Winter Springs Single Family Homes For Sale - 136 homes

Remarks: Under contract-accepting backup offers. Welcome to 408 Avondale Court, a custom estate built by Von Jacobs in 2003 & located in the highly desirable, gated Wicklow Greens community in Winter Springs. Set among just 48 custom homes, this stunning residence sits on arguably one of the best lots in Tuscawilla. This .48 acre property is situated in the rear of the neighborhood, on a quiet cul-de-sac where you can enjoy serene views of conservation & Howell Creek in the back. This home features 5 bedrooms, 4.5 bathrooms, and 3,850 square feet of thoughtfully designed living space. From the moment you enter, you’ll appreciate the elegance of wood flooring throughout the first floor, soaring ceilings, and the ideal layout for both everyday living and entertaining. The generously sized kitchen features wood cabinetry, a long center island that offers plenty of countertop space for meal prep, a wet bar, and ample seating space. All 5 bedrooms are conveniently situated on the lower level, with an oversized 650 sq ft loft & 4th full bathroom upstairs. This layout is ideal, offering several options no matter your stage of life. Step outside to your private backyard retreat, which features pavers, a pool and a gas-heated spa, surrounded by peaceful conservation views—the perfect place for relaxing evenings or weekend gatherings.This home has been meticulously maintained by its original owner and updated with major improvements including a new roof (2022), exterior paint (2022), and newer mechanical systems such as A/C units (2015 & 2016) and water heaters (2022 & 2016). A 3-car side-entry garage completes the picture, offering both convenience and curb appeal. Ideally located just minutes from the Tuscawilla Country Club, residents can enjoy convenient access to golf, dining, and social membership opportunities, making this home perfect for those seeking an elevated Central Florida lifestyle. The community is zoned for top-rated schools including Winter Springs High, Indian Trails Middle, and Rainbow Elementary, with additional private school options nearby, such as The Geneva School, Masters Academy, St. Luke’s, Trinity Prep, and Choices in Learning charter school. This is a rare opportunity to own a luxury home in one of Winter Springs’ most coveted gated neighborhoods. So hop onto your golf cart, and zip on by to see this beauty before it's too late!

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Jennifer Christ (407-474-7823)

Remarks: 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 wood cabinets with plenty of space for all those kitchen essentials and granite countertops with new stainless appliances. Along with the master suite features LVP flooring, a new vanity with granite and a tub/shower combo. Other three bedrooms include LVP flooring and ample closet space. Guest bath also has a new vanity with granite too! Close to the bus line and convenient to major highways, shopping and dining. This home is well maintained and move-in ready for a buyer like YOU! Schedule a showing today as this home wont last long! Roof is 2018 & A/C is 2025

Listing is courtesy of: HD REALTY LLC (407-260-8800)

Listing Agent: Nicole Anderson (407-461-4861)

Remarks: POOL HOME + NEW ROOF! Welcome to this beautifully upgraded 3-bedroom, 2-bath residence with a 2-car garage, perfectly positioned in one of Winter Springs’ most sought-after, established neighborhoods with NO HOA. This home features a private, fully fenced backyard oasis with a sparkling pool—ideal for entertaining, relaxing, and enjoying Florida living year-round. A brand-new roof will be installed, offering added value and peace of mind. Conveniently located just minutes from top-rated Seminole County schools, scenic parks, premier shopping, dining, and major highways for an easy commute. Rare opportunity to own a move-in-ready pool home in a prime location—schedule your showing today

Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)

Listing Agent: Melissa Maldonado (646-943-4002)

