Location: Longwood
Do Not Show Listings
749 SEMINOLE AVE, LONGWOOD, FL 32750
$289,0002 Days on yellowkey MLS ID: O6400530
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1108 Built: 1971 Tax: $2,752 (2024)Community: Lake Wayman Heights Lake AddSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,752
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Roof only one year old, Freshly Painted,All Tiled Floors,Electrical Updated,New Microwave,Some windows updated,Huge Back Yard,Great Location,Great Value
Listing is courtesy of: SOUTHERN REALTY ENTERPRISES (407-869-0033)
Listing Agent: Frank Filippelli (407-448-1042)
366 WEKIVA COVE RD, LONGWOOD, FL 32779
$550,000157 Days on yellowkey MLS ID: O6359535
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2268 Built: 1983Monthly Fee: $89 Tax: $3,707 (2024)Community: Wekiva Cove Ph 1Single Family
Taxes:$3,707
Elementary School: Wekiva Elementary
High School: Lake Brantley High
Middle School: Teague Middle
Remarks: One or more photo(s) has been virtually staged. Beautifully Refreshed Home in the Highly Desired Wekiva Cove Community! This stunning home is back on the market after significant upgrades, including a brand-new kitchen and improved open floor plan designed for modern living and effortless entertaining. Fresh interior and exterior paint, new ceilings in the kitchen and garage, and numerous updates make this home truly move-in ready. Step inside to a bright and welcoming formal living room featuring dramatic vaulted ceilings, a striking fireplace, and abundant natural light. The brand-new kitchen showcases elegant quartz countertops, stainless steel appliances, and a breakfast bar, perfectly positioned to overlook the dining and family room with seamless access to the pool area. Step outside and discover your own private backyard paradise. The in-ground pool, surrounded by lush landscaping and equipped with brand-new pool equipment, creates the perfect setting for relaxing or entertaining. Additional valuable upgrades include a fully paid solar panel system powering the entire home, a new water heater, and a new sprinkler system. The first-floor primary suite offers comfort and privacy, complete with a walk-in closet, private bath, and direct access to the pool. The primary bathroom features a beautiful skylight that fills the space with natural light, creating a spa-like atmosphere that feels like your own private retreat. Upstairs, you’ll find two spacious bedrooms with generous closets and a shared balcony overlooking the pool and the lake, along with a versatile loft/office that can easily serve as a 4th bedroom, workspace, or flex room. An additional indoor patio/flex space provides even more room for relaxing, entertaining, or creating a charming indoor garden area. Located in the picturesque lakefront community of Wekiva Cove, residents enjoy a scenic paved walking trail around the lake, a fishing pier, community pool, tennis courts, playground, sports fields, and clubhouse. The greater Wekiva area also offers 26 miles of walking trails, beautiful parks, and a vibrant community atmosphere. Ideally located near Wekiva Golf Club, Wekiva Island, and Wekiva Springs State Park, as well as shopping, dining, and major roadways. All of this is complemented by access to top-rated Seminole County schools. Experience the perfect blend of comfort, upgrades, and lifestyle in one of Central Florida’s most sought-after communities.
Listing is courtesy of: A2Z REALTY GROUP (407-401-8822)
Listing Agent: Olga Ray (407-404-2133)
107 COUNTRYSIDE DR, LONGWOOD, FL 32779
$785,0001 Day on yellowkey MLS ID: O6400805
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2838 Built: 1972Monthly Fee: $54 Tax: $4,872 (2024)Community: Sweetwater Oaks Sec 02Single Family
Taxes:$4,872
Elementary School: Sabal Point Elementary
Middle School: Rock Lake Middle
Remarks: Beautifully updated 5 bedroom, 4 bathroom pool home in the desirable Sweetwater Oaks community. This spacious home offers over 2,800 square feet, including two primary suites. Enjoy a resort-style backyard with a stunning pool, variable speed waterfall and outdoor cooking and entertaining space. Community features include private lake access with a beach, river access, kayak launch, beach volleyball, playgrounds, and the ability to take a golf cart or bike ride to the lake and amenities. Parks and top-rated schools are within walking or biking distance. Conveniently located near shopping, dining, and major roadways. Don’t miss this opportunity to own in one of Longwood’s premier communities!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Doriane Mclaughlin (407-687-5644)
2113 SILVER LEAF CT, LONGWOOD, FL 32779
$1,800,000Listed 04/22/2026 3:00PM MLS ID: O6401270
Bed: 7 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 7973 Built: 1986Monthly Fee: $104 Tax: $14,623 (2024)Community: Wingfield Reserve Ph 2Spa: YesSingle Family
Taxes:$14,623
Elementary School: Woodlands Elementary
High School: Lake Mary High
Middle School: Markham Woods Middle
Remarks: Welcome to 2113 Silverleaf Court! This is a once in a lifetime opportunity to own this Custom, Private Luxury Estate in Longwood’s Wingfield Reserve community, an upscale community of over 180 homes on oversized lots of at least 1 acre located inside the Prestigious Markham Woods Corridor! This one-of-a-kind custom luxury estate residence offers 7 oversized bedrooms, 5 full bathrooms, 7,793 square feet of living space which includes an 800 square foot indoor sports court, a 600 square foot home second floor bonus room with multi-use capabilities & includes a sauna, a primary suite that totals over 1,500 square feet & has direct elevator access. There is also an additional 600 square foot loft, a 3-car attached garage and the kind of architectural presence and resort style outdoor living that is one of a kind! The outdoor pool and entertainment area itself is approximately 3,000 sqft & can accommodate as many guests as you would like to host! Every inch of this home was imagined, designed and built to perfection. From the moment you arrive, the grand porte cochere entrance, paver circular driveway, and stately front elevation create a true estate feel. All of your family, friends and guests are sure to be impressed from the moment they arrive. Inside, the home opens to a massive and luxurious foyer with soaring ceilings, large but comfortable main living spaces, abundant natural light, and an unforgettable sense of scale throughout. This is an entertainer’s dream, designed