Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$690,000152 Days on yellowkey MLS ID: O6374007
REDUCED by $10,000 (1.4%) on 05/05/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2562 Built: 1984Monthly Fee: $40 Tax: $7,807 (2024)Community: Tuskabay Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,807
Elementary School: Keeth Elementary
High School: Winter Springs High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: This beautifully updated home blends timeless character with modern comfort, offering an inviting layout designed for both everyday living and entertaining. The light-filled interior showcases a stunning, renovated kitchen with new quartz extended countertops, a butcher block island, recessed lighting, and a full suite of high-end appliances including a JennAir refrigerator, KitchenAid pull-out refrigerator and freezer with ice maker, double oven and stovetop, wine and beverage cooler, and dishwasher. Major system upgrades add peace of mind and efficiency, featuring a newer roof installed in 2021, a fully paid off 11.745 kW (DC) solar system paired with a Tesla Powerwall 2.1 (7 kW DC battery capacity), whole-home water filtration and softener, high-efficiency heat pump water heater, new double-paned windows, Nest thermostats for upstairs and downstairs climate control, upgraded outlets with USB and modern switches, and new blinds throughout. The spacious primary bathroom has been fully remodeled with glass shower doors, new quartz countertops, and a farmhouse sink. Outside, enjoy exceptional curb appeal and a private backyard retreat with a screened-in pool, expansive paver patio, new extended paver walkway wrapping around the backyard, upgraded irrigation and sprinkler system, new gutters, and recently serviced chimney. The property is framed by mature, recently trimmed water and live oaks, enhancing both beauty and shade, while added features such as a new front door with wide extended entry, exterior Ring cameras and floodlights complete this truly move-in-ready home designed for a seamless indoor-outdoor Florida lifestyle.
Listing is courtesy of: MOMENTUM REALTY (904-903-1558)
Listing Agent: Carolina Taborda (832-349-8266)
986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$498,900151 Days on yellowkey MLS ID: O6374288
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1864 Built: 1985Monthly Fee: $3 Tax: $3,119 (2024)Community: Oak Forest Unit 4Spa: YesSingle Family
Taxes:$3,119
Remarks: 986 Turkey Hollow Circle—where comfort, style, and Florida living come together beautifully. Nestled in one of Winter Springs’ most desirable neighborhoods, this 4-bedroom, 2-bath pool home offers the perfect blend of warmth, functionality, and thoughtful updates—just minutes from Tuskawilla Road, SR-434, shopping, dining, and top-rated schools. Step inside to an open, light-filled great room where the kitchen, dining, and living spaces flow effortlessly—ideal for both everyday living and entertaining. The heart of the home is the kitchen, featuring rich cabinetry, custom backsplash, farmhouse sink, and a spacious island with cooktop and bar seating—perfect for gathering and connection. Just beyond, the inviting living room showcases vaulted ceilings, recessed lighting, tile flooring, and a stunning brick fireplace, creating a cozy yet open atmosphere. Sliding glass doors lead to your private outdoor retreat. Enjoy true Florida living outdoors with a sparkling pool, heated spa, and expansive covered lanai (10’ x 48’)—perfect for relaxing evenings, entertaining guests, or weekend poolside fun. Wood-tone decking, a fire pit area, gazebo dining space, and dedicated grill area complete this backyard oasis. The primary suite is a peaceful escape, offering private lanai access, a spacious bath, and walk-in closet. A split floor plan provides three additional bedrooms and an updated guest bath with convenient pool access—ideal for family or guests. Recent updates include: • POOL & DECK RESURFACED (2024) + new heater & pump • ROOF (2020) • Updated bedroom WINDOWS (2024) • Renovated GUEST BATH (2024) • New recessed lighting (2024) • New stainless steel refrigerator (2023) • Lanai flooring, spa lighting, gazebo & paver grill area Warm, welcoming, and move-in ready—this is the kind of home where memories are made. (All information intended to be accurate, but not guaranteed.)
