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1522 Eagle Nest Circle, Winter Springs
$849,900
4 Beds ⋅ 4 Baths ⋅ Glen Eagle Unit 4 SubDv. ⋅ 32708 Zip Code
Ideally located in the highly desirable Glen Eagle community of Tuscawilla, this Von Jacobs pool home offers a versatile three-way split floor plan with four bedrooms and three and a half bathrooms, providing plenty of space for family, guests, or a home office. The layout includes formal living and dining rooms, while the kitchen opens to the family room and breakfast nook for comfortable everyday living and entertaining. The remodeled kitchen features wood cabinetry, an expanded pantry, quartz countertops, and a wet bar area. Both secondary bathrooms have also been remodeled, while the primary bath offers an opportunity to customize to your taste. Outside, enjoy Florida living around the recently resurfaced pool (2024), complete with a new pool pump (2024) and electric heater for extended seasonal enjoyment. The spacious screened enclosure was re-screened in 2024, creating an inviting setting for relaxing or entertaining. A generous side yard and three-car garage add even more appeal. Major updates include a new water heater (2026), new garage doors (2026), replumb, and AC (2019). Glen Eagle puts you close to the Tuscawilla Country Club and its 18-hole golf course, along with several of Central Florida’s sought-after private schools, including The Geneva School, Trinity Preparatory School, The Master's Academy, and St. Luke's Lutheran School. Grab your golf cart and come take a look—this Glen Eagle gem won’t last long!

1522 Eagle Nest Circle, Winter Springs

149 Cherry Creek Circle, Winter Springs
$1,080,000
5 Beds ⋅ 5 Baths ⋅ Reserve At Tuscawilla Ph 1 The SubDv. ⋅ 32708 Zip Code
Virtually Staged. Exceptional curb appeal welcomes you to this beautiful custom pool home in the gated Tuscawilla Reserve community of Winter Springs. Surrounded by mature landscaping and stately palms, this spacious residence offers over 4,000 square feet of living space with five bedrooms, five full bathrooms, a private office or bonus room, and a three-car side-entry garage. One of the home’s standout features is its thoughtfully designed four-way split floor plan, providing exceptional privacy and separation for family members and guests. The bedroom suites are positioned throughout the home with convenient access to private bathrooms, making the layout ideal for guests, extended family, multigenerational living, or anyone who appreciates having their own private space. Inside, soaring ceilings, abundant natural light, beautiful wood flooring, and spacious living areas create an impressive yet comfortable atmosphere. The kitchen is designed for both everyday living and entertaining with JennAir appliances, double ovens, a convection oven and microwave combination, an oversized quartz island, built-in buffet with wine refrigerator, generous cabinetry, and a large walk-in pantry. The kitchen opens to the dramatic family room, creating a wonderful gathering space with views of the pool and backyard. French doors invite you outside to your private backyard oasis featuring a screened pool and spa, covered lanai, and spacious pool deck. Surrounded by mature landscaping and lush greenery, the backyard offers exceptional privacy, creating a peaceful setting for entertaining, relaxing, and enjoying the Florida lifestyle year-round. The upstairs retreat provides even more flexibility with an additional bedroom, full bathroom, and expansive bonus space ideal for a media room, game room, home gym, second office, or private guest area. Additional features include a whole-house water softener, generous storage, and a three-car side-entry garage. Located in desirable Tuscawilla Reserve, this home is convenient to the Seminole Trail, Tuscawilla Country Club, parks, shopping, dining, and highly regarded Seminole County schools. With its impressive curb appeal, private four-way split design, spacious bedroom suites, flexible living areas, private backyard, and resort-style pool setting, 149 Cherry Creek Circle offers an exceptional combination of space, privacy, and Florida living.

