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Homes for Sale in Winter Springs, FL with 4-Bedrooms

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  • /65

    $849,521

    • 4 Beds
    • 2 Baths
    • 2,350 Sq Ft

    1444 Bird Rd, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. ONE OF A KIND! Stunning Renovated Lakefront Home on Private Peninsula – Rare opportunity to own a beautifully updated lakefront home on a private 1.5-acre peninsula. IN ADDITION: THIS LISTING INCLUDES A VACANT 1/2 ACRE BUILDABLE LOT WHICH MAY BE "SOLD SEPARATELY" OR KEPT AS PART OF THE ESTATE. THE VALUE IS A CONBINATION OF THE 1.5 ACRE ESTATE

    Agent Photo

    Bobby Keen

    KEEN REALTY GROUP, INC.

    (321) 325-3174

    1444 Bird Rd, Winter Springs, FL 32708
  • /33

    $317,700

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

    702 Glasgow Ct Unit 702, 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

    Agent Photo

    Carrie Shawfield

    SHAWFIELD REALTY GROUP

    (321) 485-6741

    702 Glasgow Ct Unit 702, Winter Springs, FL 32708
  • /16

    $599,000

    • 4 Beds
    • 3.5 Baths
    • 2,502 Sq Ft

    1421 Happy Bird Ln, Winter Springs, FL 32708

    Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step

    Agent Photo

    Brent DeHoop

    RE/MAX ASSURED

    (321) 218-3692

    1421 Happy Bird Ln, Winter Springs, FL 32708
  • /39

    $709,000

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

    650 Cayuga Dr, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. 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 privacy and charm. The tranquil outdoor

    Agent Photo

    Jamie Ampel

    ALL SELLERS & BUYERS REALTY INC

    (321) 341-2960

    650 Cayuga Dr, Winter Springs, FL 32708
  • /29

    $569,900

    • 4 Beds
    • 3 Baths
    • 2,321 Sq Ft

    1054 Winding Waters Cir, Winter Springs, FL 32708

    This beautiful 4-bedroom, 3-bath one-story pool home features over 2,300 square feet of living space on a premium conservation lot with no rear neighbors, providing exceptional privacy. Important updates include roof replaced in 2019, AC updated in 2020–2021, pool resurfaced in 2022, and kitchen updated in 2022. The home offers a spacious split floor plan with high ceilings, abundant natural

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    Alexa Monasterio Flores

    KELLER WILLIAMS ADVANTAGE 2 REALTY

    (321) 450-8067

    1054 Winding Waters Cir, Winter Springs, FL 32708
  • /74

    $670,000

    • 4 Beds
    • 3 Baths
    • 2,474 Sq Ft

    214 Chestnut Ridge St, Winter Springs, FL 32708

    Owner is Mootivated! Great price for a GOLF FRONT LIFESTYLE! Welcome home to 214 Chestnut Ridge, a custom-built single-family residence located with an amazing lot DIRECTLY on the 16 hole of the Tuscawilla Country Club.PRICELESS VIEW! VIEW VIDEO WALK THROUGH TOUR. Chestnut Ridge is a serene Winter Springs community in Seminole County This exquisite property, situated on .24 acres of loads of

    Agent Photo

    Laurie Cain

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 472-3134

    214 Chestnut Ridge St, 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
  • /35

    $454,900

    • 4 Beds
    • 2 Baths
    • 1,632 Sq Ft

    859 Benchwood Dr, Winter Springs, FL 32708

    Welcome to this beautifully updated 4-bedroom, 2-bath home nestled in one of Winter Springs’ most sought-after neighborhoods! Perfectly positioned next to a quiet dead-end street, this move-in ready property offers both privacy and convenience—ideal for hosting guests with extra parking or enjoying peaceful, low-traffic surroundings. Step inside to discover a thoughtfully upgraded interior

    Chuck Valence VALENCE REALTY GROUP

    859 Benchwood Dr, Winter Springs, FL 32708
  • /27

    $625,000 Open Sun 12PM - 2PM

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

    1106 Superior Ct, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Welcome to the highly sought-after Tuscawilla community, a neighborhood known for its tree-lined streets, strong sense of community, and access to some of the top-rated Seminole County schools. From the moment you walk through the front door, you’re greeted with an abundance of natural light that fills the home and creates a warm, inviting

    David Miller KELLER WILLIAMS HERITAGE REALTY

    1106 Superior Ct, Winter Springs, FL 32708
  • /59

    $910,000

    • 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
  • /52

    $540,000

    • 4 Beds
    • 2 Baths
    • 2,113 Sq Ft

    1250 Stone Harbour Rd, Winter Springs, FL 32708

    IMMACULATE 4 bedroom, 2 bathroom home in the beautiful GATED community of Parkstone! Located on a CUL-DE-SAC, fully FENCED backyard, NO REAR NEIGHBORS with a small POND for watching the amazing wildlife. COMPLETELY REMODELED! LAMINATE flooring throughout with TILE in the wet areas. As you enter, notice the natural light that shines through the home. A SEPARATE dining room, flex space and a SPLIT

