Location: Winter Springs
Do Not Show Listings
135 W TRADE WINDS RD, WINTER SPRINGS, FL 32708
$847,50017 Days on yellowkey MLS ID: S5146734
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3100 Built: 1995 Tax: $4,421 (2024)Community: Oak Hill EstatesSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,421
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: As you arrive, you’re greeted by a circular driveway and the peace, privacy, and wide-open feel of over an acre of land. Step inside to a thoughtfully designed layout that flows with ease. To the right, a staircase leads to three spacious bedrooms, a full bathroom, and the primary suite featuring its own private bath. To the left, a cozy living room offers the perfect setting to relax and unwind. As you continue through the home, the space opens into a bright and expansive kitchen, dining, and lounge area—ideal for both everyday living and entertaining. Just off the kitchen, you’ll find a conveniently located laundry room with direct access to the pool bath. From the kitchen or laundry area, step out onto the screened-in porch overlooking a large backyard complete with an in-ground pool—perfect for enjoying Florida living year-round. One of the standout features of this property is the attached in-law suite, offering its own private entrance and single-level living. This versatile space includes a full kitchen, two bedrooms, a full bathroom, and a spacious living area. It is wheelchair accessible and ideal for extended family, guests, or even rental potential. The suite was converted from the original attached two-car garage, and there is ample room on the property to build a new garage if desired. In total, the home features 6 bedrooms and 4 bathrooms, all set on over an acre with no HOA restrictions. The backyard continues to impress with a barn capable of accommodating up to three vehicles, along with an existing slab ready for customization—whether you envision a workshop, additional storage, or something entirely your own. This property delivers space, flexibility, and endless opportunity to create the lifestyle you’ve been looking for.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Joshua Crittendon (321-616-0562)
431 S HAWTHORN CIR, WINTER SPRINGS, FL 32708
$450,000230 Days on yellowkey MLS ID: O6330022
REDUCED by $15,000 (3.2%) on 04/06/2026
Bed: 5 Bath: 2.5 Liv Area Sq Ft: 2092 Built: 1975 Tax: $5,400 (2024)Community: North Orlando Terrace Unit 2 Sec 9Single Family
Taxes:$5,400
Elementary School: Winter Springs Elementary
High School: Winter Springs High
Middle School: Indian Trails Middle
Remarks: **Single-Family Home with Detached ADU & Pool** Tucked away in a quiet cul-de-sac, this over 2,000 sq. ft. home with a detached Accessory Dwelling Unit (ADU) is a rare find in the highly desirable, non-HOA community of North Orlando Terrace! NEWER ROOF (2022), as well as a massive remodel in 2023 that consisted of NEW kitchen, bathrooms, plumbing, electrical panel, interior/exterior paint, light fixtures and luxury vinyl plank flooring throughout. WOW! Inside, modern design and timeless comfort blend seamlessly. The open-concept kitchen flows effortlessly into the dining and living spaces, creating the perfect setting for both family life and entertaining. A spacious family room, complete with a cozy fireplace, invites you to unwind, while the expansive primary suite offers a private retreat with a spa-like bath. Generously sized guest bedrooms and beautifully updated bathrooms make the home truly move in ready. Step outside and discover your own Florida oasis, a sparkling pool with elegant pavers and a screened porch designed for year-round enjoyment. And then there’s the showpiece: the detached ADU. With its open concept living/sleeping space, sleek kitchen, and full bath, it’s ideal for multi-generational living, private guests, or generating rental income to offset your mortgage. All of this comes with a central location just minutes from shopping, dining, and major roadways including SR-434 and US-17. This is more than a home, it’s a lifestyle. Don’t miss your chance to own it. Schedule your private showing today!
