Location: Winter Springs
Keyword(s): South Seminole Middle
Keyword(s) Middle School: South Seminole Middle
Do Not Show Listings
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,900,00074 Days on yellowkey MLS ID: O6388126
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6132 Built: 2026 Tax: $2,989 (2024)Community: Talis CrossingSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,989
Elementary School: Sterling Park Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: South Seminole Middle
Remarks: Discover the pinnacle of secluded luxury in this brand-new, 8,000 SF estate, nestled in picturesque Winter Springs. From the moment you arrive, the custom glass French entry doors hint at the artistry within. Stepping into the grand foyer, you are greeted by statement marble and mosaic flooring that sets a tone of elegance, a design narrative that flows seamlessly throughout the home. Designed for both grand-scale entertaining and intimate daily life, the main living spaces are simply breathtaking. The great room soars with 16-foot ceilings and celestial windows, anchored by a stunning custom fireplace and bookcase display. A bank of 18-foot sliding glass doors dissolves the line between indoors and out, opening to a sprawling 1,125 SF covered patio. The chef’s kitchen is a masterpiece of form and function, featuring a 13-foot island, floor-to-ceiling cabinetry, a pet-feeding station, electric vehicle garage hookup, and a full suite of WiFi-enabled GE Cafe appliances, including a double wall oven and a 48-inch refrigerator. The home offers a versatile and luxurious layout for multi-generational living or visiting guests, highlighted by two distinct primary suites. One wing is dedicated to a private retreat with two walk-in closets, separate vanities, and a spa-inspired wet room with a freestanding tub and a four-port shower system. On the opposite side of the home, a second primary suite offers equal luxury with a massive walk-in closet and its own spa-like wet room, ensuring complete privacy for all. Beyond the main living areas, discover a wealth of flexible spaces tailored to a modern lifestyle. A dedicated movie theater or fitness center is pre-wired for the ultimate audio-visual experience, while two separate offices with storefront glass windows provide inspiring workspaces. A butler’s pantry/kitchen, wet bar with a beverage fridge, and a flexible flex room with a half-bath complete the impeccably designed interior. Outside, your private paradise awaits upon the spacious 1-acre parcel. The pavered pool deck surrounds a white quartz pool with a sun shelf and bubbler, all secured by a sleek black metal fence. Every detail has been considered, from the 150-gallon propane tank servicing the future summer kitchen and pool heater to the 4-zone HVAC, a commercial grade 50-year life-span TPO roof and two tankless water heaters for ultimate comfort. This is more than a home; it is a fully realized vision of eloquent Florida living.
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
214 PERTH CT, WINTER SPRINGS, FL 32708
$589,9006 Days on yellowkey MLS ID: O6407533
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2247 Built: 1980Monthly Fee: $67 Tax: $5,200 (2024)Community: Highlands Sec 6Single Family
Taxes:$5,200
Elementary School: Woodlands Elementary
Remarks: Exceptional investment opportunity in the highly sought-after Highlands community of Winter Springs! This rare and one-of-a-kind duplex features two spacious 3-bedroom, 2-bath units, each offering a 2-car garage, fenced backyard, soaring high ceilings, and thoughtfully designed floor plans that create an open and inviting feel. Both sides are professionally leased, currently generating a combined $3,200/month in gross rental income, with tenants responsible for their own utilities — and there is strong potential to increase rents in today’s market, making this an even stronger long-term investment opportunity. Recent updates provide peace of mind for years to come, including a new roof (2021), fresh exterior paint (2021), HVAC systems replaced on both sides (2021), updated windows, replumbing, updated tile flooring, and freshly painted interiors (2024). Both bathrooms have been professionally re-glazed to look like new while adding long-term durability and extended life to the surfaces. This duplex is extremely hard to find and offers endless possibilities for both investors and owner-occupants alike. It is an ideal income-producing property or perfect opportunity for a first-time homebuyer utilizing FHA financing — allowing the owner to live in one unit while renting out the other side to help offset the mortgage payment. Located in The Highlands, one of Winter Springs’ most desirable communities, residents enjoy scenic walking trails, a waterfront playground, sparkling community pool, clubhouse, and a low HOA — all within an amazing neighborhood known for its lifestyle and convenience. Whether you’re expanding your portfolio, house hacking, or searching for a flexible multigenerational opportunity, this property truly stands out from the rest.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Jeffrey Osborn, Jr (407-221-7134)
