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$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
$405,000
4 Beds ⋅ 4 Baths ⋅ Wildmere Resurvey Of Blk 4 SubDv. ⋅ 32750 Zip Code
Income-Producing Duplex in the Heart of Longwood. Income-producing duplex ideally located in the heart of Longwood, near US Hwy 17-92 and SR-434, offering convenient access to shopping, restaurants, banks, supermarkets, SunRail, I-4, and major corridors. Built in 1973 and well-maintained, the property features two units, each offering 2 bedrooms and 2 full bathrooms. No HOA! Both units are tenant-occupied with under-market rents, providing an attractive opportunity for future rent growth. Unit 737 E Church Ave (2Bed/1.5Bath) is currently rented for $1,350/month with a lease in place through July 31, 2026, and includes a new dishwasher installed in September 2025 and an A/C replaced in February 2023. Unit 739 E Church Ave (2Bed/1.5Bath) is currently rented for $1,300/month on a month-to-month basis, and includes a new A/C installed in April 2024 and a new stove installed in July 2025. Tenants in both units are responsible for their electricity, water, cable, internet, and lawn maintenance. Excellent central location near everyday essentials, including Publix (2.5 miles, 6 minutes), CVS (1.1 miles, 5 minutes), and Starbucks (0.2 miles, 1 minute), and a variety of dining spots, local cafés, and takeout options. Distances and drive times are approximate. Don’t miss this outstanding opportunity; the location offers the perfect blend of convenience and comfort. Schedule a showing today!

737 E Church Avenue, Longwood
$630,000
8 Beds ⋅ 4 Baths ⋅ Wildmere Amd SubDv. ⋅ 32750 Zip Code
CHARMING LAKEFRONT DUPLEXES in Longwood!!  Listed at Appraised value. QUAINT and RUSTIC 2 Duplexes, 4 identical square ft units with covered rear porches on each unit.  Enclosed front porch is included in living area.  EACH Unit is 2-bedroom, 1 bath with 1 carport parking space, electric meter, ALL currently rented out.  Owner pays for water and gas.  Oxford Street has prime footage on Lake Wildmere, back of property faces partially wooded area and small pond owned by the City of Longwood. NO HOA! ROOF - 2013 PRIME Investment opportunity conveniently located in the heart of Longwood with easy access to major roadways - rare to find!  Management company is currently renewing leases on units 1,2, & 3 and information is subject to change from third party management.

833 Oxford Street, Longwood
$395,000
4 Beds ⋅ 4 Baths ⋅ Lake Wayman Heights SubDv. ⋅ 32750 Zip Code
Excellent investment opportunity in the heart of Longwood! This income-producing duplex features long-term tenants who have been in place for many years, providing consistent rental income. Both units include 2 bedrooms, 1 bathroom, tile flooring throughout, inside laundry, and attached garages. Enjoy easy maintenance with no HOA fees and a recent re-roof. Each unit also offers a spacious backyard. Conveniently located near Downtown Longwood with quick access to major highways, shopping, and dining.

566-568 Land Avenue, Longwood
$475,000
6 Beds ⋅ 4 Baths ⋅ Lake Wayman Heights Lake Add SubDv. ⋅ 32750 Zip Code
Unique Large Duplex, 1 unit faces Highland St and 1 unit faces Pasadena Ave,Large Corner Lot, Brand New Roof just installed,Electrical Updated,Fenced Yard, Great Value

