Between $400,000 - $500,000 Winter Springs FL Real Estate, Homes, Condos for Sale

3 Beds ⋅ 2 Baths ⋅ O6431993 MLS

Welcome home to this beautiful, move-in ready single-story residence situated in the highly desirable Greenbriar community in Winter Springs! Nestled along the manicured grounds near Tuscawilla Golf and Country Club, this updated 3-bedroom, 2-bathroom home features 1,587 sq. ft. of comfortable, functional living space with a 2-car attached garage. Major big-ticket improvements offer complete peace of mind, including a brand-new roof, new energy-efficient windows, a new water heater, and a 5-year-young HVAC system. Step inside to an inviting open layout filled with natural light and stylish upgrades throughout. The kitchen and bathrooms feature stunning quartz countertops, creating a fresh, modern aesthetic that makes daily living and entertaining a joy. The primary bedroom serves as a peaceful retreat complete with an updated private en-suite bathroom, while two additional spacious bedrooms offer perfect flexibility for guest quarters, a nursery, or a dedicated home office. Outside, enjoy a low-maintenance lot with mature landscaping and beautiful community surroundings. The Greenbriar neighborhood features tree-lined streets, a community park, and a sparkling pool—all zoned for top-rated Seminole County schools (Rainbow Elementary, Indian Trails Middle, and Winter Springs High). Conveniently located near shopping, dining, parks, and major roadways, this turn-key property is completely ready for its new owners—schedule your private showing today!

998 White Springs Lane, Winter Springs

$435,000

3 Beds ⋅ 2 Baths ⋅ O6431215 MLS

Welcome home to this beautifully updated 3 bedroom, 2 bath home offering 2,116 square feet of comfortable living space on a spacious .28 acre corner lot, directly across from Sunrise Park. This move-in-ready home combines modern updates with a functional split-bedroom floor plan that's perfect for growing families, remote work, or entertaining. Step inside to discover fresh interior paint, beautifully remodeled master bathroom, and a renovated kitchen just five years ago. The improvements provide added peace of mind, including a complete repipe and fresh exterior paint, making this home as practical as it is attractive. Enjoy the fully fenced backyard offering plenty of room for the family, pets, gardening, or weekend barbecues, on a prime corner lot. If you're searching for your first home without sacrificing space, updates, or location, this one checks all the boxes. Move right in and start making memories in a home that's been thoughtfully updated and lovingly maintained.

1298 Madelena Avenue, Winter Springs

$498,000

4 Beds ⋅ 4 Baths ⋅ O6430088 MLS

Virtually Staged. Pond view!! Beautifully maintained 4-bedroom, 3.5-bath home located in the highly sought-after Tuscawilla community. Offering nearly 2,500 sq. ft. of thoughtfully designed living space, this home features an ideal floor plan with two primary suites—one on the first floor and another upstairs—providing exceptional flexibility for multi-generational living or guests. Enjoy an outstanding lifestyle with resort-style community amenities, including a community pool and direct access to scenic walking and biking trails right within the neighborhood. Conveniently located with top-rated Seminole County schools, easy access to major highways, shopping, dining, and everyday conveniences. Surrounded by mature landscaping and a peaceful atmosphere, Tuscawilla is one of Central Florida’s most desirable communities. Property Highlights: 4 Bedrooms | 3.5 Bathrooms Nearly 2,000 Sq. Ft. Two Primary Suites (First & Second Floor) Functional, Open Floor Plan Beautifully Maintained & Move-in Ready Resort-Style Community Pool Walking & Biking Trails Within the Community Excellent School District Easy Access to Major Highways, Shopping & Dining Move in and enjoy the perfect combination of comfort, convenience, and the exceptional Tuscawilla lifestyle!

225 Gentle Breeze Lane, Winter Springs

$406,990

3 Beds ⋅ 3 Baths ⋅ O6428779 MLS ⋅ 9 BLDG.

Under Construction. Final opportunity! Don't miss your chance to make this beautiful property yours! As you step inside the Aurora, you are greeted by an inviting open-concept gathering room, seamlessly connecting the dining room and kitchen. The flowing layout creates an expansive and airy atmosphere, perfect for both entertaining guests and enjoying everyday life. The owner's suite is a true retreat, offering a sanctuary of relaxation and tranquility. The spacious bedroom is complemented by a large walk-in closet, providing plenty of storage for your wardrobe and personal items. With two additional bedrooms, this townhome provides flexibility for a growing family, a home office, or a guest room.

225 Spindle Palm Cove, Winter Springs

$425,000

3 Beds ⋅ 4 Baths ⋅ O6424117 MLS ⋅ 1380 BLDG.

Discover refined living in the sought-after Jesup's Landing community of Winter Springs. This elegant 3-bedroom, 3.5-bathroom split-level townhome offers exceptional privacy, with thoughtfully designed living spaces that maximize comfort and separation. Beautiful new wood laminate flooring enhances the home's modern appeal, while the spacious layout is ideal for both everyday living and entertaining. Outside is a freshly painted exterior and new roof! Perfectly situated near Central Winds Park, premier shopping, SR 417, Sanford International Airport, the University of Central Florida, and Seminole State College, this residence combines luxury with convenience. Residents also enjoy resort-style amenities, including a clubhouse, state-of-the-art fitness center, and sparkling community pool. Experience low-maintenance living in one of Winter Springs' most desirable communities.

