Location: Longwood , 32779
Do Not Show Listings
1890 LONG POND DR, LONGWOOD, FL 32779
$615,0003 Days on yellowkey MLS ID: O6415503
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2448 Built: 1987 Tax: $6,777 (2025)Community: Mandarin Sec 7Spa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,777
Elementary School: Woodlands Elementary
High School: Lake Mary High
Tax Year: 2025
Middle School: Markham Woods Middle
Remarks: Move-In Ready 4 Bedroom 3 Bathroom Pool Home Located on an Oversized 1 Acre Corner Lot in the Quiet Mandarin Community with NO HOA. Home has a wonderful open floorplan with a formal living room, a separate dining room plus a family room with a wood burning fireplace as the centerpiece. The kitchen has plenty of countertop and cabinet space with a full set of stainless-steel appliances and features a breakfast room. Primary bedroom suite features a walk-in closet with a private bathroom. Home also features 3 additional bedrooms, a 2-car side entry garage, an interior laundry room w/washer & dryer, ceiling fans, blinds, plenty of storage, and pool views throughout the home. Exterior has a screened in pool with baby safety fence, covered lanai area perfect for cookouts or entertaining family and friends while the backyard is fenced perfect for the pets to play. Location is excellent just minutes from all daily necessities including shopping, grocery, restaurants, entertainment, excellent schools, SR-436, I-4 and 429. Please call to schedule a showing today!
Listing is courtesy of: MIGHTY REALTY INC (407-403-6540)
Listing Agent: Joann Bonilla (317-435-5235)
901 CUTLER RD, LONGWOOD, FL 32779
$538,5008 Days on yellowkey MLS ID: O6414587
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2226 Built: 1979Monthly Fee: $54 Tax: $5,799 (2025)Community: Cutler CoveSingle Family
Taxes:$5,799
Elementary School: None
High School: None
Middle School: None
Remarks: Pull over HONEY! This home is move it ready. Roof. 2023. AC 1 2020, AC 2 2022. Look at the cute swing in the front yard. That looks like a great home to relax in. Let's take a look. As you walk up to the home you are greeted by double doors making it feel like a grand entrance. Enchanted ivy grows to the left of the entrance. Immediately upon entering the home you can access the updated kitchen. To the right of the entry you have the huge living room which can take you to the laundry room and garage. The living room features a wood burning fireplace as well as being open to the kitchen. There is a nice spot for stools so you can eat a quick breakfast without going to the dining room. The kitchen is nicely appointed with white shaker cabinets and subway tile. Also off of the living room is a HUGE family room with vaulted ceilings and plenty of natural light from large sliding doors that leads to the back yard. Off of the family room is a nice area that would make a great little office space. Back through the kitchen and down the hall you will find all three bedrooms. The master is plenty spacious and the ensuite bathroom has lots of space. There is currently a nice long double vanity and large shower. The master bath has been updated! Quartz counters, double vanity with a spot for a stool to do you facial maintenance regimen. There is a door that leads to the back yard making it easy to clean up after playing or working in the back yard. The home has fresh paint inside and out. Luxury vinyl plank throughout the home makes maintenance a breeze. Come add your personal touches to really make this home shine! Lake Brantley Beach park with all amenities including boat ramp, volleyball sand court, playground, grills, basketball court and ability to rent pavilion. The same for Riverside park which also has tennis courts, ball fields, larger covered pavilion and nature trails. The clubhouse playground and tennis courts across Wekiva Springs Rd. Maintenance of all common areas including the path to the beach by our house. Several family events throughout the yr incl Halloween costume parade, egg hunts, Christmas parade, and parties with games, bounce houses, etc. Don't miss out. Contact us today!
Listing is courtesy of: TC ORLANDO HOMES LLC (407-960-6145)
Listing Agent: Eric Soto (407-394-5651)
490 WEKIVA COVE RD, LONGWOOD, FL 32779
$579,00047 Days on yellowkey MLS ID: O6401936
1 Days Off yellowkey (back on 5/6/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2335 Built: 1985Monthly Fee: $125 Tax: $3,045 (2025)Community: Wekiva Cove Ph 3Spa: NoSingle Family
Taxes:$3,045
Elementary School: Wekiva Elementary
High School: Lake Brantley High
Middle School: Teague Middle
Remarks: Under contract-accepting backup offers. Welcome home to this BEAUTIFULLY UPDATED 3-bedroom, 2-bath residence with a spacious office/den, thoughtfully remodeled with a tasteful design that blends comfort and style throughout. From the moment you step inside, you’ll notice the bright, open floor plan filled with natural light, enhanced by soaring vaulted ceilings and skylights that create an airy, inviting atmosphere. The living area features a real wood-burning fireplace with a charming brick detail, adding warmth and character, while sliding glass doors in both the living room and kitchen seamlessly connect indoor and outdoor living. The living room showcases TRIFOLD SLIDERS that open fully, and the primary suite features BIFOLD SLIDERS, creating a true indoor-outdoor experience. The home showcases stunning tile flooring that looks like real wood, offering both durability and modern appeal. At the heart of the home, the COMPLETELY REMODELED KITCHEN shines with real wood cabinetry, elegant QUARTZ COUNTERTOPS, stainless steel appliances, a DOUBLE OVEN, and a classic subway tile backsplash—perfect for everyday living and entertaining. A dedicated formal dining room provides the ideal space for gatherings, and the spacious interior laundry room with custom cabinetry adds both convenience and functionality. The guest bathroom has been fully remodeled, while the primary suite offers a relaxing retreat complete with a soaking tub and separate shower. Step outside to your private backyard oasis featuring a SPARKLING SALTWATER POOL, along with a covered back patio and deck—perfect for relaxing or hosting year-round. The fully fenced yard offers privacy and plenty of space to enjoy outdoor living, beautifully complemented by spacious front and back patios. An oversized two-car garage provides ample storage and convenience. This home has been meticulously maintained with major upgrades including a 2018 roof and skylights, 2018 fence, 2019 exterior repaint, full home replumbing in 2022, 2022 updates to flooring, guest bedrooms, bathroom, and ceilings, and a 2023 kitchen and laundry remodel, along with a new AC unit, Hot water heater, and alarm system for added peace of mind. Located in a highly desirable community, residents enjoy access to a clubhouse, dock overlooking the scenic Wekiva Cove pond, playground, community pool, and TENNIS & PICKLEBALL COURTS, and more. With its prime location in top-rated school zones and close proximity to major roadways, shopping, and dining, this home truly has it all—MODERN UPGRADES, a spacious layout, and an incredible community. Don’t miss your opportunity to make it yours!