895 Pasadena Avenue, Longwood
$350,000
Acreage & Unrec SubDv. ⋅ 32750 Zip Code
***PRIME INVESTMENT OPPORTUNITY - TENANT OCCUPIED DUPLEX IN LONGWOOD*** Calling all investors! This well-positioned duplex at 604 Maine Ct features ALL NEW WINDOWS, UPDATED PLUMBING, and a NEW ROOF within the last three years, offering immediate cash flow potential in one of Central Florida’s most desirable rental markets. Currently tenant-occupied on one side with established rental income, this property presents an excellent opportunity to step into a proven income-producing asset. The property features 2 bedrooms and 1 bathroom on each side with 1,542 square feet of living space on a 0.23-acre lot in the heart of Longwood. The property is conveniently located near the SunRail Station at the intersection of Ronald Reagan Boulevard and ChurchAvenue, providing tenants easy access to Central Florida's commuter rail system. Longwood's Historic District, listed on the National Register of Historic Places, encompasses 190 acres with 37 contributing structures and offers charming shops, restaurants, and community events. Residents enjoy Reiter Park with walking trails, amphitheater concerts, and farmers markets, plus nearby Wekiva Island for kayaking and outdoor recreation. The Cross Seminole Trail provides 23 miles of multi-use paths, while Candyland Sports Complex offers extensive recreational facilities including tennis courts, baseball fields, and playgrounds. This established neighborhood combines small-town charm with easy access to I-4, shopping, dining, and Orlando's employment centers, making it a highly desirable rental market with proven tenant demand. Perfect for both seasoned investors looking to expand their portfolio and first-time investors seeking a manageable entry point into multi-family real estate. The established rental history, prime Longwood location, and proven tenant demand make this an ideal addition to any investment portfolio. Don't miss this opportunity to acquire a cash-flowing asset in one of Seminole County's most sought-after rental markets.

604 Maine Court, Longwood
$380,000
Longwood Square SubDv. ⋅ 32750 Zip Code
WHOLE 2 sided DUPLEX is ready for your portfolio! Whether you want to live on one side and rent out the other side OR rent out both sides for passive income, the opportunity is yours for the taking! These 2 bedroom 1 bath units feature LUXURY VINYL and TILE floors. Inside laundry, updated bathrooms, with a fenced back yard. Potential income per unit $1,000 - $1,300 or more a month. Long standing tenants in place until June 30th. Within walking distance to school, parks and shopping. Seminole County Schools, five minutes to historic downtown Longwood and the SunRail Station. Make this one yours today!!

905 Orange Avenue, Longwood
$350,000
Orange Terrace SubDv. ⋅ 32750 Zip Code
Conveniently located in Longwood-close to shopping, dining and businesses, this 2 bedroom, 2 bath each side duplex features central A/C, eat-in kitchen with nice counter space, Washer and Dryer hook-ups in single car garage, a private bath attached to the master bedroom, and a Living/Dining Combo with sliding glass doors that lead to the screen patio-nice place to sit and visit or just relax with a good book. The large shaded yard would be a nice place for a cook-out or maybe a hammock?! Each side under a lease until 8/31/25

548 Seminole Avenue, Longwood
$355,000
Orange Terrace SubDv. ⋅ 32750 Zip Code
Conveniently located in Longwood-close to shopping, dining and businesses, this 2 bedroom, 2 bath each side duplex features central A/C, eat-in kitchen with nice counter space, Washer and Dryer hook-ups in single car garage, a private bath attached to the master bedroom, and a Living/Dining Combo with sliding glass doors that lead to the screen patio-nice place to sit and visit or just relax with a good book. The large shaded yard would be a nice place for a cook-out or a game of baseball! Each side under a lease until 7/31/25

577 Seminole Avenue, Longwood
$456,000
Lake Wayman Heights Hwy Add SubDv. ⋅ 32750 Zip Code
PRICE REDUCTION! Come tour this lovely Duplex for sale at 448 & 450 Georgia Avenue, Longwood, Florida 32750. This Charming Duplex is perfect for the savvy investor and shows easily. It is in a ideal location in the heart of Longwood with a unbeatable easy access within a short distance to local shops, Candyland park, and Arbor dog park. With no HOA and HOA fees this duplex could provide a hassle free investment. Rental income is set at 34,500.00 annually with room to grow. Both leases are up for renewal on February 28, 2026. Call today to make an appointment to tour this rare find in downtown Longwood.

