Remarks: Welcome to 2494 Castlewood Road, a beautifully updated pool home situated on a spacious corner lot in one of Maitland's most established neighborhoods. This move-in-ready residence offers peace of mind with a newer roof, solar panels, updated HVAC, and extensive interior renovations throughout. Inside, you'll find an open and inviting floor plan featuring luxury vinyl flooring, updated bathrooms, modern fixtures, quartz countertops, and custom cabinetry. The spacious primary suite includes a walk-in closet and renovated en-suite bath, while the additional bedrooms provide flexibility for family, guests, or a home office. A large screened Florida room overlooks the backyard and creates the perfect space for year-round entertaining. Outside, enjoy the oversized swimming pool, expansive patio deck, fully fenced yard, and storage shed, offering plenty of room for recreation and outdoor living. Conveniently located just minutes from Downtown Maitland, Winter Park, Park Avenue, AdventHealth, shopping, dining, and major roadways including I-4, this home combines modern updates, energy-efficient features, and an exceptional location in the heart of Central Florida.

Listing is courtesy of: LA ROSA REALTY CW PROPERTIES L (407-910-2168)

Listing Agent: Neil Chetram (407-752-1597)

Remarks: This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neighborhood and is packed with standout features. Upstairs, you’ll find beautiful engineered hardwood flooring throughout the main living areas, with carpet in the bedrooms and tile in the baths. A stunning screened-in porch overlooks the backyard and pool, offering a perfect spot to relax or entertain. The bright and airy formal living room provides plenty of space, while the dining room includes sliding doors that lead out to the porch. The large eat-in kitchen offers ample cabinet storage and even features a convenient pass-through window to the porch/outside bar—ideal for hosting. The upper level includes three bedrooms two bathrooms. Just a few steps down, the lower level opens to a massive family room with tile floors set to entertain family and friends with two additional bedrooms with carpet and a full bath. Tile flooring runs throughout this level. Additional highlights include outdoor spa , updated windows, a re-piped plumbing system, updated Electrical, and a well-maintained interior full of character. The home comes with paid in full solar panels and a Terminix termite bond and Well Maintained sprinkler system on well. Washer/Dryer are located in the garage. The garage include cabinets for additional storage. The yard features mature Citrus trees and Magnolia trees adding to the home’s charm. With its flexible layout, inviting screened porch, and beautiful salt water pool area, this home truly has it all.

Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)

Listing Agent: Maydelin Munoz (407-485-4990)

Remarks: Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitland—this charming single-family home is on the market for the first time in 45 years. Built with solid block construction, this home offers exceptional durability, structural soundness, and reliable weather resistance, giving peace of mind for years to come. Situated on an expansive and highly desirable corner lot, the property provides a unique blend of privacy, space, and long-term potential. With .41 acres of land, this double lot offers endless possibilities, whether you’re looking to enjoy the generous yard or explore the option to split it into two separate parcels. Inside, the home features 3 bedrooms and 2 bathrooms across 1,623 square feet of thoughtfully designed living space. A spacious layout provides comfort and functionality, while large windows invite in natural light, creating a warm and welcoming atmosphere throughout. The 2-car garage offers ample storage and convenience, complementing the home’s practical appeal for everyday living. Outside, the oversized lot is truly the standout feature—lush, open, and full of potential for outdoor living, expansion, or future development. With its prime location, generous lot size, and first-time availability in decades, this is a one-of-a-kind opportunity you won’t want to miss.

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Joseph Sipp (407-820-7016)