1380 Mill Stream Lane, Winter Springs

$489,900

2 Beds ⋅ 3 Baths ⋅ O6426798 MLS ⋅ 1541 BLDG.

Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs

$405,000

3 Beds ⋅ 2 Baths ⋅ O6427603 MLS

A bright and welcoming Winter Springs gem tucked into the charming community of Georgetowne. This 3-bedroom, 2-bathroom home features a split floor plan that maximizes privacy and flow. The main living areas are finished in upgraded tile, while the Primary bedroom offers soft carpeting for a cozy retreat. The Primary bathroom includes double sinks and an expanded walk-in shower, creating a spacious and functional suite. The kitchen is a standout with natural lighting thru the window, gorgeous backsplash, granite countertops, ample cabinetry, and a layout perfect for everyday cooking or entertaining. Throughout the home, plantation shutters add timeless style and excellent light control. Two other secondary bedrooms both have privacy and space. Step outside to enjoy multiple outdoor living spaces: a screened-in patio ideal for morning coffee or evening relaxation, plus a pavered courtyard that feels like your own private oasis and a private trellised area outside of the dining area. Practical updates include a newer AC system and newer Hot Water Heater, offering peace of mind. The HOA covers front yard maintenance, making life a little easier. And with top-rated schools nearby and Trotwood Park that includes Pickle Ball, Tennis Courts, Playgrounds and lots of Green areas for free play, all of this is just around the corner. The Winter Springs Town Center, 417, shops, restaurants and more are also close making the location hard to beat. With its unbeatable location, thoughtful layout, and inviting features, this home truly offers the best of TUSCAWILLA LIVING.

711 Andover Circle, Winter Springs

$460,000

3 Beds ⋅ 3 Baths ⋅ O6424732 MLS

Under contract-accepting backup offers. Welcome to Winter Springs Village featuring one of the finest bungalows situated on a corner lot with a private wooded view from the cozy front porch. Many upgrades include: AC replaced in 2023 with a transferrable warranty, freshly painted exterior in 2024, crown molding throughout the living space, custom built-in cabinets in the dining room niche for additoinal storge & epoxy flooring in the 2 car garage. The kitchen has a quartz countertop, backsplash, stainless steel appliances and 42" cabinets. Upstairs features a spacious loft/flex space, generous size alternate bedrooms, laundry room with a new washer/dryer and a primary suite complete with a walk-in closet and an additional hall closet. You will enjoy the affordable utility bills due to the many energy efficient features & design with low E Vinyl dual pane, double tint windows and a foam insulated attic. The HOA includes lawn & irrigation maintenance, community pool and clubhouse, playground and secure mailboxes. Easy access to 417 for a commute downtown, University of Central Florida, Orlando International Airport or the beaches. Convenient to highly rated Seminole County Schools. This one will not disappoint!

416 Michael Blake Boulevard, Winter Springs

$464,000

3 Beds ⋅ 2 Baths ⋅ O6424605 MLS

Welcome home to this beautifully maintained 3-bedroom, 2-bath residence nestled on a picturesque lot in the desirable North Orlando Ranches community. Offering the freedom of no HOA, this move-in-ready home combines comfort, style, and an unbeatable location. Step inside to discover a bright, open floor plan highlighted by vaulted ceilings, a charming bay window in the dining room, and a modern kitchen designed for both everyday living and effortless entertaining. Throughout the home, you’ll find no carpet—only attractive ceramic tile and laminate flooring for easy maintenance. The spacious primary suite features a walk-in closet and a private ensuite bathroom complete with a large walk-in shower. An inside laundry room adds convenience with a utility sink and additional storage space. Relax year-round in the air-conditioned Florida room, where French doors open to a peaceful, shaded backyard—perfect for morning coffee, outdoor gatherings, or simply enjoying the natural surroundings. Located within the highly acclaimed Seminole County Public School district, this exceptional home is just minutes from SR 434, shopping, dining, parks, and entertainment, making commuting and daily errands a breeze. Don’t miss this wonderful opportunity to own a move-in-ready home in one of Winter Springs’ most desirable locations. Schedule your private showing today!

619 Coral Way, Winter Springs

$425,900

3 Beds ⋅ 3 Baths ⋅ O6424446 MLS

Set within Country Club Village in the heart of Tuscawilla, this spacious 3-bedroom, 2.5-bath home offers more than 2,000 square feet designed for comfortable living, easy entertaining, and room to make the space your own. Thoughtfully arranged living and dining areas provide flexibility for everyday life, while the generous floor plan creates an easy flow throughout the home. Start and end your days in a space that gives you room to gather, unwind, and linger a little longer. Located in one of Winter Springs’ most established communities, residents enjoy convenient access to golf, parks, shopping, restaurants, SR 417, UCF, Oviedo, and highly regarded Seminole County schools. With lawn maintenance included through the community association, weekends can be spent enjoying more of the lifestyle and less of the upkeep. Spacious, inviting, and positioned in a location people love to call home, this is an opportunity to bring your vision to one of Tuscawilla’s most desirable communities.

1375 Augusta National Boulevard, Winter Springs

$425,000

3 Beds ⋅ 2 Baths ⋅ O6424067 MLS

Virtually Staged. Discover 963 Sequoia Dr, recently updated with fresh interior paint and partial flooring replacement throughout the residence. The kitchen includes all stainless steel appliances, complementing the updated interior. The exterior features a patio, fully fenced in backyard, a practical storage shed, and an in ground pool. This updated residence provides comfort and an exceptional outdoor retreat ready for everyday enjoyment.. Included 100-Day Home Warranty with buyer activation

963 Sequoia Drive, Winter Springs

$450,000

3 Beds ⋅ 2 Baths ⋅ O6423515 MLS

Welcome to 1454 King Court - this is an ideal POOL home or rental property for those seeking an updated living space. This renovated home has 3 bedrooms with 2 bathrooms. The renovations include new kitchen cabinets, kitchen appliances and Quartz countertops, fully renovated luxurious bathrooms, new flooring, new lighting, new ceiling fans and more. NEW Roof in 2026 and Newer Water Heater! This home also has a newly painted interior/exterior. Quiet Neighborhood, Close to all Major Highways, and Shopping Centers. Also an excellent rental investment opportunity.

