Location: Winter Springs
Keyword(s): Winter Springs High
Keyword(s) High School: Winter Springs High
Do Not Show Listings
161 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$444,99093 Days on yellowkey MLS ID: O6386458
REDUCED by $40,000 (8.2%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2026Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,457
Elementary School: Layer Elementary
High School: Winter Springs High
Tax Year: 2025
Middle School: Indian Trails Middle
Remarks: Under Construction. A standout feature of this end-unit home is the owner’s suite, conveniently located on the first floor, providing privacy and ease of access. This inviting retreat includes abundant natural light, a generous walk-in closet, and a well-appointed private bath. The open-concept main floor features expansive living and dining areas that flow seamlessly into a thoughtfully designed kitchen—complete with stainless steel appliances, including a refrigerator, a walk-in pantry, and a spacious breakfast bar—ideal for entertaining or everyday living. Laundry room, complete with washer and dryer is conveniently located on the main floor. Upstairs, you’ll find two additional bedrooms, a versatile loft perfect for a home office or media space, along with ample storage and a dedicated laundry area. A rear-loading 2-car garage adds both functionality and curb appeal. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
Listing is courtesy of: MATTAMY REAL ESTATE SERVICES (407-440-1760)
Listing Agent: Amanda Warren (321-662-0779)
173 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$439,99093 Days on yellowkey MLS ID: O6386437
REDUCED by $45,000 (9.3%) on 06/01/2026
Remarks: Under Construction. With an open concept ground floor and spacious living areas, the Sofia is ideal for entertaining and everyday life. Dedicated as an end unit, this floorplan features 3 bedrooms, 2.5 bathrooms and a rear-loading 2-car garage. The 2nd floor features a loft, abundant storage, and laundry space. Located on the 1st floor, the owner's suite that has it all - a spacious walk-in closet, great natural light, and private bath. Stainless steel appliances, a walk-in pantry and a breakfast bar are all featured in this floorplan's thoughtfully designed kitchen.
189 BEAR SPRINGS DR, WINTER SPRINGS, FL 32708
$443,990147 Days on yellowkey MLS ID: O6372546
REDUCED by $48,000 (9.8%) on 06/01/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1704 Built: 2025Monthly Fee: $356 Tax: $1,457 (2025)Community: Hickory GroveTownhouse
Remarks: Experience luxurious living in the Sofia floorplan, where the spotlight shines on the exquisite first-floor owner's suite that exudes sophistication with a spacious walk-in closet, abundant natural light, and a private bath. This end unit boasts an open-concept ground floor, perfect for entertaining and daily life. With 3 bedrooms, 2.5 bathrooms, and a rear-loading 2-car garage, this residence offers both style and functionality. Enjoy the convenience of first-floor laundry, while the 2nd floor features a loft and two generous-sized bedrooms. The thoughtfully designed kitchen showcases stainless steel appliances, a walk-in pantry, and a breakfast bar for a truly elevated living experience. Located in desirable Winter Springs near the vibrant Town Center, residents enjoy a highly sought-after lifestyle with walkable access to shopping, dining, and community events. Known for its top-rated schools, scenic parks, and extensive trail system, Winter Springs offers a perfect balance of small-town charm and modern convenience—just a short drive from Orlando. Discover low-maintenance townhome living in one of Central Florida’s most connected and livable communities.