for both impressive gatherings and comfortable everyday living. Outside, the property transforms into a private resort. The entire outdoor entertainment area was renovated recently, creating a spectacular setting for gatherings and relaxation alike. The 52,000-gallon saltwater pool features a waterfall, two fountains, and a heated spa, & a 9.5-foot-deep end, while the backyard is fully enclosed by concrete block and stucco wall fencing for a rare level of privacy. One of the home’s most unique features is the indoor sports court, accessible from the outdoor pool and entertainment area and currently equipped with a basketball hoop while also offering flexibility for volleyball, pickleball, handball or other recreational uses. Back inside, the chef’s kitchen is as functional as it is beautiful, featuring custom cabinetry, stone countertops, a custom cooktop installed in 2026, & all the space you need! The kitchen flows seamlessly into the home’s expansive gathering spaces, making it ideal for hosting on any scale. The primary suite includes 3 balconies, 3 closets and a second laundry room totaling close to 1500 square feet by itself! The remodeled primary bathroom was updated recently & features dual vanities, a sky light, a freestanding soaking tub, a private balcony and 3 closets! This home also offers the peace of mind with major updates, including 5 HVAC systems including one recently installed in 2026, updated electrical panels, Aqua Ox whole house water filtration system installed in 2024, several windows & doors replaced in 2021, interior painting completed in 2025 & 2026 and an artesian well for irrigation! We have also completed a 4-Point Inspection and Wind Mitigation report for your peace of mind. Zoned for Woodlands Elementary, Markham Woods Middle, and Lake Mary High School, 2113 Silverleaf Court is a once in a lifetime opportunity to own an unforgettable estate where architectural grandeur, privacy, and luxury lifestyle come together in spectacular fashion.
Listing is courtesy of: CREEGAN GROUP (407-622-1111)
Listing Agent: Chris Creegan (407-622-1111)
102 N SILVER CLUSTER CT, LONGWOOD, FL 32750
$395,0005 Days on yellowkey MLS ID: O6399945
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1166 Built: 1975 Tax: $4,071 (2024)Community: Lake Searcy ShoresSpa: NoSingle Family
Taxes:$4,071
Elementary School: Longwood Elementary
High School: Lyman High
Middle School: Greenwood Lakes Middle
Remarks: Welcome to 102 Silver Cluster Ct N in Longwood, a beautifully maintained pool home under $400K offering comfort, value, and an unbeatable opportunity for first-time buyers or anyone looking for a great starter home in a desirable Seminole County location. Tucked away on a quiet dead-end street with no through traffic, this home provides both privacy and peace of mind. This solid concrete block home features a functional split floor plan with bright, open living spaces filled with natural light. The interior flows seamlessly, with French doors leading out to a screened-in patio that overlooks your private pool — perfect for relaxing weekends, entertaining friends, or enjoying Florida living year-round. The kitchen is updated with white shaker cabinets and offers a clean, modern feel, while the home’s layout makes everyday living easy and comfortable. Step outside to a fully fenced, oversized backyard complete with an irrigation system, providing plenty of space for pets, play, gardening, or future outdoor enhancements. Major updates include a new roof (2023), double-pane windows, and an HVAC system (2017), offering confidence and efficiency for years to come. The screened patio and pool area create a true backyard retreat, making this Longwood home absolutely stand out at this price point. Located in the heart of Longwood, you’re just minutes from Historic Downtown Longwood, Reiter Park, and the SunRail station, along with easy access to shopping, dining, and major roadways. Outdoor enthusiasts will enjoy nearby parks, trails, and recreational areas, while the home’s central location makes commuting throughout Central Florida simple and convenient. With its affordable price, thoughtful updates, private setting, and inviting pool, 102 Silver Cluster Ct N is a rare find and the perfect place to start your next chapter.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Abby Greenberg (407-484-2689)
351 W HORNBEAM DR, LONGWOOD, FL 32779
$750,0001 Day on yellowkey MLS ID: O6400662
0 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2778 Built: 2026Monthly Fee: $49 Tax: $2,578 (2024)Community: Sabal Point AmdSingle Family
Taxes:$2,578
Remarks: Under contract-accepting backup offers. Under Construction. Welcome to one of the most exciting new builds to hit Longwood's coveted Sabal Woods subdivision in years. This stunning 4-bedroom, 3-bathroom home with a spacious office/flex room is a rare opportunity — block construction offering superior durability, energy efficiency, and long-term peace of mind backed by a comprehensive 2/10 Builder's Warranty. From the moment you arrive, the curb appeal speaks for itself. A canopy of mature oaks lines the road leading to the home, where brick exterior accents and cedar shake detailing set an impressive first impression on a generous .32-acre lot. Step inside and discover a thoughtful floor plan designed with purpose and flow in mind — ideal for growing families or those who work from home. The large dedicated office/flex room provides the versatility today's buyers demand. Soaring coffered ceilings in the master suite add a touch of elegance, while the oversized walk-in shower and enormous walk-in closet make every day feel like a retreat. At the heart of the home, the kitchen is thoughtfully designed with crisp white shaker-style cabinets, stunning quartz countertops, designer gold hardware, and a sleek timeless backsplash — a combination that anchors the home with both style and sophistication. Brand-new energy-efficient double-pane windows keep utility costs down while flooding every room with natural light. Stainless steel appliances complete this kitchen built to impress. LVP flooring flows throughout the main living areas, with plush carpet in the bedrooms for added comfort underfoot. The oversized 2-car garage offers ample storage and parking, and the expansive backyard is a blank canvas with serious upside. The previous pool has been fully removed, meaning there are zero obstacles for future pool construction or backyard customization — just bring your vision!
