Displaying: For Sale
Location: Longwood
Property Type(s): Single Family
Price: $400,000 to $499,000
Do Not Show Listings
Longwood - 34 properties found
107 PINEAPPLE CT, LONGWOOD, FL 32750
$432,90053 Days on yellowkey MLS ID: O6390238
0 Days Off yellowkey (back on 4/20/2026)
REDUCED by $10,000 (2.3%) on 04/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1996 Built: 1975 Tax: $6,434 (2024)Community: Lake Searcy ShoresSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,434
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: One or more photo(s) has been virtually staged. This well-maintained property features three comfortable bedrooms and two full bathrooms, providing ample space for daily living. Recent major updates include a new HVAC system installed in 2024 and a complete roof replacement in 2023, ensuring reliable comfort and protection. Two expansive screen porches extend the living area, creating protected spaces for relaxation and entertainment throughout the seasons. These covered areas provide comfortable spots for dining or simply enjoying the surroundings. The backyard includes a swimming area fo recreation and exercise, while the outdoor firepit creates a natural gathering spot for evening conversations and warmth during cooler months. With no homeowners association restrictions, residents enjoy complete freedom in personalizing and maintaining the property according to their preferences. The established neighborhood setting creates a peaceful environment while maintaining easy access to local conveniences. Schedule your private showing today and experience all the comfort and convenience.
Listing is courtesy of: ELITE REAL ESTATE & FINANCE LLC (904-510-1608)
Listing Agent: Brice Gill (904-510-1608)
235 S SHADOWBAY BLVD, LONGWOOD, FL 32779
$425,000316 Days on yellowkey MLS ID: O6320596
1 Days Off yellowkey (back on 4/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1916 Built: 1981Monthly Fee: $156 Tax: $2,265 (2024)Community: Shadowbay Unit 1Single Family
Taxes:$2,265
Elementary School: Sabal Point Elementary
High School: Lake Brantley High
Middle School: Rock Lake Middle
Remarks: Under contract-accepting backup offers. This single-family home is amazing in every way and is truly a must see! Nestled in the highly coveted Shadowbay Community on Lake Brantley. Brand NEW HVAC with 10 year transferable parts warranty. Brand NEW 50 Gallon Water Heater! NEW ROOF 2023! A perfect location just minutes to everything. This residence boasts an array of desirable features. Three bedrooms and two full baths with oversized primary bedroom. As you enter through the striking front door and stunning foyer, you are mesmerized by the beauty and flow of home. Separate formal dining room and expansive living area creating a stylish, classic feel. Living room bright and open with sliding glass doors that take you out to the paved patio. Crown molding throughout and a beautiful wood burning fireplace. Skylights in kitchen, bathrooms, and laundry room. Split floorplan for privacy and convenience. Stunning, oversized primary bedroom overlooking the private back yard. Substantial closets offering more than ample storage. Additional two bedrooms with sliding glass doors leading out to private, open garden area. Enjoy your morning coffee in the breakfast nook with exquisite chair molding and picturesque Bay Window. Brand NEW stainless steel appliances. Kitchen centered between large breakfast area and spacious formal dining room. Timeless Wet Bar of living and dining room. Perfect home for entertaining. Gorgeous luxury vinyl flooring combining durability and elegance. No carpet. Throughout entire home NEW flooring, interior paint, and appealing textured ceilings. Owner with pride of ownership. Private backyard with mature landscaping and some fencing for your fury family. Oversized 2 car garage with an abundant of storage options both inside and out. This is the ideal home in so many ways. What more could you ask for!? Shadowbay Community with so much to enjoy with tennis court, basketball court, park and private boat launch. I-4 just minutes away for Disney or a day at the Beach. Close to Historical Downtown Longwood and Winter Park with desired Park Avenue and weekly Farmer’s Market. Then you have the convenient SunRail taking you around Central Florida. Supermarkets, restaurants, shopping and so much more. Excellent A-Rated Seminole County Schools. Location, Location, Location. Welcome Home!!!