    Heather Pryor KELLER WILLIAMS ADVANTAGE REALTY

    1250 Stone Harbour Rd, 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
  • /34

    $739,000

    • 4 Beds
    • 3.5 Baths
    • 3,281 Sq Ft

    613 Bonita Rd, Winter Springs, FL 32708

    Tucked beneath a canopy of mature trees in one of Winter Springs’ most charming ranch-style settings, this custom 2016 Craftsman is the kind of home buyers rarely come across. With 4 bedrooms, 3.5 baths, a dedicated office, upstairs loft, and 3,281 square feet of thoughtfully designed living space, every inch of this home blends warmth, function, and elevated style. From the oversized front porch

    Victoria Myers RE/MAX TOWN & COUNTRY REALTY

    613 Bonita Rd, Winter Springs, FL 32708
  • /22

    $375,000

    • 4 Beds
    • 2 Baths
    • 1,769 Sq Ft

    710 Briarwood Dr, Winter Springs, FL 32708

    Welcome to this beautifully updated 4-bedroom, 2-bath home in Winter Springs, FL, featuring thoughtful upgrades and a well-designed layout. Inside, you’ll find fresh interior paint, new baseboards and trim, updated lighting and ceiling fans, and custom shelving in the living room that adds both style and functionality. The layout includes multiple living areas and four well-sized bedrooms. The

    Steven Koleno BEYCOME OF FLORIDA LLC

    710 Briarwood Dr, Winter Springs, FL 32708
  • /41

    $470,000

    • 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

    $520,000 Open Sun 12AM - 3PM

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

    421 Ringwood Cir, Winter Springs, FL 32708

    Welcome to this spacious and inviting 4-bedroom, 2-bath pool home in the heart of Winter Springs. Thoughtfully designed for both everyday living and entertaining, this home offers a comfortable layout with generous living spaces and plenty of room for a growing family. The backyard is a true highlight, featuring a private pool and brand-new sod that creates a fresh, vibrant outdoor setting

    Farrah Thacker LPT REALTY LLC

    421 Ringwood Cir, Winter Springs, FL 32708
  • /39

    $495,000

    • 4 Beds
    • 3.5 Baths
    • 2,359 Sq Ft

    1254 Spotted Sandpiper Loop, Winter Springs, FL 32708

    Live luxuriously in almost New Townhouse! Immaculate 3-story townhouse (built 2023) boasts $20,000 in builder upgrades and offers a modern living experience! Unwind while sipping your morning coffee or taking a break on the front porch overlooking serene conservation. Inside, a flexible space on the first floor can be your home office, den, or 4th bedroom with a full en-suite bathroom (including

    Sylvana Minnetto CREEGAN GROUP

    1254 Spotted Sandpiper Loop, Winter Springs, FL 32708
  • /35

    $725,000

    • 4 Beds
    • 3 Baths
    • 2,724 Sq Ft

    223 Blue Creek Dr, Winter Springs, FL 32708

    Situated within an exclusive one-street enclave in highly desirable Tuscawilla, this impeccably maintained home presents a harmonious blend of privacy, comfort, and convenience. Backing to a peaceful conservation area with no rear neighbors, the property enjoys a tranquil setting framed by mature landscaping and scenic natural views. Inside, the thoughtfully designed floor plan lends itself to

    Aida Rico-Arango EXP REALTY LLC

    223 Blue Creek Dr, 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
  • /39

    $460,000

    • 4 Beds
    • 3.5 Baths
    • 2,164 Sq Ft

    608 Jesup Springs Ln, Winter Springs, FL 32708

    This END UNIT townhome has been beautifully updated and well maintained. Located in the Jesups Landing community of Winter Springs, a highly desirable part of a vibrant community, and close to shopping, dining, major roads and highways. You'll enjoy the community - small and tucked away from the hustle and bustle and the virtually maintenance free lifestyle! With 4 bedrooms and 3.5 baths, this

    Carla Stanton MAINFRAME REAL ESTATE

    608 Jesup Springs Ln, Winter Springs, FL 32708
  • /55

    $495,000

    • 4 Beds
    • 2.5 Baths
    • 1,996 Sq Ft

    632 Blenheim Loop, Winter Springs, FL 32708

    Good afternoon and welcome to your new 4 bedroom, 3 bathroom, and 2 car garage gated community home! The HOA fee is only $150 a month and covers all lawn maintenance, trimming of shrubs, fertilization, irrigation and outside pest control. The minute you walk in the front door, you will already begin to see your future holiday and family gatherings. The high ceilings are perfect for a tall

    Susan Young REALTY HUB

    632 Blenheim Loop, Winter Springs, FL 32708
  • /31

    $400,000

    • 4 Beds
    • 2 Baths
    • 1,660 Sq Ft

    110 Mockingbird Ln, Winter Springs, FL 32708

    Welcome home! This beautifully updated 4 bed, 2 bath block home sits on over 1⁄4 acre with no HOA, abundant natural light in every room and no carpets. The split floor plan offers privacy with the secondary bedrooms tucked away on the opposite side of the house featuring new closet doors, closet hardware and blinds. On the other side of the oversized living room, the spacious primary bedroom