450 Georgia Avenue, Longwood
$425,000
Longwood SubDv. ⋅ 32750 Zip Code
Fully remodeled and renovated duplex. Move in ready for you or your tenants. Completed 9/24. New kitchens and baths. Buy as an investment property or live in one side and rent the other. Ideal for multigenerational families or use one side as a mother-in-law suite. 2024 re-piped, rewired, exterior doors, updated electrical panels, exterior/interior paint, lighting, LVP floors, stainless steel appliances. 2021 connected to city sewer. 2016 roof. Unit 171 has a front room, under air, that can be used as a 3rd bedroom.  Unit 181 has a back bedroom ensuite with a separate entrance that can be used as a 1 bedroom/1 bath studio lock-off, giving you an additional rental unit. Both units have washers and dryers and separate electrical and water meters. Termite bond 11/24. Home warranty on one unit. Can be financed with FHA and conventional mortgages as a primary residence or a conventional investment loan. Close to Orlando Health South Seminole Hospital, Rt 434, I4 and Rt 17/92. Check out the 3D virtual tour. You won't find a fully renovated duplex at this price! Call me today for a private showing.

181 & 171 N Oak Street, Longwood
$411,000
Lake Wayman Heights SubDv. ⋅ 32750 Zip Code
This is an AMAZING investment opportunity. This duplex is fully renovated on both sides. Tenant recently moved into Unit 674 in May and is paying $1750/mo in rent. Unit 680 is vacant and available to be reviewed. Both sides have identical renovations. We will hold off renting 680 for a month in case any potential buyers want to owner occupy this duplex. All room dimensions should be verified by buyers.

674 Pasadena Avenue, Longwood
$410,000
4 Beds ⋅ 4 Baths ⋅ Watson Sub SubDv. ⋅ 32750 Zip Code
Back Active on 8/26 Buyer financing fell through. Appraisals and inspections completed and cleared for ALL loan types. Calling all Investors: Duplex property on large corner lot with half the duplex on 116 Clifford Ave and the other on 750 Florida Ave. Potential income of $44,400 for both if each is rented for $1850 month. Consider living on one side and renting the other. Both units are very spacious with 2 bedrooms and 1.5 baths and 1 car garage each. New paint inside and out with both homes in move in condition. 750 Florida has ceramic tile in living areas very light and bright with a very spacious master and good size 2nd bedroom. 116 Clifford Ave has laminate flooring in living areas with a good size master with carpet and tile in the second bedroom. This home also has a lovely outdoor screened patio to enjoy entertaining. Close to bus, shops, restaurants and major roads.

750 Florida Ave, Longwood
$1,092,500
5 Beds ⋅ 5 Baths ⋅ Sanlando Spgs SubDv. ⋅ 32750 Zip Code
Welcome home to your one-of-a-kind custom built estate with an attached 1465 SF income producing in-law residence added in 2013 featuring a living room, fully equipped kitchen, full bath, bedroom & an attached 2 car garage with washer, dryer & generator hook up. Nestled on a private 1.26 acre wooded lot that backs up to a nature preserve & pond, this serene sanctuary is your ideal escape after a long day; taking in the best that Florida nature has to offer from the rustling leaves of the majestic oaks to the delicate sound of a song bird. From the minute you drive up the extended private driveway your zest for life senses are engaged to take in all that this unique & energy efficient home has to offer; including solar power, concrete block construction through the 2nd floor, tankless water heater, CAD 5, Ecobee smart thermostat, 8' solid core wood doors with architectural metal inlays & custom double pane wood frame windows & sliding glass doors. The architecturally captivating solid wood double doors lead you to the foyer featuring a mud room on the right & a guest 1/2 bath on your left. Your formal living room features a cozy gas fireplace & opens up to the spacious family room offering private views of the backyard. The gourmet kitchen is a chef's dream come true & features a commercial grade 6 burner gas range & griddle, a Wolf hood, 2 dishwashers, an island with a sink & level 5 Jaguar pattern granite counter tops, a breakfast bar, coffee bar & desk & a sink featuring an Onyx backsplash wall. The oversized 9'x12' adjacent pantry is sure to satisfy the most sophistcated culinary aficionado featuring a 3rd commercial sink with pot filler & plenty of shelving to accommodate any ingredients that an exquisite recipe calls for. The adjacent dining room opens up to the screened wrap around back porch highlighted by a rich wood ceiling & features a summer kitchen with generator hook up, a barbeque pit, single burner stove & hood, making this the ideal area to entertain your guests. The master retreat is privately located in a split floor plan configuration & features an en-suite bath with dual granite top sinks, a spacious dual head shower with floor to ceiling tile & custom mosaic motif, a jetted hydro tub & private WC. 2 additional bedrooms are located on the opposite side each with their en-suite bath featuring designer glass bowl sinks & custom vanities. A private hallway leads you to the attached in-law residence offering access flexibility from the main house or through it's own private entrance, making it ideal as an income producing rental or a private parent or teen residence. The custom marble staircase leads you to the 2nd floor featuring architecturally captivating volume ceilings & triangular wood framed windows to take in all the picturesque views that this estate has to offer. The 2nd floor office is equipped with a gas & plumbing stub out to accomodate a wet bar or kitchen & the adjacent 19'x37' bonus room features a full bath, walk-in closet & another gas stub out making this the ideal flex space for another bedroom, a home theatre, gym or an art or yoga studio.The oversized 25'x34' main garage features 16' ceilings & 12' roll up doors to accommodate car lifts or an RV.<div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=RBP7HbnheJD&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