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Christopher Dunlop (321-223-0407)
1200 ROYAL OAK DR, WINTER SPRINGS, FL 32708
$499,99948 Days on yellowkey MLS ID: O6401888
REDUCED by $10,001 (2.0%) on 05/26/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2378 Built: 1981Monthly Fee: $118 Tax: $4,618 (2025)Community: Fairway Oaks Unit 1Single Family
Taxes:$4,618
Elementary School: Rainbow Elementary
Tax Year: 2025
Remarks: 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!
Listing is courtesy of: THE PALMS PROPERTY GROUP (407-476-4202)
Listing Agent: Austin Masi (407-476-4202)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$425,00029 Days on yellowkey MLS ID: O6408695
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1476 Built: 2024Monthly Fee: $356 Tax: $6,076 (2025)Community: Hickory Grove TwnhmsTownhouse
Taxes:$6,076
Elementary School: Layer Elementary
Remarks: 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.
Listing is courtesy of: RALISTO, LLC (407-493-6032)
Listing Agent: Kalex Espinosa (407-493-6032)
560 PLEASANT GROVE DR, WINTER SPRINGS, FL 32708
$425,00050 Days on yellowkey MLS ID: O6401016
REDUCED by $20,000 (4.5%) on 05/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1654 Built: 1996Monthly Fee: $78 Tax: $5,669 (2024)Community: Tusca OaksSingle Family
Taxes:$5,669
Remarks: 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.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: David Fraser (407-920-9749)
600 NORTHERN WAY #502, WINTER SPRINGS, FL 32708
$265,000460 Days on yellowkey MLS ID: O6286935
REDUCED by $4,000 (1.5%) on 06/04/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1985Monthly Fee: $397 Tax: $766 (2024)Community: Tuscany Place Ph 1Spa: NoCondo
Taxes:$766
Remarks: MOTIVATED SELLER!!! Seller offering concession toward buyer closing cost. Location! Location! Location! This pristine condo nestled in the heart of Tuscawilla offers an incredible opportunity for low maintenance living in a serene and gated community. Enjoy summer days by the beautiful community pool and relax in the cabana. Across the way you will find access to Trotwood Park, with its picturesque settings ideal for picnics and recreational activities. Featuring a pavilion, playground, splash pad, tennis courts, and sports fields, it's a hub for family fun. For outdoor enthusiasts, the nearby Seminole County Cross Trail is perfect for biking and walking. As you tour the well maintained 3-bedroom, 2-bathroom condo, it encompasses 1425 sqft of second level living with private screened balconies overlooking the courtyard. Well-appointed kitchen equipped with brand-new stainless-steel appliances: Counter-depth Smart French Door Refrigerator, Smart SLIM Microwave, Bespoke Induction Range with self and steam cleaning Air Fry Convection Oven. A generous living and dining area that are inviting and ideal for entertaining. The split floor plan offers privacy for the owner suite, complete with its own screened balcony. The secluded and spacious secondary bedrooms are delightful for guests, office space or a growing family. New AC installed 7/2025 (16 seer AC unit with 1 year maintenance and 10yr-parts/2yr-labor). Families are drawn to the area thanks to its top-rated schools, making this condo not just a home, but a gateway to a vibrant community. Recently refreshed and ready for its new owners to display their personal touches.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Bob Bretz, Pa (407-797-9500)
446 CLUB DR, WINTER SPRINGS, FL 32708
$269,000124 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
Elementary School: Highlands Elementary
Middle School: South Seminole Middle
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)
476 CLUB DR, WINTER SPRINGS, FL 32708
$275,00084 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 new roof 2026, new water heater 2026, 2020 A/C system, a full repipe completed in 2016, and a 2016 whole home water softener. 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 is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Jeff Singletary (407-383-1933)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900389 Days on yellowkey MLS ID: O6312092
2 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1450 Built: 1987Monthly Fee: $120 Tax: $1,771 (2024)Community: Georgetowne Unit 1Single Family