Listing is courtesy of: THE SHUGAN GROUP INC (407-755-7588)
Listing Agent: Elliot Shugan (407-755-7588)
130 DEER SONG DR, WINTER SPRINGS, FL 32708
$310,00012 Days on yellowkey MLS ID: O6395309
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1105 Built: 1994Monthly Fee: $127 Tax: $3,102 (2025)Community: Deersong 2Single Family
Taxes:$3,102
Elementary School: Layer Elementary
Tax Year: 2025
Remarks: Welcome to 130 Deer Song Dr in the heart of Winter Springs an exceptional opportunity to own one of the most beautifully updated homes in the community! Positioned on a desirable corner lot with ample parking, this fully renovated 3-bedroom, 2-bathroom home stands out as a rare find offering both style and convenience. From the moment you step inside, you’ll notice the thoughtful upgrades throughout, including brand-new flooring, a completely redesigned kitchen, modernized bathrooms, updated plumbing, and new energy-efficient windows. all creating a truly move-in-ready experience. Major systems have already been taken care of for peace of mind, with the roof replaced in 2015 and AC updated in 2019. Step outside to your own private, fully fenced backyard oasis, featuring a paved outdoor space and covered patio perfect for entertaining, relaxing, or enjoying Florida living year-round. The property also includes a detached storage space, offering additional functionality and convenience. Located directly across from the community pool and amenities, you’ll enjoy easy access to everything this well-maintained neighborhood has to offer, including: Community pool Tennis courts Playground Dog park Lawn care included through HOA The location is unbeatable just minutes from Winter Springs Town Center, Seminole County Bike Trail, Oviedo Mall, Publix, restaurants, and everyday essentials, along with nearby fire and police services for added peace of mind. This home checks all the boxes: location, upgrades, lifestyle, and value. Opportunities like this don’t come often, schedule your private showing today and see why this is truly one of the best homes in the neighborhood!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Yosseff Roman (407-394-5843)
104 REDTAIL PL, WINTER SPRINGS, FL 32708
$469,90073 Days on yellowkey MLS ID: O6378697
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1766 Built: 1995Monthly Fee: $170 Tax: $2,250 (2024)Community: Eagles Watch Ph 1Single Family
Taxes:$2,250
Remarks: RECENTLY PRICE REDUCED! Luxury Living Meets Trailside Adventure — with Everything Close By! WELCOME TO THE GATED COMMUNITY OF EAGLE WATCH! This beautifully presented property is a 3-bedroom, 2-bath home where comfort, style, and location come together effortlessly. It is located in the cherished well-maintained community in Winter Springs. Enjoy peace of mind with a newer roof and HVAC system, luxury engineered wood flooring throughout the home, plus fresh interior paint that gives the home a clean, modern feel. Low HOA fees also include common area landscaping maintenance and pristine curb appeal throughout the community! Eagle Watch shares a gated entrance community pool with Howell Creek Reserve to enjoy with friends and family! The home's inviting layout is perfect for everyday living and entertaining, filled with natural light and an easy, modern flow. Step outside and relax with your covered screened in porch and level up your lifestyle with direct access to the Cross Seminole Trail—a dream for avid bicyclists, hikers, and walkers who love the outdoors. Now let's talk about the location being so convenient! You’re just minutes from malls, dining, and shopping, close to SR 417, University of Central Florida, and an easy ride to the world-class parks Orlando is famous for. Adventure, entertainment, and everyday essentials are all right at your fingertips. Move-in ready, perfectly located, and packed with lifestyle perks—this one is fun, functional, and full of possibilities! DONT WAIT TOO LONG! Schedule your showing today!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Cathy Norman (407-247-7180)
717 WILSON RD, WINTER SPRINGS, FL 32708
$389,90093 Days on yellowkey MLS ID: O6372938
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1368 Built: 1981Monthly Fee: $90 Tax: $164 (2024)Community: Wedgewood Tennis VillasSingle Family
Taxes:$164
Remarks: ASSUMABLE LOW VA LOAN INTEREST RATE of 2.5% TO QUALIFYING BUYER (You DON'T have to be a veteran)!! Saving you $450 MONTHLY!! ADORABLE home located in DESIRABLE TUSCAWILLA Wedgewood Tennis Villas known for its' CHARMING TREE-LINED STREETS!! Walk to clubhouse, tennis games, and fitness center! BEAUTIFUL CURB APPEAL! Home is OPEN, LIGHT, BRIGHT, and SPACIOUS!! With BRICK FIREPLACE and VOLUME CEILINGS!! NEWER laminate wood FLOORING throughout living and bedroom area installed 2018! Kitchen features LIGHT MAPLE WOOD CABINETRY w/pullout drawers for easy reach! and GRANITE COUNTERTOPS!!And EAT-IN SPACE in kitchen! Master bedroom features LARGE WALK-IN CLOSET!! Very spacious COVERED SCREENED-IN PATIO and FENCED-IN BACKYARD!! NEWER ROOF 2018! NEWER A/C 2020!! NEW AC DUCTWORK 2024!! FRESH EXTERIOR PAINT 2024!! NEW WATER HEATER 2023!! NEW ELECTRIC PANEL 2020! NEWER ENERGY EFFICIENT WINDOWS AND DOORS!! Solar panels w/ monthly pmt of only $98, saving owner 100's of dollars monthly!! Water treatment system!! Termite Bond for protection! Vivint Security System in place.Seminole County 2025 ALL "A" SCHOOLS!!!!!