214 PERTH CT #A, WINTER SPRINGS, FL 32708
$589,9007 Days on yellowkey MLS ID: O6407330
Bed: 6 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2247 Built: 1980Monthly Fee: $67 Tax: $5,200 (2024)Community: Highlands Sec 6Apartment
Elementary School: Highlands Elementary
429 SHEOAH BLVD #12, WINTER SPRINGS, FL 32708
$180,00081 Days on yellowkey MLS ID: O6386330
REDUCED by $18,900 (9.5%) on 05/15/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1978 Tax: $2,420 (2024)Community: Baytree VillageCondo
Taxes:$2,420
Elementary School: Winter Springs Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom condo offering the perfect blend of style, comfort, and convenience in the heart of Seminole County. Inside, you’ll find quartz countertops throughout, stainless steel appliances, and stylish brick-lay tile flooring that adds character and a modern touch to the main living areas. The thoughtfully designed layout includes an interior laundry room complete with a full-size GE washer and dryer for everyday ease. The living room features double sliding glass doors that flood the space with natural light and open to your private balcony — the perfect spot for morning coffee or winding down in the evening. Enjoy a low-maintenance lifestyle with an HOA that covers exterior maintenance, roof, and common areas. Community amenities include a junior Olympic-sized pool, pickleball and basketball courts, scenic lake views with a covered pavilion, picnic areas with grills, and beautiful nature trails for outdoor enjoyment. Ideally located with easy access to UCF, 417, 17-92, SR 434, the Cross Seminole Trail, shopping, dining, and more — all while being zoned for top-rated Seminole County schools. Whether you're a first-time buyer, investor, or looking to downsize without sacrificing style, this condo checks all the boxes!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
721 GALLOWAY CT, WINTER SPRINGS, FL 32708
$359,9005 Days on yellowkey MLS ID: G5112246
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1840 Built: 1977Monthly Fee: $35Community: Highlands Sec 4Spa: YesSingle Family
Taxes:$0
Tax Year: 2025
Remarks: Welcome to this charming home with a beautiful Winter Springs address! Nestled on a quiet, tree-lined cul-de-sac in the legendary Highlands community, this updated two-story 3 bedroom, 2.5 bathroom custom home offers the perfect blend of warmth, comfort, privacy, and functionality — all backing up to a stunning natural spring preserve with trails and no rear neighbors! Offering an inviting layout filled with natural light, this home immediately makes you feel at ease the moment you walk through the door. The great room features soaring ceilings and warm wood accents that reflect character and charm rarely found at this price point. The updated kitchen is designed for both everyday living and entertaining, featuring granite countertops, recessed lighting, pantry storage, and newer modern stainless appliances. The kitchen flows seamlessly into the dining area. Sliding glass doors lead you to your private outdoor retreat. Step outside and enjoy true Florida living with a peaceful wooded view, oversized patio space, luxury hot tub spa with massage jets, grill, and patio table with umbrella— all included! Whether you're hosting guests or unwinding after a long day, this backyard setting is virtually impossible to beat. Upstairs, you’ll find three bedrooms, including a spacious Primary Suite with a huge walk-in closet. The Primary bath offers excellent potential, needing just a touch of TLC. Major updates provide peace of mind, including a Roof (2020), Hot Water Heater (2022), Electrical (2015), Kitchen Renovation (2015), first floor Windows replaced (2015), and AC (2017). Located in the amenity-rich Highlands, residents enjoy access to a community pool, clubhouse, tennis courts, playgrounds, scenic walking trails, and beautiful boardwalks — all with low HOA fees. Add in top-rated Seminole County schools and a location near shopping, dining, parks, and major roadways, and you have an incredible opportunity to own in one of Central Florida’s most loved communities. This is the kind of home buyers wait for — updated, private, full of character, and located in one of the best communities in the area. Don’t miss out!
