Location: Winter Springs
Keyword(s): Indian Trails Middle
Keyword(s) Middle School: Indian Trails Middle
Do Not Show Listings
1328 ANDES DR, WINTER SPRINGS, FL 32708
$373,00053 Days on yellowkey MLS ID: O6398729
REDUCED by $12,000 (3.1%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1582 Built: 1987Monthly Fee: $29 Tax: $3,128 (2024)Community: Sunrise Village Unit 6Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,128
Elementary School: Rainbow Elementary
High School: Oviedo High
Tax Year: 2024
Middle School: Indian Trails Middle
Remarks: Welcome to 1328 Andes Dr! Tile floors run throughout this well-maintained 4-bed, 2-bath in Sunrise Village, giving the home a clean, consistent look from room to room. The living room flows naturally into the dining area and kitchen, an open feel that works well for everyday living and entertaining. The kitchen includes stone countertops, well-maintained cabinetry, and easy access to the back lanai. The spacious master bedroom is located just off the dining room and includes a large walk in closet with in suite master bathroom. The additional bedrooms are generously sized, ideal for family, guests, or a home office. The location puts you close to everything worth being close to. Sunrise Community Park is right around the corner. Red Bug Lake Park, Trotwood Park, and Tuscawilla are all just minutes away. SR 417, Red Bug Lake Road, and Tuskawilla Road keep commutes short in every direction, with plenty of shopping and dining close by. Come see this home in one of Winter Springs' more convenient pockets!
Listing is courtesy of: AVENIR REAL ESTATE BROKERS LLC (833-412-8364)
Listing Agent: Chad Jarvis (772-486-4345)
709 SAILFISH RD, WINTER SPRINGS, FL 32708
$402,500192 Days on yellowkey MLS ID: O6364715
REDUCED by $5,000 (1.2%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1737 Built: 1984 Tax: $5,463 (2024)Community: North Orlando Ranches Sec 10Spa: NoSingle Family
Taxes:$5,463
Elementary School: Layer Elementary
High School: Winter Springs High
Remarks: Some neighborhoods offer just a house; this one delivers a true Florida lifestyle, anchored by a beautiful, deep quarter-acre lot and a home built for functional, everyday living. Tucked away in a quiet pocket of Winter Springs—one of Seminole County’s most coveted and safest communities—this 3-bedroom, 2-bathroom gem offers the rare freedom of no HOA combined with unparalleled privacy. The home provides immediate peace of mind with a roof that is only 5 years old. Set beneath a picturesque canopy of mature trees and draping Spanish moss, the curb appeal speaks to the established, friendly vibe that residents of Winter Springs enjoy. Step inside to a flexible layout built for flow, featuring dedicated living and family rooms that give everyone room to spread out. The central kitchen and dining space is positioned perfectly to serve both entertaining areas and acts as the heart of the home. The smart split-bedroom floor plan provides ideal separation, tucking the spacious primary suite on one side of the house for privacy and tranquility. The real magic happens where the indoors meets the outdoors. The home expands dramatically with a large, enclosed Florida Room (22'6" x 11'6") that is fully under A/C with its own dedicated mini-split unit—making this substantial bonus space a year-round extension of the living area, perfect for an office, gym, or sun-soaked den. This room leads directly out to a private, spacious backyard where you will enjoy the unique benefit of no rear neighbors, secured by a perimeter of mature trees and fencing. Even the garage has been elevated: the two-car garage features durable epoxy flooring and includes a dedicated laundry area and a useful closet room, perfect for home projects or tool storage. The location is the final mic drop. You are moments from the convenience of Winter Springs Town Center, Central Winds Park, and the premier amenities of the Tuscawilla area. You are also zoned for the excellent Seminole County School District. You get the quiet, safe suburban environment while maintaining effortless access to major highways (417/I-4) for a convenient commute to Downtown Orlando or Lake Mary. View the 3D Matterport tour now to fully appreciate the space and layout. This is more than a listing—it’s the home where your next chapter begins.