Listing is courtesy of: KORR REALTY CORP (407-732-6987)
Listing Agent: Denise Korrey (407-221-2801)
1040 ARDEN ST, LONGWOOD, FL 32750
$444,995214 Days on yellowkey MLS ID: O6349085
REDUCED by $4,905 (1.1%) on 04/17/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2374 Built: 1967 Tax: $1,954 (2024)Community: Sanlando SpgsSingle Family
Taxes:$1,954
Elementary School: Altamonte Elementary
High School: Lyman High
Middle School: Milwee Middle
Remarks: One or more photo(s) has been virtually staged. If no HOA and outdoor space is what you are looking for, look no further! This spacious ranch-style home is located on a large lot with plenty of room for all of your toys. Inside, this home has 4 bedrooms (potential for 5) and 2 bathrooms. The main living room leads to a large dining area, an updated, bright and airy kitchen, and a large family room with a brick fireplace overlooking the expansive back yard. The interior laundry room leads to a two-car garage, a secluded 4th bedroom, and an additional flex room that would be perfect for a secluded home office or home gym. Outside, there is room for cars, boats, rv's, or whatever you need. The asphalt parking pad/sport court behind the double-gate privacy fence has a metal carport canopy for vehicles or a covered entertainment space. This home has a country feel right in the city, with no HOA. Come see it today!
Listing is courtesy of: CARLISLE REALTY, LLC (407-557-4024)
Listing Agent: James Rouadi (407-557-4024)
307 COBLE DR, LONGWOOD, FL 32779
$475,00075 Days on yellowkey MLS ID: O6380947
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1987 Built: 1978Monthly Fee: $23 Tax: $5,763 (2024)Community: Wekiva Hills Sec 04Single Family
Taxes:$5,763
Elementary School: Wekiva Elementary
Middle School: Teague Middle
Remarks: Some homes just feel right the moment you walk in… and 307 Coble Drive is one of them. Natural light pours through the living spaces, creating a warm and inviting atmosphere that instantly feels like home. The layout flows effortlessly—giving you the perfect balance of open gathering areas and private spaces to unwind. At the heart of the home, the kitchen connects seamlessly to the main living area, making everyday living easy and entertaining even better. Whether it’s a quiet morning coffee or hosting friends and family, this space was designed for real life. The primary suite offers a comfortable retreat—ideal for recharging at the end of the day—while the additional bedrooms provide flexibility for guests, a home office, or growing needs. Step outside and you’ll find a backyard with room to relax, entertain, or simply enjoy the Florida lifestyle. It’s the kind of space where weekends feel slower and evenings last a little longer. Located in the heart of Longwood, you’re surrounded by established neighborhoods, mature trees, and convenient access to everything Central Florida has to offer—from daily essentials to major roadways that make commuting simple. Enjoy unbeatable proximity to Wekiva Golf Club, Wekiva Island, and Wekiva Springs State Park, ideal for outdoor enthusiasts. Zoned for top rated Seminole County schools and conveniently close to Publix, local parks, dining, and shopping, this home offers an exceptional balance of lifestyle and location. As part of the Wekiva community, residents enjoy access to two parks, a community center, and 26 miles of walking trails surrounding the private Wekiva Golf Course. This home is ready for its next chapter. This home presents a unique opportunity to move into a desirable area and make it your own! If you’ve been waiting for a home that offers comfort, location, and potential… this is one you don’t want to miss.
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Todd Schroth, Pa (407-641-2808)
111 DELLWOOD DR, LONGWOOD, FL 32750
$490,00089 Days on yellowkey MLS ID: V4947148
1 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2126 Built: 1973Monthly Fee: $8 Tax: $3,795 (2024)Community: Winsor ManorSingle Family
Taxes:$3,795
Elementary School: Woodlands Elementary
Remarks: Under contract-accepting backup offers. Beautifully updated Longwood home with a brand new roof, offering a tucked away, residential feel while still being perfectly positioned for everyday convenience. Located directly across from Lake Winsor, enjoy the wide sidewalks and mature trees on your way to the neighborhood’s lake access, perfect for kayaking, canoeing, paddle boarding, fishing, or boating. Just minutes from I-4 and SR 417, commuting, shopping, dining, and daily essentials are always within reach. Inside, you’re welcomed by a spacious living room with stylish accent walls and a warm, inviting feel. The kitchen features quartz countertops, a vibrant backsplash, ample prep space, and a cozy breakfast nook ideal for everyday living. The split floor plan provides both functionality and privacy, with three well-appointed bedrooms and a tastefully updated bathroom on one side, while the primary suite is set apart on the opposite end. Just outside the primary bedroom is a versatile flex space ideal for a home office, nursery, or sitting area. At the heart of the home, the oversized family room showcases a stunning brick fireplace and offers great views of the backyard. Step outside to your own retreat with a sparkling, well-maintained pool and a spacious covered porch designed for entertaining or unwinding. Zoned for Woodlands Elementary, with Rock Lake Middle School just a short walk or bike ride away. This home blends a true sense of retreat without sacrificing convenience. Schedule your private showing today.
Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)
Listing Agent: Boky Lee (407-920-8693)
1730 HIGHLAND DR, LONGWOOD, FL 32750
$475,00052 Days on yellowkey MLS ID: O6390295
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1738 Built: 1987 Tax: $3,629 (2025)Community: Myrtle Lake HillsSingle Family
Taxes:$3,629
High School: Lake Mary High
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Expect to be impressed with this fantastic renovation in the desirable Myrtle Lake Hills in Longwood. Completely transformed in 2023 with every detail accounted for. This modern layout provides incredible function with a three-way split bedroom plan and generous open living space. On a large shady lot, there is plenty of room to grow and expand the footprint. Warm wood floors invite you into this stylish space, ideal for entertaining. Light and bright and clean lined the design is timeless and ready for you to make it your own. Kitchen overlooks backyard and features shaker style white cabinets, a large working island with bar seating, quartz counters with subway tile backsplash and stainless appliances with a WOLF range. Primary suite has double doors inviting you and doors out to patio, with large walk-in closet and beautiful bath retreat with double sinks and a walk-in shower with seamless glass. One bedroom is off on its own and used as an office and other two bedrooms enjoy a separate wing with a shared renovated bath. Kitchen opens to covered screened porch and then out to backyard with is spacious and shady. Shed in the back provides terrific storage. All major systems updated roof (2018), HVAC and ducts (2023), Replumbed (2023), electrical panel (2023). This one is turnkey and move-in ready. So close to all Longwood offers. This charming home won’t last long. See for yourself.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Alison Mosley (407-304-6458)
305 PALM SPRINGS DR, LONGWOOD, FL 32750
$475,00043 Days on yellowkey MLS ID: O6392490
1 Days Off yellowkey (back on 4/12/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2391 Built: 1956 Tax: $1,784 (2025)Community: Sanlando SpringsSingle Family
Taxes:$1,784
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home, ideally situated on a desirable almost 1/2 acre corner lot with a circular driveway and former golf-front setting. Directly across the street, the former Rolling Hills Golf Course has been transformed into the newly reestablished Rolling Hills Community Park, offering playgrounds, open green space, and a relaxing outdoor setting for recreation and neighborhood enjoyment. Best of all—NO HOA! This home showcases a stunning renovation with carefully curated, high-end designer finishes and energy-efficient upgrades throughout. Step inside through elegant double front doors with leaded glass to an inviting open-concept floor plan. The bright, eat-in kitchen is the heart of the home, featuring quartz countertops, a glass subway tile backsplash, a spacious center island with seating, and custom soft-close KraftMaid cabinetry with seeded glass accents, pull-out shelves, and drawers. Enjoy upscale appliances, including a convection oven with built-in air fryer, all complemented by elegant 20” x 20” Italian ceramic tile flooring (minimal grout lines) flowing seamlessly through the kitchen, family room, and foyer—creating both beauty and easy maintenance. Plantation shutters add timeless elegance and privacy, while energy-efficient double-pane windows enhance comfort throughout. The formal living room—currently used as a music room—features crown molding, rich Brazilian hardwood flooring, and two skylights that fill the space with natural light. Built-in shelving and pocket French doors add both charm and versatility. The spacious family room with vaulted ceilings opens effortlessly to the kitchen, creating the perfect gathering space. A thoughtfully designed addition provides an interior laundry room and an impressive oversized walk-in closet with built-in cabinetry, adding approximately 411 sq ft of additional living space. Step outside and enjoy Florida living at its finest. A large paver patio is perfect for relaxing or entertaining, with French doors creating a seamless indoor-outdoor flow. The private backyard is fully enclosed with a PVC fence and two gates, and features lush, mature landscaping with your own fruit trees—including fig, lemon, bay leaf, tangerine, and mulberry. Additional highlights include a large storage shed and a RainBird 6-zone irrigation system. Conveniently located near SunRail, I-4, Altamonte Mall, Seminole Wekiva Trail, top-rated Seminole County schools, medical facilities, dining, and year-round Longwood community events. Schedule your private showing today—this one-of-a-kind home offers the perfect blend of style, comfort, and location!
