Winter Springs, FL Homes

• 

  

  

  /31

  $299,900

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,726 Sq Ft

  600 Northern Way Unit 1804, Winter Springs, FL 32708

  Welcome to Tuscany Place in the heart of sought after Tuscawilla! This well-maintained townhouse style condo offers a spacious floor plan with abundant natural light, generous living and dining areas, and a well-appointed kitchen perfect for everyday living and entertaining. Enjoy spacious bedrooms, ample storage and an outdoor patio ideal for relaxing after a long day. Located in a gated

  Sandra Moshir BHHS FLORIDA REALTY

  600 Northern Way Unit 1804, Winter Springs, FL 32708
• 

  

  /2

  $750,000

  Sold Apr 02, 2026

  1542 Wescott Loop, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 3,242 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $231/SF
  • 129 Days On Market

  Current Estimated Value $754,167

  Last Listing Agent Lalta Sanichar LIBERTY HOME SALES INC

  1542 Wescott Loop, Winter Springs, FL 32708
• 

  

  

  /33

  Est $455,827

  Not Listed For Sale

  929 Old White Way, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 1998

  929 Old White Way, Winter Springs, FL 32708

  Last Sold Summary

  • 0 Days On Market
• 

  

  

  /26

  $218,000

  Open Sun 10AM - 12PM $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  497 Club Dr, Winter Springs, FL 32708

  Beautiful 2/2 townhome in highly desirable Cypress Club community in The Highlands of Winter Springs, located in close proximity to SR 434! Light and neutral colors throughout, freshly painted approximately two years ago! *Vaulted ceiling in the spacious family/great room with a wood burning fireplace! Tile flooring in the living areas and laminate in the bedrooms. Split bedroom floorplan, with

  Edyta Olejnik WATSON REALTY CORP

  497 Club Dr, Winter Springs, FL 32708
• 

  

  /2

  $430,000

  Sold Jan 05, 2026

  821 Sheoah Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 2,185 Sq Ft
  • Built 1978

  Last Sold Summary

  • 18% Below List Price
  • $197/SF
  • 113 Days On Market

  Current Estimated Value $429,405

  Last Listing Agent Sean Calegan CFRP REALTY LLC

  821 Sheoah Cir, Winter Springs, FL 32708
• 

  

  /43

  Est $426,488

  Not Listed For Sale

  1054 Chokecherry Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,979 Sq Ft
  • Built 1986

  1054 Chokecherry Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 14 Days On Market
• 

  

  /85

  $589,900

  Pending

  • 6 Beds
  • 4 Baths
  • 2,247 Sq Ft

  214 Perth Ct Unit A, Winter Springs, FL 32708

  Under contract-accepting backup offers. Exceptional investment opportunity in the highly sought-after Highlands community of Winter Springs! This rare and one-of-a-kind duplex features two spacious 3-bedroom, 2-bath units, each offering a 2-car garage, fenced backyard, soaring high ceilings, and thoughtfully designed floor plans that create an open and inviting feel.Both sides are

  Jeffrey Osborn, Jr EXP REALTY LLC

  214 Perth Ct Unit A, Winter Springs, FL 32708
• 

  /2

  $425,000

  Sold Nov 03, 2025

  861 Big Buck Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,831 Sq Ft
  • Built 1984

  Last Sold Summary

  • 3% Below List Price
  • $232/SF
  • 46 Days On Market

  Current Estimated Value $427,545

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  861 Big Buck Cir, Winter Springs, FL 32708
• 

  /2

  Est $396,610

  Not Listed For Sale

  628 Sailfish Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1978

  628 Sailfish Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 7 Days On Market
• 

  

  /51

  $669,900

  Pending

  • 5 Beds
  • 3 Baths
  • 2,837 Sq Ft

  1208 Cheetah Trail, Winter Springs, FL 32708

  Under contract-accepting backup offers. Come fall in love with this versatile 5 bedroom 3 bath home on over 1/2 acre beautifully landscaped property with lush trees and gardens....your very own private oasis in the heart of Tuscawilla! With two large master suites, two spacious guest bedrooms plus a fifth bedroom/ home office with exterior door, the opportunities are endless! In addition, most of

