Winter Springs, FL Homes for Sale with Pool

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  /47

  $280,000

  • 3 Beds
  • 2.5 Baths
  • 1,306 Sq Ft

  3825 Black Spruce Ln, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. This beautifully updated 2 large bedroom and 2 1/2 bath townhouse is move-in ready! New carpet and luxury vinyl floor coverings, as well as brand new appliances: dishwasher, range, hood, microwave just installed in 2026. Newer AC and refrigerator ( 2 yrs.) complete this well-maintained townhouse overlooking the back patio and pond. The home boasts

  Iris Bolt Malishewsky ABSOLUTE REALTY GROUP, LLC

  3825 Black Spruce Ln, Winter Springs, FL 32708
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  /36

  $719,000

  • 4 Beds
  • 3 Baths
  • 2,562 Sq Ft

  4951 Courtland Loop, Winter Springs, FL 32708

  This beautifully updated home blends timeless character with modern comfort, offering an inviting layout designed for both everyday living and entertaining. The light-filled interior showcases a stunning, renovated kitchen with new quartz extended countertops, a butcher block island, recessed lighting, and a full suite of high-end appliances including a JennAir refrigerator, KitchenAid pull-out

  Carolina Taborda MOMENTUM REALTY

  4951 Courtland Loop, Winter Springs, FL 32708
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  /23

  $32,000

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft

  463 Ponce de Leon Cir, Winter Springs, FL 32708

  SELLER CONSIDERING ALL OFFERS! Welcome to this cozy and inviting 2-bedroom, 1-bathroom home located in the highly desirable 55+ community of Hacienda Village in Winter Springs, Florida. This peaceful, well-maintained community offers an ideal combination of comfort, convenience, and Florida living. With quick access to the 417, you can easily reach the beaches, theme parks, downtown Winter

  Bella Siracusa SUNBELT HOME SALES INC

  463 Ponce de Leon Cir, Winter Springs, FL 32708
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  /17

  $129,900

  • 3 Beds
  • 2 Baths
  • 1,272 Sq Ft

  1073 Cheyenne Trail, Winter Springs, FL 32708

  Completely and beautifully remodeled. This sparkling clean 3/2 home is ready for someone to make it their own. Large Living room and Dining Room with two adjacent screen porches. Spacious Master bedroom with garden tub and shower for your relaxing indulgence. Nice sized 2nd and 3rd bedrooms. Plenty of parking space and fenced backyard. Location is everything here at Tuskawilla Trails with

  Todd Newby NEWBY REALTY INC

  1073 Cheyenne Trail, Winter Springs, FL 32708
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  /31

  $599,000

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

  417 Dancing Water Dr, Winter Springs, FL 32708

  Welcome to your dream home in the highly sought-after Tuskawilla Crossings community! This stunning 2019-built residence offers 1,916 square feet of luxurious single-story living with 4 spacious bedrooms and 2 full baths—perfect for those seeking style, comfort, and convenience in Winter Springs! Step through the charming covered front porch and prepare to be captivated by the home's bright, open

  Tim Kitts FATHOM REALTY FL LLC

  417 Dancing Water Dr, Winter Springs, FL 32708
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  /15

  $169,900

  • 2 Beds
  • 2 Baths
  • 972 Sq Ft

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708

  Prime First-Floor Living in Prestigious Highlands of Winter Springs! Discover the ultimate in convenient living with this exceptional first-floor 2 bedroom, 2 bathroom condo in the highly sought-after Highlands community. Located in top-rated Seminole County School District, this ground-level gem eliminates the hassle of stairs while offering effortless accessibility for residents and guests

  Matt Merdian MERDIAN REALTY LLC

  10 Sheoah Blvd Unit 5, Winter Springs, FL 32708
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  /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
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  /35

  $289,999

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  150 N Edgemon Ave, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. *FLASH SALE* Motivated Seller!! Winter Springs single-family home on nearly 1⁄4 acre with A-rated schools,NO HOA, Eligible for FHA/VA financing; suitable for first-time buyers, and energy-efficient upgrades. Major improvements include NEW ROOF (2025), PAID-OFF SOLAR PANELS (installed Nov 2020) for lower monthly utility costs, NEW WINDOWS (2022), GAS

  Kathern Cox-Uvalle EMPIRE NETWORK REALTY

  150 N Edgemon Ave, Winter Springs, FL 32708
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  /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
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  /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
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  /58

  $729,900

  • 4 Beds
  • 4 Baths
  • 3,186 Sq Ft

  1149 Eagles Watch Trail, Winter Springs, FL 32708

  Beautiful and spacious 4 bed 4 bath pool home in the sought after community of Eagles Point nestled in the heart of Winter Springs! Home sits on a one of a kind oversized lot with pond views in the front, side and conservation behind! This home has been well maintained and boasts a large open kitchen with shaker cabinets, stainless appliances, custom shutters, tile throughout common areas