Listing is courtesy of: FLORIDA USA REALTY (407-493-1438)
Listing Agent: Cameron Hasan (407-493-1438)
449 GEE HAMMOCK LN, WINTER SPRINGS, FL 32708
$355,000103 Days on yellowkey MLS ID: O6370606
0 Days Off yellowkey (back on 4/4/2026)
REDUCED by $4,000 (1.1%) on 04/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1435 Built: 2016Monthly Fee: $226 Tax: $5,182 (2025)Community: Jesups LandingTownhouse
Taxes:$5,182
Remarks: Under contract-accepting backup offers. Welcome to your dream home at 449 Gee Hammock Lane, nestled in the tranquil and highly sought-after neighborhood of Jesups Landing. This stunning home boasts Stainless Steel appliances, Granite countertops, 42" Cabinets, Tiled kitchen backsplash, Pendant lighting, Walk-in pantry, Breakfast bar, and charming built-in storage shelves. This home offers a split floor-plan, giving you the option to partition the home as you please! The private, spacious balcony located on the second floor is the perfect place to enjoy relaxing moments. The community is surrounded by nature preserves, parks, and top-rated schools. You will love the easy access to Major Highways (SR 434, SR 417) for commuting to nearby cities such as Orlando, Altamonte Springs, and Sanford.
Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)
Listing Agent: Angela Magac (407-744-5557)
1815 SENECA BLVD, WINTER SPRINGS, FL 32708
$1,049,000118 Days on yellowkey MLS ID: O6368232
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3885 Built: 1989 Tax: $5,558 (2024)Community: Tuscawilla Unit 14BSingle Family
Taxes:$5,558
Elementary School: Lawton Elementary
High School: Oviedo High
Remarks: This stunning 5-bedroom pool home in the highly desirable Chelsea Woods at Tuscawilla has been completely remodeled from top to bottom. The home offers exceptional living space, including a large living room with fireplace, a spacious family room with fireplace, and a formal dining room—ideal for entertaining. A large bonus room provides flexible space for a home office, playroom, or additional living area. The brand-new kitchen is a showstopper, featuring new appliances, quartz countertops, two-tone cabinetry with open shelving, and a stylish bar area with additional shelving. The large laundry room includes a convenient butler’s pantry area, adding extra storage and functionality. Downstairs, you’ll also find two half bathrooms, all beautifully updated. All five bedrooms are located upstairs, along with three fully renovated bathrooms, including a Jack-and-Jill bath. The expansive primary suite offers a true retreat with a luxurious soaking tub, large walk-in shower, and generous space throughout. Recent upgrades also include new wood-look tile plank flooring throughout the lower level, LVP flooring upstairs, ROOF (2023), and both A/C units replaced. Step outside to enjoy the covered, screened patio overlooking the pool—perfect for relaxing or entertaining. Located in Tuscawilla, this home is zoned for top-rated schools and offers the space, updates, and location you’ve been looking for. Schedule your private showing today!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Belinda Gonzales (321-277-8994)
1513 BLACK BEAR CT, WINTER SPRINGS, FL 32708
$1,549,00041 Days on yellowkey MLS ID: O6385058
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6175 Built: 1989Monthly Fee: $142 Tax: $23,523 (2025)Community: Bear Creek EstatesSingle Family
Taxes:$23,523
Elementary School: Keeth Elementary
Remarks: Welcome to this exceptional home in the exclusive gated community of Bear Creek Estates, set on over an acre of lush wooded greenbelt with beautiful landscaping and a circular driveway that creates outstanding curb appeal. The over 6,000 sq. ft. (includes 1 car garage/hobby room of approx. 