Listing is courtesy of: ELEGANT REALTY LLC (407-985-2840)
Listing Agent: Wayne Mottley (407-741-3804)
107 GOLDEN CREST CT, WINTER SPRINGS, FL 32708
$504,00080 Days on yellowkey MLS ID: O6393850
REDUCED by $5,000 (1.0%) on 06/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1978 Built: 1995Monthly Fee: $162 Tax: $6,261 (2024)Community: Eagles Watch Ph 1Single Family
Taxes:$6,261
Elementary School: Lawton Elementary
Remarks: Located within the gated community of Eagle’s Watch in Seminole County, this well-maintained residence offers a functional layout, quality features, and a highly convenient location. Situated on a quiet cul-de-sac and backing to a greenbelt, the property provides added privacy along with direct access to the Florida National Scenic Trail system for outdoor recreation. The home features a modern open-concept floor plan with high ceilings and abundant natural light throughout the main living areas. A covered front porch enhances curb appeal, while the interior layout is designed for both everyday living and entertaining. The fenced backyard includes mature trees and usable space, creating a comfortable outdoor setting. Eagle’s Watch is a gated, tree-lined, golf cart-friendly community offering amenities such as a pool, basketball courts, and playground, with front yard maintenance included through the HOA. Conveniently located near Highway 417 and Winter Springs Town Center, the home provides easy access to shopping, dining, and everyday essentials, along with zoning for top-rated Seminole County schools. This property combines a desirable setting, thoughtful design, and low-maintenance living within one of Seminole County’s most sought-after communities.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Dianne Moore (407-494-7575)
877 BENCHWOOD DR, WINTER SPRINGS, FL 32708
$460,00017 Days on yellowkey MLS ID: O6410431
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1612 Built: 1983Monthly Fee: $3 Tax: $3,127 (2024)Community: Oak Forest Unit 3Single Family
Taxes:$3,127
Elementary School: Keeth Elementary
Remarks: Inviting curb appeal welcomes you into this beautifully maintained Winter Springs pool home tucked within the peaceful established subdivision of Oak Forest. Step inside to an open floor plan with immediate views of the backyard oasis, creating a light and airy feel perfect for everyday living and entertaining. The spacious kitchen opens seamlessly to the living and dining areas and features granite countertops, stainless steel appliances and a breakfast bar ideal for gathering with family and friends. The floor plan offers comfortable living spaces, while sliding doors lead out to the screened porch overlooking the private backyard retreat. Enjoy Florida living year-round with the screened patio, resurfaced pool featuring a PebbleTec finish completed in 2020, a fully fenced yard and plenty of room to relax or entertain outdoors. Major updates provide peace of mind, including the roof, AC, and water heater all replaced in 2015. Additional improvements include gutters added in 2020, pool pump replaced in 2016, new garage door opener in 2025, and updated microwave, dishwasher, and garbage disposal in 2026. This home sits on a spacious lot in a quiet, established neighborhood. Conveniently located near SR-417, shopping, dining, and top-rated Seminole County schools - walking distance to both the elementary and middle school. This home is also just minutes from Trotwood Park and Central Winds Park which features pickleball courts, sports fields, playgrounds, walking trails, and community events.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Melissa Condrey (407-505-9339)
1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$469,00073 Days on yellowkey MLS ID: O6395600
REDUCED by $9,500 (2.0%) on 06/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2344 Built: 2021Monthly Fee: $236 Tax: $2,985 (2025)Community: Seminole Crossing TwnhmsTownhouse
Taxes:$2,985
Tax Year: 2025
Remarks: One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity in the heart of Winter Springs, where lifestyle, location and luxury converge at 1128 Spotted Sandpiper Loop. Positioned in a thoughtfully planned community, this residence offers the ideal balance of elegance and everyday convenience. From moment you arrive, you are embraced by a neighborhood designed for connection and ease, tree-lined streets, inviting trails and a sense of community that makes this address desirable. Ideally just moments from Winter Springs Town Center, this residence offers an accessible lifestyle. Natural light fills the interiors, creating a warm and welcoming ambiance suited for relaxed living and stylish entertaining. Thoughtfully designed across three levels, the first floor offers a private retreat ideal for guests, complete with its own en suite. The second level unfolds into the heart of the home, featuring an open concept living space with a well-appointed kitchen, dining area and inviting family room. The third floor is dedicated to restful living, showcasing three bedrooms, two full baths and a convenient laundry area. Updates include new carpeting throughout with transferable warranty and fresh interior paint reflecting the home's meticulous maintenance. Beyond your doorstep, accessibility becomes a defining feature of this lifestyle. Enjoy proximity to local shops, dining, parks and top-rated Seminole County schools, all just moments away. With easy access to major roadways, commuting to downtown Orlando, nearby business hubs, or weekend destinations is simple and efficient. Amenities include community pool, trails and accessibility to area favorites.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jackie Hughes (407-247-0030)