Taxes:$1,771
Remarks: Under contract-accepting backup offers. Very well maintained home in Tuskawilla! Updated kitchen with Granite countertops, Elegant mirrored wall, Ceramic Tile throughout. Double sinks in beautiful master bathroom with garden shower tub! Owners have access to the neighborhood clubhouse and Community pool, HOA takes care of front yard lawn maintenance. Two parks and a nature trail are walking distance from the home. Walk to Trotwood Park and to Tuskawilla Country Club for a round of golf or tennis or to just socialize at the café and bar. This is a great opportunity to own an adorable low maintenance single-family home in the most affordable sought-after Country Club community in Seminole county. A rated school district! Short drive to Oviedo Marketplace and restaurants! Seller willing to contribute $2000 towards closing costs!! Don't miss this opportunity!! --
Listing is courtesy of: DIAMOND 2000 REALTY, INC (321-231-4195)
Listing Agent: Ramon Ortiz Cruz (321-231-4195)
1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708
$729,900112 Days on yellowkey MLS ID: O6384753
0 Days Off yellowkey (back on 4/2/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2908 Built: 2003Monthly Fee: $150 Tax: $2,062 (2025)Community: Parkstone Unit 3Single Family
Taxes:$2,062
Remarks: Under contract-accepting backup offers. Experience the ultimate Florida lifestyle at this stunning 4-bedroom (plus home office) or 5-bedroom, 3.5-bathroom retreat nestled in the exclusive gated community of Parkstone. Come home to soaring, high ceilings and a bright, open floorplan that’s an entertainers dream. The Chef’s kitchen features stainless steel appliances, and a breakfast bar as well as a window enjoying views of the screen patio and beautiful backyard. You will love the oversized primary suite that features stunning conservation views, and connects to a private, flexible room perfect for an office or nursery, or even a fifth bedroom. One of the additional bedrooms has an on suite bathroom and walk in closet as well. Wake up to breathtaking sunrises and spend your evenings watching wildlife. This exceptional property features a private 300ft boardwalk that winds through Florida Hammock vegetation and leads to your own personal boathouse. This incredible, covered boat dock features both electric and water access, plus a boat lift for effortless access to the scenic, expansive Lake Jesup. Enjoy relaxing on the screened lanai or the open paver patio while enjoying the sounds of nature. NEW ROOF IN 2024 (House and Boat Dock), NEW PORCH ROOF 2025, NEW WATER HEATER 2025, NEW A/C 2021, FRESHLEY PAINTED 2021, RAIN GUTTERS 2020. Relish your time at the private community fishing pier, tennis court, take a dip in the gorgeous community pool or enjoy the splash pad. Lawn Maintenance is even included in your HOA (Lawncare includes mowing of lawn, trimming of bushes and fertilizer). Parkstone is a gated community with walking trails, scenic ponds, tennis court, community dock, two playgrounds, a splash pad and community pool to enjoy. The Cross Seminole Trail borders Parkstone and you are just a short walk from Central Winds Park, the Dog park and the Newly opened Pickleball Facility! Minutes from grocery stores, The Town Center, shopping and dining, this home has it all! Welcome home!
Listing is courtesy of: SHORESTONE PROPERTY GROUP (407-452-9818)
Listing Agent: Tania Crandall (407-452-9818)
224 HIGHLANDS GLEN CIR, WINTER SPRINGS, FL 32708
$295,00028 Days on yellowkey MLS ID: O6409042
0 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1185 Built: 1986Monthly Fee: $63 Tax: $3,265 (2025)Community: Highlands GlenVilla
Taxes:$3,265
Elementary School: Winter Springs Elementary
Remarks: Welcome to 224 Highlands Glen Circle, a beautifully updated 3-bedroom, 2-bath villa with 1,185 sq. ft. of comfortable living space. This home features a modern kitchen with new countertops and appliances, along with fresh interior paint and new flooring throughout. Enjoy the ease of a move-in ready home with a 1-car garage. The community offers fantastic amenities, including a pool, tennis courts, playground, and park, perfect for active lifestyles and family fun. Ideally located in Winter Springs, this villa combines style, convenience, and comfort, schedule your showing today!