600 NORTHERN WAY #502, WINTER SPRINGS, FL 32708
$265,000449 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
Elementary School: Keeth Elementary
Tax Year: 2024
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)
600 NORTHERN WAY #906, WINTER SPRINGS, FL 32708
$290,000127 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)
724 LAKESIDE DR, WINTER SPRINGS, FL 32708
$264,9002 Days on yellowkey MLS ID: O6412679
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1168 Built: 1985Monthly Fee: $95 Tax: $2,675 (2025)Community: WildwoodSingle Family
Taxes:$2,675
Elementary School: Highlands Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to 724 Lakeside Dr, nestled in the highly sought-after Wildwood community. This beautifully maintained 2-bedroom, 2-bathroom home offers 1,168 square feet of comfortable living space and presents an excellent opportunity for first-time homebuyers, downsizers, or anyone seeking a move-in-ready home in one of Winter Springs' most established neighborhoods. As you step inside, you'll immediately notice the fresh updates throughout, including brand-new carpet that adds warmth and comfort to every room. The functional floor plan offers a spacious living and dining area filled with natural light, creating an inviting atmosphere for both everyday living and entertaining guests. The kitchen provides ample cabinet and countertop space with easy access to the main living areas, making meal preparation and gatherings effortless. The primary suite offers a private retreat complete with an en-suite bathroom and generous closet space. A well-sized secondary bedroom and full guest bathroom provide flexibility for family members, guests, or a home office setup. The guest bathroom has been enhanced with a newly installed backsplash, adding a stylish and modern touch. Step outside and enjoy all that the Wildwood community has to offer. Residents have access to a community swimming pool, tennis courts, playground, and a community clubhouse, providing plenty of opportunities for recreation and social gatherings. The neighborhood's mature landscaping, tree-lined streets, and established character create a welcoming environment that homeowners have enjoyed for years. Conveniently located in the heart of Winter Springs, this home is just minutes from the Cross Seminole Trail, Central Winds Park, Winter Springs Town Center, shopping, dining, and top-rated Seminole County schools. Easy access to major roadways makes commuting throughout Central Florida a breeze while still allowing you to enjoy the charm and tranquility of this sought-after community. Whether you're searching for your first home, looking to downsize, or seeking a low-maintenance lifestyle in a prime location, this property offers the perfect combination of comfort, convenience, and community. Schedule your private showing today and discover everything 724 Lakeside Dr has to offer.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Eric Campbell (321-279-8941)
709 SAILFISH RD, WINTER SPRINGS, FL 32708
$407,500183 Days on yellowkey MLS ID: O6364715
REDUCED by $5,000 (1.2%) on 05/01/2026
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
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)
986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$498,900140 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)
207 BIRCH TERRACE, WINTER SPRINGS, FL 32708
$297,0004 Days on yellowkey MLS ID: O6411799
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1318 Built: 1973 Tax: $4,212 (2025)Community: North Orlando TerraceSingle Family
Taxes:$4,212
Elementary School: Winter Springs Elementary
Remarks: 3 BEDROOM 2 BATH HOME LOCATED ON CUL DE SAC STREET. WOOD CABINETS, SOLID SURFACE COUNTERS IN KITCHEN. SPLIT BEDROOM PLAN. FENCED REAR YARD. NEW ROOF IN 2025. A LITTLE TLC MAKES THIS A GREAT HOME. GREAT HOME FOR OWNER OCCUPANT OR INVESTOR.
Listing is courtesy of: REILLY REALTY & MGMT. (407-658-1119)
Listing Agent: Bernard Reilly (407-658-1119)
1219 SWAN ST, WINTER SPRINGS, FL 32708
$350,00081 Days on yellowkey MLS ID: O6391011
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1848 Built: 1978 Tax: $2,327 (2024)Community: Winter Spgs Unit 4Single Family
Taxes:$2,327
Remarks: Build your dream home on this rare 0.47 acre corner lot located at 1219 Swan Street in the highly desirable Tuscawilla area of Winter Springs. This spacious homesite offers plenty of room to design a custom residence while enjoying the charm and established beauty of one of Seminole County’s most loved communities. The property is zoned for single family residential use, allowing for the construction of a custom single family home that fits your vision and lifestyle. Located in an optional HOA section of Tuscawilla, homeowners enjoy flexibility while still benefiting from the surrounding community amenities and pride of ownership. Just a short walk away is the Tuscawilla Country Club, a private club offering a full golf course with Diamond Zoysia greens surrounded by majestic Live Oak trees draped in Spanish moss. Members enjoy a well stocked Golf Pro Shop, fitness center, and The Oaks Restaurant which serves lunch, dinner, and brunch in a welcoming setting. The club also features six Har Tru clay tennis courts with LED lighting and a Jr Olympic sized swimming pool at the Aquatics Center along with numerous social activities throughout the year for both adults and children. Beyond the club, the Tuscawilla community is known for its beautiful parks, playgrounds, and scenic walking and biking trails that wind through the neighborhood, creating a peaceful and active outdoor lifestyle. With its large size, corner location, and unbeatable proximity to golf, tennis, dining, and recreation, this lot presents an exceptional opportunity to build a custom home in one of Winter Springs’ most sought after communities. Close to 417 highway which connects easily to I-4 to take you anywhere from Downtown Orlando, to Tampa or Daytona beach! Zoned for Keeth Elementary, Indian Trails Middle School, and Winter Springs High School in highly rated Seminole County Public Schools. Cash or hard-money only please.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Kristine Mckinley (407-415-2412)
214 PERTH CT, WINTER SPRINGS, FL 32708
$589,90023 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
Middle School: South Seminole Middle
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
$589,90024 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
984 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$410,0009 Days on yellowkey MLS ID: O6410083
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1821 Built: 1985Monthly Fee: $3 Tax: $3,100 (2025)Community: Oak Forest Unit 4Single Family
Taxes:$3,100
Remarks: One or more photo(s) has been virtually staged. A spacious 3-bedroom, 2-bathroom home located in the highly sought-after community of Oak Forest in Winter Springs. Known for its beautiful tree-lined streets, mature oak trees, and quiet suburban charm, this family-friendly neighborhood also offers access to top-rated schools and is conveniently located near popular restaurants, shopping, and everyday conveniences. Inside, this home features a versatile and functional floor plan with a spacious family room, separate living room, dining room, large kitchen, dedicated office space, and an indoor laundry room. The detached shed provides the perfect opportunity for extra storage, a workshop, or hobby space. Step outside to enjoy the private backyard complete with a fire pit — ideal for relaxing or entertaining guests. The garage has been split into an office and storage space but can be converted back into a two car garage. Major upgrades and improvements include an updated roof (2018), gutters(2018), HVAC system(2022), windows(2020), garage door(2020), hot water heater(2021), electrical panels(2023), and added insulation(2019). Additional features include an indoor electric fireplace (2022), and numerous updates throughout, offering peace of mind and move-in-ready convenience. Call today to schedule your private tour!