Listing is courtesy of: BEACON REAL ESTATE & ASSOC (352-253-9200)
Listing Agent: Al Spry (407-310-3064)
622 ANHINGA RD, WINTER SPRINGS, FL 32708
$398,500146 Days on yellowkey MLS ID: O6369225
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1721 Built: 1988Monthly Fee: $106 Tax: $4,083 (2024)Community: GreenspointeSingle Family
Taxes:$4,083
Remarks: NEW ROOF 2026, HVAC 2017–2018, and water heater 2022, giving buyers peace of mind from day one. This 3-bedroom, 2.5-bathroom home offers over 1,700 sqft of living space in a top-rated Seminole County school zone. The layout is highly desirable with the primary bedroom downstairs, featuring a spacious walk-in closet and a large private bathroom with dual vanities, separate shower, soaking tub, and private toilet space. The home offers a bright and open layout with high ceilings and tile flooring throughout the main living areas. The kitchen includes granite countertops, stainless steel appliances, light cabinetry, and a breakfast bar, with sliding glass doors leading to a cute shaded backyard — perfect to relax or entertain. Upstairs you’ll find a spacious loft along with two additional bedrooms and a full bathroom, offering flexibility for guests, family, or working from home. Additional features include a 2-car garage, interior laundry room, neutral finishes throughout, and the home is vacant and easy to show. Ideally located near UCF, Valencia College, SR-417, SR-434, and I-4, with easy access to shopping, dining, Downtown Orlando, and Central Florida beaches.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
126 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$769,00047 Days on yellowkey MLS ID: O6392873
REDUCED by $16,000 (2.0%) on 04/15/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3205 Built: 2000Monthly Fee: $184 Tax: $9,320 (2024)Community: Seville ChaseSingle Family
Taxes:$9,320
Remarks: **Price Improvement** and a $10,000.00 SELLER CONCESSION towards buyer's closing costs ** Welcome to Seville Chase, a quiet gated neighborhood in Winter Springs with tree-lined streets and access to great schools like South Seminole Middle and Winter Springs High Schools.This 5-bedroom, 4-bath home sits on a large 0.41-acre lot and offers over 3,000 square feet of living space, mostly on one level, with a practical 3-way split floor plan that gives everyone their own space.As you walk in through the double front doors, you’ll notice the natural light, high ceilings, and nice touches like crown molding and archways. There’s a formal living and dining area up front, and a big family room that opens right into the kitchen—great for everyday living and hanging out.The kitchen has plenty of counter space, an island with bar seating, and a bright breakfast nook that looks out over the backyard and trees.Out back, you’ve got a covered lanai and a big yard with tons of potential. It’s already set up with electric, gas, and plumbing hookups—making it easy to add a pool or build out your dream outdoor space.The primary suite is set off to one side of the home for privacy and includes two walk-in closets, a spacious bathroom, and an attached flex room that works well as an office, nursery, or quiet retreat.On the other side of the home, there are three more bedrooms and two bathrooms, giving plenty of room for family or guests. Upstairs, there’s a fifth bedroom with its own bathroom plus an air-conditioned bonus/storage room—perfect for a game room, gym, or hobby space.The home has been well taken care of, with regular A/C duct and carpet cleanings, updated lighting, fresh exterior paint, and a painted garage floor. The extra-long, wide driveway gives you plenty of parking and leads to your three car garage.You’re also in a great location—close to shopping, restaurants, Oviedo Mall and the Winter Springs Town Center, with easy access to major roads and nearby employers like University of Central Florida.If you’re looking for space, a solid layout, and the chance to make a backyard your own, this home is definitely worth a look. Come check it out and see if it feels like home. Not local? No worries, please click on the two attached links,one being a video walk through and the other is your own personal 360 degree tour of the whole house, walk through it like you are in the home! Looking forward to seeing you!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Robert Johnson (407-920-4920)