  Thomas Marchetto OPTIMA REAL ESTATE

  1149 Eagles Watch Trail, Winter Springs, FL 32708
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  /39

  $925,000

  • 4 Beds
  • 4 Baths
  • 3,499 Sq Ft

  213 Heatherwood Ct, Winter Springs, FL 32708

  Welcome to luxury living in the gated community of the Reserve at Tuscawilla! This elegant 4-bedroom, 4-bathroom estate features a dedicated home office, spacious bonus room, and a 3-car garage nestled on a generous .34 acre lot. Soaring 12–14' coffered ceilings enhance the open and airy feel throughout. The open-concept kitchen is the heart of the home, featuring a large center island, perfect

  Cynthia Davis COLDWELL BANKER REALTY

  213 Heatherwood Ct, Winter Springs, FL 32708
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  /30

  $281,500

  • 3 Beds
  • 2 Baths
  • 1,091 Sq Ft

  314 San Gabriel St, Winter Springs, FL 32708

  Welcome home to this charming 3 bedroom, 2 Bath home in the heart of Winter Springs, in centrally located Deer Song Community. This home features: Corner unit, open floor plan, high ceilings, NEW ROOF 2021, RE-PLUMBED 2021, NEW APPLIANCES 2021-2022, NEW AIR CONDITIONING SYSTEM 2022, NEW WATER SOFTENER SYSTEM 2022 AND NEW LUXURY VINYL FLOORING IN BEDROOMS 2022. Home has been well maintained and

  Linda Bain WEICHERT REALTORS HALLMARK PRO

  314 San Gabriel St, Winter Springs, FL 32708
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  /23

  $410,000

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  403 Murphy Rd, Winter Springs, FL 32708

  Welcome home to this beautiful 3 bedrooms, 2 bathrooms house with a pool. Come and enjoy the large pool, modern and updated kitchen with granite countertop and stainless-steel appliances. The spacious interior along with the bonus room will give your family enough space to grow. In the last 4 years the roof, air conditioning unit and water heater have all been replaced. The solar panels will

  Celeste Baez FLORIDA REALTY INVESTMENTS

  403 Murphy Rd, Winter Springs, FL 32708
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  /54

  $719,000

  • 5 Beds
  • 3 Baths
  • 3,287 Sq Ft

  1503 Graceful Doe Loop, Winter Springs, FL 32708

  This stunning 5-bedroom, 3-bathroom home with a three-car garage offers a perfect blend of style, comfort, and functionality. As you step inside, you are greeted by a spacious floor plan. One bedroom and a full bathroom are conveniently located downstairs, providing privacy and flexibility for guests.The main level features an open and versatile layout, including a spacious dining room that

  Gabriel Andrada FLORIDA SPIRIT HOMES

  1503 Graceful Doe Loop, Winter Springs, FL 32708
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  /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
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  /13

  $29,900

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  31 La Vista Dr, Winter Springs, FL 32708

  A must-see home that has been totally renovated with new luxury vinyl flooring, Kitchen has quartz counter tops and all new stainless-steel appliances. New baseboards freshly painted throughout. New A/C ductwork. Master bathroom has been totally remodeled. a GREAT 55+ COMMUNITY offering lots of amenities. Restaurants & major roads nearby. Vacant & ready for a new owner!!!

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  31 La Vista Dr, Winter Springs, FL 32708
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  /27

  $515,000

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

  223 Tavestock Loop, Winter Springs, FL 32708

  Great Opportunity in Winter Springs! This spacious 4-bedroom, 2.5-bath two-story home is located in the gated community of Parkstone and features an oversized backyard, perfect for future upgrades. The floor plan includes a formal living and dining area, as well as a family room with high ceilings and windows that bring in a ton amount of natural lighting. The open staircase adds volume to the

  Mary Walason MEP REALTY INVESTMENTS LLC

  223 Tavestock Loop, Winter Springs, FL 32708
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  /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
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  /36

  $469,900

  • 3 Beds
  • 2 Baths
  • 1,501 Sq Ft

  903 Torrey Pine Dr, Winter Springs, FL 32708

  Paradise found in Tuscawilla! Come fall in love with this idyllic low maintenance waterfront villa on over 1/3 acre with lawn care and community pool included. Walk out the back door of this beautiful 3 bedroom home to your “high and dry” oasis backing up to serene Bear Creek. Inside the home, you will be greeted by a cozy yet open floor plan with abundant light, high ceilings and many upgrades.