1454 King Court, Winter Springs

$450,000

4 Beds ⋅ 2 Baths ⋅ O6423576 MLS

Discover this beautiful 4-bedroom, 2-bath home in the highly desirable Oak Forest community, offering comfort, style, and a welcoming layout perfect for everyday living. The chef-inspired kitchen showcases granite countertops, a stylish tile backsplash, and abundant cabinetry, creating an ideal space for cooking and gathering. The inviting living room features a wood-burning fireplace, adding warmth and charm, while the spacious primary suite offers a large walk-in closet for exceptional storage. Enjoy Florida living year-round on the screened-in patio, perfect for morning coffee, evening relaxation, or entertaining guests. A 2-car garage provides parking and additional storage, rounding out the home’s thoughtful design. All of this just minutes from shopping, restaurants, medical facilities, and major roadways, delivering unbeatable convenience and accessibility. Homes offering this level of comfort, location, and value don’t stay available for long. Make your move before this one slips away.

930 Oak Forest Drive, Winter Springs

$420,000

4 Beds ⋅ 3 Baths ⋅ O6422840 MLS

Welcome to this versatile and beautifully updated 4-bedroom, 3-bathroom home offering both comfort and opportunity. From the moment you step inside, you’re greeted by a warm, inviting atmosphere that instantly feels like home. The rich vinyl flooring stretches seamlessly throughout, adding both elegance and durability, while the light-colored walls reflect natural light to create a bright, airy space that feels open yet cozy. The heart of the home is a stunning kitchen equipped with newer appliances, including a brand-new refrigerator, making it perfect for everyday living and entertaining. Both the guest and primary bathrooms have been tastefully updated, adding a fresh and contemporary feel. One of the standout features of this property is its flexible layout. The Florida room and back bedroom have been thoughtfully converted into a secondary living space, ideal for generating supplemental income, accommodating guests, or creating a private in-law suite. This area can also be easily reintegrated into the main home if desired. Additional highlights include a HVAC system installed in 2020, providing peace of mind and energy efficiency. Whether you're looking for a primary residence with income potential or a spacious home with adaptable living areas, this property offers incredible value and flexibility.

758 N Gretna Court, Winter Springs

$415,000

3 Beds ⋅ 2 Baths ⋅ O6421127 MLS

Under contract-accepting backup offers. Beautifully updated turn-key ranch home on a prime corner cul-de-sac lot in the desirable Highlands community! This 3-bedroom, 2-bathroom split-plan home features extensive recent updates throughout. Inside, vaulted ceilings open up the main living spaces, highlighted by brand-new wood laminate flooring, crisp new baseboards, and a strikingly updated fireplace facade. The nicely updated kitchen boasts a newly added wall pass-through for an open-concept feel, and a large pantry. Every detail has been refreshed, including new fixtures, door knobs, hinges, and wall outlet faceplates throughout the entire home. The master suite features a walk-in closet and a beautifully updated shower with new lighting, while the guest bath includes a jetted tub, newer vanity, and refreshed finishes. Step through the sliding doors to an expansive covered portico, newly elevated with a shiplap ceiling, new fans, and replaced pillars. The outdoor space includes a fully fenced backyard with professionally leveled concrete (polyrenewal), new gutters, and mature landscaping. This home offers complete peace of mind with major mechanical updates, including a brand-new HVAC system installed in 2023, a new architectural 25-year roof from 2020, and updated interior and exterior electrical panels. The property also benefits from fresh exterior paint and updated wood trim. The location is unbeatable, allowing you to Seminole county schools and the ability to walk directly to Highlands Elementary. The vibrant community features a pool, clubhouse, tennis and basketball courts, playgrounds, and miles of walking trails. Enjoy the ultimate convenience of a short drive to the Town Center for Publix, dining, and fitness, along with effortless commuting via quick access to SR 417.

740 Galloway Court, Winter Springs

$424,990

4 Beds ⋅ 3 Baths ⋅ O6419339 MLS ⋅ 9 BLDG.

Under Construction. Final opportunity! Don't miss your chance to make this beautiful property yours! 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 owner’s 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.

221 Spindle Palm Cove, Winter Springs

$401,990

3 Beds ⋅ 3 Baths ⋅ O6419352 MLS ⋅ 24 BLDG.

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 options for families, professionals, or those in need of a dedicated home office space. The loft adds an additional dimension, allowing you to customize this versatile area to suit your lifestyle.

1403 Tarflower Drive, Winter Springs

$429,900

2 Beds ⋅ 2 Baths ⋅ V4949727 MLS

Virtually Staged. Welcome home to this absolutely charming and move-in-ready 2-bedroom, 2-bathroom home nestled in one of the most desirable areas of Winter Springs! From the moment you arrive, you'll appreciate the countless updates, beautiful wood beams and inviting curb appeal that make this home truly special. Major improvements provide peace of mind, including a 4-year-old roof, brand-new water heater, new flooring throughout, fresh interior and exterior paint, new appliances, and all-new light fixtures and ceiling fans. The beautifully updated kitchen offers modern style and functionality, while both bathrooms have been thoughtfully remodeled with today's buyer in mind. The spacious and light-filled bonus room overlooks the picturesque backyard and tranquil pond, creating the perfect space for a home office, reading room, playroom, or additional living area. Step outside and enjoy your backyard retreat featuring stunning water views and majestic oak trees that provide natural shade and beauty year-round while enjoying your morning coffee and watching the family of ducks swim by daily to greet you. Located in a great walking neighborhood, you'll love being just minutes from Tuscawilla Country Club and its renowned golf course, with olympic size pool and dining. Near top-rated schools and parks. Conveniently close to everything you need such as shopping, restaurants, medical facilities and your only a short drive to Florida's famous Theme Parks and about a 45 min drive to the best Beaches around. This adorable home offers the perfect blend of comfort, style, and location. Completely move-in ready and waiting for its new owners to fall in love—don't miss this incredible opportunity to own a piece of Winter Springs paradise!