    Cami Coupland KELLER WILLIAMS ADVANTAGE REALTY

    110 Mockingbird Ln, Winter Springs, FL 32708
  • /43

    $489,000

    • 4 Beds
    • 2.5 Baths
    • 2,309 Sq Ft

    131 Lisa Loop, Winter Springs, FL 32708

    Check out this spacious 4-bedroom, 2.5 bath home in Winter Springs, located in the highly sought-after Seminole County school district! Discover comfort and space in this corner lot home in The Oaks at the Highlands Subdivision. This well-designed home offers more than 2,300 square feet of living space with a functional layout that features the primary suite on the first floor along with a flex

    Nathan Bailey BAILEY CAMPBELL PROPERTIES

    131 Lisa Loop, Winter Springs, FL 32708
  • /36

    $470,000

    • 4 Beds
    • 2 Baths
    • 2,066 Sq Ft

    1126 Trotwood Blvd, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. Top-Rated Schools! Beautiful and well-maintained 4-bedroom, 2-bath home located in desirable Winter Springs. This home features ceramic tile flooring throughout for easy maintenance and a spacious layout perfect for comfortable living. Enjoy a huge patio—ideal for family gatherings and entertaining guests. Brand new roof (2025) provides peace of

    Joyce Tang JOY ESTATE ENTERPRISE INC

    1126 Trotwood Blvd, Winter Springs, FL 32708
  • /11

    $569,000

    • 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
  • /60

    $599,900

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

    203 Wise Owl Way, Casselberry, FL 32708

    HUGE PRICE DROP! SELLERS NEED TO SELL! 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

    Lindsay Kaye Voss VOSS REALTY INC

    203 Wise Owl Way, Casselberry, FL 32708
  • /63

    $489,975

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

    1262 Spotted Sandpiper Loop, Winter Springs, FL 32708

    "VA ASSUMABLE LOAN" Imagine a home that doesn't just house your life but elevates every chapter of it. At this stunning tri-level townhouse, the story begins the moment you step across the covered front porch and through the front door.Your day begins on the third level, where light pours through the expansive windows of your primary retreat. You wake up in a sanctuary defined by a sense of

    Mark Anthony Buot ROI AVE LLC

    1262 Spotted Sandpiper Loop, 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
  • /29

    $500,000

    • 4 Beds
    • 2 Baths
    • 1,979 Sq Ft

    1201 Wolverine Trail, Winter Springs, FL 32708

    Welcome to this charming 4-bedroom, 2-bath home tucked away in a quiet, tree-lined neighborhood in desirable Winter Springs. Surrounded by mature trees, this property offers a peaceful atmosphere and a spacious backyard, ideal for entertaining, relaxing, or enjoying Florida outdoor living. Inside, you’ll find a warm and inviting layout highlighted by an original masonry fireplace, adding timeless

    Nairobi Rondon LPT REALTY, LLC

    1201 Wolverine Trail, 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
  • /40

    $315,500

    • 4 Beds
    • 2 Baths
    • 1,356 Sq Ft

    114 Sundance Ct, Winter Springs, FL 32708

    One or more photo(s) has been virtually staged. If you’ve been searching for space, location, and opportunity without overpaying, this cul-de-sac home delivers. Tucked away on a quiet cul-de-sac and backing to a peaceful conservation area with no rear neighbors, this 4-bedroom home offers a rare combination of privacy and value in one of Winter Springs’ most desirable locations. Inside, you’ll

    Nora Rios WEICHERT REALTORS HALLMARK PRO

    114 Sundance Ct, Winter Springs, FL 32708
  • /18

    $369,900

    • 4 Beds
    • 2 Baths
    • 1,312 Sq Ft

    113 Lido Rd, Winter Springs, FL 32708

    Welcome home to this 4 bedroom 2 bath in the heart of Winter Springs! Walk thru the front door to be wowed with LVP flooring and a spacious living space with large windows letting in natural light. The eat-in space in the kitchen features French doors leading out into the oversized backyard perfect for a summer game of baseball or even a firepit for those cool FL nights. Kitchen has updated real

    Nicole Anderson HD REALTY LLC

    113 Lido Rd, 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
  • /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
  • /42

    $539,900

    • 4 Beds
    • 2.5 Baths
    • 2,447 Sq Ft

    987 Kerwood Cir Unit 4, Oviedo, FL 32765

    ***PRICE IMPROVEMENT***Welcome to this beautifully maintained home in the highly sought-after Tuska Ridge community in Oviedo. Known for its prime location, this neighborhood offers convenient access to shopping, dining, major highways, and is zoned for top-rated schools. Situated on a spacious 1⁄4-acre lot with mature trees providing natural shade, this home offers both comfort and

    Renata Stare PROPERTY OUTLET INTERNATIONAL

    987 Kerwood Cir Unit 4, Oviedo, FL 32765

Home Trends in Winter Springs, FL

Housing Trends

Median Sale Price
$418,000
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$414,229
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
134
Last 12 months Home Sales
606
Months of Supply
2.70
Median List Price
$430,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
-3%
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