Homes for Sale Between $500,000 to $600,000 in Longwood, FL

4 Beds ⋅ 2 Baths ⋅ Sanlando Spgs SubDv. ⋅ 32750 Zip Code

Virtually Staged. WELCOME HOME TO THIS SPACIOUS 4-BEDROOM, 2-BATH POOL HOME OFFERING THE PERFECT BLEND OF CHARACTER, UPDATES, AND FLORIDA LIVING! Situated on a fully fenced lot with RV parking, this solid block home offers exceptional space, thoughtful updates, and plenty of room to entertain. Step through the hardwood entryway into the inviting living room, where you'll find a cozy fireplace that also connects to the primary bedroom, creating warmth and charm throughout the home. Just beyond is the beautifully remodeled kitchen featuring a large center island, farmhouse sink, ample cabinetry, pantry, and generous prep space—perfect for everyday living and entertaining. The adjoining family room flows seamlessly into the incredible climate-controlled Florida room, complete with heating, air conditioning, and its own stunning stone fireplace, making it the perfect year-round gathering space overlooking the backyard and pool. The spacious primary suite offers private access to the Florida room, a large walk-in shower, dual vanities, and generous closet space. The secondary bathroom has been beautifully remodeled with dual sinks and an updated shower. The additional bedrooms are all generously sized, including one with a walk-in closet and another featuring French doors leading to the backyard along with its own walk-in closet. The dining room includes custom built-in storage, while additional linen, utility, and pantry storage provide functionality throughout the home. Outside, you'll enjoy your own private backyard retreat featuring a sparkling pool with a new pool pump (2026), a fully fenced yard, RV parking, and plenty of space for entertaining, pets, or gardening. The climate-controlled two-car garage features a new electrical panel, laundry area, and is complemented by an additional carport. A generator transfer switch is also already installed for added peace of mind. Major updates include a new addition completed in 2024, new septic system and drain field installed in 2024, repiped plumbing, new HVAC system, roof replaced in 2017, flat roof replaced in 2021, and a new electrical panel. The home is on septic, and while a well is present, it is not currently in use. Conveniently located just minutes from Historic Downtown Longwood, SunRail, I-4, shopping, dining, top-rated Seminole County schools, Big Tree Park, and Wekiwa Springs State Park, this home offers the perfect combination of space, comfort, and convenience. Don't miss your opportunity to own this one-of-a-kind Longwood home. Schedule your private showing today!

442 Homer Avenue, Longwood

$595,000

4 Beds ⋅ 2 Baths ⋅ Sweetwater Oaks Sec 18 SubDv. ⋅ 32779 Zip Code

Welcome to Riverbend Boulevard, where spacious living, thoughtful updates, and the sought-after Sweetwater Oaks lifestyle come together. Residents enjoy private access to skiable Lake Brantley, including the community’s private beach and boat ramp—perfect for boating, paddleboarding, fishing, or simply enjoying life by the water. Inside, this four-bedroom, two-bath home offers a versatile split-bedroom floor plan with generously sized living spaces and vaulted ceilings. Updated luxury vinyl plank flooring flows throughout all four bedrooms and the formal living and dining rooms, creating a fresh, cohesive feel. The expansive living room provides the flexibility to serve as an office, playroom, or additional gathering space, while the dining room offers plenty of room for entertaining. At the heart of the home, the inviting family room features soaring vaulted ceilings and a striking stone fireplace that brings warmth and character to the space. The kitchen offers abundant cabinetry, casual dining space, and all-new stainless steel appliances. The spacious primary suite easily accommodates a king-size bed, while three additional bedrooms are conveniently located near the beautifully remodeled guest bathroom. A generous sunroom extends the home’s living space and opens to the private backyard, where an oversized pool creates the perfect setting for swimming, entertaining, and enjoying Florida’s year-round sunshine. The pool was resurfaced in 2022. Major improvements provide added confidence and convenience, including a 2022 roof, 2024 air-conditioning system, updated electrical panels, Pella replacement windows throughout, and a new garage door and opener. Sweetwater Oaks is known for its tree-lined streets, established natural beauty, sought-after schools, and exceptional private amenities. In addition to Lake Brantley access, residents enjoy tennis and pickleball courts, basketball courts, playgrounds, covered pavilions, volleyball, a fishing dock, soccer and baseball fields, community center, and private access to the Wekiva River for canoeing, kayaking, and paddleboarding. With its flexible floor plan, oversized pool, extensive improvements, and exceptional community lifestyle, Riverbend Boulevard is ready to welcome its next owners home.