280 sq.ft.) home features a new architectural tile roof (less than one year old) and 10-foot ceilings throughout the first floor, creating a bright and spacious feel. Inside, you’ll find elegant formal living and dining spaces, a private home office, and a comfortable family room overlooking the sparkling pool and lanai. The home offers oversized secondary bedrooms with seating areas, plus a large additional bedroom that can serve as an office, art studio or flex space. Entertainment is exceptional with two theater spaces, The main floor home theater is projector-ready, with acoustic panels, granite snack counter, an electronic masking screen and wiring for 7.1 sound. The upstairs primary bedroom is massive in size and the ideal retreat to unwind at end of the day! Complete with its sitting area and outdoor deck with stunning panoramic views of lush nature. The upstairs primary suite in this home also includes a projector drop-down screen and wiring for 5.1 sound. The private backyard retreat features a beautiful pool with LED lighting, waterfall feature, and updated pump and filter (2023), along with panoramic views of lush green space. Additional highlights include a smart audio system controlled by smartphone app, extensive network wiring, pre-wiring for security cameras, well-fed irrigation, and a backyard telescope pier with power and ethernet. In Winter Springs, this home offers peaceful luxury living while being close to shopping, dining and major commuting routes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Lynda Miller (407-620-2924)
986 TURKEY HOLLOW CIR, WINTER SPRINGS, FL 32708
$498,90089 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 4Single 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)
1447 BIRD RD, WINTER SPRINGS, FL 32708
$2,900,00040 Days on yellowkey MLS ID: O6388126
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 6132 Built: 2026 Tax: $2,989 (2024)Community: Talis CrossingSingle Family
Taxes:$2,989
Elementary School: Sterling Park Elementary
Middle School: South Seminole Middle
Remarks: Discover the pinnacle of secluded luxury in this brand-new, 8,000 SF estate, nestled in picturesque Winter Springs. From the moment you arrive, the custom glass French entry doors hint at the artistry within. Stepping into the grand foyer, you are greeted by statement marble and mosaic flooring that sets a tone of elegance, a design narrative that flows seamlessly throughout the home. Designed for both grand-scale entertaining and intimate daily life, the main living spaces are simply breathtaking. The great room soars with 16-foot ceilings and celestial windows, anchored by a stunning custom fireplace and bookcase display. A bank of 18-foot sliding glass doors dissolves the line between indoors and out, opening to a sprawling 1,125 SF covered patio. The chef’s kitchen is a masterpiece of form and function, featuring a 13-foot island, floor-to-ceiling cabinetry, a pet-feeding station, electric vehicle garage hookup, and a full suite of WiFi-enabled GE Cafe appliances, including a double wall oven and a 48-inch refrigerator. The home offers a versatile and luxurious layout for multi-generational living or visiting guests, highlighted by two distinct primary suites. One wing is dedicated to a private retreat with two walk-in closets, separate vanities, and a spa-inspired wet room with a freestanding tub and a four-port shower system. On the opposite side of the home, a second primary suite offers equal luxury with a massive walk-in closet and its own spa-like wet room, ensuring complete privacy for all. Beyond the main living areas, discover a wealth of flexible spaces tailored to a modern lifestyle. A dedicated movie theater or fitness center is pre-wired for the ultimate audio-visual experience, while two separate offices with storefront glass windows provide inspiring workspaces. A butler’s pantry/kitchen, wet bar with a beverage fridge, and a flexible flex room with a half-bath complete the impeccably designed interior. Outside, your private paradise awaits upon the spacious 1-acre parcel. The pavered pool deck surrounds a white quartz pool with a sun shelf and bubbler, all secured by a sleek black metal fence. Every detail has been considered, from the 150-gallon propane tank servicing the future summer kitchen and pool heater to the 4-zone HVAC, a commercial grade 50-year life-span TPO roof and two tankless water heaters for ultimate comfort. This is more than a home; it is a fully realized vision of eloquent Florida living.