Listing Agent: Tyler Deans (407-319-2493)
322 N SHADOWBAY BLVD, LONGWOOD, FL 32779
$499,900432 Days on yellowkey MLS ID: O6280309
REDUCED by $25,100 (4.8%) on 03/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1599 Built: 1993 Tax: $2,326 (2024)Community: Lake Vista At ShadowbaySpa: NoSingle Family
Taxes:$2,326
Remarks: Welcome to Lake Vista at Shadowbay - NO Homeowners Association, No Restrictions, $0 HOA dues! This beautiful and well-maintained home features three charming bedrooms, two full bathrooms, and a spacious 2-car garage, 1,599 sq. ft. of living space, the home boasts an open and airy floor plan filled with natural light, vaulted ceilings, and a stylish combination of rich solid wood floors and tile throughout. Unique architectural details and built-in niches add warmth and character. Enjoy both formal and informal living spaces, including an elegant dining room, a comfortable living room, and additional flexible living areas that flow seamlessly together, ideal for everyday living or entertaining. Step outside to your tranquil, oversized screened-in patio featuring vaulted ceilings, two wood ceiling fans with remotes, and plenty of room for outdoor gatherings. Relax with serene views of the pond and wooded conservation area, perfect for peaceful moments or entertaining guests in a private, natural setting. Located in the highly sought-after Shadowbay community, you will enjoy access to Ski Lake Brantley and exclusive amenities including a private gated beach, fishing area, picnic space, boat ramp, tennis court, basketball court, and more. This is a prime location just minutes from I-4 and Seminole County schools, walking distance to the elementary school. UPDATES include: New HVAC (2022), New plumbing (2022), Updated electrical (2022), Tankless water heater (2022), Roof (2013), New front covered porch and oversized back patio (2022), and a fenced backyard for added K-9 run and for privacy (2022). This is a must-see property! Make this fantastic house your home today! Contact the listing agent for details on buyer incentives.
Listing Agent: Diane Melody Goglas (407-690-1959)
401 BLUE LAKE DR, LONGWOOD, FL 32779
$580,00035 Days on yellowkey MLS ID: O6390986
0 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2564 Built: 1978Monthly Fee: $54 Tax: $6,950 (2024)Community: Sweetwater OaksSpa: NoSingle Family
Taxes:$6,950
Remarks: Welcome to 401 Blue Lake Drive, this is an amazing Sweetwater Oaks home that has a great location, great floorplan and tons of potential! - - This home has a very functional 4 bedroom, 2-and-a-half-bathroom split bedroom floorplan! The kitchen is large with a huge center island and stainless-steel appliances. The great room has a nice and vaulted ceiling with wonderful beams and a unique stone wood burning fireplace for those cooler days! Wood floors, french doors, huge property, privacy, this full half acre property offers many opportunities, the private fenced backyard is shaded and ready for relaxing, the giant 897 square foot side entry garage is ready for your projects/toys/cars and garage fun!! The screened pool is inviting, the 747 square foot back porch is one of the largest you will see, this is perfect for multiple televisions, game tables and football season and more!! The roof is from 2023, nearly new! The AC is a year old!! Come home and enjoy all the unique and wonderful Sweetwater Oaks amenities all with low annual HOA dues!! These amenities include access to Sweetwater Beach at Lake Brantley which offers a beautiful park and beach as well as a covered pavilion for gatherings, boating, water skiing, fishing, sailing, kayaking and fun! Eight tennis courts, 8 pickle ball courts, sand volleyball at Sweetwater Beach (right around the corner), many parks, multiple playgrounds, a beautiful community center and many community events for everyone!! Access to the Wekiva River is right down the street at Riverbend Park, enjoy soccer, baseball, kayaking, canoeing, fishing, the picnic and party pavilion, or nature walks and much more! The schools are the best in the area; Sabal Point Elementary School, Rock Lake Middle School and nationally ranked and highly regarded Lake Brantley High School!! The location, quality and condition are right, call today to see this great home!!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Mark Humphreys (407-310-5765)
1209 ROXBORO RD, LONGWOOD, FL 32750
$799,999100 Days on yellowkey MLS ID: O6373160
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3332 Built: 1969Monthly Fee: $13 Tax: $4,384 (2024)Community: Knollwood 1St AddSpa: NoSingle Family
Taxes:$4,384
Elementary School: Altamonte Elementary
Middle School: Milwee Middle
