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$575,000
4 Beds ⋅ 3 Baths ⋅ Winsor Manor SubDv. ⋅ 32750 Zip Code
A beautifully renovated, move-in ready family home with over 2,600 square feet of living space is now available in the established Winsor Manor community of Longwood. This 4-bedroom, 3-bathroom, single-story property offers the space, fresh modern finishes and long-term peace of mind every growing family deserves. Step inside to a bright, open layout featuring vaulted ceilings, plenty of natural light, brand new flooring, fresh paint and modern fixtures throughout. The fully renovated kitchen takes center stage with solid wood shaker cabinets featuring soft-close hinges, elegant Quartz countertops and brand new appliances. All bathrooms have been completely renovated with a fresh modern feel, while major improvements including a brand new roof installed just weeks ago, a newer and fully serviced AC and new water heater offer the kind of worry-free ownership that lets you focus on what really matters - making everlasting memories with your family. One of the home's most impressive features is the oversized enclosed rear porch, creating a massive additional gathering area where the entire family can come together for holidays, birthdays and weekend get-togethers without ever feeling cramped. Outside, a large backyard and spacious two-car garage provide even more room to enjoy everyday family life. Set on a 0.28-acre lot within the well-established Winsor Manor neighborhood, you'll enjoy mature surroundings and welcoming neighbors in a community that has stood the test of time. Conveniently located just minutes from SR 434, I-4, the Seminole-Wekiva Trail, shopping, dining and everyday necessities, with easy access to Altamonte Springs, Lake Mary, Maitland and the greater Orlando area, this home truly offers the ideal combination of space, comfort and location. At $575,000, this is a fantastic opportunity to plant roots in Longwood in a home that's already been completely refreshed for its next family. Reach out to your preferred real estate professional today to schedule your private showing before it's gone.

136 Glendale Drive, Longwood

$529,900
4 Beds ⋅ 2 Baths ⋅ Oakmont Reserve SubDv. ⋅ 32750 Zip Code
Fantastic Longwood location! Come tour this 4BR, 2BA 2018 Meritage home located in the charming gated community of Oakmont Reserve! This builder is known for its energy standards, which include spray foam insulation, double pane windows and Energy Star appliances. This home offers an open concept with a formal living room and dining room off the front entry anchored by neutral tile. The heart of the home features vaulted, angled ceilings and a kitchen/family room combo perfect for entertaining. This traditional kitchen features light 42" wood cabinetry with crown molding, granite countertops, and stainless steel appliances, including double ovens, a flat cooktop, and a double-door refrigerator. This split plan has 3 bedrooms sharing a full bath with dual sinks and bathtub. Enjoy the private owners suite that has a large walk-in closet and private backyard views. Primary bath has an oversized shower and dual sinks. Sliding doors off the family room open to the screened lanai. Enjoy the lush backyard views from the custom paver seating area. This fenced yard offers intentional landscaping for privacy. Inside laundry room opens to the 2 car garage with storage racks. This all-one-level home with a paver driveway and charming curb appeal is waiting for you! Close proximity to hospital, Sun Rail, shopping, I4 and the 417!

154 Oakmont Reserve Circle, Longwood

$700,000
4 Beds ⋅ 3 Baths ⋅ 32750 Zip Code
Wow! BACK ON THE MARKET! Just over TWO ACRES in the Lake Mary Longwood area! NO HOA! Two separate homes, a main home and guest home on just over two cleared and level acres in the heart of the Longwood - Lake Mary area. Main home has four bedrooms and three full baths and features three levels with original hardwood floors, plantation shutters and a wood burning fireplace. Guest house is a one bedroom, one bath with a living and dining combination and kitchen. Plenty of room for rebuilding, remodeling, or expansion plans - put your own personal touches on things and make this your family compound! Irrigation system covers entire TWO+ acres. Zoned A-1 which allows for livestock and chickens. Lot can be subdivided. This outstanding location affords copious amounts of shopping and restaurants within ten minutes' travel. Lake Emma Road connects Longwood with Lake Mary and the location is very convenient to I-4, Lake Mary Blvd, and SR 434.