Listing is courtesy of: ALL REAL ESTATE & INVESTMENTS (407-917-8206)
Listing Agent: Kelsey Payton (407-718-2967)
1128 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$478,50064 Days on yellowkey MLS ID: O6395600
REDUCED by $10,500 (2.1%) on 05/12/2026
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
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)
214 CHESTNUT RIDGE ST, WINTER SPRINGS, FL 32708
$600,000104 Days on yellowkey MLS ID: O6372400
REDUCED by $25,000 (4.0%) on 06/03/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2001Monthly Fee: $42 Tax: $5,539 (2024)Community: Chestnut Ridge In TuscawillaSingle Family
Taxes:$5,539
Elementary School: Rainbow Elementary
Remarks: WOW, BEST PRICE IN Winter Springs inside Executive TUSCAWILLA! Incredible opportunity. Here is your future DREAM HOME! Best price DIRECT GOLF FRONT HOME IN ORLANDO! Why wait to build on a 50 ft lot when you can live in a custom home Did you ever dream of drinking your Coffee daily while looking at a pristine GOLF course and Conservation view? Maintenance free yard that is DIRECTLY on the 16th hole of the Tuscawilla Golf Course. Builder of this neighborhood built this One of a kind home for himself and it has a one of a kind view. VIEW VIDEO WALK THROUGH TOUR. Energy Efficient SOLAR that is PAID FOR! Chestnut Ridge is a serene Winter Springs community in Seminole County This exquisite property, situated on .24 acres of loads of landscaping, with amazing azaleas with many colors, is the epitome of luxury living, perfect for executive families seeking a harmonious blend of comfort and elegance. Boasting an impressive 4 bedrooms and 3 bathrooms, this custom-built home offers a spacious upstairs private en suite featuring 1 bedroom and 1 bath, ideal for guests, playroom or a secluded home office. A true Gardeners Paradise. The interior is nothing short of breathtaking with soaring 10’ ceilings and solid red oak flooring that greets you in the foyer and extends through the kitchen and breakfast nook. The heart of the home, a chef's kitchen, is adorned with quality chestnut wood cabinets, sleek granite countertops, and a wet bar island, perfect for entertaining. Hallway complete with bright skylights that lead to bedroom 2 and 3 that actually both have access to the hall Jack n Jill bath. Three way split floor-plan offers loads of lifestyle options. Attention to detail is evident with 5 1/4” baseboards, recessed lighting, and a luxurious custom built-in entertainment center. Cozy up by the gas-burning fireplace or enjoy the oversized 860 SF 3-car garage/workshop, equipped with an insulated ceiling and reinforced garage doors, offering ample space for vehicles and projects alike. Custom Built pergola off the garage offers additional charm. So Many options. Complete with a direct wire for a generator access. The master suite is a sanctuary with a generous 8' x 12' walk-in closet featuring custom solid walnut cabinets. Bask in the Florida sunshine on your awning-covered rear deck with a view of the golf course and conservation area. Built in 2001 with a new roof in 2020, this move-in ready home benefits from top-of-the-line “Low E” windows, R-30 attic insulation. Yard is LOW MAINTENANCE! Location is paramount, with proximity to quality schools, shopping, dining, and major employment hubs.You are upgrading your LIFESTYLE in this neighborhood. HIGHLIGHTED EXTRAS Throughout. Along with the purchase this home comes with 20 solar panels, that are PAID FOR, which can provide 7.8 kWh are connected with the Duke power grid. The electric bill reflects how much power you use and how much you push back to the grid. You are credited equally for power pushed back in the final monthly amount due. Additionally, there is a backup battery which in the event of power outage will provide 6 dedicated circuits for the house with standby power during brief power outages."A" Rated schools, all three! A MUST SEE!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Laurie Cain (407-484-9944)
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,625,00091 Days on yellowkey MLS ID: O6388126
REDUCED by $174,000 (6.2%) on 06/03/2026
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6132 Built: 2026 Tax: $2,989 (2024)Community: Talis CrossingSingle Family
Taxes:$2,989
Elementary School: Sterling Park Elementary