Remarks: Stunning Remodeled Estate Home in Knollwood - Longwood! Welcome to this exceptionally remodeled estate home located in the highly desirable Knollwood community of Longwood. Set on a generous 0.70-acre lot, this 3,332-square-foot residence offers four bedrooms and two and a half bathrooms, blending luxury, flexibility, and everyday comfort—ideal for modern living and entertaining. From the moment you enter, you’ll appreciate the bright, open layout and desirable split floor plan designed to provide privacy for the primary suite. The inviting foyer opens to a formal dining room, where a newly added powder room is conveniently located for guests. Across the foyer, the spacious living area flows seamlessly into the heart of the home and is anchored by a cozy wood-burning fireplace, adding warmth and character. The gourmet kitchen is a true showpiece, featuring shaker-style cabinetry, luxurious quartzite countertops, and top-of-the-line appliances, including a 48-inch eight-burner double-oven gas range. Thoughtful details such as a farmhouse sink, pot filler, oversized island with seating for six, and a large pantry with open shelving make this space as functional as it is beautiful. Just off the kitchen is a dedicated laundry room with full size washer and dryer with a utility sink that is easily accessible to the garage, adding everyday convenience. Extensive renovations include a new home addition along with updated flooring, lighting, drywall, millwork, ductwork, HVAC, plumbing, and electrical systems, providing modern comfort and peace of mind throughout. Engineered hardwood flooring adds both elegance and durability. Double doors lead into the private primary bedroom suite, which features vaulted ceilings, large window, and a walk-in closet. The spa-inspired en-suite bathroom includes a dressing room and separate linen closet, granite countertops, a 1930s clawfoot soaking tub, a glass-enclosed shower with dual rain showerheads, and a private water closet. Two newly constructed bonus rooms adjacent to the primary suite provide flexibility that can be used as a home office, nursery, or additional storage. Three additional bedrooms are located on the opposite side of the home and share a beautifully renovated full bathroom, offering comfort and style for family and guests alike. Outdoor living is equally impressive, featuring a newly renovated lanai with a tongue-and-groove ceiling, a covered patio, and an expansive fully fenced backyard. The property also includes two storage sheds and a workshop with its own bathroom, providing excellent potential for a future guest suite, studio, or creative space. Additional features include double-pane windows, updated lighting, and an optional HOA with a voluntary fee of just $150 annually. Ideally located near top-rated schools, shopping, dining, healthcare, and popular destinations such as Uptown Altamonte, Wekiva Island, Altamonte Mall, and Cranes Roost, with easy access to major roadways for a smooth commute. This thoughtfully upgraded Knollwood estate offers space, style, and flexibility in an unbeatable Longwood location. Schedule your private showing today—homes like this are rarely available.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Alison Forbes (407-766-5243)
884 CUTLER RD, LONGWOOD, FL 32779
$625,00019 Days on yellowkey MLS ID: O6396152
REDUCED by $14,000 (2.2%) on 04/22/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2601 Built: 1973 Tax: $5,101 (2025)Community: Cutler CoveSpa: NoSingle Family
Taxes:$5,101
Tax Year: 2025
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully updated 5-bedroom, 3-bathroom home nestled on a quiet street in Longwood's sought-after 32779 zip code, just steps from the top-rated Sabal Point Elementary and minutes from everything the Lake Brantley area has to offer. With 2,601 square feet of thoughtfully designed living space on a generous 0.30-acre corner lot, this home delivers the space, style, and location today's buyers are searching for, with no HOA and the freedom to make it truly your own. A large private driveway leads you home, complemented by an oversized 2-car garage with ample storage. Step inside and you're greeted by an expansive open floor plan filled with natural light from large front windows, creating a bright and inviting atmosphere throughout. At the heart of the home, the kitchen is built for both everyday living and effortless entertaining. White shaker cabinets, a large island with stunning quartz countertops and waterfall edges, and stainless steel appliances. The open floor plan flows seamlessly into the living and dining areas — a layout that brings people together naturally. Peace of mind comes built in with major updates already done for you — a new roof in 2021, new AC in 2021, water heater in 2022, upgraded double-pane windows, and new LVP flooring throughout installed in 2021. The large primary suite offers a comfortable retreat complete with a double vanity and walk-in shower, while the additional bedrooms and bathrooms provide all the flexibility a modern family needs. Outside, a large covered and screened patio overlooks a fully fenced backyard with beautiful pavers — perfect for morning coffee, weekend entertaining, or simply unwinding. A 7-zone irrigation system keeps everything green with ease, and with plenty of room to add the pool of your dreams, the backyard is a blank canvas ready for your vision. Located in one of Seminole County's most desirable family-friendly communities with easy access to parks, nature, shopping, dining, and major commuter routes — this move-in-ready home is an exceptional opportunity. Corner lot. No HOA. Top-rated schools. Come see it before it’s gone.