1879 Lake Emma Road, Longwood

$725,000
Bradleys Add SubDv. ⋅ 32750 Zip Code
Absolutely Turn Key fully renovated two-story block standalone building zoned Neighborhood Commercial with 11 parking spaces located just seconds from Longwood’s Historic District. Zoning (Live/Work) allows living in the property while also running your business. This building has been meticulously maintained and is truly one of a kind. The first floor is fully ADA compliant with 8 built in cubicles, 2 offices and a conference room with Cathedral ceilings. The kitchen offers granite countertops with solid wood cabinets. There are two separate bathrooms with a utility room ready for a stackable washer & dryer. The beautiful custom millwork stairway leads to the 2nd floor which could easily be converted into a separate business office with a private entrance. It’s nicely appointed with Brazilian walnut flooring throughout and elegant crown molding. There is a large office that would make a great bedroom, a private bath plumbed for a shower and a kitchen area that is open to the living room, which could also be a large office space if desired. The many updates include: a New Roof (2023), New Exterior Paint (2023) New carpet on the first floor (2023) water heater (2017) and hurricane rated dual pane windows and shatter proof storm doors. All interior doors are solid core. All interior glass is tempered. Extremely well insulated exterior and interior walls. There are two separate HVAC systems for the first floor and second floor. Natural Gas is available on the property. The property also features a fully enclosed storage shed, providing additional secure space for equipment, inventory, supplies, or other storage needs. The Average Annual Daily Traffic (AADT) generally reaches around 12,000 vehicles per day. This is truly a one of a kind gem you must see to appreciate!

1150 N Ronald Reagan Boulevard, Longwood

$725,000
1 Beds ⋅ 3 Baths ⋅ Bradleys Add SubDv. ⋅ 32750 Zip Code
Absolutely Turn Key fully renovated two-story block standalone building zoned Neighborhood Commercial with 11 parking spaces located just seconds from Longwood’s Historic District. Zoning (Live/Work) allows living in the property while also running your business. This building has been meticulously maintained and is truly one of a kind. The first floor is fully ADA compliant with 8 built in cubicles, 2 offices and a conference room with Cathedral ceilings. The kitchen offers granite countertops with solid wood cabinets. There are two separate bathrooms with a utility room ready for a stackable washer & dryer. The beautiful custom millwork stairway leads to the 2nd floor which could easily be converted into a separate business office with a private entrance. It’s nicely appointed with Brazilian walnut flooring throughout and elegant crown molding. There is a large office that would make a great bedroom, a private bath plumbed for a shower and a kitchen area that is open to the living room, which could also be a large office space if desired. The many updates include: a New Roof (2023), New Exterior Paint (2023) New carpet on the first floor (2023) water heater (2017) and hurricane rated dual pane windows and shatter proof storm doors. All interior doors are solid core. All interior glass is tempered. Extremely well insulated exterior and interior walls. There are two separate HVAC systems for the first floor and second floor. Natural Gas is available on the property. The property also features a fully enclosed storage shed, providing additional secure space for equipment, inventory, supplies, or other storage needs. The Average Annual Daily Traffic (AADT) generally reaches around 12,000 vehicles per day. This is truly a one of a kind gem you must see to appreciate!

1150 N Ronald Reagan Boulevard, Longwood

$619,900
4 Beds ⋅ 3 Baths ⋅ North Cove SubDv. ⋅ 32750 Zip Code
Stunning 4-bedroom, 3-bathroom home featuring fresh exterior and interior paint, along with new LVP flooring and new carpet throughout. The dramatic living room impresses with soaring vaulted wood-paneled ceilings, a striking floor-to-ceiling brick fireplace, and walls of windows and French doors that flood the space with natural light. The beautifully updated kitchen boasts crisp white cabinetry, sleek black countertops, and stainless steel appliances, opening to a bright breakfast area. Bathrooms feature stylish black-framed mirrors and modern fixtures for a fresh, updated feel. Step outside to a true backyard oasis, complete with a sparkling pool, covered patio with wood-beamed ceiling, and a fully fenced yard, perfect for entertaining or relaxing in privacy. With its blend of character, space, and resort-style outdoor living, this home is a must-see.