Remarks: VIDEO/VIRTUAL TOUR AVAILABLE! This Maitland pool home features 3 bed/2 bath in the main house with a 4th room addition on the other side of the garage. The 4th room has it's own separate entrance and it's own rear door access to the pool! Use it as a home office, creative studio, home gym, or income-producing suite — with no HOA to answer to. The cozy fireplace, hardwood floors, and split bedroom floor plan makes it feel like home. The oversized rectangular pool and deck were recently resurfaced and a screen enclosure was added to make maintenance a breeze. There’s still plenty of backyard space to enjoy on the huge 0.28 acre lot equipped with a white vinyl fence and storage shed. Minutes from excellent Maitland private schools and the Winter Park private school corridor, you’ll love the area! It’s close to Trader Joe’s, Winter Park Shopping & Dining, Audubon Center for Birds of Prey, Maitland Art Center, Lake Lily Park, and Enzian Theater. The RDV Sportsplex Athletic Club — with 400+ monthly classes — is an incredible convenience as well! Highway I-4 is close by and the SunRail Maitland Station is only 1 mile away, making downtown Orlando just 24 min commute on the Sunrail. Downtown Maitland is walkable with acclaimed restaurants anchored by a weekly Farmers' Market and the annual Jazz & Blues Festival. Roof is 2020, and water heater is brand new 2026. To see more of the house, WATCH THE VIDEO/VIRTUAL TOUR!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Cece Wong (407-809-1440)

Remarks: Welcome to 502 Oak Lane in Maitland, a beautifully updated pool home that blends comfort, character, and peace of mind. This fully improved 3 bedroom, 3.5 bathroom home has been thoughtfully updated throughout, including the replacement of the cast iron plumbing, offering both charm and important system improvements. Inside, you will find a well designed layout with spacious living areas, updated finishes, and plenty of natural light. Each bedroom offers its own bathroom, creating privacy and flexibility for guests or family. The home has been meticulously maintained and improved, making it truly move in ready. Step outside to your private backyard oasis featuring a pool, perfect for relaxing afternoons or entertaining friends and family. Located on a quiet street in Maitland, this home offers a great combination of location, updates, and lifestyle. This is a rare opportunity to own a fully improved pool home in one of Maitland’s most desirable areas.

Listing is courtesy of: KRESSLER REAL ESTATE (407-864-2184)

Listing Agent: Andre Kressler (407-864-2184)

Remarks: Don't miss this Great opportunity in the Maitland-Winter Park area! There's Potential for Renovation, Expansion or Development with this property. Imagine the Improvements that can be made for the Future. This is a One Owner Home held be the same family since the 1960s. New roof in 2022. The adjacent property at 220 Alpine is also available for purchase.

Listing is courtesy of: PREMIUM PROPERTIES R.E SERVICE (407-380-2800)

Listing Agent: Beth Hathaway (407-314-1300)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This gem is situated in the Brittney Gardens gated neighborhood in desirable Maitland. When you enter the home you are greeted by beautiful, rich wood floors and loads of natural light. The dining room flows seamlessly into the kitchen for ease when entertaining. The kitchen boasts quartz countertops, stainless-steel appliances, ample cabinet and counter space, breakfast bar & closet pantry. The kitchen overlooks the living room, which provides glass doors, complete with retractable screens, leading to the screened-in patio. The primary bedroom is a true private retreat and is on the opposite side of the home from the secondary bedrooms. The primary retreat includes a walk-in closet with a closet system and a spa-like ensuite bathroom with a dual sink vanity. The secondary bedrooms are across the home and share a hallway bathroom. The screened-in patio overlooks a rear paver patio which provides the perfect outdoor space to enjoy the Florida lifestyle. Other amenities and updates include a whole house generator, recently repainted interior, LED lights, new carpet in all the bedrooms, and a new tankless water heater. HVAC was installed in 2024. This home is close to several restaurants and shops and is just a short distance from both the newer Maitland City Center and famed Park Avenue in Winter Park. Welcome Home!

Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)

Listing Agent: Beth Logullo (772-633-0670)

Remarks: One or more photo(s) has been virtually staged. NEW ROOF 2022 - NEW AC 2022 - NEW ELECTRICAL PANELS 2022 - REPLUMB 2022 - NEW SEPTIC 2023 - Seperate detached GUEST HOUSE offering built-in monthly income potential. Previously rented under market value at $900/month, the guesthouse is currently vacant and ready for a new tenant, a private space for adult children, or a comfortable in-law suite. Endless possibilities to maximize value and flexibility! The spacious single-level layout features 3 bedrooms, 2 bathrooms in the main house, plus an updated guest suite. Enjoy an open living and dining area with a stone fireplace, designer lighting, and luxury vinyl plank flooring. The upgraded kitchen includes wood cabinets, granite countertops, penny tile backsplash, and new stainless appliances. A bright family room leads to two outdoor seating areas, including a brick courtyard with a second fireplace. The oversized primary suite and additional bedrooms feature new plush carpet, while the bathrooms have been fully updated. The detached guest suite offers 1 bedroom, 1 bath, a sitting area, and a wet bar. Additional features include a washer and dryer, security cameras, and a Google/Nest doorbell, all conveying with the home. Double carport, oversized driveway, and a private lot on a quiet street. Conveniently located near downtown Maitland with easy access to I-4.