308 SMOKERISE BLVD, LONGWOOD, FL 32779
$650,00047 Days on yellowkey MLS ID: O6387465
REDUCED by $39,000 (5.7%) on 03/31/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2352 Built: 1979Monthly Fee: $108 Tax: $5,564 (2025)Community: Sweetwater Oaks Sec 12Spa: NoSingle Family
Taxes:$5,564
Remarks: Welcome to 308 Smokerise Blvd., tucked away on a quiet corner lot within a cul-de-sac in the highly sought-after Sweetwater Oaks community of Longwood. Situated on an expansive .40-acre homesite framed by majestic oak trees and mature landscaping, this 4-bedroom, 2-bath residence offers 2,352 heated square feet of inviting, thoughtfully designed living space. From the moment you step inside, the home feels warm and welcoming. Skylights fill the space with natural light, and the split floor plan provides both privacy and comfortable gathering areas. At the heart of the home is the den — a cozy yet spacious retreat featuring a wood-burning fireplace and adjoining entertaining bar area. This inviting space is what originally captured the current owners’ hearts. It’s easy to imagine evenings gathered around the fire, hosting friends at the bar, or simply unwinding at the end of the day. It’s a room designed for connection. The primary suite offers its own private escape. The ensuite bath feels like a boutique resort spa, highlighted by distinctive, whimsical wallpaper that adds personality and charm — an unexpected and delightful design statement. Step outside to your screened pool oasis surrounded by brick pavers and lush greenery. With plenty of yard space on this oversized corner lot, outdoor living comes naturally here. The Blackstone grill conveys, making the backyard perfectly set up for sunset dinners and weekend gatherings. Major updates provide valuable peace of mind: • Brand new roof • A/C replaced in 2022 • Variable-speed pool pump (2025) • Water treatment system (2021) • Three updated electrical panels (2021) Sweetwater Oaks residents enjoy private lake access and boat ramps to Lake Brantley, along with multiple parks, tennis courts, pickleball courts, a clubhouse, and scenic community spaces. Located near Wekiva Springs State Park, major highways and toll roads, Orlando attractions, beaches, shopping, and dining, the community offers both tranquility and convenience. It is also golf cart friendly :-) This is more than just a home — it’s a place where memories are made, gatherings feel effortless, and everyday living feels just a little bit special...Property has a ASSUMMABLE VA mortgage in place at 2.25%!
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: Ginny Peters (407-443-3965)
413 WILLOWBROOK LN, LONGWOOD, FL 32779
$574,99956 Days on yellowkey MLS ID: O6385431
REDUCED by $8,000 (1.4%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2740 Built: 1981Monthly Fee: $46 Tax: $4,171 (2024)Community: Cypress Landing At Sabal PointSpa: NoSingle Family
Taxes:$4,171
Remarks: Welcome home to this spacious 4-bedroom, 2-bath pool residence with dedicated office, nestled in the peaceful Cypress Landings neighborhood of Sabal Point in Wekiva Springs. From the moment you enter, you’re greeted by warm wood floors and an inviting great room with soaring vaulted ceilings and a wood-burning fireplace — the perfect gathering space for family and friends. Outside, your oversized lot transforms into a private backyard oasis featuring a sparkling pool, screened patio, firepit, and brand-new playground, creating endless opportunities for relaxation and entertainment. With all brand new appliances, including washer and dryer, a 2017 roof, 2022 A/C, and 2023 water heater, the major updates are already done for you. Enjoy miles of shaded walking and jogging trails, a scenic three-mile loop, and direct access to the Wekiva River Buffer Conservation Area, all while being minutes from highways, shopping, dining, and highly rated Seminole County schools.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Antonio Salinger (407-304-9867)
811 GREENSHIRE CT, LONGWOOD, FL 32779
$1,349,0005 Days on yellowkey MLS ID: O6399384
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4293 Built: 1989Monthly Fee: $367 Tax: $7,316 (2025)Community: Sweetwater Club Unit 7Spa: YesSingle Family
Taxes:$7,316
Remarks: Welcome to 811 Greenshire Ct, a rare opportunity to own a fully renovated private estate in the heart of Longwood, FL, where luxury, space, and multigenerational living come together on nearly 2 acres. Ideally located just minutes from Wekiva Island, Publix at Shoppes of Sweetwater, and top-rated Seminole County schools, this exceptional 5-bedroom, 4-bath residence offers 4,293 square feet of thoughtfully designed living space with no carpet throughout and a true move-in-ready feel. Designed for today’s lifestyle, this home delivers exactly what buyers are searching for—privacy, flexibility, and high-end upgrades—making it ideal for multigenerational living, extended stays, or long-term value. The standout feature is the approximately 800-square-foot attached multigenerational suite built in 2022, offering complete independence with its own full kitchen, living area, spacious bedroom, additional enclosed flex space with Murphy bed, ADA-compliant bathroom, wheelchair-accessible doors, separate septic system, private propane generator, and a dedicated washer and dryer—perfect for in-laws, guests, or private living quarters. Inside the main home, refinished travertine