1539 Grace Lake Circle, Longwood

$672,900
4 Beds ⋅ 3 Baths ⋅ Bolling Farms SubDv. ⋅ 32750 Zip Code
Virtually Staged. Set along the pond in Longwood’s established Bolling Farms community, this beautifully presented four-bedroom, three-bath pool home pairs generous living spaces with an exceptional indoor-outdoor setting. A sweeping paver driveway, manicured lawn and graceful covered entry create a memorable arrival, while double glass doors open to a bright, thoughtfully designed single-story floor plan with 2500 square feet of living area. Tall ceilings, architectural columns, arched openings and expansive windows give the formal living and dining rooms an inviting sense of scale. Wood-look flooring continues through the bedrooms and formal spaces, while tile complements the kitchen and main gathering areas. At the heart of the home, the spacious kitchen features white cabinetry, granite countertops, stainless-steel appliances, a center island, breakfast bar and abundant storage. A window-lined breakfast nook overlooks the pool, and the adjoining family room is anchored by a fireplace with broad sliding doors framing the lanai and pond beyond. The private primary suite offers direct access to the outdoor living area, generous closet storage and a spacious bath with granite-topped vanities, a jetted soaking tub and separate walk-in shower. Three additional bedrooms and two full guest baths provide flexibility for overnight guests, a home office or multigenerational living. One guest bath also offers direct access to the pool area. Outdoors, the screened pool and spa take center stage. An expansive covered lanai creates plenty of room for dining, lounging and entertaining, while a built-in serving area adds function for gatherings. Beyond the screen enclosure, the direct pond frontage delivers an open natural backdrop and peaceful water views. Major improvements include a new HVAC system installed in 2025, brand NEW ROOF - two significant upgrades for the home’s next owner. Additional features include a two-car garage and interior laundry room. From mornings beside the water to evenings around the pool, this home offers a Florida lifestyle designed to be enjoyed year-round. The Longwood location places shopping, dining, parks, Historic Downtown Longwood, the SunRail station, the Lake Mary business corridor and Wekiwa Springs State Park within easy reach.

1413 Canal Point Road, Longwood

$539,900
4 Beds ⋅ 3 Baths ⋅ Moorings The SubDv. ⋅ 32750 Zip Code
NEW ROOF as of September 2026! Paid off solar panels may also be available for purchase at an additional premium. Welcome to this beautifully established Longwood home, nestled in the desirable Moorings community just east of I-4. With mature trees, lush landscaping, no HOA, and distinctive architectural details throughout, this home offers a unique combination of character, comfort, and convenience. As you enter through the solid walnut front door featuring beautiful varicolored fused glass, you'll immediately appreciate the home's thoughtful design and timeless finishes. Jerusalem slate flooring, a charming Franklin stove, and floor-to-ceiling windows create a warm and inviting atmosphere while providing stunning views of the sparkling pool and private backyard oasis. The open concept kitchen is designed for both everyday living and entertaining, featuring quartz countertops and stainless steel appliances. The split bedroom floor plan provides privacy and flexibility, including two spacious owner's suites. The primary owner's suite features a walk-in closet and beautifully updated bathroom with a travertine shower and striking Onyx accent walls. The secondary owner's suite includes its own updated full bathroom with convenient access for guests. Numerous recent updates provide added peace of mind, including a new roof scheduled for installation in September 2026, new AC systems installed in 2022 and 2024, updated pool pump and filter, new cork-backed LVP flooring in the bedrooms, and five new windows. The property also features fresh sod surrounding the pool area. Step outside to your private backyard retreat, complete with a stunning Cobalt blue-tiled pool, updated pool equipment, fully fenced yard, and an expansive paver patio, perfect for relaxing, entertaining, or enjoying Florida's year round outdoor lifestyle. Located in the heart of Longwood, the Moorings community offers easy access to I-4 and State Road 434 and is conveniently located near shopping, dining, SunRail, walking distance to Rock Lake Middle, and more. With its spacious layout, thoughtful updates, private pool, and desirable location, this home is a rare opportunity to enjoy the best of Longwood living | Ready, refreshed, and waiting for you! All repairs are complete, so there’s nothing left to do but move in and enjoy. Come back and tour this beautiful property before someone else calls it home this one is not expected to stay on the market long! Bring your highest and best offer.

