Location: Longwood
Do Not Show Listings
2201 CAMELLIA DR, LONGWOOD, FL 32779
$389,90012 Days on yellowkey MLS ID: O6408749
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1964 Tax: $2,281 (2025)Community: Lake Brantley Isles 2Nd AddSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,281
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome home to this beautifully updated 3-bedroom, 2-bath residence located in one of Longwood's most desirable communities. Zoned for highly rated Wekiva Elementary and Lake Brantley High School, this home offers an exceptional combination of location, comfort, and convenience. Inside, you'll find updated tile flooring throughout the entire home—no carpet anywhere—creating a modern look that's both stylish and easy to maintain. The spacious layout is complemented by a roof that is less than two years old, offering added peace of mind for the new owner. Situated on an oversized lot, the property features a fully fenced backyard with plenty of space for pets, play, gardening, or future outdoor living enhancements. Enjoy life in a well-established neighborhood with access to a private boat ramp on Lake Brantley and the flexibility of no mandatory HOA. Conveniently located near popular restaurants, shopping, parks, and major commuter routes, you'll have everything you need just minutes from your doorstep.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Adam Allegroe (407-227-2831)
1837 WINGFIELD DR, LONGWOOD, FL 32779
$899,00060 Days on yellowkey MLS ID: O6398952
REDUCED by $26,000 (2.8%) on 05/27/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3000 Built: 1982Monthly Fee: $104 Tax: $9,687 (2025)Community: Wingfield Reserve Ph 1Spa: YesSingle Family
Taxes:$9,687
Elementary School: Woodlands Elementary
High School: Lake Mary High
Middle School: Markham Woods Middle
Remarks: Welcome to 1837 Wingfield Drive, a rare opportunity to own a private ranch-style retreat in the highly sought-after Markham Woods corridor. Perfectly situated on a sprawling 1.5-acre homesite, this property offers an exceptional blend of space, privacy, and natural beauty. The oversized backyard showcases wooded & pond water views, while the neighboring community tennis courts provide an added buffer—creating a uniquely secluded setting where you can relax and enjoy the peaceful sights and sounds of local wildlife. Inside, the home has been thoughtfully updated with modern touches and major system upgrades, including new windows throughout, a high-efficiency 18 SEER HVAC system, and a new water heater—offering both style and peace of mind. The expansive, open-concept family room flows effortlessly into an extended dining area, creating an ideal layout for entertaining and everyday living. A stunning sunroom and solarium feature bring the outdoors in, offering panoramic views of the pool area and tranquil pond beyond. The split floor plan provides both comfort and functionality. The primary suite is generously sized and privately positioned, while two additional bedrooms share a convenient Jack-and-Jill bathroom. On the opposite side of the home, a junior suite with its own full bath offers the perfect setup for guests, multigenerational living, or older children seeking additional privacy. Wood flooring runs throughout the main living spaces, enhancing the home’s warm and inviting feel. Located just minutes from top-rated schools, premier shopping, dining, and only a few blocks from the Seminole Trail, this home delivers the perfect combination of location, lifestyle, and livability. This is a rare chance to enjoy estate-style living in one of Central Florida’s most desirable areas—schedule your private showing today.