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Amber Zinno Adams (407-696-7908)
1833 CROWLEY CIR, LONGWOOD, FL 32779
$560,000150 Days on yellowkey MLS ID: O6369834
REDUCED by $14,900 (2.6%) on 05/22/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2742 Built: 1985 Tax: $5,474 (2024)Community: Mandarin Sec 5Single Family
Taxes:$5,474
Tax Year: 2024
Remarks: Virtually Staged. Welcome to 1833 Crowley Circle, a beautifully maintained POOL home offering comfort, freedom, and an unbeatable location — with NO HOA! This inviting property features a private backyard oasis with a lovely pool, perfect for Florida living and entertaining year-round. Enjoy peace of mind knowing the home has been thoughtfully updated, including a full replumb completed 4 years ago, new breaker boxes 4 years, a new pool pump 4 years, and an AC compressor replaced approximately 5 years ago. Stunning fireplace featured in living room to keep the whole family cozy. Enjoy the amazing kitchen in the heart of the home with serving window, breakfast bar area, and extra pull out pantry space! Ideally situated just one mile from the Seminole Wekiva Trail, this home is perfect for outdoor enthusiasts who love biking, walking, and nature, while still being close to everyday conveniences. Near major roadways including I4 making commute to theme parks, downtown, Orlando or Sandford International airports, beaches, and so much more! Whether you’re relaxing poolside, hosting friends, or enjoying nearby trails, 1833 Crowley Circle delivers the perfect blend of lifestyle, location, and long-term value. Don’t miss this opportunity to own a move-in-ready pool home! Easy to show so come see today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Christina Rampersad (407-995-6788)
110 WHITLEY BAY LN, LONGWOOD, FL 32779
$500,00010 Days on yellowkey MLS ID: O6413710
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1645 Built: 1984Monthly Fee: $125 Tax: $2,352 (2025)Community: Wekiva Cove Ph 2Single Family
Taxes:$2,352
Remarks: Nestled on a quiet cul-de-sac in the highly sought-after Wekiva Cove community, 110 Whitley Bay Lane offers something truly special—spectacular views of Sand Lake and unforgettable sunsets, without the premium price tag of direct lakefront ownership. Lovingly updated and meticulously maintained, this charming 3-bedroom, 2-bath home combines comfort, character, and one of the most picturesque settings in the neighborhood. From the moment you arrive, you'll appreciate the pride of ownership and inviting atmosphere that make this home feel instantly welcoming. Inside, natural light fills the living spaces, creating a warm and airy feel throughout. Thoughtful updates and careful maintenance mean you can move right in and start enjoying everything this exceptional home has to offer. The real magic happens outdoors. Step onto the spacious deck or relax on the patio as you take in breathtaking views across Sand Lake. Whether you're enjoying a peaceful morning coffee, hosting friends for an evening gathering, or simply unwinding after a long day, the backdrop is nothing short of stunning. Every evening brings a front-row seat to some of the most beautiful sunsets Central Florida has to offer. One of the home's most unique advantages is its incredible proximity to Wekiva Cove's resort-style amenities. Just beyond your backyard, you'll enjoy a short walk to the community pool, playground, clubhouse, tennis courts, and walking trails—giving you all the benefits of these amenities without the cost, maintenance, or responsibility of caring for them yourself. Imagine spending your weekends enjoying the pool instead of cleaning one. Zoned for highly desirable Lake Brantley schools and conveniently located near shopping, dining, parks, and major roadways, this home offers the perfect blend of natural beauty, convenience, and community. If you've been dreaming of lake views, stunning sunsets, a beautifully maintained home, and a lifestyle that feels like a retreat every day, this is a rare opportunity to enjoy the best of Wekiva Cove—without the lakefront price tag. Schedule your private showing today!