Listing is courtesy of: MAVREALTY (727-314-3942)
Listing Agent: Robert Kirkwood, Iv (321-297-6489)
1075 CONDOR PL, WINTER SPRINGS, FL 32708
$414,90028 Days on yellowkey MLS ID: O6391519
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1749 Built: 1988Monthly Fee: $28 Tax: $3,267 (2024)Community: Sunrise Estates Unit 4Single Family
Taxes:$3,267
Elementary School: Rainbow Elementary
Remarks: Under contract-accepting backup offers. Charming three bedroom, two full bathroom, two car garage home with large fully fenced backyard in the lovely community of Sunrise in Winter Springs. This home has been loved and it shows with well-maintained neutral interior throughout. The large living room offers a beautiful wood burning fireplace with mantle and flooring has been upgraded to tile or laminate throughout. The kitchen features plenty of space for cooking and overlooks the large family room making this home perfect for entertaining. The spacious master bedroom features a vaulted ceiling, walk-in closet and dual vanities in attached full bathroom. Upgrades to this home include hurricane rated dual pane windows and doors (2020), refrigerator (2021), dishwasher (2020), PEX re-pipe (2012), master bath shower doors (2022), HVAC compressor (2025) and new paint (2022). Sunrise community amenities include basketball courts, tennis courts, park and playground. View today.
Listing is courtesy of: ABSOLUTE REALTY GROUP, LLC (407-673-1400)
Listing Agent: Courtney Davis (407-493-8329)
620 STALLION CT, WINTER SPRINGS, FL 32708
$650,00014 Days on yellowkey MLS ID: O6395164
0 Days Off yellowkey (back on 4/3/2026)
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2856 Built: 1979 Tax: $3,831 (2024)Community: Winter Spgs Unit 3Single Family
Taxes:$3,831
Remarks: Under contract-accepting backup offers. Welcome to this incredible opportunity to create your own paradise on 1.8 acres in the Estate Section of Tuskawilla Country Club! This 5 bedroom home sits on a prime lot in the premier neighborhood of Winter Springs. The home is ready for a complete renovation to bring it up to modern standards. You are working with a solid floor plan and a property that has had some of the major items addressed: Roof replaced 2017, HVAC 2014, Septic serviced 2024. If your goal is to build your dream home, then this beautiful, majestic area of Tuskawilla is perfect for you! Professional photos to follow next week after the estate sale process is complete. Please forgive the current condition, listing still being prepared for public viewing. Limited access granted this week to accommodate interest prior to the official launch. Call for early access. This property will be sold AS-IS only. No repairs will be offered or systems warranted. This rare find will be gone soon!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Claudia Davidson (850-294-0199)
791 ANDOVER CIR, WINTER SPRINGS, FL 32708
$435,00040 Days on yellowkey MLS ID: O6386689
5 Days Off yellowkey (back on 3/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 1994Monthly Fee: $124 Tax: $2,326 (2024)Community: Georgetowne Unit 3Single Family
Taxes:$2,326
Remarks: Welcome home to Georgetowne in the heart of Tuscawilla — where lifestyle, location, and top-rated schools come together to create one of the most desirable places to call home in Seminole County. Living here means being surrounded by the very best the area has to offer. Spend your mornings walking or biking along the scenic Seminole Trail, or head over to Trotwood Park for tennis, pickleball, playgrounds, and open green space the whole family can enjoy. On warm Florida afternoons, the community pool provides the perfect place to relax and cool off close to home. Golf enthusiasts will appreciate being just a golf cart ride away from the private Tuscawilla Country Club, offering championship golf, dining, and social events. Families are drawn to Georgetowne not only for its charm but also for access to highly rated Seminole County schools — a major highlight of this established and well-loved community. Conveniently located near SR 417, commuting is effortless whether you’re heading to the airport, the beaches, or Central Florida’s world-famous theme parks. Plus, you’ll enjoy an abundance of nearby shopping and dining options, giving you everything you need just minutes from your doorstep. Georgetowne in Tuscawilla isn’t just a neighborhood — it’s a lifestyle defined by community, convenience, and everyday enjoyment.