floors and new wood flooring in every bedroom create a seamless blend of elegance and warmth, complemented by an updated kitchen with refinished cabinetry and newer appliances, a luxurious primary suite with a spa-inspired bath and Roman tub, and a beautifully remodeled guest bath featuring a custom stained-glass window, new tile shower, and updated cabinetry. Hunter Douglas Roman shades are installed throughout, and all windows and doors were replaced between 2021 and 2022, adding both efficiency and peace of mind. The outdoor living experience is equally impressive, featuring a saltwater pool with a variable speed pump and computer-controlled lighting, an enclosed courtyard for added privacy, and an expansive fenced backyard with an additional cleared half-acre—ideal for entertaining, future expansion, or simply enjoying the space. A whole-home audio system extends to the pool, deck, and porch, creating a seamless indoor-outdoor lifestyle. Additional highlights include a heated and air-conditioned garage with epoxy flooring, smart sprinkler system, newer roof, dual-zone HVAC, and a full alarm system. Homes offering this level of land, upgrades, and true multigenerational flexibility in Longwood are rare, making this a standout opportunity for buyers seeking space, luxury, and long-term value. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Gina Hutchinson (386-793-4262)
501 SWEETWATER CLUB CIR, LONGWOOD, FL 32779
$1,222,00071 Days on yellowkey MLS ID: TB8473605
1 Days Off yellowkey (back on 3/19/2026)
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4709 Built: 1975Monthly Fee: $367 Tax: $5,855 (2024)Community: Sweetwater Club Unit 1Spa: NoSingle Family
Taxes:$5,855
Remarks: Under contract-accepting backup offers. **Seller extremely movtivated** Some homes offer space. Few offer presence. This timeless Spanish Mediterranean estate in Sweetwater Club delivers both, an acre of privacy, refined architecture and a setting designed for a life well lived. Ideally in the prestigious, gated community and enhanced by its own private estate entrance, the residence rests on a rare, just over one-acre home site surrounded by approximately 46 mature live oak trees. The result is an atmosphere of natural beauty, tranquility and seclusion that feels worlds away while remaining effortlessly connected. From the moment you arrive, the home’s classic design and serene setting create a lasting impression. Inside, a grand foyer opens to a thoughtfully designed interior with an expansive, versatile layout suited for elegant entertaining and everyday living. Formal living and family rooms are anchored by a wood-burning fireplace, while a traditional dining room provides an inviting setting for gatherings. The newly updated kitchen features beautiful stone countertops, generous cabinetry and refined modern finishes that balance style with function. The primary suite is a retreat, offering generous proportions and a peaceful ambiance designed for restoration. Its en-suite bath features dual vanities and a spa-like atmosphere. A second primary suite also awaits, including an updated bath, ideal for guests or multigenerational living. Both offer direct lanai access. Upstairs, three additional bedrooms and two full baths provide flexible space for family, work or evolving lifestyle needs. A private guesthouse with its bath adds exceptional versatility for extended family, visitors or a secluded studio. Expansive interior living spaces transition effortlessly outdoors, embracing Florida’s signature indoor-outdoor lifestyle. Beneath a canopy of mature oaks, the grounds offer open space, privacy and the rare sense of calm that defines estate living. Sweetwater Club is among Central Florida’s sought-after communities, known for its serenity, exclusivity and proximity to country clubs, Wekiwa Springs State Park, Wekiva Island, top-rated schools, and premier shopping plus dining. Blending privacy, scale and location, this remarkable property presents a rare opportunity to own a private sanctuary.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (813-217-5288)
Listing Agent: Colin Kennedy (727-677-9777)
214 SHERIDAN AVE, LONGWOOD, FL 32750
$425,0001 Day on yellowkey MLS ID: O6400828
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1707 Built: 1976 Tax: $4,935 (2024)Community: Winsor Manor 1St AddSingle Family
Taxes:$4,935
Remarks: Welcome to your next home—where comfort, style, and everyday living come together effortlessly. This beautifully maintained 3-bedroom, 2-bathroom home offers over 1,700 square feet of thoughtfully designed space, featuring a desirable split floor plan with two separate living areas—perfect for both relaxing and entertaining. At the heart of the home, you’ll find a flawlessly upgraded kitchen complete with sleek stainless steel appliances, modern finishes, and plenty of space to cook, gather, and create memories. Step outside and enjoy your morning coffee on the charming front porch, or unwind in your private backyard oasis. The brand-new paver patio and perfectly designed fire pit set the stage for cozy evenings, all while taking in peaceful water views that make this home truly special. Conveniently located just minutes from major highways, airports, shopping, and dining, you’ll have easy access to everything Central Florida has to offer while still enjoying your own serene retreat. This one checks all the boxes—come see it for yourself!