Remarks: Under contract-accepting backup offers. 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 featuring brand-new luxury vinyl plank (LVP) flooring installed in 2025 and elegant 5½-inch baseboards throughout. The heart of the home is the STUNNING, FULLY REMODELED KITCHEN (2022), designed for both everyday living and entertaining. It boasts STAINLESS STEEL APPLIANCES, a LARGE QUARTZ ISLAND WITH BUILT-IN CABINETRY, 42-inch maple wood cabinets in a rich cashew finish with cabinet molding, SOFT CLOSE DRAWERS, and abundant horizontal storage with convenient pull-outs. A double oven, eat-in kitchen space, and open flow into the family room make this layout as functional as it is inviting. Both bathrooms were tastefully updated in 2025, featuring custom lighting and soft-close cabinetry, creating a modern feel in both the primary and secondary baths. Major system upgrades provide peace of mind, including a roof replaced in 2016, ANDERSON DOUBLE PANE LOW-E WINDOWS, Andersen French sliding patio door added in 2021, enhancing energy efficiency and natural light throughout the home. Step outside to your expansive 27’ x 10’ covered and screened lanai—perfect for relaxing or entertaining—with no rear neighbors for added privacy. The backyard also includes a storage shed on a durable 4-inch concrete slab, installed in 2018. With its extensive upgrades, prime location, and turnkey condition, this home truly checks every box. Don’t miss your opportunity to own a beautifully maintained property in the heart of Winter Springs!

Listing is courtesy of: VALENCE REALTY GROUP (407-797-5034)

Listing Agent: Chuck Valence (407-797-5034)

Remarks: Under contract-accepting backup offers. Short Sale. This property has significant potential and is located in the highly desirable Tuscawilla Country Club area. This home features three bedrooms, two bathrooms, and a practical two-car garage. It's important to note that this property needs some tender loving care, and it may need a new roof. The current asking price has been strategically set to acknowledge the present condition of the home and the necessary improvements. This presents a unique opportunity for those looking to create a personalized living space in a fantastic location. The Tuscawilla Country Club area is well-regarded for its appealing amenities and its proximity to various local points of interest. We are confident that this property holds considerable promise for the Buyers who are prepared to invest in its renovation and make it their own.

Listing is courtesy of: INT'L PROFESSIONAL REALTY INC (407-699-7718)

Listing Agent: Maria Gonzalez Ortiz (407-545-9060)

Remarks: Under contract-accepting backup offers. Don’t miss the opportunity to see this exceptional property! Located in the desirable Ranchlands neighborhood of Winter Springs, this exceptional property sits on over 1.5 acres of land, offering both space and privacy. A large circular driveway provides easy access and ample parking. This well-maintained home features 4 bedrooms, 2 bathrooms, and over 2,100 square feet of living space, with a split floor plan ideal for both everyday living and entertaining. As you enter, you’re welcomed by a bright, open interior showcasing tile flooring throughout the home, high ceilings, and an abundance of natural light. The upgraded kitchen is a standout, featuring stainless steel appliances, granite countertops, plenty of cabinet storage and a kitchen nook. The spacious family room includes a cozy fireplace, along with a mounted TV and surround sound system that will convey with the home. The primary suite offers private access to the backyard through sliding glass doors, a walk-in closet, and a generously sized en-suite bathroom complete with dual sinks, and a tub/shower combo. Step outside to enjoy the expansive covered lanai—perfect for relaxing or entertaining—along with a 30' above-ground pool to enjoy Florida’s warm weather and a play area for the little ones. Additional upgrades include a home generator, AC and septic tank and pump all installed in 2017, a water heater in 2018, pool in 2020, roof in 2021 and pool pump in 2026. In addition to the attached 2-car garage, the property also features a 25' x 30' detached garage equipped with electricity and AC—ideal for extra vehicles, a workshop, or storage. A side-entry gate provides access for RV or boat parking to store in your backyard. With no HOA, you’ll enjoy the flexibility to use the property as a primary residence, investment, or income-producing opportunity. This hidden gem offers a peaceful, country-style setting while still being conveniently located near major roads, shopping, and dining. Come see it today and make it yours!

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Zac Hernandez (407-576-7622)

Remarks: Welcome home to this cozy 3-bedroom, 2-bath bungalow-style home located in the resort-like Highlands community, offering 1,178 sq. ft. of living space. This home features vaulted ceilings, ceramic tile throughout, fresh interior paint, and a newly renovated kitchen with granite countertops, solid wood shaker-style cabinets, and black appliances. Major updates include a 2025 water heater and a new electrical panel inside and outside. The generously sized primary bedroom includes a built-in California Closets system, providing stylish and highly functional custom storage. The secondary and third bedrooms are also well-sized—perfect for guests, family, or easily converted into a home office. Washer and dryer are included in the sale. Enjoy the covered and screened lanai overlooking a charming New Orleans-style courtyard with pavers, a firepit, and a lamp post. The oversized, fully fenced, and cleared backyard offers plenty of space to relax, entertain, or garden, providing a strong sense of privacy. The Highlands is a highly sought-after, established community with low HOA fees and beautiful mature trees throughout. Amenities include an Olympic-size community pool, walking trails, playground, tennis court, volleyball court, and a clubhouse. Ideally situated just off State Road 434 Florida and Tuskawilla Road, this home offers quick access to Winter Springs Town Center for shopping and dining, and is just a short stroll from Torcaso Park—a lively neighborhood park featuring basketball courts, soccer and football fields, playgrounds for all ages, a splash pad, sand play areas, and picnic pavilions, perfect for both active days and relaxed family outings.

