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Winter Springs, FL Homes for Sale with Private Pool

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  • /47

    $624,900

    • 3 Beds
    • 2 Baths
    • 1,882 Sq Ft

    1096 Dyson Dr, Winter Springs, FL 32708

    Welcome to 1096 Dyson Drive, a truly one-of-a-kind pool home in the heart of Winter Springs, FL! This spacious and well-maintained property is packed with unique features and thoughtful upgrades, offering the ideal Florida lifestyle—both inside and out.Step inside and you’ll immediately notice the charm and craftsmanship, including solid wood interior doors in a timeless Craftsman style. The

    Agent Photo

    Lorena Cabal Ospina

    EXP REALTY LLC

    (321) 516-0796

    1096 Dyson Dr, Winter Springs, FL 32708
  • /38

    $399,999 Open Sun 1PM - 4PM

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

    340 Inglenook Cir Unit 1, Winter Springs, FL 32708

    Buyer changed there 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

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (689) 399-2598

    340 Inglenook Cir Unit 1, Winter Springs, FL 32708
  • /39

    $724,000

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

    650 Cayuga Dr, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. 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 privacy and charm. Designed for both comfort and entertaining, the outdoor

    Agent Photo

    Jamie Ampel

    ALL SELLERS & BUYERS REALTY INC

    (321) 341-2960

    650 Cayuga Dr, Winter Springs, FL 32708
  • /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
  • /32

    $685,000

    • 4 Beds
    • 3 Baths
    • 2,353 Sq Ft

    1113 Citrus Oaks Run, Winter Springs, FL 32708

    Welcome to 1113 Citrus Oaks Run, a beautifully maintained home offering timeless style, functional space, and a private backyard retreat. This spacious 3-way split floor plan features wood flooring throughout, 8-foot doors, high ceilings, and elegant beams in the dining room, creating a warm and inviting atmosphere from the moment you enter. The living room/den showcases added French doors, while

    Abby Nelson RE/MAX 200 REALTY

    1113 Citrus Oaks Run, Winter Springs, FL 32708
  • /49

    $849,000

    • 4 Beds
    • 4 Baths
    • 2,801 Sq Ft

    1502 Eagle Nest Cir, Winter Springs, FL 32708

    Classic Tuskawilla Pool Home with Remodeled Kitchen and First Floor Primary Suite. Welcome to 1502 Eagle Nest Circle, a timeless two-story pool home located in the desirable Glen Eagle section of Tuskawilla, one of Winter Springs’ most established and sought-after planned communities. Known for its tree-lined streets, golf course lifestyle, and convenient Seminole County location, Tuskawilla

    Dione Collier-Larkin ADAIR REALTY INC

    1502 Eagle Nest Cir, Winter Springs, FL 32708
  • /66

    $965,000 Open Sat 11AM - 1PM

    • 5 Beds
    • 4.5 Baths
    • 3,660 Sq Ft

    702 Golfpoint Dr, Winter Springs, FL 32708

    Set on a prominent corner lot in Glen Eagle, this spacious pool home makes an immediate impression with standout curb appeal, mature oak trees, lush landscaping, and a winding front walkway leading to a natural slate entry. Located in the sought-after Tuscawilla golf community, the home offers a rare blend of presence, warmth, and flexibility in one of the area’s most desirable settings. Inside,

    Blake Murphey RE/MAX 200 REALTY

    702 Golfpoint Dr, Winter Springs, FL 32708
  • /59

    $910,000 Open Sat 12:30PM - 2:30PM

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

    213 Heatherwood Ct, Winter Springs, FL 32708

    Welcome home to 213 Heatherwood Circle, nestled within the highly sought-after gated community of Reserve at Tuscawilla, where lifestyle meets luxury. From the moment you arrive, you’re greeted by lush Florida landscaping, an oversized driveway, and a desirable side-entry three-car garage. Situated on a generous 0.34-acre pond-front lot, this exceptional property offers a private pool and spa,

    Virginia Bellhorn WATSON REALTY CORP

    213 Heatherwood Ct, Winter Springs, FL 32708
  • /82

    $735,000

    • 4 Beds
    • 3 Baths
    • 2,711 Sq Ft

    1825 Seneca Blvd, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to 1825 Seneca Blvd in the heart of Tuskawilla, a rare opportunity to own a spacious one-story pool home on an almost half-acre lot in one of Seminole County’s most sought-after locations. Owned by the same family for 37 years, this 4-bedroom, 3 full bathroom block home offers 2,711 square feet of living space, a 2-car garage, soaring