630 FALCON CT, WINTER SPRINGS, FL 32708
$419,00033 Days on yellowkey MLS ID: O6396134
2 Days Off yellowkey (back on 5/13/2026)
REDUCED by $6,000 (1.4%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1360 Built: 1986Monthly Fee: $64 Tax: $1,454 (2024)Community: GreenspointeSingle Family
Taxes:$1,454
Remarks: Under contract-accepting backup offers. PRICE IMPROVEMENT! Welcome to 630 Falcon Ct in the Greenspointe section of The Highlands community in Winter Springs. Located just north of Orlando, this beautiful three-bedroom, two-bathroom home is now available. It features an open layout with abundant natural light, a cozy fireplace, and a custom chef’s kitchen designed for entertaining. One of the property's standout features is the screened-in back porch, which provides a peaceful setting to enjoy sunsets and nature within the large, partially fenced-in backyard. For added peace of mind, the home includes a brand-new tile roof and a clean four-point inspection completed in February 2026. As a resident of The Highlands, you will enjoy access to a private clubhouse, pool, pickleball and tennis courts, and a nature trail. For outdoor enthusiasts, there is also a public mountain bike trail located directly behind the clubhouse. The location is ideally situated for a well-connected lifestyle, offering easy access to the 417, I-4, 17-92, and 434, and is just minutes from the Winter Springs Town Center. Don’t Miss This Exceptional Opportunity - Schedule Your Private Showing Today!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Lisa Eichenblatt (407-595-2592)
140 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$779,90047 Days on yellowkey MLS ID: O6395594
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3129 Built: 1999Monthly Fee: $184 Tax: $5,857 (2024)Community: Seville ChaseSingle Family
Taxes:$5,857
Remarks: Welcome to a residence that truly embodies the phrase "NEIGHBOR'S ENVY, OWNER'S PRIDE" - an exceptional opportunity to own a showpiece home in the gated enclave of Seville Chase where smart living meets timeless elegance. This impeccably maintained, Solar-Powered SMART home offers an unparalleled blend of luxury, comfort, and sustainability. With Fully Paid Solar Panels keeping monthly electric cost under $45. The property greets you with commanding curb appeal, an extra-wide driveway, and an oversized side-entry garage, setting the tone for what lies within. Step inside to discover a designer-inspired interior adorned with gleaming cherry hardwood floors, elegant French doors, soaring tray ceiling, gracefully rounded architectural walls, and refined crown molding- each detail curated for those with a taste for elevated living. The heart of the home, a chef's kitchen, showcases Granite countertops, luxurious 42" cherry cabinetry with crown molding, a built-in desk, ample storage, and sleek stainless-steel appliances-perfectly blending form and function. A thoughtful 3-way split floor plan ensures privacy and space for all, with the primary suite offering a serene retreat complete with his and her walk-in closet and shared linen cabinetry. The fifth bedroom, with its custom-built-in shelving, is ideally suited for a nursery, personal library, or a quiet study. At the Rear, a True Showstopper awaits - an Expansive 1,000+ sq ft screened and paved lanai, fully outfitted with a complete outdoor kitchen, with ADDITIONALD NEW FULL SIZE REFRIGERATOR, Gas hook-up with Range, Microwave, etc. ready to host unforgettable evenings under the stars. Surrounded by Fresh landscaping, New Sod, and vibrant plantings with a gazebo this home has been lovingly updated with a new roof in 2016, solar in 2021, and two high-efficiency A/C systems (5-ton in 2016 and 3-ton in 2014). Ideally located in the highly acclaimed Seminole County School District, and just minutes from premium shopping and places to worship, this is more than a home, it's a lifestyle. Experience the beauty, serenity, and elegance this exceptional property has to provide. Your home awaits. DO NOT FORGET TO CLICK THE LINK TO SEE THE VIDEO WALK-THROUGH.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PROPERTIES (407-644-5385)
Listing Agent: Joji Jacob (407-747-3681)
506 CLUB DR, WINTER SPRINGS, FL 32708
$232,000180 Days on yellowkey MLS ID: O6362326
REDUCED by $5,000 (2.1%) on 05/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1002 Built: 1987Monthly Fee: $398 Tax: $1,908 (2024)Community: Cypress ClubTownhouse