Listing is courtesy of: MILLENIUM REALTY GROUP (407-277-1400)

Listing Agent: Irina Carp (407-969-9937)

Remarks: A truly rare find in Winter Springs. This equestrian-friendly, lakefront estate is complete with its own private tennis court, a solid block-constructed horse barn, and room to enjoy every part of the lifestyle. All of this, tucked in a quiet setting that keeps you close to the heart of Orlando, with the added benefit of being just 2 miles from The Geneva School, one of the area’s premier private education options. Originally built in 1964, the home was thoughtfully expanded in 1994, creating a larger, more functional layout while preserving its character. Today it offers over 3,000 SF overlooking the shimmering waters of Little Lake Howell. Enjoy west-facing sunset views framed by mature cypress trees. Host friends for tennis or pickleball right in your backyard. The sizeable horse barn was engineered for exceptional durability, built with block construction and poured concrete for maximum strength. The main home includes a 3-car garage, and the barn adds an oversized carport that can easily double as covered boat storage.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Kris Kennedy (813-947-3509)

Remarks: Warm and inviting home located in the highly sought-after Highland Village community of Winter Springs—where residents love to live and rarely want to leave. This 2-bedroom, 2-bath home features an open floor plan, abundant natural light, and no carpet throughout. The spacious living and dining areas open a comfortable layout, perfect for everyday living or entertaining. The primary bedroom is generously sized with a large walk-in closet, and the primary bathroom has been updated with a sink, faucet and mirror. The secondary bedroom is also well-sized and versatile. The guest bathroom has been updated with a new vanity and mirror. The kitchen offers ample storage, includes all appliances, and opens directly to the private backyard—complete with a covered patio and ceiling fan, ideal for relaxing outdoors. Seller has recently updated the following: replace all interior doors, all new faux window blinds for all windows and crown molding in living areas. All appliances will stay including the washer and dryer! Enjoy living in a vibrant, well-maintained community with top-rated schools and fantastic amenities including a pool, tennis and pickleball courts, volleyball court, playground, and scenic walking trails and low HOA costs. Conveniently located near SR 434 and Tuskawilla Road, just minutes from Winter Springs Town Center, shopping, dining, and a short walk to Torcaso Park. Schedule your private showing today.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Dan Goodman (407-212-1012)

Remarks: Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to own one of the most beautifully updated homes in the community! Positioned on a desirable corner lot with ample parking, this fully renovated 3-bedroom, 2-bathroom home stands out as a rare find offering both style and convenience. From the moment you step inside, you’ll notice the thoughtful upgrades throughout, including brand-new flooring, a completely redesigned kitchen, modernized bathrooms, updated plumbing, and new energy-efficient windows. all creating a truly move-in-ready experience. Major systems have already been taken care of for peace of mind, with the roof replaced in 2015 and AC updated in 2019. Step outside to your own private, fully fenced backyard oasis, featuring a paved outdoor space and covered patio perfect for entertaining, relaxing, or enjoying Florida living year-round. The property also includes a detached storage space, offering additional functionality and convenience. Located directly across from the community pool and amenities, you’ll enjoy easy access to everything this well-maintained neighborhood has to offer. The location is unbeatable just minutes from Winter Springs Town Center, Seminole County Bike Trail, Oviedo Mall, Publix, restaurants, and everyday essentials, along with nearby fire and police services for added peace of mind. This home checks all the boxes: location, upgrades, lifestyle, and value. Opportunities like this don’t come often, schedule your private showing today and see why this is truly one of the best homes in the neighborhood!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Yosseff Roman (407-394-5843)