717 Adidas Road, Winter Springs

$479,000

3 Beds ⋅ 2 Baths ⋅ O6417280 MLS

Welcome to the desirable city of Winter Springs, where 114 Stone Gable Cir sits on a beautiful corner lot with peaceful pond views to the rear and side of the home. Just minutes from shopping, restaurants, theme parks, major roads, and the airport, this move-in ready residence puts convenience right at your fingertips. Inside, 1,814 square feet of bright living space welcomes you with high ceilings and an open floor plan that flows naturally from room to room. Hard flooring runs throughout, keeping upkeep easy while adding a clean, modern look. The kitchen is ready for everything from casual breakfasts to weekend gatherings, featuring sleek granite countertops and stainless steel appliances. This thoughtfully designed home offers three comfortable bedrooms and two full bathrooms. The smart split layout tucks the primary bedroom away on its own side for added privacy, creating a quiet retreat at the end of the day, while two additional bedrooms provide flexible space for family, guests, or a home office. The real showstopper waits out back. Step onto the screened-in porch and enjoy your own private pool, perfect for cooling off under the Florida sun or relaxing as you take in the serene water views. The corner-lot setting adds extra elbow room and a sense of openness rarely found. With its prime location, modern finishes, and resort-style outdoor living, this Winter Springs gem checks every box. Schedule your private showing today and make it yours before it's gone!

114 Stone Gable Circle, Winter Springs

$475,000

4 Beds ⋅ 4 Baths ⋅ A4696204 MLS ⋅ Seminole Crossing BLDG.

Perfectly positioned in one of Winter Springs' most convenient and desirable locations, this fabulous home offers a sophisticated blend of modern design, flexible living spaces, and low-maintenance comfort. Situated within a beautifully maintained community just steps from Winter Springs Town Center, this three-story residence places shopping, dining, entertainment, and everyday conveniences right at your fingertips. Designed with both functionality and style in mind, the thoughtfully crafted floor plan offers exceptional versatility. The first level features a private bedroom suite, ideal for guests, a home office, multigenerational living, or anyone seeking additional privacy. Upstairs, the main living level serves as the centerpiece of the home, where an open-concept design seamlessly connects the kitchen, dining area, and spacious gathering room. The open floor plan creates an inviting atmosphere perfect for both everyday living and entertaining. The upper level is dedicated to comfort and relaxation, featuring three additional bedrooms, two full bathrooms, and a conveniently located laundry room. The spacious primary suite provides a peaceful retreat, while the secondary bedrooms offer flexibility for family, guests, or workspace needs. Beyond the home itself, residents enjoy access to community amenities including a sparkling pool, walking trails, and beautifully landscaped common areas. Top-rated Seminole County schools, local parks, and major commuter routes are all nearby, providing easy access to downtown Orlando, area employers, and Central Florida's many attractions. Whether you're seeking a primary residence, a lock-and-leave lifestyle, or a home that offers both convenience and comfort, this wonderful home delivers an exceptional opportunity in the heart of Winter Springs.

1320 Spotted Sandpiper Loop, Winter Springs

$499,900

4 Beds ⋅ 3 Baths ⋅ O6413206 MLS

Under contract-accepting backup offers. Welcome to 472 Dewars Court, a beautifully maintained 4-bedroom, 2.5-bath pool home offering over 2,200 square feet of living space in one of Winter Springs' most desirable communities. Tucked away at the end of a quiet cul-de-sac, this exceptional property provides the perfect combination of privacy, comfort, and convenience with a serene wooded backdrop and no rear neighbors. Inside, you'll find a spacious and functional floor plan designed for both everyday living and entertaining. The kitchen features a gas stove for the home chef, while the home's whole-house Generac gas generator provides peace of mind and uninterrupted comfort year-round. Recent major updates include a brand-new air conditioning system installed in June and a completely resurfaced pool completed this month, offering added value and years of worry-free enjoyment. Multiple living and dining spaces provide flexibility for growing families, remote work, or hosting guests. Step outside to your private backyard oasis featuring a sparkling newly resurfaced pool, expansive patio space, and tranquil wooded views—perfect for relaxing, entertaining, or enjoying Florida's beautiful weather. Located within The Highlands, one of Winter Springs' most sought-after communities, residents enjoy access to incredible amenities including a large Olympic-sized community pool, scenic nature trails, multiple parks, playgrounds, and recreation areas surrounded by mature oak trees that create a picturesque neighborhood setting. The Highlands is known for its strong sense of community, low-traffic streets, and family-friendly atmosphere. Winter Springs consistently ranks among the most desirable places to live in Seminole County thanks to its highly rated schools, beautiful parks, excellent shopping and dining options, and convenient access to Lake Mary, Oviedo, Winter Park, Downtown Orlando, and major highways. This is a rare opportunity to own a private pool home on a cul-de-sac lot with wooded views in one of Central Florida's most established and sought-after communities. With a brand-new A/C, a freshly resurfaced pool, and a whole-house generator already in place, this move-in-ready home offers comfort, peace of mind, and exceptional value. Schedule your private showing today!

472 Dewars Court, Winter Springs

$490,000

3 Beds ⋅ 2 Baths ⋅ O6413841 MLS

Beautiful pool home located in the highly desirable Amherst community of Winter Springs! Situated on an oversized .34-acre lot, this well-maintained 3-bedroom, 2-bath home offers a spacious split-bedroom floor plan with vaulted ceilings, abundant natural light, and a cozy wood-burning fireplace in the oversized family room. Updated bathrooms and ceramic wood looking flooring in main living areas. The screened with an large pool and covered lanai create the perfect setting for year-round outdoor living and entertaining, and no rear neighbors for privacy. Property has fiber optics, 50 amp car charger in garage, and nest thermostat for A/C. The primary suite features a walk-in closet and spacious bath with dual sinks newly remodeled. Additional highlights include a 2-car garage, irrigation system, rain gutters, public utilities, and low annual HOA dues. New Roof (2025), New Water Heater & A/C (2024). Conveniently located near top-rated Seminole County schools, parks, shopping, dining, major roadways, and the 417.