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Deborah Perry, Pa (407-310-3015)
1328 N MARCY DR, LONGWOOD, FL 32750
$449,00038 Days on yellowkey MLS ID: O6389549
0 Days Off yellowkey (back on 3/31/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1831 Built: 1984Monthly Fee: $14 Tax: $5,239 (2025)Community: Bay Lagoon Unit 1Single Family
Taxes:$5,239
Remarks: Under contract-accepting backup offers. Welcome to an exceptional opportunity in Longwood’s highly sought-after Bay Lagoon community—where charm, comfort, and convenience come together seamlessly. This immaculate 1984-built residence showcases a unique and thoughtfully designed split floor plan, highlighted by soaring ceilings and an abundance of natural light that create a warm, inviting atmosphere throughout. At the heart of the home, the eat-in kitchen flows effortlessly into a spacious family room featuring a cozy fireplace and double doors that open to a screened-in porch—perfect for embracing Florida’s indoor-outdoor lifestyle. The private primary suite offers a tranquil retreat with generous space, and a well-appointed ensuite bath. Outdoors, the large yard provides endless possibilities for entertaining, gardening, or simply relaxing in the sunshine. Additional features include a 2-car garage and rain gutters, all contributing to the home’s impeccable presentation. Ideally located just minutes from shopping, dining, I-4, Seminole Wekiva Trail, and top-rated Seminole County schools—this home truly offers a refined blend of lifestyle, location, and livability. Call today to schedule your private showing before this one is GONE!
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Renee Holt (407-474-5552)
170 CITRUS TREE LN, LONGWOOD, FL 32750
$439,90090 Days on yellowkey MLS ID: O6378389
1 Days Off yellowkey (back on 4/4/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1763 Built: 1987Monthly Fee: $37 Tax: $1,848 (2024)Community: Longwood GreenSingle Family
Taxes:$1,848
Remarks: Outstanding 3 BD/ 2 Bath. Open concept, single story with a lot of natural light. Gourmet Updated Kitchen, with Stainless steel Refrigerator New Roof 2023! New Hot Water Heater, Beautiful Laminate flooring. Vaulted Ceilings, Wood burning Fireplace. Skylights, Surrounding the back porch with French doors. Hard Wired Alarm System. Located in the Longwood Green neighborhood with tree lined streets & top-rated Seminole County schools. Located just minutes away from Historic Longwood with community events in Reiter Park. There is easy access to the Cross Seminole Trail and Spring Hammock Preserve for scenic walks, biking, and nature exploration. Quick access to I-4 and SR 417. Move in Ready! Hurry! Won't Last!!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Caroline Moffitt Lawton (407-670-9797)
320 FERDINAND DR, LONGWOOD, FL 32750
$450,00048 Days on yellowkey MLS ID: O6391269
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1852 Built: 1979Monthly Fee: $29 Tax: $3,988 (2025)Community: Columbus HarborSingle Family
Taxes:$3,988
Elementary School: Longwood Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom home located in the highly desirable Columbus Harbor community in Longwood. Known for its friendly atmosphere and vibrant neighborhood events, residents enjoy access to pickleball courts, a private boat ramp, and unforgettable holiday gatherings that make this community truly special. Inside, the home features beautiful tile flooring throughout and a spacious open-concept living and dining area that is perfect for entertaining or relaxing with family. The kitchen offers an inviting eat-in space, granite countertops, and elegant crown molding, creating both style and functionality. A dedicated laundry room adds convenience to everyday living. The generous primary suite provides a peaceful retreat and features French doors that open directly to the large back patio. Step outside to enjoy the screened-in pool—perfect for year-round Florida living. The expansive backyard offers plenty of space for pets, play, or even a future playground. With its welcoming layout, wonderful outdoor space, and location in a sought-after community, this Longwood home is a fantastic opportunity to enjoy comfort, convenience, and neighborhood charm.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Joanne Otero (407-310-0856)
105 KILKENNY CT, LONGWOOD, FL 32779
$435,00032 Days on yellowkey MLS ID: O6387619
0 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1562 Built: 1975Monthly Fee: $23 Tax: $4,048 (2024)Community: Wekiva Hunt Club 1 Fox Hunt Sec 1Single Family
Taxes:$4,048
Remarks: Welcome to 105 Kilkenny Ct and this beautifully updated Wekiva home nestled on a quiet cul-de-sac. Step inside this 3 bedroom 2 bath home with tile flooring, lots of natural lighting, cozy fireplace in the family room and a remodeled kitchen with new appliances and breakfast bar. Recent upgrades include: 2024 kitchen remodel, 2022 new roof, 2022 new A/C, 2022 new electrical panel, 2025 new sod and plants in the front and irrigation updated. Wekiva is known for it's location and lifestyle and is zoned for all the top rated Seminole County Schools. Wonderful Golf Community with a low HOA and the community offers tennis/pickleball courts, playgrounds and a community room. Central Florida living at its best with easy access to I-4, 436 and Wekiva Springs State Park. Call for your private showing today!