734 Riverbend Boulevard, Longwood

$590,000

4 Beds ⋅ 3 Baths ⋅ Woodlands Sec 4 SubDv. ⋅ 32750 Zip Code

Back on the Market! Buyer financing last minute fell through. VA appraisal was done and approved. Second chance for you to grab this fabulous house with in-law suite. Absolutely Everything You’ve Been Looking For — in the Sought-After Woodlands Community of Longwood! This lovingly maintained home has been cherished by the same owners for 39 years and is now ready to welcome new memories. With an ideal multigenerational floor plan, in-law suite, sparkling pool with natural gas heater, and huge yard, this home truly has it all. Key Features Spacious Layout: Bright, open floor plan with flexible living spaces — perfect for entertaining or quiet family living. Gourmet Kitchen: A chef’s dream with an abundance of rich wood cabinetry featuring 42" cabinets, soft-close drawers, granite countertops and backsplash, stainless appliances featuring double ovens with convection, 5 burner gas cooktop 2024, microwave, and ample amounts of counter space. A large window overlooks the pool, and the breakfast bar is ideal for casual meals. Comfortable Gathering Spaces: The kitchen opens to a large family room with French doors leading to a massive 30-foot screened lanai with gorgeous wood ceiling and huge paddle fans, perfect for summer barbecues and poolside relaxation. A separate dining area features elegant built-in cabinetry. Versatile Living Room: A huge formal living room (or flex space) features a gorgeous gas fireplace surrounded by beautiful stone and framed by custom shelving—ideal for a game room, home theater, or play area. Private Primary Suite: The spacious primary retreat includes French doors overlooking the pool, dual closets, and an ensuite bath with double sinks and walk-in shower. Large Bedrooms: Spacious secondary bedrooms with large closets and conveniently located near full bath with pool access. In-Law Suite: Thoughtfully designed newer addition with its own private entrance, full bath, dual sinks, walk-in shower, and a generous 23’ x 12’ living space—perfect for guests or multigenerational living. Outdoor Oasis: Enjoy the 8-foot-deep screened pool and spa with heater for year-round swimming. The 30’ x 17’ lanai has a natural gas hookup for grilling and entertaining. Despite the large pool, there’s still ample green space on your .29-acre yard for gardening. Seller added a separate Well for Irrigation System to keep your plants lush and green and watering costs low!. Bonus size indoor laundry room, extra storage closets throughout and large two car garage. Updates include: Brand-new plumbing, new electrical panels, 2020 roof, replaced windows, Kitchen update, bathroom showers retiled, pool resurfaced within last 10 years, exterior paint and freshly painted living areas. Four-point inspection available. Location & Lifestyle In the heart of Seminole County, zoned for top-rated schools and just minutes from I-4, world-famous attractions, dining, and shopping. This home blends classic character with modern comfort in one of Longwood’s most desirable neighborhoods. Come see why this home truly has everything you’ve been searching for—and more!