1055 Chesterfield Circle, Winter Springs

$445,000

3 Beds ⋅ 2 Baths ⋅ O6410431 MLS

Under contract-accepting backup offers. Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool home tucked within the peaceful established subdivision of Oak Forest. Step inside to an open floor plan with immediate views of the backyard oasis, creating a light and airy feel perfect for everyday living and entertaining. The spacious kitchen opens seamlessly to the living and dining areas and features granite countertops, stainless steel appliances and a breakfast bar ideal for gathering with family and friends. The floor plan offers comfortable living spaces, while sliding doors lead out to the screened porch overlooking the private backyard retreat. Enjoy Florida living year-round with the screened patio, resurfaced pool featuring a PebbleTec finish completed in 2020, a fully fenced yard and plenty of room to relax or entertain outdoors. Major updates provide peace of mind, including the roof, AC, and water heater all replaced in 2015. Additional improvements include gutters added in 2020, pool pump replaced in 2016, new garage door opener in 2025, and updated microwave, dishwasher, and garbage disposal in 2026. This home sits on a spacious lot in a quiet, established neighborhood. Conveniently located near SR-417, shopping, dining, and top-rated Seminole County schools - walking distance to both the elementary and middle school. This home is also just minutes from Trotwood Park and Central Winds Park which features pickleball courts, sports fields, playgrounds, walking trails, and community events.

877 Benchwood Drive, Winter Springs

$410,000

3 Beds ⋅ 2 Baths ⋅ O6411321 MLS

Under contract-accepting backup offers. Welcome home to this beautiful, move-in-ready residence nestled in the highly sought-after Greenbriar at Tuscawilla community! This charming 3-bedroom, 2-bath home offers a highly functional single-story layout with an open floor plan and split-bedroom design, creating both comfortable everyday living and added privacy. The spacious living and dining areas feature vaulted ceilings and abundant natural light, making the home feel bright and inviting. The oversized primary suite offers a relaxing retreat complete with a large walk-in closet and private bath. Enjoy low-maintenance living with a low HOA that includes lawn maintenance, plus access to the community pool. As an added option, Tuscawilla Country Club offers dining, fitness facilities, a junior Olympic pool, tennis courts and leagues, pickleball, golf, and social events. Conveniently located near SR 417, SR 434, and Red Bug Lake Road, you'll have easy access to shopping, dining, and entertainment. Don’t miss your opportunity to own this sweet home in one of Winter Springs’ most desirable communities. Schedule your private showing today!

907 Glen Abbey Circle, Winter Springs

$420,000

3 Beds ⋅ 3 Baths ⋅ O6408695 MLS ⋅ 1406 BLDG.

Welcome to this almost-new townhome in beautiful Winter Springs! Located in the desirable Hickory Grove community, where you will find a maintenance free living, relaxing pool and cabana, playground for the little ones and a dog park for your furry friend, all just a few steps away and NO CDD to pay. The monthly HOA dues also include: landscaping, irrigation, weed control, exterior paint, roof, 1GB of high speed internet and cable premium package. This stunning residence has been tastefully decorated and offers the perfect blend of modern style, comfort, and convenience. Your front door opens up to the serene parks, fountains and walkways just across the street from your favorite stores and restaurants. Enjoy an open-concept layout with plenty of natural light, a modern kitchen with state of the art SS appliances, quartz counters and a beautiful island to entertain your guests. 3 bedrooms, 2.5 bathrooms, and a 2-car garage, and much more. This home is move-in ready and designed for easy living. Upstairs, the generous primary suite offers a private retreat with an en-suite bath and ample closet space. Built with today’s lifestyle in mind, this home also includes the peace of mind of a builder warranty, this is a fantastic opportunity to own a like-new home in one of Central Florida’s most sought-after areas with top-rated schools.

1406 Blumberg Boulevard, Winter Springs

$469,000

3 Beds ⋅ 2 Baths ⋅ O6407546 MLS

Under contract-accepting backup offers. Welcome to 143 Hayes Rd, Winter Springs a rare opportunity to own a beautifully renovated home in one of the area’s most exclusive and sought-after locations. Situated on a huge corner lot surrounded by mature trees, this property offers privacy, space, and the freedom of no HOA with low property taxes. This home has been recently updated and is truly move-in ready, featuring a 2017 roof, brand-new AC system, fresh interior and exterior paint, new carpet, and a newly finished driveway. Every detail has been thoughtfully refreshed to provide comfort and peace of mind for the next owner. Step outside and imagine yourself enjoying your own private pool while being surrounded by peaceful natural scenery — the perfect setting for relaxing weekends, entertaining guests, or simply enjoying Florida living at its best. Conveniently located near top-rated schools, shopping, dining, and major highways while still offering the tranquility of a private retreat. Homes like this in Winter Springs rarely hit the market!

143 Hayes Road, Winter Springs

$409,990

4 Beds ⋅ 3 Baths ⋅ O6407275 MLS ⋅ 10 BLDG.

Under Construction. The Catalina II offers a spacious and modern open-concept design on the main level, creating the perfect setting for entertaining, everyday living, and gathering with family and friends. This thoughtfully designed townhome features 4 bedrooms, 2.5 bathrooms, and a rear-loading 2-car garage, blending functionality with contemporary style in desirable Winter Springs, FL. The owner’s suite serves as a private retreat, complete with a well-appointed ensuite bathroom and a generous walk-in closet. The chef-inspired kitchen is designed for both beauty and performance, showcasing stainless steel appliances, a walk-in pantry, and a convenient breakfast bar ideal for casual dining and hosting.

1270 Tarflower Drive, Winter Springs

$475,000

3 Beds ⋅ 2 Baths ⋅ O6396980 MLS

Beautifully maintained 3-bedroom, 2-bathroom home located in the highly sought-after Highlands community in Winter Springs, FL. Real hardwood floors flow through the main living areas, adding warmth and timeless appeal. The spacious kitchen features elegant stone countertops, ample cabinetry, and plenty of room for cooking and entertaining. The primary suite serves as a relaxing retreat with an en suite bathroom that includes a dual sink vanity, a large soaking tub, and a walk-in closet. The split-bedroom layout offers added privacy, while the two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to enjoy the oversized lot, offering plenty of space for outdoor living and activities. The screened-in lanai is perfect for enjoying Florida’s weather year-round, whether you're relaxing or hosting guests. A 2-car garage adds convenience and extra storage. Residents also enjoy access to a community pool, as well as tennis courts, pickleball courts, and scenic nature trails, perfect for an active and social lifestyle. Ideally located in Winter Springs, this home is close to top-rated Seminole County schools, beautiful parks and trails, shopping and dining options, and provides easy access to major roadways for commuting to Orlando and surrounding areas. Enjoy a balance of peaceful suburban living with everyday conveniences just minutes away.