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Tiffany Yates (321-684-2399)
342 COBLE DR, LONGWOOD, FL 32779
$530,000131 Days on yellowkey MLS ID: O6379074
REDUCED by $5,000 (0.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2596 Built: 1978Monthly Fee: $23 Tax: $2,766 (2024)Community: Wekiva Hills Sec 04Spa: NoSingle Family
Taxes:$2,766
Remarks: Virtually Staged. Prepare to fall in love with this gorgeous POOL home located in the heart of quiet and serene Wekiva Hills. This stunning home delivers charming curb appeal, soaring ceilings, ample skylights flooding the interior in natural light. The living room is anchored by the dramatic stone wood burning fireplace. The formal dining room flanking the kitchen and living room, creating the perfect backdrop for effortless entertaining. You'll love the beautifully updated kitchen blending style and function with a separate spacious walk-in pantry, and bright, cheerful breakfast nook. Stay organized with interior indoor laundry room encompassing a folding table and extra storage cabinets above. Upstairs, the airy primary suite feels like a retreat—complete with additional skylights, versatile sitting area, generous walk in closet, and an updated ensuite bath with tiled shower. From the living room area through french doors is a lovely SCREENED patio with fans. The sparkling open private pool is surrounded by beautiful landscaping for all gardeners to appreciate. A well maintained large side yard and private rear gate leads directly to a serene walking trail, ideal for morning strolls, evening unwinding, or simply enjoying nature right from your backyard. Roof 2016. AC 2020. Electrical 2024. Pool equipment 2023. Flooring 2023. Kitchen remodeled 2016. Fence 2023. Golf, tennis, restaurants and shopping in community. Nature is nearby... conveniently located near Wekiwa State Park's natural springs, hiking trails and the popular Wekiva Island, ideal for picnics, kayaking, paddelboarding, swimming and canoeing. Thoughtfully updated, open layout, generous square footage, and a peaceful setting in an ideally located well-established community.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Veronica Parker (407-718-6983)
136 HABERSHAM DR, LONGWOOD, FL 32779
$539,99912 Days on yellowkey MLS ID: A4695578
REDUCED by $5,501 (1.0%) on 06/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3089 Built: 1978Monthly Fee: $20 Tax: $7,077 (2025)Community: Wekiva Hills Sec 06Single Family
Taxes:$7,077
Remarks: 4 Bed / 3 Bath home in the highly desirable Wekiva Hunt Club community in Longwood, FL. Prime opportunity on a mature, established street with strong community demand, excellent schools, parks, shopping, and quick highway access. This home features a 6-year-old roof with plenty of life remaining, two A/C units (the primary unit is 5 years old, and the second unit, which serves the primary bedroom and three additional bedrooms, is only 2 years old), and two hot water heaters. The property also includes an in-ground pool that is ready to be enjoyed. With a solid layout and strong lot potential, this home is perfect for an owner-occupant or investor.
Listing is courtesy of: JOSEPH WALTER REALTY LLC (248-294-7850)
Listing Agent: Scott Fader (248-294-7850)
175 CROWN POINT CIR #175, LONGWOOD, FL 32779
$206,500129 Days on yellowkey MLS ID: O6371436
REDUCED by $8,500 (4.0%) on 06/12/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1581 Built: 1985 Tax: $2,678 (2024)Community: Crown Point By The SpgsCondo
Taxes:$2,678
Elementary School: Sabal Point Elementary
Remarks: Ideal for buyers who value price and speed over perfection. Being sold as-is, it is well-suited for buyers looking to maximize value and make improvements over time. A great option for those seeking flexibility, long-term upside, and a practical entry point into homeownership or investment. This is a strong value opportunity in a highly convenient Seminole County location. Welcome to 175 Crown Point Circle, located in the established Crown Point community of Longwood. This clean, move-in ready condo offers a functional and flexible layout, featuring two bedrooms upstairs and one downstairs—ideal for guests, a home office, or multi-generational living. The main living area is bright and comfortable, with an easy flow into the kitchen that supports both everyday living and casual gatherings. Well-proportioned bedrooms provide comfortable living space, while the primary suite offers privacy and ample storage. The home presents a great opportunity to move in as-is while allowing room to personalize over time. Enjoy outdoor space for relaxing or entertaining, all within close proximity to shopping, dining, parks, and major roadways—making day-to-day living simple and accessible. A great opportunity for buyers seeking location, functionality, and long-term value in the 32779 area.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Darryl Dziedzic (407-446-3791)
628 E CLUB CIR, LONGWOOD, FL 32779
$995,00032 Days on yellowkey MLS ID: O6400643
0 Days Off yellowkey (back on 5/30/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4026 Built: 1988Monthly Fee: $367 Tax: $5,748 (2024)Community: Sweetwater Club Unit 7Spa: YesSingle Family
Taxes:$5,748
Middle School: Rock Lake Middle
Remarks: Under contract-accepting backup offers. Custom Built Estate Residence by Jones Clayton Construction showcases timeless elegance in architecture, style and livability. Begin your next chapter in this beautiful home featuring one story, a screened pool with approximately 4026 sq ft, of living space with 4 Bedrooms, 4 Baths. Located in Sweetwater Club Seminole County's Premier 24 hour Guard Gated Community with more nature than homes and spacious estates spanning 1 - 11 acres. This Mediterranean Style residence blends classic architectural charm with today's most desired features. From the moment you pull into your circular driveway you're greeted by a professionally landscaped lawn spanning approximately one acre with an oversized side entry 3 car garage. Your foyer and entry hallway features marble floors and picturesque views through the Living Room of the tropical pool and lanai. There is a formal Dining Room with a Window Bench Seat off the Entry. In the Living Room there are soaring ceilings and a wet bar area for entertaining. There is a nearby Powder Bathroom for guests. You''ll notice abundant Custom millwork, moldings and built in features throughout the home. Recent Updates include: Beautiful New Tile Roof in 2022, Two Brand New Air Conditioning Units with Ecobee Thermostats. New Luxury Vinyl Plank flooring in main living areas, Pool Enclosure Rescreened, New Ceiling Fans, New Sundeck Pool Deck, All New Recessed Lighting throughout! Your Private Backyard adds to the peace and tranquility of this property. The pool is large enough for your lap swimming excercise. Primary Bedroom Suite is very spacious with access to the pool lanai area and a separate walk in closet. The Primary Bath is also very spacious with a double sided fireplace. 