149 Cherry Creek Circle, Winter Springs

1436 Winter Wharf Lane, Winter Springs
$399,000
3 Beds ⋅ 4 Baths ⋅ Jesups Landing SubDv. ⋅ 32708 Zip Code
Virtually Staged. Welcome to easy, stylish living in Jesup’s Landing, one of Winter Springs’ most desirable communities. This spacious 3 Bedroom, 3 1/2 Bath Townhome features a versatile split-level design that creates a comfortable sense of separation between living areas while still offering plenty of room to gather and entertain. The beautifully appointed kitchen features 42-inch cherry cabinetry, granite countertops, and a spacious prep island, creating an inviting and functional space for cooking, baking, and entertaining. Upstairs, the primary suite offers a generous bedroom, a spacious walk-in closet, and a well-designed primary bath with a double-sink vanity, separate shower, and soaking tub. A second upstairs bedroom also features its own en-suite bath with a walk-in shower and a large walk-in closet, providing added privacy and convenience. The lower level includes an additional secondary bedroom with its own en-suite shower bath, along with access to the two-car garage and extra storage space. New Carpet in the Bedrooms and Stairways was just installed for a MOVE-IN READY transition for the new Owner. The exterior has also been refreshed with New Paint, New Screen on Balcony and the home features a New Roof for added value and peace of mind. The location offers exceptional convenience with Central Winds Park, shopping, dining, SR 417, Orlando Sanford International Airport, UCF, and Seminole State College all within easy reach. Jesup’s Landing residents enjoy a variety of community amenities, including a clubhouse, fitness center, and inviting swimming pool. With its spacious floor plan, recent updates, convenient location, and low-maintenance lifestyle, this home offers a wonderful opportunity to enjoy all that Winter Springs has to offer. ROOF - 2026, A/C and Water Heater - 2014.

1436 Winter Wharf Lane, Winter Springs

992 Sleeping Rock Court, Winter Springs
$750,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 12a SubDv. ⋅ 32708 Zip Code
CHARACTER YOU CAN’T BUILD INTO A COOKIE-CUTTER HOME—welcome to 992 Sleeping Rock Ct, a distinctive 4-bedroom, 2.5-bath POOL HOME tucked away on an oversized .38-ACRE CUL-DE-SAC LOT with NO HOA in the heart of Tuscawilla. Originally built as a CUSTOM PARADE OF HOMES MODEL, this residence offers approximately 2,701 SQ FT and immediately separates itself with architectural details rarely found in newer construction. Dramatic VAULTED WOOD CEILINGS bring warmth and character to both the family room and primary suite, while an updated WOOD-BURNING FIREPLACE creates a natural centerpiece for the main living space. The SPLIT FLOOR PLAN offers privacy and functionality, complemented by updated flooring, crown molding, baseboards, interior doors, custom closet systems, a WALK-IN PANTRY, dedicated laundry room, and thoughtful smart-home upgrades throughout. The primary suite feels like its own retreat beneath the vaulted wood ceiling, complete with custom closet shelving and an en-suite bath overlooking a PRIVATE ATRIUM. Then step outside and discover what may be the most memorable part of the property: a HUGE COVERED LANAI overlooking the PRIVATE POOL with a NATURAL ROCK WATERFALL, surrounded by mature landscaping and an expansive backyard that gives you room to actually enjoy the .38-acre homesite. New brick pavers and updated fencing further enhance an outdoor setting made for entertaining, relaxing, and Florida living year-round. Just as important, many of the major components have already been addressed, including ROOF & SKYLIGHTS (2019), A/C, ELECTRICAL PANEL & DUCTWORK IMPROVEMENTS (2020), WINDOWS & THREE SLIDING GLASS DOORS (2023) WITH HOME DEPOT LIFETIME WARRANTY, FRONT DOOR (2023), WATER HEATER (2024), plus updated pool equipment including a Pentair pump and smart WiFi-controlled irrigation. The home is also equipped with FIBER INTERNET and CAT8 wiring throughout, along with Nest and Ring smart-home features. CUSTOM MODEL HOME. .38 ACRES. CUL-DE-SAC. PRIVATE POOL & WATERFALL. MATURE LANDSCAPING. MAJOR UPDATES. NO HOA. 992 Sleeping Rock Ct offers the space, privacy, architectural personality, and freedom that are becoming increasingly difficult to find in Winter Springs. Schedule your private showing and experience this one in person.