105 Cedar Oak Trail, Longwood

$589,900

4 Beds ⋅ 3 Baths ⋅ Wekiva Club Estates Sec 08 SubDv. ⋅ 32779 Zip Code

Virtually Staged. Close before the end of the year on this gorgeous home and take advantage of significant savings! Reach out to us and ask us how! Welcome to this beautifully updated 4-bedroom, 2.5-bath pool home in the highly sought-after Wekiva Club Estates! Offering 2,477 square feet of living space on a spacious .32-acre lot, this home blends comfort, style, and functionality in one of Seminole County's most desirable communities. Step inside to discover soaring ceilings, an open and inviting floor plan, wood and tile flooring throughout, and a stunning floor-to-ceiling stone fireplace that serves as the centerpiece of the living space. The updated kitchen opens seamlessly to the main living and dining areas, creating the perfect setting for everyday living and entertaining. The spacious primary suite features a beautifully renovated NEW PRIMARY BATH, walk-in closet, and private en-suite retreat, while three additional bedrooms provide plenty of room for family, guests, or a home office. Major updates provide peace of mind, including NEW WINDOWS and a NEW FENCE. Outside, your private backyard oasis awaits. Enjoy Florida living year-round with a sparkling in-ground pool, above-ground spa, lush landscaping, and a cozy fire pit area. Whether you're hosting gatherings, relaxing with family, or enjoying a quiet evening outdoors, this backyard was designed for making memories. Additional features include a two-car garage, wood fencing, public utilities, and low HOA dues. Residents of Wekiva enjoy access to community amenities including parks, playgrounds, tennis courts, sidewalks, and a golf course. Located within the highly rated Wekiva Elementary, Teague Middle, and Lake Brantley High School districts, this home offers convenience, recreation, and an exceptional lifestyle. Don't miss the opportunity to make this move-in-ready Wekiva gem your own!

351 Needles Trail, Longwood

$587,000

4 Beds ⋅ 3 Baths ⋅ Knollwood 3rd Add Amd SubDv. ⋅ 32750 Zip Code

Your Dream Home Awaits! Discover the perfect combination of space, comfort, and endless possibilities in this charming ranch-style home, ideally positioned on an impressive 0.71-acre corner lot in the highly sought-after Knollwood community of Seminole County. Offering 4 spacious bedrooms, 2.5 bathrooms, and 2,416 square feet of living space, this home is designed for growing families, entertaining, and creating memories that will last a lifetime. From the moment you arrive, you'll appreciate the oversized driveway with abundant parking and the expansive yard that provides limitless opportunities to design your own private retreat—whether you envision a sparkling pool, outdoor kitchen, garden, playground, or the ultimate backyard entertainment space. Step inside to a warm and welcoming interior where timeless charm meets modern comfort. The inviting living room features elegant crown molding, a cozy wood-burning fireplace, and beautiful rustic barn doors that lead into the heart of the home—an updated kitchen complete with stainless steel appliances, sleek countertops, generous cabinetry, and abundant natural light, making it the perfect place to gather with family and friends. Built with the quality and craftsmanship of a classic 1974 ranch, this home offers solid construction, spacious living areas, and incredible potential to personalize and make it uniquely yours while enjoying its timeless character. Perfectly located within one of Seminole County's most desirable school districts, you'll enjoy convenient access to premier shopping, dining, parks, major highways, and everything Central Florida has to offer. Homes with this much land, this much living space, and this prime location rarely become available. Whether you're searching for your forever home or an exceptional investment, this property offers a rare opportunity to own one of Knollwood's most desirable homes. Don't miss your chance to make this incredible property yours—schedule your private showing today before it's gone!

1200 Waverly Way, Longwood

$575,000

4 Beds ⋅ 2 Baths ⋅ Wildmere Amd SubDv. ⋅ 32750 Zip Code

Great for an investor! Property is being sold with the other 2 properties on the same premises of which both already have tenants in place and are self-contained with their own kitchen, laundry and living space. Property needs some TLC. Combined all 3 properties Lot size is over 1 acre. Great news, No HOA!! The home is nestled between 2 lakes and conservation with a large backyard that allows for lots of privacy. Close to major highways, shopping and restaurants. If you need peace, quiet and a place to relax from the daily stress of everyday life to come home to. This one is just waiting for you to call home!