629 Ryan Court, Winter Springs

$488,000

4 Beds ⋅ 3 Baths ⋅ TB8504998 MLS

Motivated sellers *** Seller offering up to $8,000 toward buyer’s closing costs! Take advantage of this incredible opportunity to reduce your out-of-pocket expenses and make homeownership more attainable. THIS IS THE ONE you’ve been waiting for in Winter Springs. This spacious 4-bedroom, 2.5-bath home with 2,152 SqFt offers the perfect combination of space, flexibility, and income potential. Located in a non-flood zone with low HOA and NO rental restrictions, this is a rare find for both homeowners and savvy investors. Featuring a unique three-level layout, the home includes formal living and dining areas plus a versatile Family room—perfect for movie nights, game days with friends, or even unforgettable family karaoke evenings. Step outside and get ready to fall in love. The fully fenced backyard is built for lifestyle: the spacious covered and screened terrace invites you to enjoy your morning coffee by a charming gas fire pit, unwind with evening cocktails, roast marshmallows around a natural fire pit, or host the perfect BBQs. The outdoor space also features a small play area, while still offering ample room for pets to run freely. This is Florida living done right. Freshly painted, meticulously maintained, with updated bathrooms and a functional kitchen ready for immediate enjoyment. For added value and peace of mind, the property includes a water softener system throughout the home and an alkaline water filtration system at the kitchen sink—features today’s buyers truly appreciate. Located near top-rated Seminole County schools, parks, shopping, and major highways with easy access to Orlando. Opportunities like this are rare and move FAST. Schedule your private showing TODAY before it’s gone.

1304 Ortega Street, Winter Springs

$404,000

3 Beds ⋅ 2 Baths ⋅ O6404240 MLS

Beautiful 3-bedroom, 2-bath pool/spa home located in the highly desirable Sunrise Estates in Winter Springs, featuring a split floor plan on nearly ¼ acre with no front neighbors for added privacy. This home boasts a newer roof and newer pool/spa heater, making it perfect for entertaining family and friends, while the oversized backyard and large covered screened-in patio provide an ideal outdoor living space. Inside, enjoy a wood-burning fireplace for warmth and ambiance on cooler evenings, along with no carpet throughout for easy maintenance. Sunrise Estates offers open parks, tennis courts, basketball courts, and softball fields, and is zoned for A-rated Seminole County schools, making it perfect for a growing family. Conveniently located near major highways, dining, shopping, and just minutes from Oviedo and Winter Park—schedule your private tour today!

1024 Dinero Drive, Winter Springs

$499,999

3 Beds ⋅ 3 Baths ⋅ O6401888 MLS

Welcome to the highly sought after Fairway Oaks at Tuscawilla community, where homes like this rarely come available! This spacious home features 3 bedrooms and 3 full bathrooms, 2,378 square feet of thoughtfully designed living space, and a private pool in the generously sized, fenced-in backyard oasis. As you enter through the private courtyard, discover the details that make this home so special. The luxury vinyl floors throughout the first floor are not only beautiful but designed for durability. The great room features a floor to ceiling wood burning stone fireplace, soaring cathedral ceilings, and stunning oversized windows which fill the home with natural light throughout. Granite countertops, a breakfast bar, ample storage, and ALL NEW black stainless-steel appliances are just some of the reasons you’ll love this kitchen, which flows naturally into the formal dining room. The first bedroom is situated downstairs, and includes its own ensuite full bathroom, perfect for those needing an in-law suite or multigenerational living. Upstairs you’ll find another full bathroom with a shower/tub combo, the second bedroom, and the primary suite. The primary bathroom includes a walk-in shower and separate bathtub, and the bedroom showcases a private balcony with recently updated flooring; the perfect place to relax and unwind while overlooking the 15th hole of the Tuscawilla golf course! At the back of the house an enclosed Florida room adds additional flex space to fit any lifestyle. Enjoy Florida living in the private pool and large fenced-in backyard, with peace of mind knowing that lawncare (front and back) is covered by the very reasonable, low-cost HOA! Additional features include updated electric panel (2024), new vent fans in all 3 bathrooms, and UV lights installed in both AC intakes to improve the air quality throughout the house and increase energy efficiency. Zoned for some of the best schools Central Florida has to offer, just minutes away from the Oviedo Mall, and right around the corner from the Tuscawilla country club which offers a fitness center, tennis courts, a junior Olympic sized swimming pool, and an 18-hole golf course, you really can’t beat this location! Schedule a showing today!

1200 Royal Oak Drive, Winter Springs

$410,000

3 Beds ⋅ 2 Baths ⋅ O6401016 MLS

Under contract-accepting backup offers. Welcome to Tuska Oaks—a well-established community in the heart of Winter Springs known for its convenience and neighborhood feel. Tucked away on a quiet cul-de-sac, this 3-bedroom, 2-bath home offers over 1,600 square feet of comfortable living space with a smart, open layout and soaring vaulted ceilings. The kitchen features granite countertops, stainless steel appliances, and ample cabinet space, opening seamlessly into the dining room area—ideal for everyday living and entertaining. Tile flooring runs throughout the home with laminate or LVP in the bedrooms and bathrooms, making maintenance simple and clean. Major updates have already been handled for you, including a roof replaced in 2018, A/C replaced in 2020, newer water heater (2024), and interior and exterior paint completed just 3 years ago. The secondary bathroom has been fully remodeled, adding a fresh, updated touch. Step outside to a screened-in back porch overlooking a fully fenced backyard, offering privacy and space for pets, play, or outdoor gatherings. Residents of Tuska Oaks enjoy a low HOA and access to a community pool , all while being conveniently located near shopping, dining, and top-rated Seminole County schools.

