2025

  1525 Eagle Nest Cir, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,853 Sq Ft
  • Built 1993

  Last Sold Summary

  • $296/SF
  • 1 Day On Market

  Current Estimated Value $838,617

  Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY

  1525 Eagle Nest Cir, Winter Springs, FL 32708
• 

  

  /2

  Est $411,632 Not Listed For Sale

  509 Shane Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,802 Sq Ft
  • Built 1979

  509 Shane Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $230/SF
  • 10 Days On Market

  • Last Sold Price $415,000
  • Apr 30, 2025

  Last Listing Agent Jane Fochler ONE LUXURY INTERNATIONAL LLC
• 

  

  

  /62

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  440 Buckskin Ct, Winter Springs, FL 32708

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** PAID-OFF 15kW SOLAR + 10Gb whole-home Ethernet — corner lot in the heart of Winter Springs! This 4BR/2.5BA Deer Run home blends colonial charm and fresh curb appeal with smart upgrades new construction can't touch.

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 329-3872

  440 Buckskin Ct, Winter Springs, FL 32708
• 

  

  /20

  $2,560 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 $2704.90. That covers your base rent, $2560.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  (321) 467-7687

  1172 La Mesa Ave, Winter Springs, FL 32708
• 

  /2

  $622,000 Sold Oct 15, 2025

  659 Cayuga Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,492 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $250/SF
  • 4 Days On Market

  Current Estimated Value $624,841

  Last Listing Agent Laura Leigh Wood RE/MAX TOWN & COUNTRY REALTY

  659 Cayuga Dr, Winter Springs, FL 32708
• 

  /2

  Est $596,565 Not Listed For Sale

  81 Sable Ct, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,153 Sq Ft
  • Built 1977

  81 Sable Ct, Winter Springs, FL 32708

  Last Sold Summary

  • $276/SF
  • 3 Days On Market

  • Last Sold Price $595,000
  • Apr 23, 2025

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
• 

  

  /33

  $317,700

  • 4 Beds
  • 2.5 Baths
  • 1,878 Sq Ft

  702 Glasgow Ct, Winter Springs, FL 32708

  Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends comfort, functionality, and

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  (321) 638-5391

  702 Glasgow Ct, Winter Springs, FL 32708
• 

  

  /16

  $2,155 Per Month

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

  109 N Alderwood St, 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.

  (321) 320-6605

  109 N Alderwood St, Winter Springs, FL 32708
• 

  

  /12

  $433,244 Sold Dec 30, 2025

  1284 Crab Apple Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $258/SF
  • 208 Days On Market

  Current Estimated Value $413,785

  Mattamy Homes Hickory Grove

  1284 Crab Apple Ln, Winter Springs, FL 32708
• 

  /2

  Est $467,076 Not Listed For Sale

  134 Woodleaf Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,654 Sq Ft
  • Built 1995

  134 Woodleaf Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $284/SF
  • 9 Days On Market

  • Last Sold Price $470,000
  • May 01, 2025

  Last Listing Agent Laura Leigh Wood RE/MAX
• 

  

  /24

  $470,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,579 Sq Ft

  562 Pleasant Grove Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. **Seller willing to provide buyer with a temporary rate buy down of 5-6% interest rate!** Step into this beautifully updated home in Tusca Oaks where modern comfort meets everyday convenience. The open-concept layout features soaring vaulted ceilings, skylights, and plenty of natural light that flows seamlessly through the living, dining, and kitchen areas.

  

  Evelyn Tejada

  REGENCY REAL ESTATE LLC

  (321) 342-1010

  562 Pleasant Grove Dr, Winter Springs, FL 32708
• 

  

  /17

  $2,179 Per Month

  • 3 Beds
  • 2 Baths
  • 1,255 Sq Ft
  • House for Rent

  1239 La Mesa Ave, Winter Springs, FL 32708

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,255 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental

  (321) 522-4359

  1239 La Mesa Ave, 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 $606,087

  Last Listing Agent Valentina Vakhova LA ROSA REALTY KISSIMMEE

  338 Wooded Vine Dr, Winter Springs, FL 32708
• 

  /2

  Est $410,587 Not Listed For Sale

  1404 Barcelona Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • Built 1979

  1404 Barcelona Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $269/SF
  • 3 Days On Market

  • Last Sold Price $415,000
  • Apr 18, 2025

  Last Listing Agent Michelle Richardson KELLER WILLIAMS CLASSIC
• 

  

  /38

  $399,999 Pending

  • 3 Beds
  • 2 Baths
  • 1,762 Sq Ft

  340 Inglenook Cir Unit 1, Winter Springs, FL 32708

  Buyer changed their mind! New Price!!! Welcome to 340 Inglenook Cir, a beautifully maintained pool home in the heart of Winter Springs offering the perfect blend of comfort, privacy, and Florida lifestyle living. This 3-bedroom, 2-bath residence features a light-filled, open layout designed for both everyday living and effortless entertaining. At the heart of the home, spacious living areas flow

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 399-2598

  340 Inglenook Cir Unit 1, Winter Springs, FL 32708
• 

  

  /16

  $2,420 Per Month

  • 4 Beds
  • 3 Baths
  • 1,462 Sq Ft
  • House for Rent

  644 Cypress Ln, 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.

  (321) 465-7218

  644 Cypress Ln, 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 $172,297

  Last Listing Agent Richard Sherrod Jr EXP REALTY LLC

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

  /2

  Est $725,002 Not Listed For Sale

  1510 Wescott Loop, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,738 Sq Ft
  • Built 2004

  1510 Wescott Loop, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $267/SF
  • 3 Days On Market

  • Last Sold Price $730,000
  • Apr 25, 2025

  Last Listing Agent Angela Rodriguez DREAM FINDERS REALTY GROUP CORP
• 

  