    Chris Creegan CREEGAN GROUP

    1825 Seneca Blvd, Winter Springs, FL 32708
  • /41

    $470,000 Open Sat 12PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,917 Sq Ft

    632 Tuskawilla Point Ln, Winter Springs, FL 32708

    Welcome to this beautifully maintained home nestled in the desirable Tuskawilla area of Winter Springs! This lovely 4-bedroom, 2-bath, 1,917 square foot pool home is situated in a quiet, tree-lined neighborhood and offers the perfect blend of comfort, charm, and Florida living. Step inside to discover a spacious and inviting floor plan filled with natural light, featuring laminate floors

    Harry Narvaez-Mercado KELLER WILLIAMS ADVANTAGE 2 REALTY

    632 Tuskawilla Point Ln, Winter Springs, FL 32708
  • /38

    $528,000 Open Sat 12AM - 3PM

    • 4 Beds
    • 2 Baths
    • 2,029 Sq Ft

    421 Ringwood Cir, Winter Springs, FL 32708

    Welcome to 421 Ringwood in Winter Springs. This spacious 4-bedroom home offers the perfect setup for a growing family, with plenty of room to spread out and enjoy. Step outside to your own private pool and freshly resodded backyard, creating an ideal space for relaxing, entertaining, and making the most of Florida living. Important updates add peace of mind, including a roof replaced in 2017, A/C

    Farrah Thacker LPT REALTY LLC

    421 Ringwood Cir, Winter Springs, FL 32708
  • /12

    $349,900 Open Sat 11:30AM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,053 Sq Ft

    214 N Alderwood St, Winter Springs, FL 32708

    Completely remodeled 3-bedroom, 2 bathroom home located located in the heart of Winter Springs, offering convenience , comfort , and modern upgrades throughout. Situated on an oversized lot, this property features a large private pool, perfect for entertaining or relaxing in your own backyard oasis. Inside , you'll find a brand -new kitchen with modern finishes ,complemented by all-new appliances

    Krasimira Kakarova WORLD PROPERTIES GROUP

    214 N Alderwood St, Winter Springs, FL 32708
  • /20

    $649,999

    • 5 Beds
    • 3 Baths
    • 3,408 Sq Ft

    363 Twelve Oaks Dr Unit 5, Winter Springs, FL 32708

    Outstanding 5-bedroom, 3-bathroom home with a Screened Pool and a beautiful Water view. Open concept, 2 story with a lot of natural light.Large kitchen overlooks the Spacious Family room. Spacious Great room, Living & Dining combo! Plus a Grand-sized Bonus room upstairs for the family to all enjoy! Tall Ceilings. 3-car garage! Ready for quick occupancy! Great Schools! Hurry! Won't Last!

    Caroline Moffitt-Lawton KELLER WILLIAMS HERITAGE REALTY

    363 Twelve Oaks Dr Unit 5, Winter Springs, FL 32708
  • /41

    $499,999

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft

    1356 Via Villa Nova, Winter Springs, FL 32708

    Your private oasis awaits on a PREMIUM WATERFRONT LOT. Forget the stress... MOVE-IN READY to this completely stunning fully remodeled home with luxury finishes throughout! *** Welcome to your 3 Bedroom 2 full Bathroom, split plan Saltwater pool home. This home is also fully wheelchair accessible. The interior is elevated by curated designer upgrades, freshly redone walls and stylish new flooring

    Tori Nguyen LOKATION

    1356 Via Villa Nova, Winter Springs, FL 32708
  • /60

    $865,000

    • 5 Beds
    • 3.5 Baths
    • 2,660 Sq Ft

    1692 Wingspan Way, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Nestled within the prestigious Glen Eagle community of Tuscawilla, this exceptional executive-style single-story custom home offers luxury, space, and an unbeatable location. Set along picturesque tree-lined streets, this 5-bedroom, 3.5-bath residence with a 3-car side-entry garage and additional gated parking (perfect for a boat) is designed for