  Colleen Kahl RE/MAX TOWN & COUNTRY REALTY

  1208 Cheetah Trail, Winter Springs, FL 32708
• 

  /2

  $437,000

  Sold Dec 19, 2025

  1010 Chokecherry Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,984 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 34 Days On Market

  Current Estimated Value $445,242

  Last Listing Agent Suzanne Crudo COLDWELL BANKER REALTY

  1010 Chokecherry Dr, Winter Springs, FL 32708
• 

  

  /25

  Est $448,854

  Not Listed For Sale

  999 El Lago Terrace, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,846 Sq Ft
  • Built 1989

  999 El Lago Terrace, Winter Springs, FL 32708

  Last Sold Summary

  • 53 Days On Market
• 

  

  /32

  $219,500

  $10K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,224 Sq Ft

  502 Club Dr, Winter Springs, FL 32708

  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

  502 Club Dr, Winter Springs, FL 32708
• 

  /2

  $360,000

  Sold Dec 16, 2025

  3876 White Birch Run, Winter Springs, FL 32708

  • 5 Beds
  • 3.5 Baths
  • 1,966 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Below List Price
  • $183/SF
  • 17 Days On Market

  Current Estimated Value $363,022

  Last Listing Agent Elaine Masood HEARTFELT REALTY HOMETEAM

  3876 White Birch Run, Winter Springs, FL 32708
• 

  

  /40

  Est $454,674

  Not Listed For Sale

  3955 Biscayne Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,092 Sq Ft
  • Built 1988

  3955 Biscayne Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 5 Days On Market
• 

  /2

  $380,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  665 Murphy Rd, Winter Springs, FL 32708

  This well-maintained 3-bedroom, 2-bath Winter Springs home delivers the Florida lifestyle you've been looking for — and with no HOA fees. Inside, you will find tile flooring throughout the living spaces and carpet in the bedrooms. The primary bedroom features vaulted ceilings with plenty of room for a king size bed. The bathrooms have been renovated, with a walk-in shower in the primary bath. The

  Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  665 Murphy Rd, Winter Springs, FL 32708
• 

  /2

  $740,000

  Sold Apr 22, 2026

  1777 Seneca Blvd, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $316/SF
  • 50 Days On Market

  Current Estimated Value $737,034

  Last Listing Agent Chandler Williams EXIT REALTY PREMIER LEGACY

  1777 Seneca Blvd, Winter Springs, FL 32708
• 

  /2

  Est $445,989

  Not Listed For Sale

  1022 E Pebble Beach Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft
  • Built 1994

  1022 E Pebble Beach Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 12 Days On Market
• 

  

  /31

  $34,500

  • 2 Beds
  • 2 Baths
  • 1,344 Sq Ft

  308 Casa Grande Ct, Winter Springs, FL 32708

  2 bEDROOM 2 BATH- A LOT OF THE MAIN WORK DONE! ALL NEW DUCTING,PLUMBING IS GOOD, ELECTRIC GOOD, CARPETING PULLED UP, SUB FLOORING DONE. KITCHEN SOME CABINETS HAVE PULL OUTS. NEW ALL YOU HAVE TO DO IS PUT YOUR OWN PERSONAL TOUCH. THIS IS ONE OF THE MOST POPULAR FLOOR PLANS. YHIS DOES HAVE A SPRINKLER SYSTEM(AS IS) HACIENDA VILLAGE IS FULL OF AMENITIES-2 POOLS, PICKLE Ball. centrally located-base

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  308 Casa Grande Ct, Winter Springs, FL 32708
• 

  /2

  $600,000

  Sold Nov 12, 2025

  604 Timberwilde Ct, Winter Springs, FL 32708

  • 5 Beds
  • 3 Baths
  • 2,899 Sq Ft
  • Built 1995

  Last Sold Summary

  • 8% Below List Price
  • $207/SF
  • 116 Days On Market

  Current Estimated Value $615,167

  Last Listing Agent Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

  604 Timberwilde Ct, Winter Springs, FL 32708
• 

  