439 Wilford Avenue, Longwood
$384,900
4 Beds ⋅ 2 Baths ⋅ Lake Wayman Heights SubDv. ⋅ 32750 Zip Code
Cute concrete block duplex located in a quiet Longwood residential district. Each side of the duplex has 2 bedrooms and 1 bath with a fenced back yard. Tile flooring throughout makes this easy to rent and take care of. New roof is being permitted and installed in the next few weeks. Each side is metered separately for water and electricity. No HOA. A short drive from US 17-92, north of 434 with a quick drive or bike ride to downtown Longwood and the Sunrail commuter rail station. Turnkey investment property.

564 N Wayman Street, Longwood
$297,000
4 Beds ⋅ 4 Baths ⋅ Longwood SubDv. ⋅ 32750 Zip Code
GREAT INVESTMENT OPPORTUNITY in Longwood, Florida! CASH ONLY. NO HOA! Each unit (171 & 181 N. Oak St. ) features 2 bedrooms, 2 bathrooms with an inside laundry area. Each unit is separately metered for electric and City water. The tenants in both units recently vacated. The net rental income for 2023 is lower due to the tenant's leases being well under market value. This duplex offers convenience and easy accessibility to shopping, medical centers and major roads. Walking distance to S.R. 434, U.S.17-92, and C.R.427. The Longwood SunRail Station is 3 blocks away and Longwood Elementary school is just 4 blocks away. The roof was replaced in 2016. Room measurements and city restrictions should be verified by the buyer and buyer agent. Contact us today to schedule a viewing and seize your place in the real estate investment market!