917 Oxford Street, Longwood

$575,000

2 Beds ⋅ 1 Baths ⋅ Wildmere Amd SubDv. ⋅ 32750 Zip Code

Great for an investor! Property already has a tenant in place and is being sold with the other 2 properties on the same premises of which one also has a tenant in place and one needs some TLC. Combined all 3 properties Lot size is over 1 acre. Great news, No HOA!!. This property was fully renovated 2 years ago and is very cozy and spacious with 2-bedroom/1 bath with lake view in the lovely Wildmere Community. Property features quartz counter top, stainless steel appliances, shaker cabinets and pantry, lots of natural light throughout the home, luxury vinyl flooring and ceiling fans and updated light fixtures. The 2 bedrooms have large closet space and the laundry room has washer and dryer for your convenience. The home is nestled between 2 lakes and conservation with a large backyard that allows for lots of privacy. Close to major highways, shopping and restaurants. If you need peace, quiet and a place to relax from the daily stress of everyday life to come home to, this one is just waiting for you!!

923 Oxford Street, Longwood

$569,000

4 Beds ⋅ 3 Baths ⋅ Wekiva Hills Sec 08 SubDv. ⋅ 32779 Zip Code

Welcome to this spacious and beautifully maintained family home in the highly desirable Wekiva Hills community, where comfort, functionality, and location come together. Offering 4 bedrooms, 3 full bathrooms, and an abundance of versatile living space, this home is designed to accommodate today's busy lifestyle. Roof (2022), new windows (2022), Water Heater (2023), Pool re-surfaced and tiled (2022), fence (2023). Freshly painted inside and featuring hard-surface flooring throughout with no carpet, the interior offers a clean, modern feel that's both stylish and easy to maintain. Multiple living areas include formal living and dining rooms, wood-burning fireplace, a generous bonus space, and an oversized family room centered around a classic wood-burning fireplace. The formal dining room is currently used as a home office, showcasing the flexibility of the floor plan to fit your needs. The spacious family room opens to a covered lanai and private screened swimming pool, creating the perfect setting for entertaining or relaxing year-round. The large fenced backyard is beautifully landscaped with mature fruit and flowering trees, providing plenty of room for outdoor activities and gardening. Additional features include an inside laundry/utility room, updated bathrooms, tile flooring in all wet areas, a whole-home water filtration system, AC system (2015), and all major appliances convey with the home, making it truly move-in ready. Located in the heart of Wekiva, residents enjoy miles of scenic walking and biking trails, parks, playgrounds, sports courts, and a vibrant community atmosphere. Zoned for highly sought-after Brantley High School and conveniently located near shopping, dining, Wekiva Springs State Park, and major roadways, this home offers the perfect balance of peaceful living and everyday convenience. This is a wonderful opportunity to own a spacious pool home in one of Central Florida's most established and sought-after communities. Schedule your private showing today.

165 Duncan Trail, Longwood

$565,000

4 Beds ⋅ 3 Baths ⋅ Meadows Unit 1 SubDv. ⋅ 32750 Zip Code

POOL HOME ON NEARLY HALF AN ACRE WITH TWO PRIMARY SUITES. A 3.5% ASSUMABLE LOAN may offer qualified buyers a valuable financing opportunity. Set at the end of a cul de sac, this distinctive Longwood home pairs flexible living with exceptional outdoor space. A COURTYARD ENTRY leads into multiple living areas, while the kitchen overlooks the pool. The main primary suite features a PRIVATE SCREENED LANAI and DUAL SIDED FIREPLACE shared with the living room, while a SECOND PRIMARY SUITE adds flexibility. Outside, TWO CONNECTED BACKYARD AREAS include a fenced pool area opening through a gate to a LARGE CLEARED YARD with AVOCADO TREES. Improvements include LVP FLOORING approx. 1 year old, WHOLE HOME GENERATOR and poolside fencing approx. 3 years old, one HVAC system approx. 4 years old, and ROOF and GAS WATER HEATER approx. 7 years old. OUTDOOR SHOWER added in 2024. Furniture may be negotiated with the sale. Loan assumption subject to lender approval, buyer qualification, existing loan terms and applicable requirements.