    Suzanne Giambruno COLDWELL BANKER REALTY

    1692 Wingspan Way, Winter Springs, FL 32708
  • /68

    $1,549,000

    • 4 Beds
    • 6 Baths
    • 6,175 Sq Ft

    1513 Black Bear Ct, Winter Springs, FL 32708

    Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings

    Lynda Miller PREMIER SOTHEBYS INT'L REALTY

    1513 Black Bear Ct, Winter Springs, FL 32708
  • /64

    $822,800

    • 5 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    422 Sandringham Ct, Winter Springs, FL 32708

    Nestled at the end of a peaceful cul-de-sac within an exclusive gated community, this exceptional lakefront residence offers breathtaking water views and direct access from your own private dock. Just a short walk from the community pool, playgrounds, and tennis courts, this home perfectly blends tranquility with convenience.Boasting 5 bedrooms and 3.5 bathrooms, including two expansive

    Yujie Jiang INTOP REALTY LLC

    422 Sandringham Ct, Winter Springs, FL 32708
  • /33

    $448,997

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    872 Falkirk Dr, Winter Springs, FL 32708

    Beautifully maintained home located in one of the most desirable areas of Winter Springs, offering the perfect blend of comfort, convenience, and outdoor living. Surrounded by scenic walking and biking trails throughout the neighborhood, this home delivers a peaceful setting while staying close to everything you need. This property features 3 bedrooms and 2 bathrooms with a bright open floor plan

    Elizabeth Rodriguez CAISSA REALTY INVESTMENT INC

    872 Falkirk Dr, Winter Springs, FL 32708
  • /11

    $569,000 Open Sun 1PM - 4PM

    • 4 Beds
    • 2.5 Baths
    • 2,674 Sq Ft

    30 Sable Ct, Winter Springs, FL 32708

    REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated

    Julie Bailey HOME SOLD NETWORK LLC

    30 Sable Ct, Winter Springs, FL 32708
  • /51

    $764,900

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

    1534 Wescott Loop, Winter Springs, FL 32708

    Now offered at an ADJUSTED price of $764,900 for this 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,

    Denise Pohlmann PALMANO GROUP RE BROKERAGE LLC

    1534 Wescott Loop, Winter Springs, FL 32708
  • /25

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,044 Sq Ft

    222 W Panama Rd, Winter Springs, FL 32708

    Well-maintained 3-bedroom, 2-bath home located in sought-after Winter Springs. This property offers a fully fenced backyard with a private pool, providing excellent privacy and space for outdoor entertaining. A brand-new roof will be installed adding value and peace of mind. Situated in a quiet, established neighborhood with no HOA restrictions. Conveniently located near local parks, shopping

    Melissa Maldonado CENTURY 21 MCBRIDE REALTY GROUP

    222 W Panama Rd, Winter Springs, FL 32708
  • /47

    $1,299,900

    • 4 Beds
    • 3 Baths
    • 4,464 Sq Ft

    120 E Bahama Rd, Winter Springs, FL 32708

    This property offers a rare opportunity to own a home with true flexibility, privacy, and long-term value—perfect for today’s evolving lifestyles. Designed with flexibility in mind, this home features a private in-law or guest suite with its own separate exterior entrance and full bathroom, creating an ideal setup for multigenerational living, visiting guests, or a private home office. The in-law

    Alma Merrill EXP REALTY LLC

    120 E Bahama Rd, Winter Springs, FL 32708
  • /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
  • /56

    $498,900

    • 4 Beds
    • 2 Baths
    • 1,864 Sq Ft

    986 Turkey Hollow Cir, Winter Springs, FL 32708

    986 Turkey Hollow Circle—where comfort, style, and Florida living come together beautifully. Nestled in one of Winter Springs’ most desirable neighborhoods, this 4-bedroom, 2-bath pool home offers the perfect blend of warmth, functionality, and thoughtful updates—just minutes from Tuskawilla Road, SR-434, shopping, dining, and top-rated schools. Step inside to an open, light-filled great room

    Christopher Dunlop CALL IT CLOSED INTL REALTY

    986 Turkey Hollow Cir, Winter Springs, FL 32708
  • /36

    $700,000

    • 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
  • /33

    $1,049,000

    • 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
  • /30

    $804,900

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

    124 Blue Creek Dr, Winter Springs, FL 32708

    Welcome to this 5 bedroom, 3 bathroom pool home in the highly desirable Tuskawilla neighborhood of Chestnut Estates. This home offers open-concept living with pool access from the primary bedroom, living room, and family room. As you walk through the front door, the dining room and spacious living room open to the lanai and screened-in pool area. The master bedroom and 5th bedroom are located on