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Brian Hyser (407-951-2472)
126 SEVILLE CHASE DR, WINTER SPRINGS, FL 32708
$769,00075 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
Elementary School: Sterling Park Elementary
Remarks: **Price Improvement** and a $20,000.00 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)
805 LEOPARD TRL, WINTER SPRINGS, FL 32708
$565,00040 Days on yellowkey MLS ID: O6405925
REDUCED by $10,000 (1.7%) on 05/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2608 Built: 1978 Tax: $2,946 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$2,946
Remarks: Welcome to 805 Leopard Trail in Winter Springs, a 4-bedroom, 2-bath pool home located in a quiet, established no HOA community. Situated on approximately half an acre, this property offers a rare combination of space, privacy, and natural surroundings. The home features a functional layout with comfortable living areas, while large windows and sliding glass doors provide natural light and seamless access to the backyard. Step outside to a truly special outdoor setting, where mature trees, natural surroundings, and the sounds of nature create a peaceful and private atmosphere. The backyard is a standout feature, complete with a private pool and plenty of space to relax or entertain. The pool area is also plumbed for a future outdoor kitchen, offering additional potential. With a generous lot size, there is ample room for recreation, storage, or future improvements. Conveniently located near University of Central Florida, Central Winds Park, Oviedo Mall, as well as shopping, dining, and major roadways including SR 434 and SR 417, this property offers both tranquility and accessibility in a desirable Winter Springs location.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Wilfred Sierra Sosa, Pa (863-588-8303)
214 PERTH CT, WINTER SPRINGS, FL 32708
$589,90034 Days on yellowkey MLS ID: O6407533
1 Days Off yellowkey (back on 6/3/2026)
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: Under contract-accepting backup offers. 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
$589,90035 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
600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708
$269,90069 Days on yellowkey MLS ID: O6396912
REDUCED by $5,100 (1.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1425 Built: 1981 Tax: $4,268 (2025)Community: Tuscany Place Ph 1Condo
Taxes:$4,268
Remarks: One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to Tuscany Place, a GATED COMMUNITY in the heart of Tuskawilla – one of Winter Springs’ most desirable and established areas! This UPDATED second-floor condo delivers the perfect blend of modern style, LOW MAINTENANCE LIVING, and an unbeatable Central Florida location. Major updates are already done for you, including the kitchen and both bathrooms, plus a NEWER A/C (2020), giving peace of mind from day one. Inside, the home has been tastefully updated with modern finishes and fixtures, creating a clean, MOVE-IN READY space that feels both fresh and inviting. WOOD LAMINATE FLOORING flows throughout the entire unit, enhancing the seamless, low-maintenance lifestyle. The OPEN CONCEPT living and dining area is filled with NATURAL LIGHT thanks to a wall of SLIDING GLASS DOORS that lead to a SCREENED BALCONY overlooking peaceful green space – perfect for morning coffee or winding down in the evening. The UPDATED KITCHEN stands out with a fresh, modern color palette and a pop of personality, featuring sleek countertops, STAINLESS STEEL APPLIANCES, ample cabinet storage, a breakfast bar, and a window that brings in even more natural light. The SPLIT BEDROOM layout offers both comfort and privacy with the primary suite tucked away at the back of the home, complete with a WALK-IN CLOSET, updated en-suite bath, and its own private access to a SECOND BALCONY. Two additional bedrooms are positioned at the front of the unit and share a beautifully updated full bath, ideal for guests, family, or a home office setup. Tuscany Place residents enjoy a gated entrance along with added conveniences like lawn care and pest control, making this a truly low-maintenance option. The location is hard to beat – just minutes from Tuskawilla Road, SR 434, and 417, with easy access to TROTWOOD PARK, Central Winds Park, Tuscawilla Country Club, and all the shopping and dining options in Winter Springs and nearby Oviedo. Whether you are looking for your next home or a smart investment, this updated condo is priced to sell and ready for its next owner. Call today to schedule a tour!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
4991 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$750,00026 Days on yellowkey MLS ID: O6409511