2nd Bedroom/Office has an ensuite full bathroom. Bright Kitchen and Nook area opens to spacious Family Room. Down the hall there are two bedrooms and a full bath. There are many French Doors to the Screened Pool Lanai for seamless indoor outdoor living. Separate Laundry Room with sink and exit door to a covered porch out to side entry 3 car garage parking area. There's pure potential for the next owner to renovate kitchen and baths. In mid Spring you'll enjoy a multitude of Azaleas, Gardenias and Magnolia Flowers. In Fall/Winter you'll have gorgeous Camelias. You'll have Deeded Lake Access to Lake Brantley and walking distance to over 7000 acres at the Wekiwa State Park. There are Tennis and Pickle Ball Courts and Gazebo Park. Seminole County Excellent Schools, close to the 429 and !-4 Freeways. Disney and Beaches are 40- 60 minute drives.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Carolyn Kickhofel (407-538-4210)
3591 TERRA OAKS CT, LONGWOOD, FL 32779
$1,200,00023 Days on yellowkey MLS ID: NS1088208
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3810 Built: 2002Monthly Fee: $169 Tax: $5,617 (2024)Community: Terra OaksSpa: YesSingle Family
Taxes:$5,617
Elementary School: Forest City Elementary
Remarks: Tucked behind the gates of one of Longwood’s most desirable communities, this beautifully maintained four-bedroom, five-bath estate blends timeless elegance with modern luxury. From the moment you enter, soaring elevated ceilings, refined architectural details, and expansive living spaces create an immediate sense of sophistication and comfort. Designed for both everyday living and exceptional entertaining, the home features a thoughtfully crafted floor plan, upscale finishes throughout, and a stunning chef’s kitchen appointed with high-end appliances, custom cabinetry, and generous gathering space at the heart of the home. Includes a whole house generator and security system. The spacious primary suite offers a private retreat with spa-inspired amenities, while each additional bedroom provides comfort, privacy, and its own distinctive character. Multiple living and entertaining areas flow seamlessly to the outdoor oasis, where a sparkling pool and beautifully maintained surroundings invite year-round Florida living at its finest. Set within a secure gated neighborhood in the heart of Longwood, this exceptional residence delivers luxury, privacy, and convenience in one extraordinary offering.
Listing is courtesy of: ENGEL & VOLKERS NEW SMYRNA (386-213-6899)
Listing Agent: David Dell'Olio (407-228-4613)
3946 VILLAS GREEN CIR, LONGWOOD, FL 32779
$434,50039 Days on yellowkey MLS ID: O6402630
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $5,000 (1.1%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1967 Built: 1993Monthly Fee: $175 Tax: $2,296 (2025)Community: Wekiva VillasSingle Family
Taxes:$2,296
Remarks: Under contract-accepting backup offers. Virtually Staged. Seminole County, where "Old Florida" charm mixes with modern suburban convenience, and this Wekiva golf course home on the 9th hole is no exception. This beautiful Wekiva area is away from the hustle, but minutes to grocery stores, restaurants & home improvement options. Well cared for throughout the years with only one owner. The home underwent a 2020 makeover that included the kitchen & appliances, all 3 bathrooms, and the water heater. The roof was replaced in 2022 and reinspected this year. Wekiva offers some of the best schools in Seminole County, with "The Natural Choice" being one of the best Counties to live in the state of Florida. Convenient to all the expressways to get around Central Florida. Do not miss the amenities that Weikva offers: the continual sidewalks, local playground, tennis courts & pickleball courts, and a community center. 3946 Villas Green Cir is your next stop to homeownership!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Karen Pfannerstill (407-947-5717)
1722 MARKHAM GLEN CIR, LONGWOOD, FL 32779
$849,0003 Days on yellowkey MLS ID: O6414162
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2726 Built: 1997Monthly Fee: $100 Tax: $6,817 (2025)Community: Markham GlenSingle Family
Taxes:$6,817
Remarks: With over 4,400 sq. ft. under roof, this gorgeous 4 bedroom, 3 full bath pool home with over $75k in just finished upgrades has it all! Seller is offering up to a $20k credit for the new owner to add their personal touches. Situated on a full acre estate lot in one of the most desirable neighborhoods along Markham Woods Road, you'll enjoy all the best North Orlando has to offer and top notch Seminole County schools. At home, enjoy the privacy and serenity of being surrounded by lush greenery and sounds of nature. Within minutes, be in town with easy access to I-4 putting you at the doorstep of some of the most sought-after and exciting dining, shopping, and entertainment venues. This home boasts a new roof (2026), new plumbing (2026), new heat pump AC system (2026), newly re-tiled and refinished pool (2026), and re-screened pool enclosure (2026), and newer water heater (2024). Additional peace of mind comes from its concrete block construction and updated gutter system. The open concept living space allows for flexible use options and the extra large glass doors leading out to the 52 foot wide covered lanai make the space feel even more expansive. The lanai has a wet bar pre-wired with 220V for a cooking appliance, making a true outdoor kitchen well within reach. The sparkling pool dazzles from the main living areas, which is made even more impressive by the depth of the backyard. There's plenty of room to add an ADU with appropriate approvals. The Seminole Wekiva Trail runs directly behind the lot. Easily jump onto the trail for your morning walk or evening bike ride. High ceilings with knockdown finish (no popcorn) throughout. All 4 bedrooms feature wood laminate flooring and large closets. The ensuite primary bedroom has ample space for an office setup or searing area. The extra large 825 sq. ft. 3-car garage has a BMW EV charger (which works with other brands) conveniently located between the two garage doors for easy charging access on both sides. Solid across all 4 points (new roof / new AC / newer electrical panel / new plumbing) for insurability purposes and more manageable premium, this home's overall costs of ownership can be kept in check - especially since there is no sewer bill to pay. A central vacuum system adds to ease of maintenance. Call today for a private showing of this exquisite home!