  /51

  $769,000

  • 5 Beds
  • 4 Baths
  • 3,205 Sq Ft

  126 Seville Chase Dr, Winter Springs, FL 32708

  **Price Improvement** and a $10,000.00 SELLER CONCESSION towards buyer's closing costs ** Welcome to Seville Chase, a quiet gated neighborhood in Winter Springs with tree-lined streets and access to great schools like South Seminole Middle and Winter Springs High Schools.This 5-bedroom, 4-bath home sits on a large 0.41-acre lot and offers over 3,000 square feet of living space, mostly on one

  Robert Johnson KELLER WILLIAMS ADVANTAGE REALTY

  126 Seville Chase Dr, Winter Springs, FL 32708
• 

  

  /20

  $2,249 Per Month

  • 3 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • House for Rent

  120 N Alderwood St, Winter Springs, FL 32708

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,037 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental

  (321) 430-1842

  120 N Alderwood St, 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 $250,232

  Last Listing Agent Sharyon Neilen COLDWELL BANKER REALTY

  565 Green Spring Cir, Winter Springs, FL 32708
• 

  /2

  Est $344,207 Not Listed For Sale

  1395 San Luis Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft
  • Built 1982

  1395 San Luis Ct, Winter Springs, FL 32708

  Last Sold Summary

  • $267/SF
  • 207 Days On Market

  • Last Sold Price $345,000
  • Apr 29, 2025

  Last Listing Agent Ericburt Rodriguez COLLECTIVE GROUP REALTY, CORP
• 

  

  /58

  $485,000 Pending

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

  1379 Tarflower Dr, Winter Springs, FL 32708

  Under contract-accepting backup offers. RARE END UNIT MOVE IN READY townhome with the PRIMARY BEDROOM DOWNSTAIRS in the heart of the Winter Springs Town Center! This beautifully maintained 3-bedroom, 2.5-bath home features a screened porch, custom California Closets in the primary suite, a rear-entry 2-car garage, and a bright open floor plan just steps from the Cross Seminole Trail, community

  Melanie Miller PREMIUM PROPERTIES R.E SERVICE

  1379 Tarflower Dr, Winter Springs, FL 32708
• 

  

  /17

  $1,995 Per Month

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • House for Rent

  404 Edwin St, 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 $2139.90. That covers your base rent, $1995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  (689) 264-6526

  404 Edwin St, 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 $329,539

  Last Listing Agent Dean Erlandson LIVE FLORIDA NOW LLC

  5 Gumtree Ct, Winter Springs, FL 32708
• 

  /2

  Est $252,015 Not Listed For Sale

  464 Green Spring Cir, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,363 Sq Ft
  • Built 1987

  464 Green Spring Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 4% Above List Price
  • $178/SF
  • 2 Days On Market

  • Last Sold Price $242,500
  • Apr 23, 2025

  Last Listing Agent Lenny Migliaccio RE/MAX
• 

  

  /68

  $2,900,000 New Construction

  • 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
• 

  

  /19

  $2,435 Per Month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  337 Riunite Cir, 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.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  (321) 495-6125

  337 Riunite Cir, 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 $355,525

  Last Listing Agent Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

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

  /2

  Est $348,556 Not Listed For Sale

  351 Lansbrook Ln, Winter Springs, FL 32708

  • 2 Beds
  • 2 Baths
  • 1,129 Sq Ft
  • Built 2007

  351 Lansbrook Ln, Winter Springs, FL 32708

  Last Sold Summary

  • $310/SF
  • 5 Days On Market

  • Last Sold Price $350,000
  • May 02, 2025

  Last Listing Agent Tania Crandall SHORESTONE PROPERTY GROUP
• 

  

  /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
• 

  

  /16

  $3,035 Per Month

  • 4 Beds
  • 2 Baths
  • 2,078 Sq Ft
  • House for Rent

  1400 Ponce de Leon Blvd, 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

  (689) 399-3532

  1400 Ponce de Leon Blvd, 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 $939,926

  Last Listing Agent Walter Givens LPT REALTY, LLC

  704 Forest View Ct, Winter Springs, FL 32708
• 

  /2

  Est $280,941 Not Listed For Sale

  600 Northern Way Unit 1406, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,377 Sq Ft
  • Built 1997

  600 Northern Way Unit 1406, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Below List Price
  • $207/SF
  • 79 Days On Market

  • Last Sold Price $285,000
  • May 05, 2025

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP
• 

  

  /54

  $519,000

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

  934 Torrey Pine Dr, Winter Springs, FL 32708

  One or more photo(s) has been 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

  James Clark CENTURY 21 ALTON CLARK

  934 Torrey Pine Dr, Winter Springs, FL 32708
• 

  

  /20

  $2,089 Per Month

  • 3 Beds
  • 2 Baths
  • 1,161 Sq Ft
  • House for Rent

  107 Sundance Ct, Winter Springs, FL 32708

  Experience the perfect blend of modern style and functional living in this impressive 1,161 sq ft residence, designed for a seamless single-story layout. The inviting interior features a bright, open-concept layout with stylish wood-look flooring and soaring vaulted ceilings, where the spacious living area flows directly into a contemporary kitchen fully equipped with a complete suite of

  (321) 419-1566

  107 Sundance Ct, 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 $198,430

  Last Listing Agent Marielle Parra COMPASS FLORIDA LLC

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

  /2

  Est $437,114 Not Listed For Sale

  621 Daron Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft
  • Built 1979

  621 Daron Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 1% Above List Price
  • $236/SF
  • 17 Days On Market

  • Last Sold Price $432,600
  • May 07, 2025

  Last Listing Agent Sheryl Webster VENTURE HOME REALTY

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