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)
Listing Agent: Jenny Wemert (407-809-1193)
207 LONESOME PINE DR, LONGWOOD, FL 32779
$559,9004 Days on yellowkey MLS ID: O6416580
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1908 Built: 1977Monthly Fee: $54 Tax: $5,568 (2025)Community: Sweetwater Oaks Sec 08Spa: NoSingle Family
Taxes:$5,568
Elementary School: Sabal Point Elementary
High School: Lake Brantley High
Middle School: Rock Lake Middle
Remarks: FANTASTIC OPPORTUNITY IN SWEETWATER OAKS! Nestled under a canopy of mature trees in one of Longwood’s premier neighborhoods, this pristine 4-bedroom, 2-bathroom pool residence flawlessly showcases true pride of ownership! Exceptionally maintained: ROOF 2016, REPIPED w/PEX, NEWER ELECTRICAL PANEL & OUTLETS, REMODELED KITCHEN AND BATHS, NEWER GARAGE DOOR and Freshly Painted Pool Decking! PERFECT for both everyday living and grand-scale entertaining, the traditional floor plan offers a seamless flow, featuring spacious living areas, neutral decor throughout, soaring ceilings, a welcoming atmosphere, inviting wood burning fireplace and beautiful architectural touches! GOURMET kitchen with granite counters, convenient pass through window to patio, ample cabinets and SS appliance package (3 yrs new!). The heart of the home effortlessly transitions to a private backyard oasis with spacious covered patio and sparkling screen-enclosed pool serving as your personal Florida retreat. Enjoy the fenced in dog run/pet area with your 4 leg best friend(s). Home boasts a generous size corner lot at .32 acres with definite curb appeal along with convenient side facing garage and utility door access to garage! Beyond the property line lies the unparalleled lifestyle of Sweetwater Oaks, giving you exclusive access to the private Sweetwater Beach on Lake Brantley (for boating and skiing), tennis, playground/picnic area and Riverbend Park’s kayak launches onto the Wekiva River. Complete with top-tier Seminole County schools including Sabal Point Elementary, Rock Lake Middle, and Lake Brantley High, this MOVE-IN-READY gem offers the ultimate blend of timeless comfort and luxury community living. Incredible Longwood location with easy access to 434, 436, I4 plus close to multiple Publix, schools, shopping, dining, Wekiva Island, Wekiwa Springs Park, Uptown Altamonte, Orlando Health, Advent Health and so MUCH MORE!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Laura Toppin (407-489-0415)
1890 LONG POND DR, LONGWOOD, FL 32779
$615,0005 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
Taxes:$6,777
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)
490 WEKIVA COVE RD, LONGWOOD, FL 32779
$579,00049 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
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)
1405 CRICKET CT, LONGWOOD, FL 32750
$299,90065 Days on yellowkey MLS ID: O6397641
REDUCED by $15,100 (4.8%) on 06/12/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1372 Built: 1984Monthly Fee: $68 Tax: $3,994 (2024)Community: Westlake Manor Unit 2BTownhouse
Taxes:$3,994
Tax Year: 2024
Remarks: BIG PRICE DROP...and Ask about CREDIT FOR DECK REPLACEMENT for buyer. Wake up to tranquil lake views in this beautifully updated Coventry home, where comfort meets effortless elegance. This 3-bedroom, 2-bath residence offers a spacious design and a 2-car garage, complemented by thoughtful upgrades throughout. At the heart of the home, newer luxury vinyl plank flooring in living, dining and kitchen in addition to a fully remodeled kitchen that shines with quartz countertops, custom cabinetry, new appliances, and refined finishes—perfect for both quiet mornings and stylish entertaining. Recent improvements, including a new A/C and water heater (2023), add lasting peace of mind. Set within a well-kept community featuring a pool, tennis, and basketball courts, this home delivers a rare blend of scenery, sophistication, and value. Buyer and buyer agent to verify all data/measurements.
Listing is courtesy of: CFRP REALTY LLC (407-682-8686)
Listing Agent: Tonya Giddens (321-277-3291)
1006 CROSS CUT WAY, LONGWOOD, FL 32750
$569,90010 Days on yellowkey MLS ID: O6413921
0 Days Off yellowkey (back on 6/12/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2301 Built: 1987Monthly Fee: $43 Tax: $4,990 (2025)Community: Hidden Oak EstatesSingle Family
Taxes:$4,990
Elementary School: Longwood Elementary
High School: Lyman High
Middle School: Greenwood Lakes Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated 4-bedroom, 2.5-bath pool home in the highly desirable Hidden Oaks community of Longwood. Situated on a spacious homesite in an established neighborhood known for its mature landscaping, community pond with dock access, and convenient Seminole County location, this home combines extensive updates, functional living space, and exceptional outdoor amenities. Step inside to discover all-new wood flooring throughout the first floor and new carpet throughout the second floor. The remodeled kitchen (2023) serves as the heart of the home and features a gas range, abundant cabinetry, and generous prep space for everyday living and entertaining. The spacious great room is anchored by a wood-burning fireplace, while the formal dining room provides an inviting setting for gatherings and special occasions. The first-floor primary suite offers comfort and privacy with a walk-in closet and en-suite bath. Upstairs, you'll find three additional bedrooms and a full bath, providing flexibility for guests, hobbies, a home office, or additional living space. Major improvements provide peace of mind and set this home apart, including a remodeled kitchen (2023), whole-home replumb (2023), tankless water heater (2023), most windows replaced (2025), irrigation system (2020), paver driveway (2024), resurfaced pool deck (2024), new wood flooring throughout the first floor, and new carpet throughout the second floor. Outdoor living shines with a screened patio overlooking the sparkling pool, beautifully updated pool deck, and fire pit area. Whether hosting gatherings or enjoying a quiet evening outdoors, this backyard offers the perfect setting to enjoy Florida's year-round lifestyle. Hidden Oaks offers the appeal of an established Longwood neighborhood with mature landscaping, spacious homesites, and a community pond with dock access, while remaining conveniently located near shopping, dining, parks, SunRail, major roadways, and many of Central Florida's most popular destinations. Combining thoughtful updates, major system improvements, versatile living space, and a resort-inspired outdoor setting, this move-in-ready home is ready for its next owner.