Listing is courtesy of: DEGREE REALTY LLC (407-310-5456)
Listing Agent: Brandy Hill (407-310-5456)
125 RAINTREE DR, LONGWOOD, FL 32779
$410,0003 Days on yellowkey MLS ID: O6408649
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1671 Built: 1981Monthly Fee: $140 Tax: $4,407 (2025)Community: Springs Whispering Pines Sec 2Townhouse
Taxes:$4,407
High School: Lyman High
Middle School: Milwee Middle
Remarks: Welcome to THE SPRINGS! This beautiful 3-bedroom, 2.5-bathroom townhouse is located in the highly desirable Whispering Pines Village. Step inside this bright and inviting two-story home featuring beautiful wood flooring throughout the living room, dining room, and primary bedroom. The spacious living room features a cozy wood-burning fireplace and opens to a private enclosed patio. The beautifully paved outdoor living space includes a fire pit and fenced backyard, creating the perfect setting for entertaining or unwinding. Beyond the backyard fence, you'll find Whispering Pines Village's private tennis court and community pool, offering a rare backyard-adjacent amenity experience that feels like an extension of your own outdoor space. The dining room has been thoughtfully converted into a private office, creating an ideal workspace for remote professionals or anyone needing a dedicated home office. The oversized primary suite is conveniently located on the first floor and features a walk-in closet. The primary bathroom offers dual vanities and a walk-in shower. Upstairs, you'll find two additional bedrooms and a full bathroom with a shower/tub combination. This home also provides abundant storage, including a large storage area beneath the stairs, as well as a separate indoor laundry room. The interior has been freshly repainted, and major updates provide peace of mind, including a roof installed in November 2020, AC replaced in 2021, and a newer water heater. Residents of The Springs enjoy exclusive access to the community's natural crystal-clear spring and river, along with an impressive collection of resort-style amenities. The Springs is a spectacular 24-hour guard-gated community with hourly patrols and resort-style amenities, including tennis courts, pickleball courts, a swimming pool, basketball court, horse stables, playground, clubhouse, RV and boat storage, walking and jogging trails, nature trails along the Little Wekiva River, picnic and barbecue areas, and the stunning natural spring. This vibrant community hosts year-round events and activities, including movie nights under the stars, holiday celebrations, food truck nights, and more. Located within a top-rated school district and offering convenient access to I-4, shopping, dining, major highways, amusement parks, outlet malls, and Florida's beautiful beaches, this home combines comfort, convenience, and an exceptional lifestyle. Schedule your private tour today!
Listing is courtesy of: U R HOME REALTY GROUP LLC (407-602-5377)
Listing Agent: Mia Diercks (407-595-5899)
1808 WINGFIELD DR, LONGWOOD, FL 32779
$799,90016 Days on yellowkey MLS ID: O6411497
0 Days Off yellowkey (back on 6/11/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4440 Built: 1984Monthly Fee: $104 Tax: $11,518 (2025)Community: Wingfield Reserve Ph 1Spa: YesSingle Family
Taxes:$11,518
Remarks: Under contract-accepting backup offers. Tucked away beneath a canopy of mature trees on an expansive homesite in one of Longwood's most established communities, this custom pool home offers a rare combination of privacy, character, and space. From the moment you arrive, the circular driveway, natural setting, and distinctive architecture create a memorable first impression. Inside, soaring wood-beamed ceilings, extensive hardwood flooring, and dramatic floor-to-ceiling stone fireplaces add warmth and architectural interest throughout the home. The spacious living areas are filled with natural light and designed for both everyday living and entertaining, with multiple gathering spaces and walls of glass overlooking the screened pool and lush backyard. The kitchen features abundant cabinetry, generous workspace, granite countertops, a center island, and a functional layout that flows seamlessly into the surrounding living areas. The primary suite offers a private retreat complete with a spa-inspired bath, oversized walk-in shower, soaking tub, and tranquil outdoor views. Step outside to enjoy the screened pool enclosure, expansive paver deck, and beautifully landscaped surroundings. The oversized lot provides exceptional privacy while still offering plenty of room to enjoy the outdoors. Conveniently located, this home offers easy access to Interstate 4, SR 434, shopping, dining, golf courses, and everyday conveniences. Residents enjoy proximity to popular destinations including Wekiwa Springs State Park, Cranes Roost Park, Altamonte Mall, and the shops and restaurants of Lake Mary. A unique opportunity to own a distinctive property with timeless architectural details, generous living spaces, and an exceptional Longwood location.