  /26

  Est $396,500

  Not Listed For Sale

  523 Shane Cir, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,908 Sq Ft
  • Built 1979

  523 Shane Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 9 Days On Market
• 

  

  /26

  $404,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  445 Gee Hammock Ln, Winter Springs, FL 32708

  Under contract-accepting backup offers. WELCOME HOME!! Located in the highly desirable Jesups Landing community, this impeccably maintained end-unit townhome features 3 bedrooms, 2.5 bathrooms, a versatile loft, and 1,682 square feet of thoughtfully designed living space. Its premium end-unit location offers exceptional natural light through 15 windows, creating a bright and inviting

  Austin Lanpher MAROON REALTY GROUP LLC

  445 Gee Hammock Ln, Winter Springs, FL 32708
• 

  

  /23

  $339,900

  Sold Dec 22, 2025

  409 Murphy Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Built 1977

  Last Sold Summary

  • 7% Below List Price
  • $291/SF
  • 140 Days On Market

  Current Estimated Value $337,277

  Last Listing Agent Edwin Reyes Tower Team Realty, LLC

  409 Murphy Rd, Winter Springs, FL 32708
• 

  

  /37

  Est $613,805

  Not Listed For Sale

  1192 Falling Pine Ct, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,568 Sq Ft
  • Built 1998

  1192 Falling Pine Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 12 Days On Market
• 

  

  /82

  $3,998,000

  $2M PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 8,685 Sq Ft

  1112 Orange Ave, Winter Springs, FL 32708

  Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its

  Brian Hyser THE AGENCY FL

  1112 Orange Ave, Winter Springs, FL 32708
• 

  /2

  $340,000

  Sold Sep 26, 2025

  269 Buttonwood Ave, Winter Springs, FL 32708

  • 3 Beds
  • 3 Baths
  • 1,506 Sq Ft
  • Built 1972

  Last Sold Summary

  • $226/SF
  • 5 Days On Market

  Current Estimated Value $347,872

  Last Listing Agent Maria Peralta CHARLES RUTENBERG REALTY ORLANDO

  269 Buttonwood Ave, Winter Springs, FL 32708
• 

  

  /31

  Est $676,521

  Not Listed For Sale

  674 Vistawilla Dr, Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • Built 1987

  674 Vistawilla Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 9 Days On Market
• 

  

  /15

  $419,900

  $5K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,658 Sq Ft

  820 Wakulla Ln, Winter Springs, FL 32708

  Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath home offers bright, comfortable living with fresh interior paint, new carpet, and new light fixtures throughout. The open main living area flows easily into the kitchen, where new quartz countertops, a new range, microwave, and dishwasher add style and everyday functionality. A new roof provides valuable peace of mind, while the

  Robert Jones OFFERPAD BROKERAGE FL, LLC

  820 Wakulla Ln, Winter Springs, FL 32708
• 

  /2

  $585,000

  Sold Oct 14, 2025

  121 Partridge Cir, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,002 Sq Ft
  • Built 1977

  Last Sold Summary

  • 7% Below List Price
  • $292/SF
  • 9 Days On Market

  Current Estimated Value $575,837

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  121 Partridge Cir, Winter Springs, FL 32708
• 

  

  /38

  Est $1,065,030

  Not Listed For Sale

  150 E Bahama Rd, Winter Springs, FL 32708

  • 3 Beds
  • 3.5 Baths
  • 2,956 Sq Ft
  • Built 2018

  150 E Bahama Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 3 Days On Market
• 

  

  /34

  $415,000

  Coming Soon

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  1437 Ponce de Leon Blvd, Winter Springs, FL 32708

  Welcome to this beautifully updated 4-bedroom pool home located in sought- after Winter Springs. Featuring an open yet cozy floor plan, this home offers the perfect blend of comfort, functionality, and style. The spacious kitchen provides ample cabinet storage and overlooks the main living and dining areas, creating an inviting space for everyday living and entertaining. Updated finishes