181 N Oak Street, Longwood
$470,000
4 Beds ⋅ 4 Baths ⋅ Evergreen Place SubDv. ⋅ 32750 Zip Code
MULTIPLE OFFERS RECEIVED-PLEASE SUBMIT HIGHEST/BEST OFFERS BY 6 PM 12/11/23. Excellent opportunity to purchase a meticulously maintained full duplex at 327 and 329 Evergreen Avenue featuring 2 bedrooms/2 baths in each unit. You won't find a better maintained property due to the long term occupancy of the same family for over 50 years. Tenants are vacating at end of 2023 and rent was below market but unit is in good overall condition. Rent both sides and reap the benefits of a rental in this desirable Longwood community or live in one and rent the other, you decide. The owner’s unit at 327 is largest with the addition of a 29X16 bonus room added in 1989. No expense has been spared to keep the systems up to date including NEW ROOF in 2019 and complete electrical re-wire in 2022, replumbing Nov. 2023 (unit 327) and 2009 (unit 329). AC units were replaced in 2019 and 2015 and blown in attic insulation was added in 2014. Even better, ALL the windows and the sliding glass door (329) were replaced in 2006/2017 with Andersen white vinyl double paned argon gas insulated units. Both units have propane gas water heaters. Ceiling fans are present in many rooms of both units. The garage on 327 is wired for a whole house portable generator which conveys with the home. Plumbed propane heaters serve as a backup heat source if power should fail. In fact, a 150 gallon propane tank supplies fuel for the gas ranges, water heaters and propane heaters. The spacious floorplan of the owner’s unit offers a great place to entertain in the bonus room with lots of natural light. The master suite was enlarged with a 16X5 California closet with built in floor safe, in addition to the original walk-in closet and a full en-suite bath with low flow commode and tiled tub/shower. The second bedroom shares the full hall bath with seamless walk-in shower, low flow commode and new luxury vinyl flooring. The centralized living/dining room offers more room to relax. The galley kitchen overlooks the front yard and has direct access to the single car garage and huge laundry room with extended storage room. The tenant occupied unit 329 is smaller than the owner's side but the enclosed garage creates a den plus a large storage/laundry room. Washer and dryer will convey. The bedrooms and living areas are comfortably sized too. The galley kitchen includes a newer Bosch dishwasher and Maytag refrigerator. Similar luxury vinyl flooring covers the kitchen, foyer and hallway with carpet in the bedrooms and living area. Just off the living room is a large 20X16 screened porch which has detachable metal hurricane shutters and solar shades. The entire duplex custom hurricane shutters that can be rolled down from inside the units to secure it for storms. A large shared backyard with fencing on 3 sides has two sheds for lawn equipment or extra storage. The entire yard is mulched for easy maintenance. A two car covered carport with parking space for 4 vehicles plus a one car garage and one detached carport insure plenty of parking for both units. Both units are separately metered for water, power, and propane gas. The owners handled all maintenance for the rental unit. Entire duplex was converted to city sewer several years ago and re-wired with copper more recently. The propane gas lines are plumbed in each unit but electric heat is available too. This fantastic location and home is close to plenty of shopping, dining, employers, major roadways, and is ready for the next generation.

327 E Evergreen Avenue, Longwood
$407,000
4 Beds ⋅ 2 Baths ⋅ Watson Sub SubDv. ⋅ 32750 Zip Code
Wow! Don't miss out on this fantastic Duplex investment property. You can live in one side and earn strong cash flow on the other or just add it to your rental portfolio for steady returns renting out both units. The property is located on a large lot down the street from Longwood Elementary. You are just off US 17-92, north of 434 with a quick drive or bike ride to downtown Longwood and the Sunrail commuter rail station. The building is sturdy concrete block construction with a metal roof and terrazzo floors in both units. Each unit has 2 bedrooms, 1 bath and a large indoor utility room. The exterior offers covered carports, large rear covered porches, a storage shed and an extra large driveway for plenty of parking. Both units are rent-ready. The seller just installed a brand new roof on the rear porches. Major renovations were completed in 2014-2015 which include plumbing repipes, water heaters, electrical panels and HVAC systems for both units, kitchen cabinets, new septic drainfield for the 753 unit and insulated windows for the whole building. Each unit is separately metered for electric and City water. There is no HOA. Make your offers today! This great income property won't last long!

751-753 Highland Street, Longwood
$465,000
4 Beds ⋅ 3 Baths ⋅ Oak Arbor SubDv. ⋅ 32750 Zip Code
VACANT and Turn Key - both sides as of 10/1/23. INVESTOR ALERT, convert garages to extra bedrooms to maximize potential profit in these! This beautiful duplex was updated in 2019 and is a great investment. Featuring Newer roof - 2019, interior remodel 2019, New ACs in both units 2019 and so much more. Both sides feature 2 bedrooms, large fenced in yard, laundry room, one car garage and private driveway. The biggest highlight of this property is having it zoned for Lake Mary schools but paying lower Longwood taxes! Owners have taken meticulous mechanical care of the property. FHA Eligible investment!

961-965 Lake Lane, Longwood
$384,000
4 Beds ⋅ 2 Baths ⋅ Lake Wayman Heights Lake Add SubDv. ⋅ 32750 Zip Code
Currently tenant occupied. Please do not disturb the tenant by walking the property, looking in the windows or knocking on door. Great investment property! Large corner lot, each unit is a 2/1 with a carport, mixed flooring (carpet & tile), inside utility room with hookups. Newer AC system in one unit. Properties are leased thru 1/2024 & 6/2024.

775 N Wayman Street, Longwood