Remarks: 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 one side of the home, while the remaining bedrooms and baths are off the family room, offering a functional split floor plan. The kitchen comes equipped with all appliances, granite countertops, extra storage, and a large breakfast bar, and is open to the family room. The master bedroom measures approximately 29’ x 15’ and features a large walk-in closet plus a linen closet, double vanities, a separate shower, and a jetted tub. There is a Jack-and-Jill bathroom between two of the bedrooms, and the third bathroom opens directly to the pool area. All bathrooms and the kitchen have been updated. All five bedrooms are carpeted, and the main living areas are tiled. The backyard features mature landscaping with fruit trees and is fully fenced for privacy. Additional features include an alarm system and keypad near the garage entry. This home is available for immediate move-in.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Ryan Langley (407-802-6462)

Remarks: Under contract-accepting backup offers. 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 the updated kitchen overlooks the family room and features refinished cabinetry with soft-close features, updated countertops, pantry storage, and a cozy dinette area. The primary suite opens to the pool through sliding doors and includes a walk-in closet and an en-suite bath with updated counters, while the secondary wing offers two bedrooms with a beautifully remodeled bathroom and linen storage, plus a third bedroom and another fully renovated bath. Plantation shutters throughout add charm and privacy, and the laundry room is conveniently located just off the garage. Outside, enjoy a fully fenced wrought-iron yard and a screened pool area with a recently redone pool cage, perfect for relaxing or entertaining. Additional highlights include a 3-car garage with shelving and attic storage, water softener, A/C approximately 3 years old, and roof approximately 6 years old—making this move-in-ready home an exceptional opportunity in a desirable Winter Springs location.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: Abby Nelson (407-571-1445)

Remarks: 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 space used as an office or guest room plus 2 additional bedrooms upstairs. Inside, you’ll find a bright, open floor plan that seamlessly connects the main living areas. The kitchen is equipped with stainless steel appliances (new double door fridge) and a convenient breakfast bar overlooking the great room, making it perfect for both casual mornings and entertaining guests. Step outside through French doors to a screened patio and cozy fire pit area, creating an inviting space to unwind year-round. The spacious primary suite includes a walk-in closet and an en-suite bath with dual vanities, a soaking tub, and separate shower. Updates include a 2018 roof, energy-efficient windows, water softener, rain gutters, and irrigation system. Residents enjoy access to community amenities including a pool, clubhouse, park, and scenic walking trails, all just minutes from major roadways, shopping, and dining. Schedule your private tour today!

Listing is courtesy of: BAILEY CAMPBELL PROPERTIES (321-228-7985)

Listing Agent: Nate Bailey (321-331-8658)

Remarks: 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 mind for years to come. Prime location close to shopping, restaurants, and supermarkets, offering both convenience and lifestyle.

Listing is courtesy of: JOY ESTATE ENTERPRISE INC (321-754-9131)

Listing Agent: Joyce Tang (407-666-9388)

Remarks: Welcome to this charming 3-bedroom, 2-bath home nestled on a spacious cul-de-sac lot in the heart of Winter Springs. Offering added privacy and room to spread out, the oversized homesite provides a peaceful setting while still being close to everything you need. Inside, you’ll find a warm and inviting interior with tile and wood flooring throughout, complemented by neutral tones that make it easy to personalize. The kitchen features solid wood cabinetry and updated appliances, blending functionality with classic style. Conveniently located near local shopping, dining, and everyday amenities in Winter Springs, this home offers the perfect balance of comfort, privacy, and accessibility. Don’t miss the opportunity to make it your own!

Listing is courtesy of: THE AGENCY FL (407-335-4119)

Listing Agent: Amanda Brown (386-248-5754)

Remarks: Under contract-accepting backup offers. Looking for a move in ready & affordable home in Winter Springs? This home features new paint and updated LPV flooring, with block construction, 2 Car Garage and an updated roof. You will enjoy a large backyard with no rear neighbors, a pond view, and Boat / RV Parking. With No HOA restrictions, you have the freedom to customize and personalize your space. Perfect for the family looking for the local Winter Springs / Seminole County Schools. *All information is intended to be accurate but is not guaranteed.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Ryan Minadie (407-765-9990)