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  1437 Ponce de Leon Blvd, Winter Springs, FL 32708
• 

  /2

  $520,000

  Sold Feb 20, 2026

  337 Ringwood Cir, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,931 Sq Ft
  • Built 1983

  Last Sold Summary

  • 10% Below List Price
  • $269/SF
  • 20 Days On Market

  Current Estimated Value $531,087

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  337 Ringwood Cir, Winter Springs, FL 32708
• 

  

  /30

  Est $310,991

  Not Listed For Sale

  711 Lakeside Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,426 Sq Ft
  • Built 1979

  711 Lakeside Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 3 Days On Market
• 

  

  /29

  $290,000

  $20K PRICE DROP

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

  600 Northern Way Unit 906, Winter Springs, FL 32708

  Turnkey townhouse in Tuscany Place is totally move-in ready. The townhouse style is limited to only a few homes in the new phase of this wonderful, gated community. Built in 2016 and much newer than many competing condos/townhomes. All 3 bedrooms have their own private full bathrooms. The first-floor bedroom with en-suite bath is great for guests, home office, or multigenerational living. Brand

  John Vincent JR REALTY GROUP LLC

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

  /2

  $718,900

  Sold Oct 15, 2025

  422 Dancing Water Dr, Winter Springs, FL 32708

  • 5 Beds
  • 3.5 Baths
  • 3,014 Sq Ft
  • Built 2019

  Last Sold Summary

  • 1% Below List Price
  • $239/SF
  • 10 Days On Market

  Current Estimated Value $713,848

  Last Listing Agent Cindy Sosa-Castro COLDWELL BANKER REALTY

  422 Dancing Water Dr, Winter Springs, FL 32708
• 

  

  /61

  Est $836,570

  Not Listed For Sale

  1005 Nancy Cir, Winter Springs, FL 32708

  • 4 Beds
  • 3.5 Baths
  • 3,361 Sq Ft
  • Built 1990

  1005 Nancy Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 2 Days On Market
• 

  

  /28

  $570,000

  Pending

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft

  1107 Winter Springs Blvd, Winter Springs, FL 32708

  Under contract-accepting backup offers. Welcome to this beautifully maintained, freshly painted 4-bedroom, 3-bathroom home situated on a picturesque wooded lot in the heart of Tuscawilla, one of Winter Springs' most sought-after communities. Built with quality craftsmanship and designed for comfortable living, this spacious residence features brand-new engineered wood flooring, generously sized

  Laura Leigh Wood RE/MAX TOWN & COUNTRY REALTY

  1107 Winter Springs Blvd, Winter Springs, FL 32708
• 

  /2

  $380,000

  Sold Aug 05, 2025

  535 Crimson Ln, Winter Springs, FL 32708

  • 3 Beds
  • 3.5 Baths
  • 1,872 Sq Ft
  • Built 2007

  Last Sold Summary

  • 5% Below List Price
  • $203/SF
  • 259 Days On Market

  Current Estimated Value $387,686

  Last Listing Agent Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

  535 Crimson Ln, Winter Springs, FL 32708
• 

  /2

  Est $318,703

  Not Listed For Sale

  762 S Edgemon Ave, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1979

  762 S Edgemon Ave, Winter Springs, FL 32708

  Last Sold Summary

  • 106 Days On Market
• 

  

  /25

  $170,000

  • 2 Beds
  • 1.5 Baths
  • 1,080 Sq Ft

  70 Moree Loop Unit 63, Winter Springs, FL 32708

  Two story condominium in Winter Springs. The two bedroom, 1 and 1/2 bath unit is located in the Highlands Community. Tile and laminate flooring, fresh paint, spacious layout, kitchen has a pass thru window to the dining area. Combo living/dining with sliding glass doors which offers natural sunlight and opens to an exterior patio. Two bedrooms, master full bath and laundry utility on the second

  Joyce Gary PAINE-ANDERSON PROPERTIES, INC

  70 Moree Loop Unit 63, Winter Springs, FL 32708

Showing Results 641 - 680, Page 17 of 18