120 Slade Drive, Longwood

$599,900
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

$519,995
3 Beds ⋅ 2 Baths ⋅ Woodlands SubDv. ⋅ 32750 Zip Code
Welcome to this well-maintained 3-bedroom, 2-bath home featuring a desirable split-bedroom floor plan and a versatile layout with both formal living and comfortable gathering spaces. The kitchen and living areas flow seamlessly toward the screened lanai, creating an ideal setting for entertaining or relaxing by the sparkling saltwater pool. The fenced yard provides added privacy and outdoor enjoyment. Notable updates and features include a 2023 roof, newer windows, and a 2021 HVAC system with new ductwork. The home is equipped with leased solar panels and two Tesla backup batteries for added energy efficiency and peace of mind. Additional highlights include natural gas heating, a whole-home water purifier and softener, custom closets, and no irrigation system. Enjoy the Florida lifestyle with a private screened outdoor retreat and inviting in-ground saltwater pool.

127 Rose Briar Drive, 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

$625,000
4 Beds ⋅ 3 Baths ⋅ Meadowridge Estates SubDv. ⋅ 32750 Zip Code
PRICED REDUCTION!! SELLER OFFERING BUY DOWN OPTION FOR BUYER !! Welcome to this beautiful 4 bedroom 2 ½ bath 2 STORY home in the exclusive gated community of Meadowridge Estates located in the heart of Longwood. This home has everything that you need: an oversize master bedroom, an open kitchen and family room, an FLEX ROOM that can be used as office/den and dining room located on the first level, three bedrooms and a large bonus room upstairs, with 8’ doors and volume ceilings throughout the home. 20 inch porcelain tile, large baseboards throughout the home. The kitchen is perfect for the family chef, featuring plenty of granite counter space, STAINLESS STEEL APPLIANCES built-in double ovens, a built-in microwave, a breakfast bar and island, and 42” cabinets , all open to the family room and breakfast nook. You’ll feel relaxed in the master retreat, with his and her closets, split vanities in the bathroom, a walk-in shower with dual heads and separate garden tub. Three secondary bedrooms are upstairs and share a bathroom with dual sinks and a raised vanity. This home also features a 3 CAR GARAGE, DOUBLE PANE WINDOWS and AC 2020 . Located right off Lake Emma Dr near Lake Mary Blvd, close to top-rated schools, highways, restaurants and shopping. The search is over, make your appointment today!

421 Meadowridge Cove, 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

$580,000
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

$680,000
Longwood SubDv. ⋅ 32750 Zip Code
Seller's financing is available!Prime commercial property on SR 434 in the heart of Longwood’s Gateway District. Seller's financing is available! This 0.44-acre lot offers excellent visibility with approx. 100 feet of frontage along SR 434. Surrounded by restaurants, retail, and new luxury apartments, this site is ideal for retail, office, or restaurant development. Zoned Gateway Commercial (GW), allowing for a variety of commercial and mixed-use projects designed to enhance the city’s main corridor. Convenient access to US 17-92, SR 436, and I-4. Level site with utilities available and strong traffic counts. Great opportunity for investors, developers, or owner-users in a rapidly growing area of Seminole County.

217 E State Road 434, 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