560 Pleasant Grove Drive, Winter Springs

$459,900

4 Beds ⋅ 4 Baths ⋅ O6395600 MLS ⋅ Na BLDG.

One or more photo(s) has been virtually staged. SELLER CONCESSION 6 MONTHS PAID HOA FEES!!! Welcome to an exceptional opportunity in the heart of Winter Springs, where lifestyle, location and luxury converge at 1128 Spotted Sandpiper Loop. Positioned in a thoughtfully planned community, this residence offers the ideal balance of elegance and everyday convenience. From moment you arrive, you are embraced by a neighborhood designed for connection and ease, tree-lined streets, inviting trails and a sense of community that makes this address desirable. Ideally just moments from Winter Springs Town Center, this residence offers an accessible lifestyle. Natural light fills the interiors, creating a warm and welcoming ambiance suited for relaxed living and stylish entertaining. Thoughtfully designed across three levels, the first floor offers a private retreat ideal for guests, complete with its own en suite. The second level unfolds into the heart of the home, featuring an open concept living space with a well-appointed kitchen, dining area and inviting family room. The third floor is dedicated to restful living, showcasing three bedrooms, two full baths and a convenient laundry area. Updates include new carpeting throughout with transferable warranty and fresh interior paint reflecting the home's meticulous maintenance. Beyond your doorstep, accessibility becomes a defining feature of this lifestyle. Enjoy proximity to local shops, dining, parks and top-rated Seminole County schools, all just moments away. With easy access to major roadways, commuting to downtown Orlando, nearby business hubs, or weekend destinations is simple and efficient. Amenities include community pool, trails and accessibility to area favorites.

1128 Spotted Sandpiper Loop, Winter Springs

$479,000

3 Beds ⋅ 2 Baths ⋅ O6393850 MLS

Located within the gated community of Eagle’s Watch in Seminole County, this well-maintained residence offers a functional layout, quality features, and a highly convenient location. Situated on a quiet cul-de-sac and backing to a greenbelt, the property provides added privacy along with direct access to the Florida National Scenic Trail system for outdoor recreation. The home features a modern open-concept floor plan with high ceilings and abundant natural light throughout the main living areas. A covered front porch enhances curb appeal, while the interior layout is designed for both everyday living and entertaining. The fenced backyard includes mature trees and usable space, creating a comfortable outdoor setting. Eagle’s Watch is a gated, tree-lined, golf cart-friendly community offering amenities such as a pool, basketball courts, and playground, with front yard maintenance included through the HOA. Conveniently located near Highway 417 and Winter Springs Town Center, the home provides easy access to shopping, dining, and everyday essentials, along with zoning for top-rated Seminole County schools. This property combines a desirable setting, thoughtful design, and low-maintenance living within one of Seminole County’s most sought-after communities.

107 Golden Crest Court, Winter Springs

$400,000

3 Beds ⋅ 2 Baths ⋅ O6391915 MLS

A home with its very own private oasis. This home boasts a 2019 AC UNIT and a 2021 ROOF REPLACEMENT. Enjoy the simple living that Seminole County offers. An updated kitchen centers the floorplan of 1307 Ortega St with an adjoining living room, dining room, and fully enclosed Florida room with attractive cedar plank built in storage. The true showstopper of the home sits in the backyard though. Escape through French doors off the Florida room into a backyard that presents itself immediately with a majestic and well loved Oak Tree that towers over the backyard. Enjoy a quiet morning coffee as you contemplate life over your fish holding pond or decide to stay at the small seating area that resides in the far corner of the backyard. Sunrise in Winter Springs is a well established neighborhood with a community park within a short walk of this home! Rainbow Elementary, the zoned school, is an A-Rated school! 1307 Ortega St has been owned by the same family since construction and is now available on the market for the first time ever! Other enjoyable features of 1307 Ortega include a bonus storage room, a garage with AMPLE built in storage, and cheaper sprinkler bills thanks to the environmental meter attached to the home. Come see this well maintained home, just minutes to schools, food, grocery, and more, today!

1307 Ortega Street, Winter Springs

$410,900

3 Beds ⋅ 2 Baths ⋅ O6387051 MLS

Virtually Staged. Location, comfort, and functionality come together in this well-designed 3-bedroom, 2-bath home in desirable Winter Springs! Featuring a sought-after split-bedroom floor plan, this home offers privacy and a layout that's perfect for everyday living. The open kitchen includes a casual eat-in dining area and flows effortlessly into both the formal dining room and spacious living room, creating an inviting space for entertaining family and friends. Step outside to an oversized covered porch overlooking a large backyard with endless possibilities for outdoor living, gardening, play, or future enhancements. An added convenience is the garage's direct access to the backyard, making it easy to move equipment, work on projects, or enjoy the outdoor space. Ideally located in the heart of Winter Springs, you'll appreciate the convenience of being close to top-rated Seminole County schools, parks, shopping, dining, and major roadways, all while enjoying the charm and sense of community that make this area one of Central Florida's most desirable places to call home. This home offers the space, layout, and location buyers have been searching for. Schedule your private showing today!

1012 Forest Circle, Winter Springs

$484,900

4 Beds ⋅ 3 Baths ⋅ O6386347 MLS

JUST REDUCED 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 Christmas tree! Can you see it? You will also notice that the entire home has been freshly painted with the woodgrain tile downstairs and the plush new carpeting upstairs! The kitchen, future home for all those family and friends baking, has been updated with quartz countertops, soft close cabinets, lighting and a stainless steel refrigerator. Don’t like Florida water, well you’re in luck, this home comes with a whole house water filtration system! To add to that, the roof and gutters are only 2-3 years old. Replaced in 2023! The A/C is 2015 and has had annual maintenance performed. So you’re thinking that you like to be outside. Gotcha covered there too. This home has an oversized porch with a fenced in backyard that has a banana, avocado and papaya tree. You also have access to a pool, tennis/pickleball courts and a park. If walking trails are your thing, there’s one in the Oviedo/Lake Mary area. To top your day off, enjoy downtown Winter Springs that is only a mile away!! What else could you possibly ask for! This home really has everything and it’s waiting for you. SELLERS PUT IN A NEW WATER HEATER!!!!! SELLERS ARE GIVING A HOME WARRANTY FOR 1 YEAR!!!!!