Taxes:$1,908
Remarks: Move-in ready 2-bedroom, 2-bathroom single-level townhome in the heart of Winter Springs! Enjoy an updated kitchen with granite countertops, freshly painted interior, and new flooring. Relax on the screened and tiled lanai overlooking serene greenspace. This quiet, secluded community offers two assigned parking spaces and a community pool just steps from your front door. Residents enjoy amenities including community pool, tennis courts, lush parks, and scenic walking trails throughout the neighborhood. Conveniently located near shopping, dining, entertainment, major highways, and all the area’s conveniences.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Kathleen Harrison (407-435-9565)
446 CLUB DR, WINTER SPRINGS, FL 32708
$269,00096 Days on yellowkey MLS ID: O6380694
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1994Monthly Fee: $520 Tax: $886 (2024)Community: Cypress ClubTownhouse
Taxes:$886
Remarks: Discover effortless living in this immaculate 3-bedroom, 2-bath townhome nestled in the desirable Cypress Club at The Highlands. Thoughtfully maintained and beautifully updated, this residence offers the perfect blend of comfort, style, and convenience with a desirable split-bedroom floor plan—featuring one bedroom and a full bathroom on the main level, and the primary suite along with a third bedroom upstairs. Sliding glass doors open to a private screened porch, ideal for morning coffee, evening relaxation, or entertaining guests. This inviting space offers seamless indoor-outdoor living along with additional storage. The upgraded kitchen is a true highlight, showcasing solid wood cabinetry, modern countertops, and a breakfast bar perfect for casual dining or hosting friends and family. Two reserved parking spaces are conveniently located directly at your front door. Enjoy the resort-style lifestyle The Highlands is known for, offering a community pool, recreational building, tennis courts, and scenic hiking trails. Ideally located near I-4 and SR-417, commuting and weekend adventures are effortless. HOA fees provide exceptional value, covering exterior building and grounds maintenance, community amenities, —delivering peace of mind and truly low-maintenance living. IMPORTANT MESSAGE- While this townhouse HOA fees may seem higher, it covers roof replacement and maintenance (brand new 2026), exterior maintenance, landscaping, and more. A single-family home may have lower HOA fees, but usually comes with higher maintenance costs, more upkeep, and added stress - making the overall expense very similar in the end, with far less hassle in a townhouse community. Schedule your private showing today and make this exceptional townhome yours.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Hanoi Burgos (407-342-1539)
872 FALKIRK DR, WINTER SPRINGS, FL 32708
$438,99789 Days on yellowkey MLS ID: O6383538
REDUCED by $10,000 (2.2%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1554 Built: 1978Monthly Fee: $35 Tax: $2,381 (2024)Community: Highlands Sec 1Spa: NoSingle Family
Taxes:$2,381
Remarks: BACK ON THE MARKET DUE TO BUYERS FINANCING FALL TROUGH!! Beautifully maintained home located in one of the most desirable areas of Winter Springs, offering the perfect blend of comfort, convenience, and outdoor living. Surrounded by scenic walking and biking trails throughout the neighborhood, this home delivers a peaceful setting while staying close to everything you need. This property features 3 bedrooms and 2 bathrooms with a bright open floor plan ideal for both everyday living and entertaining. The kitchen is equipped with stainless steel appliances and flows seamlessly into the main living areas, creating a spacious and inviting atmosphere. Step outside to your private screened pool area, perfect for relaxing or hosting gatherings, all within a fully fenced backyard that provides excellent privacy. Whether enjoying Florida sunshine or evening outdoor dining, this space is designed for year-round enjoyment. Conveniently located near shopping centers, restaurants, and major highways, offering easy access to Orlando, employment hubs, and surrounding communities while still enjoying the charm of a sought-after residential area. This home combines a desirable location, functional layout, and outdoor lifestyle — making it an excellent opportunity for homeowners and long-term value. Some photos were virtually staged.