992 Sleeping Rock Court, Winter Springs

855 Benchwood Drive, Winter Springs
$499,000
4 Beds ⋅ 3 Baths ⋅ Oak Forest Unit 3 SubDv. ⋅ 32708 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 855 Benchwood Drive in Winter Springs, a spacious 4-bedroom, 3-bathroom home situated in the established Oak Forest community. Offering approximately 2,268 square feet of living space, the home features an open floor plan designed to bring the main gathering areas together while providing flexibility for everyday living and entertaining. One of the four bedrooms is currently used as a home office, creating a dedicated workspace that can easily adapt to other needs. The interior offers generous living areas filled with natural light, along with a functional connection between the kitchen, dining, and main living spaces. The bedrooms provide plenty of room for family and guests, while three full bathrooms add convenience throughout the home. The flexible office can also serve as a guest room, hobby space, or additional bedroom as needed. Outside, the backyard is designed for enjoying the Florida lifestyle with a private in-ground pool and spa, surrounded by an expansive pool deck with plenty of space for lounging and entertaining. A covered patio provides a shaded area for outdoor dining and relaxing, while mature landscaping adds character to the outdoor setting. Public listing records also note the property sits on approximately 0.37 acre, providing additional yard space around the outdoor living areas. Located in Oak Forest, the home is close to neighborhood recreation, including Trotwood Park, as well as shopping, dining, and everyday conveniences throughout Winter Springs. The location also provides convenient access to Tuskawilla Road, SR 434, SR 417, and I-4, making surrounding Seminole County and Greater Orlando destinations easily accessible.

855 Benchwood Drive, Winter Springs

1067 Chokecherry Drive, Winter Springs
$415,000
3 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 2b SubDv. ⋅ 32708 Zip Code
Nestled in the desirable Oak Forest at Tuscawilla community, this 3 bedroom, 2 bathroom home is located near local parks, trails, shops, restaurants, and highly rated Seminole County schools. Inside, a spacious, open floor plan flows effortlessly between the living and dining areas, elevated throughout by custom crown molding and rich wood detailing that add a timeless, tailored feel rarely found at this price point. The lovely kitchen anchors the home with a center island and breakfast bar, perfect for casual meals or entertaining guests. The primary suite offers a peaceful retreat with a generous walk-in closet, while the additional bedrooms are equally impressive, each offering generous space and an abundance of natural light. The home also features a brand NEW roof (2026). Outside, a screened patio invites year-round outdoor living, and an attached 2 car garage completes this beautiful Winter Springs residence.

1067 Chokecherry Drive, Winter Springs

1541 Corkery Court Unit 1541, Winter Springs
$489,900
2 Beds ⋅ 3 Baths ⋅ Greens At Tuscawilla SubDv. ⋅ 32708 Zip Code
Welcome to the exclusive gated enclave know as The Greens of Tuscawilla. This luxury townhome delivers a rare combination of superior construction, premium finishes, prime location, and a maintenance-free lifestyle. Nestled amongst the trees in the heart of Tuscawilla is The Portofino II Model with Golf, Water and Conservation Views. Level One offers Open Concept Living with the ability for a future Elevator. (Elevator closets are located on both floors and are currently used as walk in storage closets). Level Two allows for privacy with all bedrooms located on this floor. Throughout the unit you will find soaring volume ceilings, crown molding, tall doors, recessed lighting, wood or tiled floors, fresh paint, granite countertops, 42 inch cabinets, designer lighting, fans, fire safety sprinkler system and much more. Start and end each day on your private screened porch where the views are unparralleled. The Greens consists of 15 buildings and 60 units. Residents enjoy lush landscaping, manicured lawns and a private dog park. Partake in the Country Club lifestyle with the private Golf Cart path that leads to Tuscawilla Country Club. Membership provides access to championship golf, Har-Tru clay tennis courts, pickleball court, Jr. Olympic-sized pool, fitness center, private restaurant/bar, and social calendar. The Tuscawilla Community has parks, sports courts and fields, playgrounds, hiking trails and splash pads. Walk, run, or ride while taking in the many natural areas throughout the 3500 acre community.

1541 Corkery Court Unit 1541, Winter Springs

216 Tavestock Loop, Winter Springs
$605,000
5 Beds ⋅ 2 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Enjoy waterfront views and your own private pool in this spacious 5-bedroom, 2-bath home located in the highly sought-after gated community of Parkstone in Winter Springs. Perfectly positioned with tranquil pond views, this home offers a desirable three-way split floor plan, open living spaces, and an ideal blend of comfort, functionality, and outdoor living. Inside, you’ll find luxury vinyl plank flooring throughout the main living areas, a beautifully updated kitchen featuring granite countertops, refinished cabinetry, and a stylish backsplash, along with tastefully remodeled bathrooms showcasing shaker-style vanities, updated fixtures, and wood-look tile flooring. Energy-efficient upgrades include Low-E double-hung windows, an updated roof (2021), Carrier HVAC system, LED lighting, a whole-house water filtration system, two mini-split air conditioning systems (2025), and an energy-efficient year-round. The backyard is also been fully fenced, creating a private space for pets, play, and outdoor enjoyment. Step outside to your own backyard retreat featuring a sparkling pool, relaxing spa, and picturesque water views. Whether you’re entertaining guests or enjoying a quiet evening watching the sunset over the pond, this outdoor space is sure to impress. Additional features include pool deck speaker pre-wiring and a 220-volt outlet ready for an electric vehicle charger. Parkstone residents enjoy an exceptional lifestyle with lawn maintenance included in the HOA, a community pool, fishing pier, tennis courts, playgrounds, walking trails, scenic ponds, and gated security. The community borders the Cross Seminole Trail and is just a short walk to Central Winds Park and the dog park. Located in Seminole County with highly rated A-rated schools and convenient access to shopping, dining, and major roadways, this home truly offers the best of Florida living. Don’t miss your opportunity to own this exceptional waterfront home in one of Winter Springs’ most desirable communities!