    Ryan Langley FLORIDA REALTY INVESTMENTS

    124 Blue Creek Dr, Winter Springs, FL 32708
  • /41

    $728,500

    • 5 Beds
    • 3 Baths
    • 3,385 Sq Ft

    1553 Cranston St, Winter Springs, FL 32708

    Reduced! Nestled in the heart of Winter Springs, this lovely 5-bedroom, 3-bathroom pool home offers the perfect blend of comfort and convenience. Located in a serene and gated neighborhood with easy access to major roadways, Downtown Orlando, UCF and other top-rated schools, this home is ideal for those looking to experience the best of suburban living in Central Florida. Interior features

    Ari Rokh LEGACY REALTY & BROKERS LLC

    1553 Cranston St, Winter Springs, FL 32708
  • /37

    $450,000

    • 5 Beds
    • 2.5 Baths
    • 2,092 Sq Ft

    431 S Hawthorn Cir, Winter Springs, FL 32708

    **Single-Family Home with Detached ADU & Pool**Tucked away in a quiet cul-de-sac, this over 2,000 sq. ft. home with a detached Accessory Dwelling Unit (ADU) is a rare find in the highly desirable, non-HOA community of North Orlando Terrace! NEWER ROOF (2022), as well as a massive remodel in 2023 that consisted of NEW kitchen, bathrooms, plumbing, electrical panel, interior/exterior paint,

    Elliot Shugan THE SHUGAN GROUP INC

    431 S Hawthorn Cir, Winter Springs, FL 32708
  • /77

    $750,000

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

    1204 Swan St, Winter Springs, FL 32708

    Great location, No HOA..69 acres , 4 bedrooms,2 bathrooms, one half bathroom out door shower, kitchen, living room, family room, huge Florida room, huge enclosed pool, 2 car garage, enclosed out door kitchen, game room, storage. Close to major Roads, sipping centers, , schools, hospitals, 17 minutes to Sanford Airport, 11 minutes to Oviedo mall, 20 minutes to UCF. 20 minutes to Orlando Health

    Rosa Rodriguez STIRLING INTERNATIONAL REAL ES

    1204 Swan St, Winter Springs, FL 32708
  • /44

    $847,500 Pre-Foreclosure

    • 6 Beds
    • 4 Baths
    • 3,100 Sq Ft

    135 W Trade Winds Rd, Winter Springs, FL 32708

    As you arrive, you’re greeted by a circular driveway and the peace, privacy, and wide-open feel of over an acre of land. Step inside to a thoughtfully designed layout that flows with ease. To the right, a staircase leads to three spacious bedrooms, a full bathroom, and the primary suite featuring its own private bath. To the left, a cozy living room offers the perfect setting to relax and unwind.

    Joshua Crittendon EXP REALTY LLC

    135 W Trade Winds Rd, Winter Springs, FL 32708
  • /43

    $585,000 Pre-Foreclosure

    • 4 Beds
    • 2 Baths
    • 2,608 Sq Ft

    805 Leopard Trail, Winter Springs, FL 32708

    Welcome to this beautifully updated 4-bedroom, 2-bath custom home located in the desirable Tuskawilla community—known for its top-rated schools and family-friendly charm. Set on a nearly half-acre lot, this 2,608 sq ft residence offers the perfect mix of comfort, character, and everyday convenience. Step inside and you’ll immediately notice the inviting warmth of the engineered hardwood floors

    Miguel Anastacio COLDWELL BANKER REALTY

    805 Leopard Trail, Winter Springs, FL 32708
  • /84

    $970,000

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

    2297 Blossomwood Dr, Oviedo, FL 32765

    Experience refined living in this fully renovated 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 multigenerational living or extended

    Michelle Torrente ROBERT SLACK LLC

    2297 Blossomwood Dr, Oviedo, FL 32765
  • /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

Home Trends in Winter Springs, FL

Housing Trends

Median Sale Price
$416,634
Median Single Family Sale Price
$424,871
Median Townhouse Sale Price
$413,459
Median 2 Bedroom Sale Price
$175,000
Median 1 Bedroom Sale Price
$180,000
Average Price Per Sq Ft
$244
Number of Homes for Sale
143
Last 12 months Home Sales
614
Months of Supply
2.80
Median List Price
$429,900
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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