Listing is courtesy of: CAISSA REALTY INVESTMENT INC (407-364-3056)
Listing Agent: Elizabeth Rodriguez (407-480-8829)
10 MOREE LOOP #3, WINTER SPRINGS, FL 32708
$135,00097 Days on yellowkey MLS ID: O6381696
1 Days Off yellowkey (back on 5/8/2026)
REDUCED by $10,000 (6.9%) on 04/02/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1080 Built: 1973Monthly Fee: $413 Tax: $2,066 (2024)Community: Bay Tree Sec 10Condo
Taxes:$2,066
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. You will LOVE living in Baytree, a towhome styled condominium community in the desirable Highlands of Winter Springs! This home has been well loved and owned by the same owner for many years and is ready for YOU to make it YOURS. Offering a great floor plan and lots of space with a screen enclosed back porch and covered entry. Two large bedrooms on the 2nd floor and a convenient half bath on the first floor. Ample storage space! Appliances include NEW water heater (2026), washer/dryer, refrigerator, range and dishwasher! The Highlands community offers great amenities including a community pool, tennis/pickleball courts and walking trails! Located in Winter Springs and VERY close to Lake Mary, Maitland and major roads, shopping and dining. Ready to make your dreams of homeownership a reality? Schedule a tour today!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Carla Stanton (321-356-3370)
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00056 Days on yellowkey MLS ID: O6392856
2 Days Off yellowkey (back on 5/8/2026)
REDUCED by $10,000 (3.5%) on 04/22/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1460 Built: 1995Monthly Fee: $520 Tax: $1,765 (2025)Community: Cypress ClubTownhouse
Taxes:$1,765
Remarks: Under contract-accepting backup offers. Welcome to 476 Club Drive, a beautifully cared-for townhome nestled in the highly sought-after Cypress Club section of The Highlands in Winter Springs—a community known for its incredible amenities and natural surroundings. This spacious 3-bedroom, 2-bath residence blends comfort, functionality, and peace of mind with key updates already completed. Enjoy the benefits of a 2020 A/C system, a full repipe completed in 2016, a 2016 water softener, and an electric water heater approximately 9 years old. Even better, a brand-new roof is currently being installed and is fully covered by the HOA—adding long-term value and convenience. Inside, you’ll find an inviting layout with knockdown ceilings throughout the main level and an open living and dining area tucked toward the rear of the home for added privacy. Updated recessed lighting enhances the space, creating a warm and welcoming atmosphere. Just beyond, a step-down enclosed patio offers a serene retreat overlooking wooded views—perfect for relaxing or entertaining. The flexible floor plan includes a downstairs bedroom with an adjacent full bath, ideal for guests, a home office, or multi-generational living. Upstairs, two generously sized bedrooms feature soaring ceilings and abundant natural light. The primary suite offers ample closet space and tranquil views of the surrounding greenery, along with a spacious en-suite bath complete with a Jacuzzi tub and separate shower—perfect for unwinding after a long day. Cypress Club stands out as the only neighborhood within The Highlands with its own private pool, in addition to access to the community’s extensive amenities. Residents enjoy multiple pools, tennis courts, scenic walking trails, parks, pavilions, BBQ areas, a clubhouse, as well as volleyball and basketball courts—delivering a true Florida lifestyle right outside your door. Don’t miss this opportunity to own a move-in-ready home in one of Winter Springs’ most desirable communities!
