Location: Longwood
Keyword(s): Rock Lake Middle
Keyword(s) Middle School: Rock Lake Middle
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235 S SHADOWBAY BLVD, LONGWOOD, FL 32779
$425,000390 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,265
Elementary School: Sabal Point Elementary
High School: Lake Brantley High
Tax Year: 2024
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)
4 WOODEN SHOE LN, LONGWOOD, FL 32750
$350,000245 Days on yellowkey MLS ID: O6360634
0 Days Off yellowkey (back on 11/17/2025)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2682 Built: 1974Monthly Fee: $25 Tax: $7,731 (2024)Community: Sleepy Hollow 1St AddSingle Family
Taxes:$7,731
Elementary School: Altamonte Elementary
High School: Lyman High
Remarks: Under contract-accepting backup offers. Short Sale. Must See 4 bed, 2 bath home in the established community of Sleepy Hollow. This spacious residence sits quietly at the end of a cul de sac where mature trees and wide lawns create a sense of privacy. Inside, the layout unfolds with generous gathering spaces including a family room large enough for game nights and holiday celebrations, a living room anchored by a wood burning fireplace, and a kitchen that keeps everyone connected with its easy flow to the dining area. Skylights draw in natural light and the split bedroom design offers comfort with a private primary suite featuring dual walk in closets and its own full bathroom. Step outside to a deep backyard designed for relaxed Florida living. A screened and covered rear-porch overlooks the lush lawn, creating a great place for morning coffee, weekend barbecues, or quiet afternoons at home. The large homesite offers room to play and the community adds even more with nearby parks, sports courts, and walking paths. With 2,682 square feet of living space, an attached two-car garage and a prime Longwood location near top rated Seminole County schools this home offers a chance to create the lifestyle you envision. This is a short sale and an excellent opportunity for buyers or investors who appreciate space character and potential.
Listing is courtesy of: THE AGENCY FL (407-335-4119)
Listing Agent: Cristina Porretto (407-264-1870)
8201 OLYMPIA CT #8201, LONGWOOD, FL 32779
$195,000135 Days on yellowkey MLS ID: O6385064
REDUCED by $5,000 (2.5%) on 05/22/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1365 Built: 1984Monthly Fee: $488 Tax: $2,537 (2025)Community: Clubside At Sabal Point A CondoCondo
Taxes:$2,537
Tax Year: 2025
Remarks: Incredible opportunity to own in Clubside at Sabal Point in the Longwood Wekiva area. This gorgeous corner unit condo is located on the second floor with calming views of natural Florida from every window. This move in ready home features a split bedroom floor plan providing privacy and peace and quiet for everyone. Your kitchen has ample room for an island or a bistro table perfect for coffee, breakfast and catching up on the latest news of the day with your family. Your new living and dining rooms are open and bright, perfect for entertaining over the holidays or just hosting movie night on the couch. This home is not only beautiful but also easy to clean- all tile and luxury vinyl flooring throughout. And of course, the location simply can't be beat. Clubside at Sabal Point is in the heart of Longwood and just around the corner from Wekiva Island, Publix, Starbucks and so much more! Hop on 1-4 or 434 and be anywhere you want to be quickly- including Daytona and New Smyrna beaches and Downtown Orlando for an Orlando Magic game or show at the Dr.Phillips Center for the performing Arts. Seminole county really is the ideal blend of natural Florida and convenience to all things commerce. You don't have to settle- schedule your private viewing of this stunning condo today!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Christina Rordam (407-928-8294)
441 WILD OAK CIR, LONGWOOD, FL 32779
$770,00070 Days on yellowkey MLS ID: O6405462
0 Days Off yellowkey (back on 5/15/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 1982Monthly Fee: $54 Tax: $3,972 (2024)Community: Sweetwater Oaks Sec 13Single Family
Taxes:$3,972
Remarks: Under contract-accepting backup offers. Tucked beneath a canopy of mature oaks on a quiet street, 441 Wild Oak Circle offers the space, privacy, and lifestyle that define Sweetwater Oaks living. Set on an expansive .64-acre homesite, this 4-bedroom, 3-bathroom residence spans over 2,800 square feet and has been thoughtfully maintained and updated throughout—offering both comfort and peace of mind. From the moment you arrive, the circular driveway and side-load 2-car garage create a welcoming presence, while the generous lot and natural surroundings set the tone for what’s inside. The home features an open, easy-flow layout designed for both everyday living and effortless entertaining, with spacious living areas and seamless connection to the outdoors. Natural light fills the interior, highlighting the home’s functional layout and inviting feel. Whether hosting guests or enjoying a quiet night in, the home lives comfortably with well-proportioned spaces and views that draw you outside. Step into your private backyard retreat, where a resurfaced pool is surrounded by an expansive paver patio, complete with a covered gazebo—creating the perfect setting for poolside entertaining, shaded lounging, and year-round gatherings. With over half an acre, the outdoor space offers a rare combination of privacy and flexibility, with plenty of room to expand, play, or simply unwind. Beyond its charm, this home has been meticulously cared for with major updates already completed, including new windows and doors, a whole-house generator, complete replumbing, and updated systems—providing true peace of mind for the next owner. Living in Sweetwater Oaks means embracing a lifestyle that’s hard to replicate. Residents enjoy access to a private, skiable Lake Brantley with a neighborhood boat ramp and beach, tennis and pickleball courts, playgrounds, and access to the Wekiva River for kayaking and outdoor adventures. All of this, zoned for top-rated Seminole County schools and conveniently located near shopping, dining, and major roadways. A rare combination of size, setting, and thoughtful upkeep—this is the kind of home that offers both immediate enjoyment and long-term value in one of Longwood’s most sought-after communities.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Tiffany Yates (321-684-2399)