  Colleen Kahl RE/MAX TOWN & COUNTRY REALTY

  903 Torrey Pine Dr, Winter Springs, FL 32708
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  /20

  $258,900

  • 2 Beds
  • 1.5 Baths
  • 1,130 Sq Ft

  543 Green Spring Cir, Winter Springs, FL 32708

  This charming townhome is a rare find! Meticulously maintained by a single owner, this 2-bedroom, 1.5-bathroom gem offers the perfect blend of comfort and peace of mind in a quiet, established community. Step inside to a bright, airy floor plan that feels like home the moment you enter. Beyond the aesthetics, this property boasts major "big-ticket" upgrades, ensuring a low-maintenance lifestyle

  Tracy Phillips COLDWELL BANKER REALTY

  543 Green Spring Cir, Winter Springs, FL 32708
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  /55

  $569,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  758 Seneca Meadows Rd Unit 4, Winter Springs, FL 32708

  Beautiful Park Stone 4 bedroom, 2.5 bathroom pool home with major recent upgrades and move-in availability March 2, 2026. Key improvements include a new roof (2022), new A/C system (October 2024), new pool pump and chlorinator (October 2024), and a pool enclosure fully re-screened in 2024.The remodeled kitchen (2022) features a stunning design with nearly floor-to-ceiling cabinetry offering

  Ken Pozek REAL BROKER, LLC.

  758 Seneca Meadows Rd Unit 4, Winter Springs, FL 32708
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  /57

  $120,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  18 La Vista Cir, Winter Springs, FL 32708

  2018 Clayton Built 3-bedroom 2 bath Home- Private backyard, quiet end of street. Lots of space-Great kitchen all modern appliances-Location, Location close to all highways. Near restaurants, shopping, medical. Community soon will have new things to do. 55+Community. Hacienda Village a Legacy Community-Monthly rent $1025.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  18 La Vista Cir, Winter Springs, FL 32708
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  /55

  $190,000

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

  429 Sheoah Blvd Unit 1, Winter Springs, FL 32708

  One or more photo(s) has been virtually staged. Stunning upgraded corner-unit with extra privacy and garden views! Enjoy wood-look flooring, an open kitchen with granite countertops, stainless steel appliances, bar area plus a wet bar with built-in wine cooler, perfect for entertaining. Plantation shutters throughout the living room, tinted windows, and a newer tankless electric water heater add

  Marielle Parra COMPASS FLORIDA LLC

  429 Sheoah Blvd Unit 1, Winter Springs, FL 32708
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  /60

  $624,900

  • 4 Beds
  • 3 Baths
  • 2,531 Sq Ft

  203 Wise Owl Way, Casselberry, FL 32708

  WALK ON IN AND CALL IT HOME! Welcome to this stunning 4-bedroom, 3-bathroom home nestled in the highly sought-after Tuskawilla Crossings community of Winter Springs. From the moment you step inside, you’ll be greeted by a tastefully decorated foyer that opens up into a spacious living room and a beautifully designed open kitchen, perfect for entertaining and everyday living. On the first floor,

  Lindsay Kaye Voss VOSS REALTY INC

  203 Wise Owl Way, Casselberry, FL 32708
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  /49

  $999,900

  • 4 Beds
  • 2.5 Baths
  • 3,522 Sq Ft

  930 Arabian Ave, Winter Springs, FL 32708

  Welcome to your dream home, a stunning estate style home on 1.2 acres of beautifully landscaped grounds located in the highly desirable Tuscawilla area of Winter Springs, FL. Nestled on a tree-lined street, this four bedroom, two and one half bathroom home is designed for comfort and entertaining, offering the perfect blend of elegance and tranquility, backing up to Howell Creek. Stepping inside,

  Lou DiBerardino KELLER WILLIAMS WINTER PARK

  930 Arabian Ave, Winter Springs, FL 32708
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  /50

  $110,000

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

  65 Majorca Dr, Winter Springs, FL 32708

  Located close to an entrance, "solar Panels" paid for. Open, Modern 2 Entrances, Shows Well, Crown Molding-SUPER KITCHEN is a must see! GREAT LOCATION, close to major roads, Doctors, Fire Dept. Restaurants, Shopping & more! Updated Amenities-2 Pools, Pickle Ball, Putt Putt Golf, Doggy Park & More, Never a dull moment, always something to do! Base Mo. lor rent is $1025.00.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  65 Majorca Dr, Winter Springs, FL 32708
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  /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
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  /59