Listing Agent: Jeff Singletary (407-383-1933)
335 KIRKCALDY DR, WINTER SPRINGS, FL 32708
$339,90014 Days on yellowkey MLS ID: O6400818
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1178 Built: 1984Monthly Fee: $36 Tax: $3,693 (2025)Community: Highland Village 1Single Family
Taxes:$3,693
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)
706 LAKESIDE DR, WINTER SPRINGS, FL 32708
$279,50018 Days on yellowkey MLS ID: O6402320
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1092 Built: 1979Monthly Fee: $95 Tax: $2,209 (2024)Community: WildwoodTownhouse
Taxes:$2,209
Remarks: Welcome to this charming 2-bedroom, 2-bath end-unit residence that lives like a single-family home. While classified as a townhome, this rare detached end-unit offers no shared walls, providing added privacy and quiet. A 2-car attached garage and a scenic homesite with tranquil pond and fountain view completes the setting. Step onto your patio and enjoy the fountain on the pond, or walk a few steps to the grill and community pavilion. Step inside to a spacious, open layout highlighted by vaulted ceilings, creating a bright and airy atmosphere that feels welcoming from the moment you enter. The home has been thoughtfully updated, including a new roof (2024), new hot water heater (2026), and a new dishwasher and range hood. The primary suite is generously sized and features an updated en-suite bath with a custom walk-in shower. Additional upgrades include new carpet in the bedrooms and living room, luxury vinyl flooring in the kitchen, dining and hallway, and fresh interior and exterior paint. Enjoy peaceful mornings or unwind in the evenings on your private patio overlooking the pond. Located in the Wildwood community of Winter Springs, residents enjoy a variety of amenities, including a community pool, tennis and pickleball courts, volleyball court, playground, pavilion, dog park and an outdoor fitness station. Conveniently situated near Highlands Elementary and just minutes from parks, shopping, and restaurants, this home offers the perfect blend of low-maintenance living with space and privacy at an affordable price! Welcome home!
Listing is courtesy of: REALTY WORLD PREFERRED (407-834-7368)
Listing Agent: Stefanie Wollam (321-303-7653)
50 SHEOAH BLVD #33, WINTER SPRINGS, FL 32708
$179,50015 Days on yellowkey MLS ID: O6404380
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 972 Built: 1973 Tax: $1,726 (2025)Community: Sheoah Sec 1Condo
Taxes:$1,726
Remarks: WELCOME HOME! This elegant, bright, and open first-floor, single-story 2-bedroom, 2-bath condo is located in the highly desirable Winter Springs community. From the moment you step inside, you’ll feel right at home in the spacious living and dining area featuring custom-built shelving and an inviting layout perfect for relaxing or entertaining. The split-bedroom floor plan offers added privacy, with sliding doors from the primary suite leading to a charming brick patio, ideal for enjoying your morning coffee or unwinding in the evening. The kitchen has been beautifully renovated with new appliances, updated countertops, and ample workspace. The primary bathroom features a walk-in shower with safety grab bars, while the guest bathroom includes a tub, with a convenient laundry area located in the guest bath closet. A bright and airy enclosed Florida room with A/C provides flexible space for a home office, reading nook, or additional living area. Step outside to your private patio with room for outdoor furniture, plants, or even your own garden retreat, all overlooking a peaceful wooded conservation area. Additional highlights include approximately 1,196 square feet including the enclosed porch, a newer A/C and water heater, fresh interior paint in a modern light gray, and no carpet throughout. Located in The Highlands, a quiet and friendly community offering a pool, tennis courts, parks, walking trails, scenic water views, reserved parking, and community mailboxes. HOA fees include high-speed internet, cable, pest control, and full grounds maintenance, with weekly lawn care and twice-weekly trash pickup. The home is situated in a top-rated school district with schools nearby and is just minutes from shopping, dining, and everyday conveniences. Schedule your private showing today, this one won’t last long!
Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)
Listing Agent: Fanny Stollmeyer (704-905-0698)
4910 E LAKE DR, WINTER SPRINGS, FL 32708
$2,399,00018 Days on yellowkey MLS ID: O6398929
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3657 Built: 1964 Tax: $6,256 (2024)Community: NaSingle Family
Taxes:$6,256
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)
502 CLUB DR, WINTER SPRINGS, FL 32708
$219,50060 Days on yellowkey MLS ID: O6390697
REDUCED by $10,000 (4.4%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1987Monthly Fee: $520 Tax: $3,355 (2025)Community: Cypress ClubTownhouse
Taxes:$3,355
Remarks: Beautiful 2 bedroom, 2 bathroom townhome in Winter Springs, located in the sought-after Cypress Club at The Highlands community, known for its lush landscaping, fantastic amenities, and serene walking trails. Step inside to a spacious open floor plan with soaring vaulted ceilings and tile flooring throughout the main living areas. The living room features a cozy wood-burning fireplace, creating a warm and inviting focal point. The galley kitchen is fully equipped with all appliances, a glass tile backsplash, and a closet pantry for added storage. This home offers double suites, thoughtfully split between the two levels, each with its own private bathroom. The upstairs loft provides the perfect flex space for a home office, reading nook, or creative studio. Step out back to a lovely screened patio overlooking a private, park-like setting with no rear neighbors, creating a peaceful outdoor retreat. An exterior storage closet offers convenient space for bikes, tools, or gardening supplies. Recent updates include a full professional re-pipe (2026), new water heater (2025), new refrigerator (2024), new interior paint in modern greige tones (2023), and new carpet in bedrooms and stairs (2023). This townhome includes two reserved parking spaces, side-by-side, including one covered carport space. Cypress Club residents enjoy their own private community pool along with full access to The Highlands’ amenities, including a lap pool, tennis courts, playground, BBQ/picnic areas, and more. Ideally located with easy access to SR-434, 17-92, SR-417, and I-4, and zoned for top-rated Seminole County schools. Outdoor recreation and weekend adventure are just minutes away with convenient access to the Cross Seminole Trail and Central Winds Park, offering miles of scenic biking and walking paths, sports fields, and community events. Everyday conveniences are equally close by, with Winter Springs Town Center and other major shopping plazas just a short drive away, providing easy access to grocery stores, fitness centers, banks, restaurants, and all your daily essentials.
Listing is courtesy of: INFINITY REAL ESTATE GROUP (407-760-0835)
Listing Agent: Tamara Martin (407-760-0835)
510 SONATA CT, WINTER SPRINGS, FL 32708
$849,90021 Days on yellowkey MLS ID: O6402358
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2381 Built: 1999Monthly Fee: $184 Tax: $6,415 (2024)Community: Seville ChaseSingle Family
Taxes:$6,415
Remarks: SELLER MOTIVATED!! Make OFFER! Seller is willing to give a 20k Credit for Paint! Walk in and feel instantly at home! This beautifully renovated 4-bedroom, 3-bathroom triple-split pool home sits on nearly half an acre in the gated community of Seville Chase and is completely move-in ready. Step inside to soaring ceilings and a thoughtfully designed open layout that still offers comfortable separation of space. You’ll immediately notice the stunning porcelain tile floors and a high-end, fully updated kitchen featuring custom cabinetry, pull-out shelving, soft-close drawers and doors, and sleek quartz countertops—perfect for both everyday living and entertaining. Recent upgrades provide peace of mind, including: New tile roof (2025) with a 50-year warranty AC replaced in 2022 Water softener (2022) New pool pump Out back, enjoy your own private retreat with a screened pool overlooking a serene conservation area with a lake—ideal for relaxing or even bass fishing. The expansive yard also features mature fruit trees, including avocado, mango, lemon, and a cherry bush. All of this is conveniently located near Winter Springs, major highways (417 & 434), UCF, Seminole State College, and major employers like Lockheed Martin and Siemens. This home truly has it all—style, space, and location. Schedule your private showing today before it’s gone!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
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