126 Heather Hl, Longwood

$559,789

3 Beds ⋅ 3 Baths ⋅ Meredith Manor Nob Hill Sec SubDv. ⋅ 32779 Zip Code

Welcome to this stunning colonial-style house in Longwood, FL, offering convenient access and limited views of beautiful Lake Brantley. This recently fully renovated 3-bedroom with office den loft study area with closet, 3-bathroom home boasts a multitude of upgrades, ensuring a comfortable and energy-efficient living experience. As you step inside, you'll immediately notice the meticulous attention to detail throughout. The house features a brand-new roof, air conditioning system, and windows, providing peace of mind and enhancing the overall aesthetic appeal. With its energy-efficient design, you can enjoy lower utility bills while minimizing your carbon footprint. The circular driveway offers unparalleled convenience, particularly for those weekends spent enjoying your boat on the lake. Imagine effortlessly parking and launching your boat, setting the stage for endless fun and relaxation. This home truly embraces the quintessential Florida lifestyle. Situated on an oversized lot, this property offers abundant space for outdoor activities and future expansion possibilities. Two of the upstairs bedrooms boasts its own private balcony. Whether it's sipping your morning coffee or unwinding after a long day, these balconies provide the perfect sanctuary to immerse yourself in the beauty of nature. Additionally, the area offers a myriad of recreational amenities, including parks, golf courses, shopping centers, and dining establishments. Longwood provides the perfect balance of suburban tranquility and easy access to the vibrant city life of nearby Orlando. Don't miss this incredible opportunity to own a fully renovated colonial-style home. Schedule a showing today and make this dream home your own. 1 year Home Warranty Included.

219 Nob Hill Circle, Longwood

$555,000

6 Beds ⋅ 4 Baths ⋅ Longwood Plantation SubDv. ⋅ 32750 Zip Code

Amazing pool home in Longwood is the perfect multi-generational home. This home has 2 master suites, one downstairs and one upstairs with the downstairs master suite perfect for a mother in law living space. Also unique is 3 living spaces, one of which is upstairs so the kids can play upstairs and not disturb whoever is downstairs. The home has been remodeled with upgraded luxury vinyl flooring and granite countertops. You will enjoy the covered pool and lanai, with a backyard large enough with for your pets and no rear neighbor. Have peace of mind with the Roof and AC replaced in 2019 and 2020. You will be able to save money each month with solar panels that keep the electricity bill affordable, and a low HOA each month. *All information is intended to be accurate but is not guaranteed.

502 Freeman Street, Longwood

$550,000

3 Beds ⋅ 2 Baths ⋅ Spring Hammock SubDv. ⋅ 32750 Zip Code

Rare 3.39-Acre Income-Producing Estate in Sought-After Seminole County Discover 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 lifestyle that's increasingly hard to find. Turnkey Income Generation This is more than a home — it's a smart investment. The property generates $3,200 monthly in rental income from a fully tenanted duplex featuring a 2-bedroom unit and a 1-bedroom unit, both with a newly renovated kitchen and modern appliances. With financials already in place, buyers need only a down payment — the rental income takes care of the rest. (Detailed financial analytics available upon request.) Endless Possibilities Zoned with flexibility in mind, this property is a rare blank canvas: Homestead your dream lifestyle with room to grow Launch a boutique farm — farm animals are welcome Develop commercially — strong rezoning potential for industrial or office use Open a Farm to Table Gourmet Restaurant Location That Has It All Nestled alongside the iconic Big Tree Park, you'll enjoy the tranquility of nature while remaining moments from city conveniences. Just minutes to Ronald Reagan Boulevard and Lake Mary Boulevard, with quick access to: Longwood SunRail Station — 4 min Lake Mary SunRail Station — 7 min Altamonte Springs — 10 min Orlando Sanford International Airport — 16 min Orlando International Airport — 39 min Lake Mary and Altamonte Springs Shopping Malls — 7-10 minutes away A Lifestyle, Not Just a Listing Owners are relocating, creating a rare window of opportunity for the right buyer. Whether you're an investor, entrepreneur, homesteader, or developer — opportunities of this caliber rarely come to market. How to Submit Your Interest With strong interest anticipated, buyers are encouraged to submit their highest and best interest using an escalation addendum. All interests will be reviewed no later than May 30th, 2026. Serene country living. Strong rental income. Commercial upside. All just minutes from the heart of the city.

1735 Timocuan Way, Longwood

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