Listing Agent: Jackie Hopkins (407-970-5170)
1310 RIDGE RD, LONGWOOD, FL 32750
$485,00035 Days on yellowkey MLS ID: S5146759
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1520 Built: 1978 Tax: $4,506 (2024)Community: Myrtle Lake HillsSingle Family
Taxes:$4,506
Remarks: Welcome to your own private oasis in the highly desirable Longwood area! This beautifully maintained home is nestled in a great neighborhood and offers the perfect blend of comfort, style, and outdoor living. Step outside to a backyard designed for entertaining and relaxation. Enjoy the sparkling pool, ideal for cooling off on warm Florida days, or unwind at the charming tiki bar that brings a true resort-style feel to your home. Gather with family and friends around the cozy fire pit, creating the perfect setting for evening conversations and lasting memories. The fully equipped outdoor kitchen makes hosting effortless, providing the perfect space for grilling, dining, and enjoying the Florida lifestyle year-round. With its inviting atmosphere and exceptional outdoor features, this home is perfect for those who love to entertain or simply relax in their own private retreat. Don’t miss the opportunity to own a slice of paradise in one of Longwood’s most sought-after communities!
Listing is courtesy of: VYLLA HOME (407-377-5900)
Listing Agent: Amanda Lindsey (407-617-0067)
112 DES PINAR LN, LONGWOOD, FL 32750
$419,00040 Days on yellowkey MLS ID: O6393707
0 Days Off yellowkey (back on 3/30/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1604 Built: 1975 Tax: $4,416 (2024)Community: Woodlands Sec 5Single Family
Taxes:$4,416
Remarks: Under contract-accepting backup offers. Fully Remodeled Luxury Pool Home | No HOA | Priced Below Appraisal Stunning fully remodeled 4-bedroom, 2-bath pool home in Longwood with NO HOA, priced below recent appraised value for immediate equity and a quick sale. This move-in ready home has been completely upgraded with new roof, windows, sliding glass doors, HVAC, plumbing, and luxury vinyl flooring throughout. The designer kitchen features 42” shaker cabinets, granite countertops, brand-new stainless steel appliances, and a stylish white and gold color palette with a custom backsplash—creating a clean, modern, high-end feel. Both bathrooms have been fully renovated with luxury granite countertops and custom tile shower work, offering a spa-like experience. The home offers a desirable split floor plan, with a private primary suite and walk-in closet, plus three additional bedrooms with dual sinks on the opposite side. The family room with fireplace flows seamlessly to the outdoor space, opening to a large pool deck and private pool. Situated on nearly ½ acre with a fully fenced backyard, this property is ideal for entertaining, with plenty of space and privacy. Additional features include a 2-car garage and extended driveway with ample parking. Located just minutes from Orlando, major highways, shopping, and dining, while still enjoying the quiet charm of Longwood. Fully remodeled, luxury finishes throughout, and priced to sell quickly—don’t miss this opportunity.
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Ken Claytor (352-278-4715)
410 GEORGIA AVE, LONGWOOD, FL 32750
$435,00041 Days on yellowkey MLS ID: O6393221
1 Days Off yellowkey (back on 3/30/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1588 Built: 2006 Tax: $4,470 (2024)Community: Lake Wayman Heights Hwy AddSingle Family
Taxes:$4,470
High School: Winter Springs High
Remarks: Under contract-accepting backup offers. This fully renovated home blends style and functionality with a bright, open layout designed for today’s lifestyle. From the moment you step inside, you’ll notice the fresh finishes, updated flooring, and abundant natural light that create a warm and inviting atmosphere. The kitchen has been completely upgraded and serves as the centerpiece of the home, featuring sleek countertops, modern cabinetry, stainless steel appliances, and ample prep space, perfect for both everyday living and entertaining. The spacious living and dining areas flow seamlessly, making the home feel open yet comfortable. The primary suite offers a private retreat with an updated en-suite bathroom and two additional bedrooms, providing flexibility for guests. Both bathrooms have been thoughtfully remodeled with contemporary finishes. With major updates already completed, this home offers the peace of mind today’s buyers are looking for, move-in ready and designed for low-maintenance living. Conveniently located in Longwood, just minutes from major highways, shopping, dining, and entertainment, this property combines modern upgrades with an unbeatable location. If you’re searching for a fully renovated home in Longwood with 3 bedrooms and nearly 1600 square feet, 410 Georgia Ave is one you won’t want to miss. New roof (2026), New AC (2026), Water Heater (2026).
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Mario Zendeli (407-325-3893)
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