Listing is courtesy of: SHORES REAL ESTATE (407-353-0106)
Listing Agent: Phil Herman (407-587-6049)
762 SHEOAH BLVD, WINTER SPRINGS, FL 32708
$360,00053 Days on yellowkey MLS ID: O6384572
REDUCED by $10,000 (2.7%) on 04/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1686 Built: 1977Monthly Fee: $40 Tax: $1,514 (2024)Community: Highlands Sec 4Single Family
Taxes:$1,514
Elementary School: Highlands Elementary
Remarks: PRICE REDUCTION. SOLD “AS IS”. This home is located in one of the most desired communities in the Winter Springs area. The home offers 3 bedrooms and 2 bathrooms, an open floor plan, a Florida Room, split bedrooms, high ceiling, crown molding and much more. It is located close to all major highways making easy access to shopping centers and restaurants offering convenient travel to all areas of Central Florida. All kitchen appliances will convey, along with the refrigerator in the garage. New beautiful bamboo wood flooring in secondary bedrooms.
Listing Agent: Beverly Curry (407-493-0673)
552 SHADOW GLENN PL, WINTER SPRINGS, FL 32708
$264,90057 Days on yellowkey MLS ID: O6382972
1 Days Off yellowkey (back on 4/3/2026)
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1359 Built: 1991Monthly Fee: $493 Tax: $2,016 (2025)Community: Deer Run Unit 19BTownhouse
Taxes:$2,016
Remarks: Under contract-accepting backup offers. Welcome to 552 Shadow Glenn Pl, a beautifully maintained 2-bedroom, 2.5-bath END UNIT townhome offering 1,359 sq ft of comfortable living space in the highly sought-after Deer Run community of Winter Springs. RECENTLY UPDATED WINDOWS AND SIDING! Built in 1991, this residence combines practicality with thoughtful updates and a layout ideal for modern living. Step inside to discover an open and inviting floor plan featuring a spacious living and dining room combo on the first floor, perfect for entertaining or everyday life. The well-appointed kitchen includes ample cabinetry, a cozy eat-in nook, and convenient in-home laundry. Natural light streams through large windows and French doors, enhancing the bright and airy feel throughout. Upstairs, you will find two generous bedrooms with double closets and ceiling fans. The primary bedroom features a private en suite bathroom, while the second bedroom is conveniently located near an additional full bath. Outdoors is an enclosed, screened-in patio and fully fenced backyard, ideal for relaxing, BBQs, or playtime. The community offers easy access to Red Bug Lake Rd, SR-434, SR-417, and nearby parks, shopping, dining, and top-rated Seminole County schools. Whether you are a first-time buyer, investor, or looking to downsize, this delightful townhome presents exceptional value in a prime Winter Springs location. ROOF 2018 - REPLUMBED CPVC 2019 - WATER HEATER 2022 - HVAC 2009
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
1233 STONE HARBOUR RD, WINTER SPRINGS, FL 32708
$729,90050 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)
203 HERRELL RD, WINTER SPRINGS, FL 32708
$573,000155 Days on yellowkey MLS ID: O6358036
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3566 Built: 1987 Tax: $5,127 (2024)Community: North Orlando Ranches Sec 06Single Family
Taxes:$5,127
Remarks: **Seller will contribute towards buyer closing costs that buyer can use towards renovations. This number is negotiable.** Incredible opportunity to own this fantastic 5 bedroom, 3.5 bathroom home with OVER 3,500 square feet of living space and NO HOA in the highly sought after Ranchlands community. This home has a beautiful covered front porch, circular driveway with lots of parking space, an OVERSIZED primary bedroom located on the 1st floor with TWO WALK-IN CLOSETS, primary bathroom that doubles as a SAUNA, a large kitchen with stainless steel appliances, interior laundry room, a whole home WATER FILTRATION SYSTEM, large totally enclosed back porch WITH AC, and beautiful oversized lot with a view of a small lake nearby. The original garage was enclosed and converted into a HUGE workspace that can be a workshop, man cave, or even an extra bedroom, and an ADDITIONAL TWO CAR GARAGE was ADDED, so you still have a full 2 car garage with covered parking/storage. This neighborhood has the most beautiful, tranquil, tree-lined streets, quiet and away from the hustle and bustle of the city, but close enough that anything you need is just a few moments away. Don’t miss this opportunity to own such a wonderful home in an incredible location. All with NO HOA!!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Margeaux Eddy (407-970-3798)