632 Blenheim Loop, Winter Springs

$423,997

3 Beds ⋅ 2 Baths ⋅ O6383538 MLS

PRICE IMPROVED + SELLER CONTRIBUTES TO CLOSING COSTS! Back on Market Financing Fell Through, Not the Home. Heated Pool | Winter Springs | Move-In Ready. Welcome to this well-maintained 3-bedroom, 2-bath home in an established Winter Springs neighborhood, featuring a private, heated pool with screen enclosure ready to enjoy year-round. The updated kitchen with gas range flows into a bright, open living area anchored by a cozy wood-burning fireplace, a rare find in Central Florida. Step outside to your screened pool and fully fenced backyard, ideal for entertaining or quiet weekends at home. A 2-car garage and tree-lined streets complete the setting. HOA dues are just $35.35/month notably low for a community with this level of amenity access. Zoned for Seminole County schools (buyer to verify assigned schools with the district). Minutes from walking and biking trails, shopping, and major roadways. Seller will contribute toward buyer's closing costs. FHA | VA | Conventional | Cash all financing welcome. Schedule your showing today.

872 Falkirk Drive, Winter Springs

$499,900

O6376787 MLS

DRIVE BY ANYTIME/ANY DAY! This property is one of the last C-2 zoned properties in Seminole County (unincorporated) that has allowance for autobody and paint (since 1981 and still active!). There is a nice log cabin style office modular near the entrance with ac and power. The entire lot is security fenced and it has 2 huge rolling gates!! Currently rented to auto professionals in the front lot, and back lot is vacant. Perfect to keep the tenants up front and use the back-lot yourself!! Or..The tenants have a clause in their lease to vacate if sold, so you can keep them or use the entire property yourself!!! ***************************************************************************************************************** Body Shop Property next door is ALSO available for sale and listed on the MLS (MLS # O6380976--PENDING). Buy one, buy both, buy all, buy some!!! SELLER FINANCE WITH JUST 200k DOWN AND EASY TERMS!!!!! I would love to answer any questions or help get you in this place!! LEASE OPTION is also an option!!! Happy property hunting!

1050 Nursery Road, Winter Springs

$500,000

4 Beds ⋅ 2 Baths ⋅ O6374676 MLS

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 character and charm. Skylights in the living room and hallway flood the home with natural light, creating a bright and airy feel throughout the main living spaces. Conveniently located near schools, parks, shopping, dining, and major roadways, this home offers the perfect blend of tranquility and accessibility in an established community.

1201 Wolverine Trail, Winter Springs

$449,000

3 Beds ⋅ 3 Baths ⋅ O6340870 MLS

Virtually Staged. PRICED TO SELL AT 449,000!! *** A 4 BEDROOM-FOOTPRINT IS ALREADY RECORDED IN SEMINOLE COUNTY RECORDS, SO THIS 3 BEDROOM HOUSE CAN EASILY GIVE YOU THE ADDED VALUE AND OPPORTUNITY OVERLOOKING SERENE CONSERVATION & POND VIEW. *** WELCOME TO A BEAUTIFULLY MAINTAINED HOME OFFERING UNMATCHED LAYOUT FLEXIBILITY, AND PEACE OF MIND WITH A STRONG MECHANICAL FOUNDATION: FEATURING ROOF, A/C & WATER HEATER UPDATED IN 2017. STEP INSIDE TO AN INTERIOR THAT FEELS FRESH AND BRAND NEW WITH FRESH INTERIOR PAINT THROUGHOUT, GORGEOUS NEW WOOD FLOORING AND PRISTINE NEW CARPET UPSTAIRS. EVERY WINDOW IS ELEVATED WITH CLASSIC, HIGH-END WOOD SHUTTERS. THE SPACIOUS, LIGHT-FILLED KITCHEN IS A CHEF'S DELIGHT, BOASTING PREMIUM STONE COUNTERS, STONE BACKSPLASH AND SLEEK STAINLESS STEEL APPLIANCES THAT COMPLEMENT A GOURMET GAS RANGE AND ENOUGH ROOM FOR A KITCHEN TABLE. THE ADJACENT FAMILY ROOM OFFERS DURABLE, ELEGANT TRAVERTINE FLOORING, WHICH FLOWS TOWARD A STRIKING STAIRCASE ADORNED WITH CUSTOM IRON AND WOOD RAILING. STEP OUT THE SLIDING DOORS INTO A CUSTOM SANCTUARY FEATURING A PREMIUM ARCHITECTURAL TRELLIS SYSTEM THAT ALLOWS YOU TO SHIFT THE LOUVERED BLADES FOR INSTANT SHADE OR FULL FLORIDA SUN. THIS PRIVATE BACK YARD PERFECTLY FRAMES AN UNTOUCHED CONSERVATION AREA AND SCENIC NEIGHBORHOOD POND. THE 2ND FLOOR HOUSES A GRAND PRIMARY SUITE COMPLETE WITH VAULTED CEILINGS AND A PEACEFUL PRIVATE WINDOW VIEW OVERLOOKING THE BACKYARD OASIS. THE 2ND FLOOR LOFT/FLEX ROOM MAY BE MADE INTO A 4TH BEDROOM OR OFFICE. COMPLETE WITH CLEAN 2 CAR GARAGE. THIS MOVE-IN WINTER SPRINGS GEM OFFERS THE PERFECT BLEND OF MODERN COSMETIC UPDATES, SOLID MECHANICAL HISTORY AND SERENE PRIVACY. LOCATION OFFERS TOP-RATED SCHOOLS, DINNING AND SHOPPING. THIS PROPERTY IS A RARE FIND! SCHEDULE YOUR SHOWING BEFORE IT IS GONE!!

122 Stone Gable Cir, Winter Springs

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