Listing is courtesy of: EXIT GLOBAL REALTY (407-725-7180)
Listing Agent: Wendy Wagner (407-947-6879)
110 WHITLEY BAY LN, LONGWOOD, FL 32779
$500,00012 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
$530,000133 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
$539,99914 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
$206,500131 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
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
$995,00034 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
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
$1,200,00025 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)
1722 MARKHAM GLEN CIR, LONGWOOD, FL 32779
$849,0005 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
$410,0005 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
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)
106 SPRINGWOOD CIR #B, LONGWOOD, FL 32750
$148,00063 Days on yellowkey MLS ID: O6399098
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1973 Tax: $666 (2024)Community: Springwood VillageCondo
Taxes:$666
Elementary School: Altamonte Elementary
Remarks: Virtually Staged. This darling condo is located in the Springwood community and offers wonderful natural light. The entry way flows right into the living room which provides sliding doors to the screened-in patio. The kitchen boasts granite counters, tile backsplash and eat-in area. The primary bedroom offers ample space. The primary and secondary bedroom share a hallway bathroom. The secondary bedroom is perfect for a guest room, office or craft room. The screened-in patio overlooks wonderful green space and includes a storage closet. This condo is close to many area restaurants and shops. Welcome Home!
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Beth Logullo (772-633-0670)
1808 WINGFIELD DR, LONGWOOD, FL 32779
$799,90018 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
$759,90064 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
$2,785,00060 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)
231 RUTH BLVD, LONGWOOD, FL 32750
$339,00011 Days on yellowkey MLS ID: O6414044
2 Days Off yellowkey (back on 6/10/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1334 Built: 1983 Tax: $540 (2025)Community: Longwood ParkSingle Family
Taxes:$540
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to this well-maintained 3-bedroom, 2-bathroom home located in the desirable Longwood Park community. This property offers a spacious fenced backyard, a two-car garage, and an additional covered carport—providing plenty of room for vehicles, recreational equipment, or additional parking flexibility. Inside, the home features a freshly painted living and dining area with French doors leading to a large, screened-in covered lanai—perfect for year-round outdoor enjoyment. The updated eat-in kitchen offers modern convenience, while the primary bedroom includes its own set of French doors opening to the lanai, creating a private and relaxing retreat. Outdoors, you’ll find a hand-built wooden storage shed, ideal for tools, hobbies, or additional workspace. The front of the home also features a painted concrete area that can easily be set up as an inviting outdoor seating space—perfect for enjoying the neighborhood and connecting with neighbors. Ideally situated near the Cross Seminole Trail, offering miles of paved paths perfect for biking, walking, and outdoor recreation, and just minutes from downtown Lake Mary, where you’ll find local shops, restaurants, and a popular weekend farmers market. Zoned for top-rated Seminole County schools and within walking distance to the YMCA, Lake Mary High School, Greenwood Lakes Middle School, and the Seminole County Public Library, this location offers both convenience and a relaxed, practical lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Carmen Quintana (407-340-3932)
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