Listing is courtesy of: ACME REAL ESTATE FLORIDA LLC (407-601-4958)
Listing Agent: Heather Unger, Pa (407-810-6304)
208 ORANGE RIDGE CIR, LONGWOOD, FL 32779
$759,90062 Days on yellowkey MLS ID: O6394394
1 Days Off yellowkey (back on 6/2/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2847 Built: 1984 Tax: $4,035 (2024)Community: Orange Ridge FarmsSpa: YesSingle Family
Taxes:$4,035
Remarks: Under contract-accepting backup offers. Tucked away on over 1.3 acres beneath a canopy of majestic trees, this exceptional residence offers a rare blend of refined living, privacy, and timeless elegance—without the constraints of HOA living. Ideally located off Long Pond Road and Markham Woods Road, this is Central Florida luxury at its most serene The property offers a 4-bedroom, 2.5-bath split floor plan, an oversized two-car garage, and an additional detached garage/workshop. The spacious kitchen features modern wood cabinetry and granite countertops. Amenities include a heated saltwater pool with spa, a Florida room adjacent to the family area complete with custom built-in bookcases (currently serving as a large office with panoramic backyard views), cathedral ceilings with recessed lighting throughout, and a brick wood-burning fireplace in the great room. A separate stand-alone building with water access and partial electrical infrastructure provides potential for conversion into in-law quarters or income property. Additional upgrades comprise a new roof (2019), solar panels-fully paid (2019), Tesla Power Wall (2025) for continuous electricity supply, double-pane storm-rated windows and doors (2020), new A/C unit (2014), upgraded flooring (2024), Hardy Plank siding (2026), and other enhancements. The grounds feature mature oak trees on a generous 1.3+ acre lot. No HOA dues. Perfectly positioned just minutes from the Seminole/Wekiva Trail and zoned for top-rated Heathrow/Lake Mary schools, this residence offers both exclusivity and convenience. A rare offering where space, sophistication, and lifestyle converge.
Listing is courtesy of: PARKER REALTY GROUP (407-845-0333)
Listing Agent: Ed Parker (407-617-0356)
2228 EARLEAF CT, LONGWOOD, FL 32779
$2,785,00058 Days on yellowkey MLS ID: O6399964
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 7696 Built: 1990Monthly Fee: $104 Tax: $11,667 (2024)Community: Wingfield Reserve Ph 3Spa: YesSingle Family
Taxes:$11,667
Remarks: At the end of a quiet cul-de-sac and backing to the protected beauty of Wekiwa Springs State Park, this extraordinary waterfront estate offers a rare blend of privacy, scale and natural serenity in the desired Markham Woods Corridor. Fully fenced and positioned to capture sweeping conservation and water views, the setting alone places this residence in a category few can match. Impressive private gates and a brick paver circular drive introduce a dramatic arrival, where a grand porte-cochere and expansive six-car motor court set the tone. Inside, the home has been completely reimagined through a comprehensive renovation, unveiling soaring ceilings, walls of glass and abundant natural light. A striking 5-by-8-foot pivot door opens to a refined foyer with porcelain tile and white oak flooring, immediately drawing the eye to the shimmering pool and tranquil pond beyond. Designed for grand entertaining and effortless living, the main areas unfold in a seamless open-concept layout. With 14-foot ceilings and expansive living, dining, family and kitchen spaces flowing together, the home offers impressive volume and connectivity. Anchoring the heart of the home, a dramatic double-sided wood-burning fireplace creates a warm focal point between kitchen and family room. The chef’s kitchen is a showpiece, featuring Wolf appliances, built-in refrigeration and an oversized island with seating for six, finished with elegant waterfall-edge countertops. Outdoor living is equally captivating. A vast travertine lanai transitions to an oversized resort-style pool, all set against a breathtaking backdrop of water and untouched conservation. Nearly every room is oriented to capture these remarkable views, creating a constant connection to the landscape. The primary suite is a sanctuary of grand scale, offering serene water and wooded vistas. Its bespoke bath features leather-finished stone countertops, dual vanities, a soaking tub, and picture windows framing the natural setting. A spa-inspired steam shower with multiple shower heads and a built-in bench completes the experience. Dual custom walk-in closets elevate functionality, one with a center island and scenic window, the other concealing a hidden safe room. Versatility defines the additional spaces. A dedicated office with walk-in closet and direct bath access can serve as an additional bedroom. A generously sized bonus room is ideal for a home theater, library or lounge, while a separate gym with luxury vinyl flooring can easily function as a second office. A thoughtfully positioned flex space between the main residence and guest quarters opens to the lanai and pool bath, ideal for a cabana lounge or wellness retreat. The guest quarters is a residence unto itself, featuring two bedrooms, two baths, a spacious great room, full kitchen with center island, separate motor court access, and its laundry, offering exceptional accommodations for guests or multigenerational living. Homes of this caliber rarely come to market. The extensive renovation, remarkable scale, and exceptional attention to detail are paired with Seminole County’s desirable locations. Zoned for top-rated schools and ideally positioned near Longwood and Lake Mary, with convenient access to major highways, regional hospitals, airports, beaches and Central Florida’s world-renowned attractions, this is a legacy property that defines elevated Florida living.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Mel Bernstein (407-810-4726)