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)
538 CRIMSON LN, WINTER SPRINGS, FL 32708
$379,90015 Days on yellowkey MLS ID: O6409571
REDUCED by $5,000 (1.3%) on 06/03/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1854 Built: 2007Monthly Fee: $300 Tax: $5,370 (2025)Community: Jesups Reserve Twnhms RepTownhouse
Taxes:$5,370
Remarks: Price improvement. Welcome to 538 Crimson Lane, a beautifully designed townhome located in the highly desirable community of Jesup’s Reserve. Meticulously maintained, this 3-bedroom, 3.5-bathroom home with a 2-car garage showcases numerous upgrades and distinctive features throughout. Ideally situated in the heart of Winter Springs, this property offers the perfect blend of comfort, style, and convenience. From the moment you arrive, the manicured landscaping and spacious front porch create inviting curb appeal. Inside, the first floor features a generously sized bedroom complete with a private bathroom and walk-in closet, making it ideal for guests, a home office, or a quiet retreat. The second floor serves as the main living space, offering an open and airy layout filled with natural light from an abundance of windows. The spacious living and dining areas flow seamlessly into the kitchen, which features granite countertops, a center island, closet pantry, breakfast bar, and ample room for entertaining family and friends. The kitchen is further enhanced with beautiful maple cabinetry. On the third floor, you’ll find the private primary suite, designed for relaxation and comfort. The oversized bedroom includes a large walk-in closet, while the ensuite bathroom features a separate shower and a luxurious oversized soaking tub. This home also includes several valuable updates and bonus features, including a new AC unit installed in 2025, a roof replaced in 2023, and fresh interior paint completed in 2026. The HOA provides added peace of mind by covering exterior maintenance, including grounds care, roof maintenance, and exterior painting. Residents of Jesup’s Reserve also enjoy access to a resort-style pool and hot tub. Conveniently located directly across from Winter Springs Town Center, you’ll have easy access to shopping, dining, fitness centers, and entertainment. The area is also known for its top-rated public and private schools, scenic parks, and walking trails, with quick access to major roadways and State Road 417. This exceptional property truly offers everything you need to feel right at home. Schedule your private showing today!
Listing Agent: Hang Kendall (407-929-8664)
1406 BLUMBERG BLVD, WINTER SPRINGS, FL 32708
$425,00018 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)
600 NORTHERN WAY #302, WINTER SPRINGS, FL 32708
$269,90058 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)
934 TORREY PINE DR, WINTER SPRINGS, FL 32708
$514,000243 Days on yellowkey MLS ID: O6349893
REDUCED by $5,000 (1.0%) on 06/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1678 Built: 2000Monthly Fee: $126 Tax: $2,280 (2024)Community: Greenbriar Sub Ph 2Single Family
Taxes:$2,280
Remarks: One or more photo(s) has been virtually staged. Beautifully remodeled golf course home in the highly desirable Tuscawilla community! This move-in ready residence has been extensively updated with a fresh modern design throughout, including all new flooring, new interior paint, new granite countertops, custom designer backsplash, stainless steel appliances, and an updated interior lighting package. The spacious primary suite features a fully renovated bath with a new granite vanity, updated hardware and lighting, and a completely redesigned custom glass-enclosed walk-in shower. The guest bath has also been tastefully updated with a new vanity. Enjoy peaceful golf course living with scenic surroundings and a spacious screened patio perfect for relaxing or entertaining. The roof has been recently inspected and is reported to be in fantastic condition, providing added peace of mind for the next owner. Conveniently located near top-rated Seminole County schools, parks, shopping, dining, and major roadways, this is an exceptional opportunity to own a beautifully updated home in one of Tuscawilla’s most sought-after golf course communities.
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: James Clark (407-575-7011)
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