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Trevor Zwick (863-303-6114)
136 GLENDALE DR, LONGWOOD, FL 32750
$350,00011 Days on yellowkey MLS ID: O6398306
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2616 Built: 1973Monthly Fee: $6 Tax: $1,633 (2024)Community: Winsor ManorSingle Family
Taxes:$1,633
Remarks: Opportunity knocks with this investor’s dream “Diamond in the Rough”—priced to reflect its incredible potential and ready for your vision. With a current Zestimate of $521,700 (as of 4/8/26), this 4-bedroom, 3-bath home offers the kind of upside savvy buyers are always searching for. Situated on a desirable corner lot, the property features a 2-car garage, cozy fireplace, inside utility room, and a spacious enclosed rear patio—providing a solid foundation for renovation or rental income potential. Recent improvements like a new driveway and sidewalk add immediate curb appeal, while the generous layout opens the door to countless value-add possibilities. Location is a standout here—just minutes to I-4, SR 434 shopping and dining, and the popular Seminole-Wekiva Trail, making this an attractive option for future occupants or tenants alike. This property is being sold AS-IS, with no utilities or inspection contingencies provided by the seller. Buyers are strongly encouraged to submit proof of funds, and use of the attached escalation addendum is highly recommended in this competitive offering. Don’t miss your chance to transform this hidden gem into something truly special.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: John Muccigrosso, Pa (407-234-6330)
1498 MARKHAM WOODS RD, LONGWOOD, FL 32779
$1,870,0003 Days on yellowkey MLS ID: O6399260
Bed: 7 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 7675 Built: 1991Community: Markham Woods CorridorSingle Family
Taxes:$0
Tax Year: 2026
Remarks: One or more photo(s) has been virtually staged. Looking for a private, multi-acre estate with the flexibility to expand, entertain, or create a true multi-generational compound? Welcome to the prestigious Markham Woods Corridor. Set on a cleared, high-and-dry 5+ acre homesite with no HOA restrictions, this property offers rare freedom and tranquility, feeling like your own private park complete with gorgeous mature oak trees, lush living privacy walls, and a dual-gated entrance. The beautifully renovated main residence spans nearly 5,600 square feet and has been meticulously updated within the last year to offer ultimate peace of mind. Major recent upgrades include completely brand-new plumbing throughout the entire home, four new HVAC units, and fully modernized bathrooms featuring pristine new tile, hardware, lighting, and vanities. Luxurious Main Residence Features include a Flexible Layout with up to 7 bedrooms (including 5 en-suites) and 8 bathrooms. Three spacious primary suites feature private baths and walk-in closets, plus a separate in-law suite with its own entrance, living area, kitchenette, and full bath. The Gourmet Kitchen is The heart of the home and boasts granite countertops, a massive center island, and premium appliances, including a Samsung 3-door refrigerator, Samsung dishwasher, and an Electrolux Icon dual oven/freezer stack. With Smart Home Technology; Enjoy automated luxury blinds on the main floor, smart-controlled exterior fountains, and customizable, color-changing boundary wall lighting. With Unrivaled Entertainment & Outdoor Living features include a separate Ballroom / Theater with a $30,000 state-of-the-art automated LED lighting system that transforms this exceptional space. Featuring smart-controlled curtains, an LG mini-beam short-throw projector, a dedicated stage, and eight surrounding screens, it is perfect for hosting large-scale events, weddings, yoga retreats, or epic movie nights. Outdoor Entertaining doesn't get any better than this. Step out onto +/- 4,000 square feet of luxury brick pavers. The outdoor summer kitchen area is a chef's dream, featuring a commercial Vulcan convection oven complete with a full-sized pizza stone for authentic, restaurant-quality entertaining. *BONUS*- Exclusive Custom Pool Opportunity: While the expansive grounds offer a blank canvas, the seller—a commercial pool contractor—is offering an exclusive buyer incentive to build a custom pool to your exact specifications at their direct cost, allowing you to design your dream oasis without the retail markup! The Detached Guest Quarters is Connected to the main home by a beautiful red-tiled covered breezeway. The massive two-story detached building offers a fully climate-controlled space. Upstairs features a 3-bedroom, 1-bath apartment with a spacious lounge. Downstairs boasts a beautiful stainless steel kitchen, a storage room, and a garage—ideal for guests, staff, or incredible income-producing potential. Zoned for horses and offering ample space for boats, RVs, and recreational vehicles, this estate is perfectly suited for a variety of uses. Conveniently located near Heathrow shopping, top-rated schools, area golf courses, and just 30 minutes from Orlando and the East Coast beaches. This is more than a home; it’s an investment in endless possibilities. Properties with this level of versatility, luxury, and land in this corridor rarely hit the market, and they never stay long. Call Today!
Listing Agent: David Warren (407-928-3760)
454 SPRINGWOOD CT, LONGWOOD, FL 32750
$349,9996 Days on yellowkey MLS ID: O6399680
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1175 Built: 1980 Tax: $333 (2024)Community: SpringwoodSingle Family
Taxes:$333
High School: Winter Springs High
Remarks: Charming Renovated 3-Bedroom Home with Spacious Yard — Move-In Ready! Welcome home to this beautifully updated 3-bedroom, 2-bath residence full of charm and modern touches! Perfectly situated in a friendly, working-class neighborhood, this home offers the perfect blend of comfort, style, and everyday practicality. Step inside to find a bright, open layout featuring fresh paint, updated flooring, and a thoughtfully renovated kitchen and bathrooms. Every detail has been designed to make daily living easy and enjoyable — from the comfortable living spaces to the convenient single-car garage for parking or extra storage. Outside, you’ll love the .24-acre lot with no trees and a huge shed INCLUDED, offering a wide-open yard that’s perfect for pets, play, or creating your dream outdoor space. There’s plenty of room to add a patio, garden, the possibilities are endless! Whether you’re a first-time buyer, small family, or someone looking to downsize, this home offers an affordable and move-in-ready opportunity to put down roots and make it your own. Don’t miss your chance to own this charming, renovated gem — schedule your showing today!