4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$690,000150 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
Taxes:$7,807
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
$498,900149 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
$499,99946 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
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
$425,00027 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
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
$425,00048 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
$265,000458 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)
724 BARRINGTON CIR, WINTER SPRINGS, FL 32708
$399,900387 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)
30 SABLE CT, WINTER SPRINGS, FL 32708
$569,000121 Days on yellowkey MLS ID: O6382648
REDUCED by $10,000 (1.7%) on 04/12/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2674 Built: 1976 Tax: $3,043 (2024)Community: TuscawillaSpa: NoSingle Family
Taxes:$3,043
Remarks: REDUCED! Beautiful Executive 4 bedroom POOL home in Tuscawilla Country Club Golf Community! NO HOA! Mediterranean feel with wrought iron accents and courtyard. Huge Kitchen with island in the middle. All appliances. Hot water heater 2017. Lots of cabinet space. Spacious eat-in area beside kitchen. Formal Dining and Living rooms. Large bedrooms. Big Owners bedroom with walk-in closet and updated bath. Inside laundry room. Large Pool (updated to salt system) 8 feet deep. Big fenced yard. Screened in porch. Oversized 2 car side entrance garage (currently part of garage is an office but could easily be converted back). Community allows golf carts. Plenty of room to park jet skis, boats, and RV. Great location near shopping, restaurants, hospital, and major roads. Good schools. Country Club has golf, tennis, swimming, and dining membership. Trotwood park has basketball and tennis courts, soccer field, and covered picnic area. Many parks in neighborhood. Close to Seminole Trail for walking and bike riding. Move right in! Must Seee!
Listing is courtesy of: HOME SOLD NETWORK LLC (407-257-6223)
Listing Agent: Julie Bailey (407-257-6223)
1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708
$729,900110 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)
805 LEOPARD TRL, WINTER SPRINGS, FL 32708
$565,00038 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)
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$290,000136 Days on yellowkey MLS ID: O6375918
REDUCED by $20,000 (6.5%) on 06/01/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1609 Built: 2016 Tax: $4,259 (2024)Community: Tuscany Place Ph 1Condo
Taxes:$4,259
Remarks: Turnkey townhouse and prestige product in Tuscany Place located in beautiful Winter Springs. The townhouse style is limited to only a few homes in the new phase of this great community. Spacious open-concept kitchen and overall excellent layout—all bedrooms have their own private full bathroom—one of the bedrooms with en-suite full bath is on the ground level so it’s perfect for an office or a mother-in-law suite. This home's natural focal point is the kitchen with granite countertops, and there's an extra-large kitchen island, which provides essential counter space and storage, cabinets and drawers, and room for a breakfast bar. The kitchen leads to the rest of the living and family room combination, which features glass sliding doors to the patio and a staircase to a great split plan layout for the bedrooms upstairs. This home has all the features you’re looking for including a laundry room with large-size appliances, walk-in closets, a huge refrigerator, dedicated trash drawer in the kitchen, blinds and window treatments, and modern fixtures throughout the home. HVAC 2020, water heater 2017, and a new roof as of March 2026. Low monthly fee covers access to the community pool, exterior maintenance and landscaping, sewer, and trash services. Very close to all the shopping and restaurants at Winter Springs Town Center, and Trotwood Park is right at your doorstep. Contact us today to schedule a private tour!
Listing is courtesy of: JR REALTY GROUP LLC (407-920-4624)
Listing Agent: John Vincent (407-534-9764)
600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708
$269,90067 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
$750,00024 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 is courtesy of: KELLER WILLIAMS ADVANTAGE REALTY (407-977-7600)
Listing Agent: Jean Scott (407-759-5320)
114 SUNDANCE CT, WINTER SPRINGS, FL 32708
$305,500212 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
Elementary School: Winter Springs Elementary
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)
1281 NATURES WAY, WINTER SPRINGS, FL 32708
$1,200,00044 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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