116 SPRINGWOOD CIR #D, LONGWOOD, FL 32750
$169,99977 Days on yellowkey MLS ID: O6403702
2 Days Off yellowkey (back on 5/8/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1973Monthly Fee: $370 Tax: $523 (2025)Community: Springwood VillageCondo
Taxes:$523
Remarks: Welcome to this beautifully updated 2-bedroom, 1-bath condo tucked away in a quiet, well-maintained community—perfect for both homeowners and investors. This move-in-ready unit features brand new vinyl flooring throughout, a fully renovated kitchen with modern cabinetry, sleek granite countertops, and a clean, contemporary design that truly stands out. The bathroom has been tastefully remodeled, offering a fresh and modern feel. What makes this unit truly unique is its private in-unit washer and dryer room—a rare feature in this community where most units rely on shared laundry. Enjoy peaceful mornings and relaxing evenings on your screened-in patio, the perfect space to unwind with coffee, tea, or a glass of wine in a quiet setting. The community offers an affordable HOA that includes water, garbage pickup, on-site management, maintenance, and security, providing both value and peace of mind. Residents also enjoy access to two swimming pools, a clubhouse with fitness center and party room, a lighted tennis court, basketball half court, multiple laundry facilities, and bike storage. With low property taxes and strong rental potential, this property is an excellent opportunity for both end-users and investors. Opportunities like this don’t last—schedule your showing today before it’s gone.
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)
Listing Agent: Ayoub Seffari (407-497-4015)
7302 OLYMPIA CT, LONGWOOD, FL 32779
$249,90073 Days on yellowkey MLS ID: O6405170
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1365 Built: 1984 Tax: $2,457 (2025)Community: Clubside At Sabal Point A CondoCondo
Taxes:$2,457
Remarks: Welcome home to this beautifully maintained and move-in ready condo in the desirable Clubside at Sabal Point community in Longwood. Offering nearly 1,400 square feet of thoughtfully designed living space, this light-filled upper-level unit combines comfort, style, and convenience in one inviting package. Step inside to discover a spacious open floor plan with tile and laminate flooring throughout - no carpet for easy maintenance. The welcoming foyer leads to a convenient half bath, an in-unit laundry room with full-sized appliances, and a large closet straight ahead. The living and dining areas flow seamlessly into a generously sized kitchen featuring ample counter space, a pantry, and eat-in area, making it perfect for both everyday living and entertaining. The split-bedroom layout provides ideal privacy, with two oversized primary suites located on opposite sides of the home. Each bedroom includes its own ensuite bathroom - one with a tub/shower combination and the other with a walk-in shower - as well as large walk-in closets and additional linen storage. Whether for guests, roommates, or multi-generational living, this layout offers flexibility and comfort for all. Step outside to your private screened-in balcony or lanai, where you can relax with morning coffee or unwind in the evening while enjoying peaceful community views. Residents enjoy a low-maintenance lifestyle with HOA fees covering exterior maintenance, water, trash, pest control, and landscaping. Community amenities include a resort-style pool, fitness center, clubhouse, tennis courts, and beautifully maintained grounds with mature trees and walking paths. Ideally located just minutes from shopping, dining, parks, and outdoor recreation, with quick access to I-4, this home offers the perfect balance of natural Florida beauty and everyday convenience. Whether you're a first-time buyer, downsizing, or seeking an investment, this condo is a wonderful opportunity in a prime location.
Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)
Listing Agent: Cheryl Roda-Wu (407-595-9580)
1469 GRACE LAKE CIR, LONGWOOD, FL 32750
$560,000263 Days on yellowkey MLS ID: O6355680
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2174 Built: 1982Monthly Fee: $40 Tax: $5,031 (2025)Community: North CoveSingle Family
Taxes:$5,031
Elementary School: Woodlands Elementary
High School: Lake Mary High
Remarks: An ideal blank canvas for those seeking top-rated schools and a fantastic neighborhood! This 4-bedroom, 2.5 bath home features a screened-in pool, a cozy family room with beamed ceilings, and tile flooring throughout. The expansive sunroom, complete with a kitchen service window, is perfect for relaxing or entertaining. The large primary suite includes a spacious closet and an en suite bathroom. With a 2-car garage,this home sits on a desirable corner lot with mature tree coverage, a lovely manicured lawn in the highly sought after North Cove community.
Listing is courtesy of: MOREHOUSE REALTY INC (407-331-4444)
Listing Agent: Alvin Moore (407-331-4444)
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