309 HICKORY DR, LONGWOOD, FL 32779
$520,0009 Days on yellowkey MLS ID: O6413953
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1852 Built: 1976Monthly Fee: $54 Tax: $3,232 (2025)Community: Sweetwater Oaks Sec 06Single Family
Taxes:$3,232
Remarks: Virtually Staged. NEW ROOF Prior to closing on this Move-In Ready Pool Home in Sweetwater Oaks! Welcome to highly desirable Sweetwater Oaks, where this beautifully maintained 4-bedroom, 2-bathroom home offers the perfect blend of space, and comfort, with RECENT UPGRADES. The functional floor plan features separate living, dining, and family rooms, an eat-in kitchen, utility room, and walk-in pantry. Enjoy Florida living at its best with a large screened pool and covered lanai, ideal for relaxing or entertaining. The fully fenced backyard also features a new storage shed added in 2024. Major recent updates, all within the last year, provide peace of mind, including a new HVAC system, electrical panel, water heater, and microwave, plus a new dishwasher, flooring and baseboards in the living and dining rooms, fresh interior paint, painted pool deck, new blinds, updated lighting, and new electrical outlets and switches throughout . Additional improvements include a new pool patio roof and pool light (2020). With the new roof being installed prior to closing, this home offers peace of mind with all the recent improvements. Sweetwater Oaks residents enjoy deeded access to skiable Lake Brantley with a boat ramp, tennis and pickleball courts, picnic pavilion, and access to the Wekiva River, parks, and playgrounds. Conveniently located near top-rated Seminole County schools, shopping, dining, and major highways, this move-in-ready home is one you won't want to miss.
Listing is courtesy of: CHAMBERLAIN REALTY LLC (407-542-3033)
Listing Agent: Carol Pennington (407-335-0907)
36 STONE GATE S, LONGWOOD, FL 32779
$1,100,00010 Days on yellowkey MLS ID: O6413256
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3443 Built: 1991Monthly Fee: $17 Tax: $10,594 (2025)Community: Ravensbrook 2Nd AddSpa: YesSingle Family
Taxes:$10,594
Remarks: Virtually Staged. Offered for the first time in 25 years, this exceptional Southern Traditional estate presents a rare opportunity to own one of Longwood's most distinguished residences. Originally designed as the builder’s personal model home, this home showcases timeless craftsmanship, architectural charm, and meticulous pride of ownership throughout. Nestled on a professionally landscaped 1.01-acre homesite within the coveted Ravensbrook community, an intimate enclave of nearly 80 custom homes, treasured for its spacious lots and tree-lined streets shaded by a mature canopy of oaks. Impressive curb appeal sets the tone from the moment of arrival. A welcoming front porch, framed by lush mature landscaping, creates an elegant first impression. Encompassing 3,443 square feet of thoughtfully designed living space, the home features 5-bedrooms, 4.5 bathrooms, and a highly desirable floor plan with both the primary suite and an additional bedroom located on the main level. A dramatic two-story entry welcomes guests with soaring 20-foot vaulted ceilings, marble tile floor, refined crown molding, Colonial trim details, raised-panel doors, plantation shutters, and exquisite beveled-glass transoms adorning every downstairs doorway. Designed for both everyday comfort and gracious entertaining, the heart of the home is highlighted by a stunning double-sided wood-burning fireplace, showcasing exceptional brick craftsmanship and engineered hardwood flooring. The kitchen boasts distinctive tongue-and-groove oak ceiling, granite countertops, a center island, stainless steel appliances, and a dining area for casual meals and gathering. Traditional swinging doors provide convenience to the separate formal dining room, creating an ideal flow for hosting dinners. The private primary suite serves as a luxurious retreat, complete with a beautifully renovated spa-inspired bathroom. Upstairs, 3 generously sized bedrooms, each enhanced by character-rich vaulted ceilings. One bedroom includes its own private ensuite bath and spacious walk-in closet. Completing the second floor is a separate bonus room located above the garage, featuring rich wood parquet flooring and a closet, offering flexibility as a media room, home office, fitness studio, playroom, or guest suite. French doors lead to a screened lanai overlooking the sparkling swimming pool and spa, complemented by a summer kitchen for storage and entertainment. Additional highlights include a well-appointed laundry room with built-in cabinetry, utility sink, washer and dryer, a three-car garage with epoxy-finished flooring and custom storage cabinets, and an expansive paver driveway that provides a grand arrival experience. For nature lovers and outdoor enthusiasts, Ravensbrook offers a unique lifestyle amenity through exclusive access to Cushman Park, a community waterfront lot named in honor of the original developer. Residents may enjoy Rice Lake for kayaking, paddleboarding, and other recreational pursuits. Ideally situated along the prestigious Markham Woods Corridor, residents enjoy convenient access to an array of shopping, dining, premier golf courses, and nature trails, all while zoned for Seminole County's highly sought-after public schools. Just minutes away is the renowned Seminole Wekiva Trail, a nearly 14-mile paved recreational trail, for walking, running, cycling, and enjoying Central Florida's natural beauty.