1 Days Off yellowkey (back on 5/24/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3217 Built: 1983Monthly Fee: $40 Tax: $6,752 (2025)Community: TuskabaySpa: NoSingle Family
Taxes:$6,752
Remarks: Under contract-accepting backup offers. MULTIPLE OFFERS : HIGHEST AND BEST DUE BY SATURDAY, MAY 23 at 5PM. Welcome to this beautifully updated 4-bedroom, 2.5-bath pool home in the highly sought-after Winter Springs community of Tuskabay, offering the perfect blend of style, comfort, and convenience. Ideally located near shopping, dining, and major commuter routes, this home boasts lush landscaping, exceptional curb appeal, and a desirable side-entry 2-car garage. Inside, you’ll find neutral paint and flooring, abundant natural light, and an open floorplan designed for both everyday living and entertaining. The inviting foyer showcases stunning custom woodwork that flows seamlessly into the spacious dining area, while custom wood ceilings in both the foyer and loft up above add warmth and character. Elegant wrought iron railings accent the staircase and dining space for a sophisticated touch. The thoughtfully designed kitchen is situated at the front of the home and features an oversized opening to the living areas for great lines of sight, 42” cabinetry, granite countertops, tile backsplash, stainless steel appliances including built-in microwave, oven, and cooktop, plus a dinette area and walk-in pantry with convenient laundry access. The oversized family room is truly the heart of the home, highlighted by vaulted ceilings, a cozy wood-burning fireplace, two skylights, and French doors that open to the covered patio for seamless indoor/outdoor living. The spacious upstairs primary suite is a private retreat complete with its own wood-burning fireplace, custom accent wall, French doors leading to a private balcony, and a large walk-in closet with custom organization system. The luxurious en-suite bath offers a wrap-around, double-sink vanity, jacuzzi tub, and oversized shower. Adjacent to the primary suite are a versatile loft and an office/nursery space perfect for working from home or additional flexibility. Downstairs, three generously sized bedrooms feature large closets and ceiling fans. One bedroom includes a private half bath with direct access to the pool deck, making it an ideal cabana bath. An additional full hall bath features an oversized vanity, linen closet, and shower/tub combination. Step outside to your own backyard oasis featuring a large, screened and covered paver patio with custom wood ceiling overlooking the spacious, heated, chlorine pool. Beyond the screened enclosure, there’s still plenty of yard space to enjoy, all enclosed by a vinyl fence for added privacy. Additional upgrades include newer AC, crown molding, plantation shutters, engineered wood flooring, and added lighting and electrical outlets throughout. This exceptional home offers the perfect combination of timeless character, modern updates, and resort-style outdoor living.
Listing Agent: Jean Scott (407-759-5320)
114 SUNDANCE CT, WINTER SPRINGS, FL 32708
$305,500214 Days on yellowkey MLS ID: O6359275
3 Days Off yellowkey (back on 6/1/2026)
REDUCED by $10,000 (3.2%) on 04/23/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1356 Built: 1997Monthly Fee: $120 Tax: $4,059 (2024)Community: Seasons TheSpa: NoSingle Family
Taxes:$4,059
Remarks: One or more photo(s) has been virtually staged. If you’ve been searching for space, location, and opportunity without overpaying, this cul-de-sac home delivers. Tucked away on a quiet cul-de-sac and backing to a peaceful conservation area with no rear neighbors, this 4-bedroom home offers a rare combination of privacy and value in one of Winter Springs’ most desirable locations. Inside, you’ll find a functional split-bedroom layout, vaulted ceilings, and an open living and dining space designed for everyday comfort. The kitchen flows into a bright dining nook and screened patio, creating an ideal setup for indoor-outdoor living. With major updates already completed, including a 2022 roof, and 2026 water heater, buyers can move in with confidence while still having the flexibility to personalize finishes over time. Additional highlights include dedicated driveway parking for two vehicles, low HOA, and access to community amenities such as a pool, tennis courts, and playground. Located within top-rated Seminole County school zones and just minutes from parks, trails, shopping, and major roadways, this home is perfectly suited for buyers looking to maximize space, location, and long-term value. Back on market due to buyer financing — no inspection concerns.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-841-0888)