Listing Agent: Uwem Akpan (689-837-2197)
3311 HORSESHOE BEND CT, LONGWOOD, FL 32779
$1,725,000109 Days on yellowkey MLS ID: O6370391
2 Days Off yellowkey (back on 4/18/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6259 Built: 2002Monthly Fee: $353 Tax: $19,471 (2025)Community: Alaqua Lakes Ph 3Spa: YesSingle Family
Taxes:$19,471
Elementary School: Heathrow Elementary
Remarks: One or more photo(s) has been virtually staged. Experience the pinnacle of luxury living in the guard-gated community of Alaqua Lakes, one of Longwood’s most coveted enclaves, ideally situated between Heathrow and Lake Mary, where Central Florida’s elite reside, work, and thrive. This two-story estate offers 5 bedrooms, 7 bathrooms, over 6,300 square feet, and is set on more than half an acre with exceptional privacy and curb appeal. A circular paver driveway, oversized three-car garage, and fully fenced backyard frame the home’s timeless elegance and grand scale. Meticulously maintained and extensively upgraded, recent improvements include over $28,000 in roof enhancements, three brand-new HVAC systems (2024) plus a newer fourth unit, Google Nest thermostats, whole-home surge protection and an Orbi mesh WiFi system providing strong, seamless coverage throughout. Inside, fresh designer paint, upgraded luxury vinyl flooring, and energy-efficient LED lighting enhance the home’s refined interiors. Formal living and dining rooms create an elegant setting for entertaining, while a dedicated private office offers a quiet workspace. The inviting family room features a gas fireplace and flows effortlessly into the expansive chef’s kitchen, complete with a large island, walk-in pantry, stone countertops, glass tile backsplash and updated cooking appliances—perfect for gatherings of any size. The primary suite is a true retreat, offering dual walk-in closets, private pool access, and a spa-inspired bath with soaking tub, split vanities, separate makeup area, and modern finishes. Upstairs, a private home theater provides an exceptional space for entertainment and relaxation. Step outside to a resort-style backyard oasis featuring a sparkling pool and spa, new pump and heater, stainless steel LED fixtures, refreshed pavers, and a fully equipped outdoor kitchen—all accented by custom LED lighting that automatically illuminates at dusk. A beautifully updated front fountain with a new underground reservoir adds a serene finishing touch to the home’s impressive curb appeal. Residents of Alaqua Lakes enjoy 24-hour guarded security and access to a 7-acre private park, resort-style pool, tennis courts, basketball court, playground, and more—along with proximity to top-rated Seminole County schools, championship golf, fine dining, and major highways. This move-in-ready estate seamlessly blends timeless sophistication with modern upgrades—offering exceptional indoor-outdoor Florida living in one of Central Florida’s premier luxury communities.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Hussein Kermalli (914-661-9646)
420 W WEKIVA TRL, LONGWOOD, FL 32779
$448,0004 Days on yellowkey MLS ID: O6398480
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1787 Built: 1978Monthly Fee: $21 Tax: $4,216 (2025)Community: Wekiva Hills Sec 06Single Family
Taxes:$4,216
Remarks: Under contract-accepting backup offers. A RARE opportunity in Wekiva awaits! Every major update has already been thoughtfully completed—offering a level of ease, confidence, and comfort that’s increasingly hard to find. Ideally positioned directly across from the Wekiva Golf Club, this light-filled three-bedroom, two-bath residence pairs meaningful upgrades with a warm, functional layout designed for modern living. Inside, an open and airy floor plan creates effortless flow between living spaces, with natural light pouring in and highlighting the striking stone fireplace—a true centerpiece that brings both character and comfort. Soft, neutral tones throughout provide a refined and versatile backdrop, ready to complement any style. The primary suite offers a standout feature: a private office just off the bathroom. Whether working remotely, creating, or simply seeking a quiet retreat, this flexible space adds a layer of intentional living that today’s buyers value. Major system updates include a 2023 roof, 2023 hurricane-impact windows. The HVAC system is scheduled for replacement, with installation pending by a licensed Florida contractor and expected to be completed in April—offering added peace of mind. Additional improvements continue throughout, including a brand-new kitchen refrigerator (2025), a second newer garage refrigerator (within the past two years), updated washer and dryer, and a newer garage door enhancing both convenience and curb appeal. For added confidence, a recent four-point inspection has already been completed. Outdoors, a fully fenced backyard invites year-round enjoyment, complete with a screened-in porch and spacious patio—ideal for relaxing, entertaining, or embracing the Florida lifestyle with ease. Set within the established and highly desirable Wekiva Springs community, just moments from parks, trails, and everyday conveniences, this home offers a rare combination of thoughtful upgrades, flexible living, and true move-in-ready appeal. This opportunity will not last!
Listing Agent: Sarah Tomlinson (407-721-7823)
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