Longwood, FL Homes for Sale with Acreage

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

Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

Privately on 1.7 acres along one of the sought-after corridors of Markham Woods Road in Longwood, this exceptional property presents a rare opportunity to enjoy space, flexibility and modern upgrades without restrictions of an HOA. Tucked behind private entry gates at the front and rear of the property, the estate offers a unique sense of privacy and convenience while remaining just moments from

Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

CRUISING THE WATERWAYS of the MAJESTIC SPRING FED LAKE BRANTLEY await you. Stroll around your sculptured & manicured gardens. Elegant entry features include PORTE-COCHERE. Biltmore GAS LANTERNS, SHUTTERS, BALCONIES & TOWERING tree canopies as you approach this MEDITERRANEAN-RIVIERA style estate. The cultivated beauty of this "one-owner home". Impressive CUSTOM-BUILT SHOWPLACE is nestled back on a

Suzanne Crudo COLDWELL BANKER REALTY

Almost a $1,000,000 of asking is an assumable loan at 4.75. Dream home with beautiful environment galore. Flowing open floor plan with high ceilings and crown molding throughout. Theater room, Florida room with indoors grill, 2 wood burning fireplaces, beautiful sought after community, gated with guards 24/7, wide large lots. Must see this picturesque environment filled with wealth and luxury.

Leslie Golliday DOVER INTERNATIONAL CO., INC.

Located behind the gates of the exclusive, guard-gated Sweetwater Club Tennis Community, this secluded luxury POOL estate sits on nearly 1.5 acres of lush, tree-lined grounds, offering exceptional privacy and tranquility.The nearly 5,000 sq ft residence features 4 bedrooms, 4.5 updated bathrooms, multiple living areas, and two versatile bonus rooms with a private entrance—ideal for a home

Beatriz Terrassa EMPIRE NETWORK REALTY

Priced below appraisal. Welcome to 1805 Meadowbend Dr, a small gated enclave of 6 estate homes. This impressive property offers a unique blend of country living within city limits. Spanning over 4,000 sq ft on a sprawling 5-acre lot, this residence is priced at $1,400,000. The home showcases a downstairs master bedroom complete with a sitting area. The master suite features double California

Christy Fauquher PERFECT FIT PROPERTIES

Welcome to this EXQUISITE, one-of-a-kind estate nestled within the highly regarded community of WINGFIELD RESERVE. Set on a sprawling 1.4-ACRE LOT in one of Longwood’s most sought-after enclaves, this STELLAR 6,300+ SQ. FT. home offers unparalleled grandeur and privacy. The journey begins as you traverse a FULLY PAVED CIRCULAR DRIVEWAY, framed by towering mature trees and meticulously manicured

Daniel Betancourt EXP REALTY LLC

One or more photo(s) has been virtually staged. Owner Financing Options Available...Call For Details. 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

David Warren CHARLES RUTENBERG REALTY ORLANDO

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

Gina Hutchinson KELLER WILLIAMS WINTER PARK

Welcome to Alaqua Drive, Luxurious Upgraded Excutive Home Reflects Timeless Appeal **Sprawling Over An Acre of Tropical Green & Fresh Landscape**Enclaved in the Estate Gates of Alaqua- the Areas Most Respected Gold Gated Communities**Features Include:Sun-filled Home**Natural Stone &Hardwood Floors on a spectacular Open Space that Boasts **5 Bedrooms* & *a Family Lounge. Large cathedral ceilings**

Louis Joachim DOVER INTERNATIONAL CO., INC.

Once-in-a-lifetime opportunity to own a privately gated estate on acreage(12 total acres, approx 3 dry) along the pristine shores of Lake Brantley. This astounding 5-bedroom, 5.5-bath estate welcomes you through a striking private gated entrance, featuring a grand circular driveway, lush landscaping, and a tranquil fountain. Enjoy the pinnacle of true privacy with seemingly endless land.

Frank Benevento COLDWELL BANKER REALTY

DOWNSIZING! Almost empty nesters! Expansive one-level executive home of 4200+ sf nestled on an unbelievable 1+ ACRES in highly desirable Markham Meadows; MINIMAL HOA FEE of only $780/yr!! This beautiful home offers an ideal blend of comfort and style. Boasting 4 spacious bedrooms (incl second master suite or in-law suite) and 5 full baths, this residence provides ample room for both relaxation

Robert Brown PREFER 1 REAL ESTATE, INC.