216 Tavestock Loop, Winter Springs

335 Lansbrook Lane, Winter Springs
$323,000
2 Beds ⋅ 2 Baths ⋅ Jesups Reserve Twnhms Rep SubDv. ⋅ 32708 Zip Code
*Buyers Financing Fell Through* Opportunity Knocks! Welcome Home to 335 Lansbrook Lane! This move-in ready 2 Bed/2 Bath townhouse is ready for its new owner. Enjoy the ultimate Florida lifestyle with peaceful water views right from your front porch. Inside, you’ll find a functional and inviting layout featuring a downstairs bedroom and full bath, while upstairs offers the primary suite, kitchen, and spacious living area. Conveniently located in highly sought-after Seminole County, you’ll be just minutes from shopping, dining, entertainment, and everyday conveniences. Recent updates include a (2023) Roof and (2025) Appliances, making this home truly move-in ready. Come see all this home has to offer! Call Today to schedule your private showing!

335 Lansbrook Lane, Winter Springs

1112 Orange Avenue, Winter Springs
$3,700,000
5 Beds ⋅ 7 Baths ⋅ Lake Jessup SubDv. ⋅ 32708 Zip Code
Opportunities like this are almost impossible to find in Central Florida. Situated on 5.33 pristine lakefront acres with no HOA, this extraordinary estate is commercially zoned, creating a unique opportunity for a variety of potential business uses, including a luxury wedding venue, private event space, corporate retreat, boutique hospitality concept, or an exceptional live-work estate. With its breathtaking setting, grand architecture, and resort-style amenities, the property offers a level of versatility rarely available in today's market. Inspired by the elegance of the Italian countryside, the residence makes a lasting first impression with a dramatic front waterscape, lush gardens, and timeless architectural details. Inside, guests are welcomed by a grand foyer featuring exquisite marble finishes and a spectacular custom-painted 24-karat gold dome. Designed for both entertaining and everyday luxury, the expansive living spaces showcase panoramic views of beautiful Lake Jessup, soaring ceilings, stunning chandeliers, and a grand marble fireplace. The thoughtfully designed "H" floor plan encompasses more than 8,000 square feet of air-conditioned living space, offering five spacious bedrooms and six-and-a-half bathrooms, all conveniently situated on a single level. The primary suite is a true private retreat, featuring eight sets of French doors opening directly to the pool and lakefront, a custom-designed closet that doubles as a safe room, and a spa-inspired bathroom complete with a tranquil garden retreat. The gourmet chef's kitchen is equipped with top-of-the-line appliances, custom cabinetry, and an oversized walk-in butler's pantry designed to accommodate large-scale entertaining. Additional luxury amenities include a temperature-controlled wine cellar, private movie theater, dedicated nanny or guest quarters, and a six-car garage with extensive attic storage. Outside, the estate transforms into a private resort. A spectacular sports pool with multiple water features serves as the centerpiece, complemented by a summer kitchen, wet bar, outdoor fireplace, and expansive covered veranda overlooking the serene waters of Lake Jessup. Whether hosting elegant weddings, unforgettable events, corporate gatherings, or private family celebrations, the setting is simply unmatched. Combining custom craftsmanship, Tuscan and Greek-inspired design elements, commercial zoning flexibility, and an irreplaceable waterfront location, this remarkable estate offers a truly rare opportunity to own one of Central Florida's most unique properties. Schedule your private tour today to experience the endless possibilities and extraordinary lifestyle this one-of-a-kind property provides.

1112 Orange Avenue, Winter Springs