229 BENNETT ST, WINTER SPRINGS, FL 32708
$335,00073 Days on yellowkey MLS ID: O6378070
5 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1164 Built: 1971 Tax: $3,852 (2024)Community: North Orlando Townsite 4Th Add RepSingle Family
Taxes:$3,852
Remarks: Under contract-accepting backup offers. This spacious 4-bedroom, 2-bathroom home offers a comfortable living experience with 1164 sq. ft. of space. The kitchen is equipped with stainless steel appliances, including a refrigerator, microwave, range oven, and dishwasher. The property also features window coverings, a ceiling fan, a bathtub, and an attached garage. Located conveniently close to restaurants, grocery stores, schools, and retail services, this home meets a variety of lifestyle needs. You will love living here! Schedule a tour today!
Listing is courtesy of: RISE 24 REAL ESTATE LLC (480-636-9896)
Listing Agent: Chantel Gutierrez-Davis (480-636-9896)
4951 COURTLAND LOOP, WINTER SPRINGS, FL 32708
$700,00090 Days on yellowkey MLS ID: O6374007
REDUCED by $14,000 (2.0%) on 04/02/2026
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)
1262 SPOTTED SANDPIPER LOOP, WINTER SPRINGS, FL 32708
$489,97568 Days on yellowkey MLS ID: O6380617
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2353 Built: 2023Monthly Fee: $236 Tax: $5,937 (2024)Community: Seminole Crossing TwnhmsTownhouse
Taxes:$5,937
Remarks: "VA ASSUMABLE LOAN" Imagine a home that doesn't just house your life but elevates every chapter of it. At this stunning tri-level townhouse, the story begins the moment you step across the covered front porch and through the front door. Your day begins on the third level, where light pours through the expansive windows of your primary retreat. You wake up in a sanctuary defined by a sense of total calm. The morning routine feels like a spa visit as you step into the frameless glass shower of your ensuite bath. Choosing your outfit is an experience in itself within the "HUGE" walk-in closet, where custom shelving keeps your world perfectly organized. As the workday begins, you descend to the first level. Here, tucked away from the main living areas, lies your dedicated office. It is a quiet, professional haven where you can focus on remote work, though its attached full bath makes it an equally welcoming guest suite for visiting family or In -Law Suite. By midday, the heart of the home calls you to the second level. This is the social hub—an open-concept masterpiece where warm wood-look tile floors glow under fashionable lighting. You find yourself in the chef’s kitchen of your dreams, pulling ingredients from a walk-in pantry so VAST it feels like a secret room. You prep lunch on the oversized quartz island, perhaps glancing toward the conservation view as the sun hits the trees. When the laptops close, the adventure starts just steps from your Front door. You don’t just have a backyard; you have direct access to the Cross Seminole Trail. Whether it’s a sunset bike ride or a peaceful walk through the preserved green space, nature is your constant neighbor. As night falls, you might walk—not drive—over to the Winter Springs Town Center. Perhaps a coffee at Foxtail, a quick stop at Publix, or a relaxed dinner with friends. You return home to a community that feels like a resort, passing the sparkling pool and pet-friendly pathways that make this neighborhood feel like a true collective. This is more than a "Like New" property; it is a lifestyle of effortless transitions. With top-rated schools for the kids, easy access to the SR-417 for the commute, and the luxury of three distinct levels of privacy, the story of your life fits perfectly here. Is this the next chapter you’ve been waiting to write? Schedule Your Private Tour To experience the flow of this home in person.
Listing is courtesy of: ROI AVE LLC (321-663-7276)
Listing Agent: Mark Anthony Buot (407-925-1716)
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