Listing Agent: Nora Rios (407-274-1174)
622 ANHINGA RD, WINTER SPRINGS, FL 32708
$384,900174 Days on yellowkey MLS ID: O6369225
REDUCED by $13,600 (3.4%) on 05/18/2026
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 TILE ROOF INSTALLED APRIL 2026 + TRANSFERABLE 4-POINT INSPECTION + APPROXIMATELY 5-MINUTE WALK TO HIGHLANDS ELEMENTARY! Welcome to 622 Anhinga Road, a move-in-ready home located in the highly desirable Greenspointe community of Winter Springs. One of the most expensive updates a homeowner can face has already been completed with a BRAND-NEW TILE ROOF installed in April 2026, providing long-term value, durability, and peace of mind for years to come. To make the buying process even easier, the seller has already completed a transferable 4-Point Inspection available to the new owner. This beautiful 3-bedroom, 2.5-bathroom home offers over 1,700 square feet of living space and a highly desirable floor plan with the primary suite conveniently located on the first floor. The spacious owner's retreat features a large walk-in closet and a private bathroom with dual vanities, a soaking tub, separate shower, and private water closet. As you enter the home, you'll immediately notice the soaring ceilings, abundant natural light, and open-concept layout that creates a bright and welcoming atmosphere. The main living areas feature tile flooring throughout, while the kitchen offers granite countertops, stainless steel appliances, light cabinetry, a breakfast bar, and views of the living and dining areas—perfect for everyday living and entertaining. Sliding glass doors lead to a shaded backyard, creating the perfect space for relaxing, grilling, entertaining guests, or simply enjoying Florida evenings. Upstairs, you'll find a spacious loft that can easily serve as a home office, media room, playroom, gym, or second living area, along with two additional bedrooms and a full bathroom. Families will love the location within the highly rated Seminole County School District. Highlands Elementary School is just a short walk from the home, allowing many residents to enjoy the convenience of walking their little ones n to school in approximately 5 minutes. South Seminole Middle School and Winter Springs High School are also nearby. Residents enjoy access to The Highlands community amenities, including a community pool, tennis courts, pickleball courts, basketball courts, playgrounds, parks, clubhouse, walking trails, and recreational facilities designed for an active Florida lifestyle. Conveniently located near Winter Springs Town Center, UCF, Valencia College, shopping, dining, SR-417, SR-434, I-4, Downtown Orlando, and Central Florida attractions, this home offers both comfort and convenience in one of Seminole County's most sought-after communities. Vacant and easy to show. Major updates already completed, including a NEW TILE ROOF (April 2026), HVAC (2017–2018), WATER HEATER (2022), and a TRANSFERABLE 4-POINT INSPECTION. A rare opportunity to own a move-in-ready home in Winter Springs with top-rated schools, outstanding community amenities, and important updates already taken care of.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Alexa Monasterio Flores (786-915-9294)
1281 NATURES WAY, WINTER SPRINGS, FL 32708
$1,200,00046 Days on yellowkey MLS ID: O6404018
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3212 Built: 1972 Tax: $2,240 (2024)Community: TuscawillaSpa: NoSingle Family
Taxes:$2,240
Remarks: Experience the beauty of city living on 2.3 acres in the highly desirable city of Winter Springs with no HOA—where open space, natural surroundings, and an equestrian friendly lifestyle come together. This unique property offers the freedom of rural living while remaining conveniently located near the Tuscawilla area. The fully usable acreage is ideal for horses, cattle, or other livestock. If livestock isn’t your preference, the expansive space is perfect for recreational vehicles, racing cars, or other outdoor hobbies. The 5 bedroom, 3 bath home is solid and ready for your personal updates. A standout feature is the 1,500 sq. ft. garage, offering ample room for a boat, race cars, or additional storage. This 2.3 acre parcel is one of the few remaining equestrian friendly properties in the city of Winter Springs, providing a rare combination of comfort, privacy, and natural surroundings. The home is zoned for highly rated Seminole County schools, offering the perfect blend of private country living and excellent educational opportunities. Seller motivated!
Listing is courtesy of: EQUITY REAL ESTATE BROKERS (407-252-5276)
Listing Agent: David Owji (407-252-5276)
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