Making its debut on the market in the sought-after Markham Woods area, 1652 Rutledge Road in Longwood is a charming one-owner home with much to offer. Sitting on one full acre, this spacious 5-bedroom, 3-bath pool home welcomes you with gorgeous pool views as you step through the front double doors. Sunlight fills the rooms and the family room’s stone-front wood-burning fireplace offers a cozy

Melissa Stalzer LPT REALTY, LLC

Pre-Construction. To be built. Property is currently a vacant lot, go and show anytime. This pre-construction Bedford 3 Model by Wettermann Homes includes both the land and the beautifully designed home to be built on it. The price also encompasses budgets for flooring, cabinets, tiling, and countertops, allowing buyers to personalize their selections at our trade partner's design showroom. This

Richard Wettermann EXP REALTY LLC

One or more photo(s) has been 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

Christina Rampersad KELLER WILLIAMS ADVANTAGE 2 REALTY

Behind three private gates, this extraordinary home offers a rare opportunity to own one of Central Florida’s most impressive luxury residences located in the gated Enclave within the guard-gated community of Alaqua Lakes! This compound is sited on 1.55 acres overlooking the 8th hole of the Legacy Club golf course and no neighbors on three sides is truly a buyer’s dream come true. The property

Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

A Private European Estate in the Heart of Longwood!! Hidden beyond iron gates and a winding brick drive shaded by timeless-old oaks, this 5.13-acre estate emerges with quiet authority — a residence designed not to follow trends, but to transcend them. Spanning more than 7,600 square feet, the architecture draws inspiration from European manor homes, where craftsmanship was paramount and every

Luke Miller COLDWELL BANKER REALTY

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 sereneThe property offers a 4-bedroom, 2.5-bath split floor plan, an oversized two-car

Ed Parker PARKER REALTY GROUP

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

Jennifer Wemert WEMERT GROUP REALTY LLC

Rare 3.39-Acre Income-Producing Estate in Sought-After Seminole CountyAccepting Backup Interest Through May 30th, 2026Discover an exceptional opportunity where wide-open freedom meets unbeatable value on this 3.39-acre property in one of Central Florida's most desirable locations. Built in 1982, this versatile estate seamlessly blends modern comfort with rural charm — providing a

Sukumar Haldar AVANTI WAY REALTY LLC

Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated on 2 acres of agricultural land in Longwood with Lake Mary city limits. Originally designed as an equestrian estate, this unique property offers the perfect blend of modern living and rural charm.The home was completely updated in 2022 and features a stylish kitchen with newer cabinetry, granite

Yanet Garcia-Rodriguez HOME WISE REALTY GROUP, INC.

Exceptional Opportunity to own a home off the celebrated Markham Woods Road, the area once recognized as the "Beverly Hills “of Central Florida. *** This premier location provides great versatility to owners who may wish to build an in-law quarters, multiple garages, a boat house, a recreational vehicle storage or just make future additions to the home. *** Home features: A one-acre lot, No HOA,

Alberto Rodriguez WEICHERT REALTORS HALLMARK PRO

One or more photo(s) has been virtually staged. The Estate at Markham Woods. Set behind private electronic gates and a guarded entry, a rare sense of arrival unfolds across more than seven acres of secluded, high and dry landscape in the heart of Markham Woods. Here, architecture, land, and infrastructure converge to create something far beyond a residence, a fully realized, multi generational

Matt McKee COMPASS FLORIDA LLC

Fully RENOVATED 4 bdm/3 bath home !!! New Roof, New AC, New Kitchen, New Bathrooms, New Floors, New Electrical Panel, New Paint (interior and exterior), New Water Heater. Located in one of Longwood’s most established and highly sought-after communities, Sweetwater Oaks. PRICED TO SELL! This beautifully updated home offers the perfect blend of modern upgrades, spacious living, and an incredible

Jorge Trejo KELLER WILLIAMS ADVANTAGE III