Listing Agent: Amanda Salazar (407-917-0706)
3116 CLUBSIDE DR, LONGWOOD, FL 32779
$215,0004 Days on yellowkey MLS ID: O6413117
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1365 Built: 1984Monthly Fee: $44 Tax: $2,537 (2025)Community: Clubside At Sabal Point A CondoSpa: NoCondo
Taxes:$2,537
Remarks: Virtually Staged. This beautifully appointed and updated condo features new kitchen cabinets and granite countertops, TWO bedrooms each with an ensuite bath and huge walk in closet plus linen closes, and a spacious great room that looks out to the screen rear porch and tranquil green space. There is a half bath and large closet in the foyer and a laundry room with washer and dryer. Excellent Seminole County schools and easy access to shopping, dining, golf and I-4 makes this a prime location. Welcome to Clubside at Sabal Point in desirable Wekiva Springs! This updated 2-bedroom, 2.5-bath end-unit condo offers an abundance of natural light and a convenient first-floor location. The spacious great room flows seamlessly to a tranquil screened back porch through sliding glass doors, creating the perfect space to relax or entertain. The beautifully updated kitchen features new cabinetry and a functional layout ideal for everyday living. A thoughtfully designed split floor plan provides privacy, with two en suite bedrooms perfect for roommates or multigenerational living. A convenient hall half-bath and laundry closet are located just off the foyer. With great updates, an excellent layout, and priced to sell, this one is not to be missed!
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-862-9966)
Listing Agent: Kathleen Bousquet (508-982-7879)
2160 MARKHAM WOODS RD, LONGWOOD, FL 32779
$1,990,0004 Days on yellowkey MLS ID: O6415194
Bed: 4 Bath: 6.0 Gar: 12 Liv Area Sq Ft: 6546 Built: 1997 Tax: $12,937 (2025)Community: Hopkins EstatesSpa: YesSingle Family
Taxes:$12,937
Remarks: Welcome to an extraordinary custom-built estate where exceptional craftsmanship, privacy, and luxury come together on 2.5 gated and fully fenced acres in the heart of Longwood. Designed and constructed with meticulous attention to detail by builder Neil Hughes, this remarkable residence showcases superior quality throughout, from the grand entryway and soaring ceilings to the intricate custom tilework and thoughtfully designed living spaces. The impressive foyer opens to elegant formal living and dining rooms, while the expansive family room features custom built-ins, a beautiful wood-burning fireplace, and seamless access to the heart of the home. Designed for both everyday living and grand-scale entertaining, the chef's kitchen boasts dual sinks, two dishwashers, stunning emerald pearl granite countertops throughout the kitchen, a six-burner cooktop with commercial-grade ventilation, double ovens, extensive custom cabinetry, under-cabinet lighting, pull-out pantry systems, and an abundance of storage. Nearby, a custom dry bar adds both style and convenience for entertaining guests. The luxurious primary suite is a private retreat featuring its own sitting room, expansive bedroom, two walk-in closets with custom his-and-hers closet systems and dedicated dressing areas, and a spa-inspired bath complete with dual vanities, dual water closets, linen storage, granite countertops, and generous space throughout. A secondary en-suite bedroom is conveniently located on the first floor, along with a dedicated office, spacious game room with adjoining equipment room and sink, pool bath, a formal living room, and a large laundry room with utility sink. Upstairs, you'll find a fully equipped theater room with sink and beverage area, additional bedrooms and baths, walk-in closets, extra-wide hallways, 9-foot ceilings, oversized 6-foot-8-inch doors, and exceptional storage throughout. Bedroom #2 on the second level features two closets. Granite countertops continue throughout every bathroom in the home. Step outside to your private resort-style oasis featuring a spacious lanai, sparkling pool and spa, and peaceful natural surroundings that create an incredible sense of privacy and tranquility. Modern conveniences include a whole-home Lutron lighting system, a new pool heater, new water softener, multiple air-conditioning systems, interior air handlers, high-capacity septic system pumps, well-fed irrigation for the sprinkler system, and a brand-new roof with a transferable warranty. A transferable termite bond provides additional peace of mind for the next owner. Car enthusiasts will appreciate the attached air-conditioned two-car garage as well as the impressive 1,605-square-foot air-conditioned workshop/garage featuring multiple bays, lifts, pull-through access, an interior wash bay, and space for up to 12 vehicles when utilizing the two vehicle lifts (10 spaces not including the lifts), with potential for future conversion to additional living space if desired. The home's floor coverings consist of carpet and tile throughout. Exterior construction includes a frame-built second level. Hurricane-impact doors and windows, along with garage doors rated for 100 MPH winds, provide additional durability and peace of mind. Offering an unmatched combination of luxury, functionality, privacy, and craftsmanship, this one-of-a-kind estate delivers a lifestyle rarely found in Central Florida.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Abby Nelson (407-571-1445)
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