  $799,000

  • 5 Beds
  • 4 Baths
  • 3,130 Sq Ft

  1816 Seneca Blvd, Winter Springs, FL 32708

  Set on nearly half an acre with pond views and no rear neighbors, this beautifully maintained Tuscawilla pool home offers privacy, space, and a layout that truly lives well. With over 3,100 square feet, five bedrooms, and four bathrooms, the home balances everyday comfort with effortless entertaining. A circular driveway, mature landscaping, and strong curb appeal create a welcoming first

  Beth Hobart MAINFRAME REAL ESTATE

  1816 Seneca Blvd, Winter Springs, FL 32708
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  /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
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  /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
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  /47

  $39,900

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  293 Casa Grande Dr, Winter Springs, FL 32708

  Beautiful Home all Remodeled-New HVAC, all new ductwork, freshly painted-Move in Ready! New Kitchen-corner Lot, No Flood Zone, Phase III. Clubhouse , Recreation Hall, 2 Pools (one heated), Pickle Ball Court, Putt, Putt, Doggy Park and more. Close to all major Highways, close to Restaurants, Shopping, Parks & Beaches (45 minutes away) lot of activities-You won't be bored. Mo. Base Lot Rent $1025.

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  293 Casa Grande Dr, Winter Springs, FL 32708
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  /54

  $789,000

  • 6 Beds
  • 4 Baths
  • 3,426 Sq Ft

  1534 Wescott Loop, Winter Springs, FL 32708

  Stunning six-bedroom, four-bath home in a gated community, perfectly positioned with a view of a conservation lot without rear neighbors. Winter Springs address, with top-rated Oviedo Schools! Soak up the Florida lifestyle in this stunning backyard retreat with a sparkling pool and spa. Brand new pool heater plus a spacious outdoor kitchen, complete with a dedicated gas grill area, seating space,

  Denise Pohlmann PALMANO GROUP RE BROKERAGE LLC

  1534 Wescott Loop, Winter Springs, FL 32708
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  /47

  $44,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  219 El Camino Real Cir, Winter Springs, FL 32708

  Brand New Inside - Completely redone, Beautiful new floors, repainted inside and out, New Front Door, Screened-in Porch redone, nice size storage room. Hacienda Village is a Legacy Community - 55+.Monthly rent $1025 Base

  Frank Filippelli SOUTHERN REALTY ENTERPRISES INC

  219 El Camino Real Cir, Winter Springs, FL 32708
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  /43

  $769,900

  • 4 Beds
  • 3 Baths
  • 2,757 Sq Ft

  1121 Arbor Glen Cir, Winter Springs, FL 32708

  WELCOME TO PARADISE! Unbeatable price for this stunning, move-in ready custom pool home in Tuscawilla. Arbor Glen is a small, very exclusive community of just 38 custom homes located in the city of Winter Springs, which has been ranked among the best places to live nationwide for decades. Well-designed formal areas feature travertine, porcelain tile and engineered hardwood flooring and lots of

  Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

  1121 Arbor Glen Cir, Winter Springs, FL 32708
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  /32

  $1,099,000

  • 5 Beds
  • 5 Baths
  • 3,885 Sq Ft

  1815 Seneca Blvd, Winter Springs, FL 32708

  This stunning 5-bedroom pool home in the highly desirable Chelsea Woods at Tuscawilla has been completely remodeled from top to bottom. The home offers exceptional living space, including a large living room with fireplace, a spacious family room with fireplace, and a formal dining room—ideal for entertaining. A large bonus room provides flexible space for a home office, playroom, or additional

  Belinda Gonzales RE/MAX TOWN & COUNTRY REALTY

  1815 Seneca Blvd, Winter Springs, FL 32708
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  /65

  $949,000

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft

  450 Terravista Place, Oviedo, FL 32765

  Welcome to your dream home! This exquisite residence nestled on a cul-de-sac within the small gated community of Terralago boasts stunning curb appeal, with a Spanish style roof and an extended paver driveway leading to a spacious three car garage. As you step inside, the beautiful foyer with soaring ceilings and crystal chandeliers in the formal living and dining spaces welcome you home. The

  Noor Masri LA ROSA REALTY PREMIER LLC

  450 Terravista Place, Oviedo, FL 32765
• 

  

  /49

  $1,150,000

  • 5 Beds
  • 4.5 Baths
  • 4,104 Sq Ft

  2297 Blossomwood Dr, Oviedo, FL 32765

  Experience refined living in this fully renovated (with finishing touches underway) luxury single-family home located in the highly sought-after Tuska Ridge subdivision of Oviedo, FL. Set on a private 1-acre lot, this exceptional residence offers 5 bedrooms, 5 bathrooms, and 4,104 square feet of thoughtfully designed living space, including a dedicated second-generation/in-law suite ideal for

  Michelle Torrente ROBERT SLACK LLC

  2297 Blossomwood Dr, Oviedo, FL 32765

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