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Greg Roberts, Llc (407-927-5303)

Remarks: A lovely well designed 4bdr. 2 bath home with an eat in kitchen open to a spacious family rm. A formal din.rm. and formal lvg.rm. are ready for any occasion. The long 2 lane brick driveway can accommodate multiple vehicles. Nearby schools for all levels and the amenities for recreation and entertainment are too numerous to list. This house should be added to your list when searching for your new home.

Listing is courtesy of: REALTY OF RIVERVIEW LLC (813-863-3948)

Listing Agent: Stephen Hachey (813-863-3948)

Remarks: Welcome to this beautifully maintained two-owner concrete block home offering the perfect blend of comfort, character, and exceptional Florida outdoor living — all with NO HOA and a prime Central Florida location. A majestic Kapok tree creates impressive curb appeal while a lush, vine-covered trellis welcomes you to the front entrance, setting the stage for the charm found throughout. Inside, the open-concept floorplan is designed for both comfortable everyday living and effortless entertaining. The heart of the home is the stunning kitchen, highlighted by a tongue-and-groove ceiling, stylish pendant lighting, and a chef-inspired gas range that makes cooking and gathering a pleasure. Bright, open living spaces create an inviting atmosphere from the moment you walk in. The spacious primary suite provides a relaxing retreat, while three additional bedrooms and two full bathrooms offer flexibility for family, guests, or work-from-home needs. An oversized two-car garage provides abundant storage and functionality. Step outside and discover your own private backyard oasis. Enjoy year-round outdoor living from the screened patio and pergola-covered entertaining area overlooking a beautifully terraced backyard leading down to peaceful pond frontage and a sparkling inground pool — creating the perfect setting for relaxing, entertaining, or enjoying tranquil water views. Conveniently located just minutes from Full Sail University, shopping, dining, and major commuter routes, with easy access to Winter Park, Casselberry, Winter Springs, and Altamonte Springs, this home combines privacy, convenience, and lifestyle in one exceptional package. Major update: Roof replaced in 2021. Schedule your private showing today and experience Florida living at its finest.

Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)

Listing Agent: John Muccigrosso, Pa (407-234-6330)

Remarks: Nestled in the heart of highly desirable Maitland, this spacious 4-bedroom, 2-bath pool home offers the perfect blend of location, functionality, and outdoor living on an oversized .28-acre lot with more than 12,000 square feet of property. Surrounded by mature trees and established neighborhoods, this prime location places you just minutes from Downtown Maitland, Historic Winter Park, Downtown Orlando, world-class shopping, dining, entertainment, and Central Florida’s renowned attractions. Maitland is loved for its charming restaurants, weekend farmer’s market, beautiful lakes, and scenic tree-lined streets, all while bordering some of the most prestigious real estate in Central Florida.The backyard is truly the showstopper of this property, featuring a sparkling open pool, beautiful vinyl fencing, and an expansive yard that is far larger than many homes in the area. Recent landscaping enhancements include a hardscaped entertaining space and decorative stone half wall, creating the perfect setting for relaxing, hosting guests, or enjoying Florida outdoor living under the shade of the beautiful oak tree.Inside, the home features a desirable split-bedroom floor plan with formal living and dining rooms, plus a spacious family room offering plenty of flexibility for everyday living and entertaining. The galley-style kitchen is equipped with granite countertops and overlooks the living areas for easy functionality. Attractive laminate wood flooring and tile flow throughout the home, while all bedrooms have been updated with new ceiling fans. Additional improvements include electrical upgrades, new exterior doors, a new roof installed in 2020, and added attic insulation for enhanced energy efficiency. Built with sturdy concrete block construction, this home offers lasting durability and peace of mind. The indoor laundry room includes the washer and dryer for added convenience. This is a rare opportunity to own a pool home with a large backyard in one of Central Florida’s most established and desirable locations.

Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)

Listing Agent: Kelly Hildebrand (407-310-5035)

Remarks: Dommerich Woods gem! Tucked away on a cul-de-sac street in one of Maitland’s most sought-after neighborhoods, this beautifully updated 3-bedroom, 2-bath block home is the one you’ve been waiting for. Move-in ready and genuinely charming from the moment you walk in. The open floor plan feels airy and welcoming, with vaulted ceilings and natural light pouring through every room. The living room centers around a classic brick fireplace that anchors the space perfectly, while the kitchen is a true standout-quartz countertops, stainless appliances, 40-inch soft-close shaker cabinets and a built-in pantry. The layout flows effortlessly between living, dining and family spaces, making it as functional as it is inviting. The split bedroom layout offers great privacy for everyone. The primary suite is a real retreat- vaulted ceiling, spacious walk-in closet and a completely redone en-suite bath with a lovely garden window. Both bathrooms have been given a fresh, modern look that feels clean and polished. The updates list is long and impressive: newer LVP flooring throughout, AC (2022), water heater (2023), roof replaced in 2016, replumbed in 2008, newer paint inside and out, newer light fixtures and ceiling fans. Laundry is indoors and connects right to the two-car garage-a detail you’ll appreciate daily. Out back, the expansive yard is a genuine sanctuary. Mature trees, lush landscaping and total privacy make it the kind of space you’ll actually use. A large shed with 50-amp power is ready for a workshop, hobby space or serious storage-and with NO HOA, bring the toys too! Just minutes from Kewannee Park, the Seminole bike trail and easy access to major roads and local shops and restaurants. It’s a rare find in a neighborhood where homeowners rarely leave. Come take a look.

Listing is courtesy of: BOWERBIRD REALTY (407-716-0239)

Listing Agent: Stephanie Doucette (407-716-0239)

Remarks: Under contract-accepting backup offers. Fully renovated pool home on a desirable corner lot in the highly sought-after English Estates with NO HOA! This move-in-ready 3-bedroom, 2 and 1/2 bath residence showcases extensive recent upgrades and modern finishes throughout, offering the perfect blend of style, comfort, and functionality. Brand-new roof, new fence, new flooring throughout, fresh interior and exterior paint, updated electrical, updated windows and doors, modernized kitchen and bathrooms, upgraded lighting and fixtures, updated cabinets and countertops, and new appliances. Additional enhancements include new baseboards, plumbing updates for an added half bath, professional landscaping with new mulch and plants, and pool equipment upgrades including a new motor and pool pump. The inviting open floor plan features spacious living areas filled with natural light, a beautifully updated eat-in kitchen, and thoughtfully renovated bathrooms designed for modern living. The garage laundry area adds convenience, while the expansive corner lot provides excellent curb appeal and additional outdoor space for entertaining, relaxing, or future enhancements. Ideally located just minutes from Highway 436, shopping, dining, schools, parks, and everyday conveniences, this property offers both exceptional lifestyle appeal and strong long-term value. Whether you are searching for a primary residence, seasonal home, or investment opportunity, this extensively upgraded property is truly move-in ready. Schedule your private showing today and experience the quality, upgrades, and convenience this exceptional English Estates home has to offer!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Angela Worachek Pllc (503-381-1575)

Remarks: Welcome to 1776 Bobtail Drive — the kind of home that doesn’t just check boxes… it creates emotion, urgency, and that unmistakable “we need this one” reaction the moment your buyers walk through the door. From the very first glance, the curb appeal sets the stage with a warm, polished presence that immediately stands out from the competition. Inside, you’re welcomed by a light-filled, open-concept layout that feels expansive yet comfortable — the perfect balance of elegance and livability. Every space has been thoughtfully designed to flow effortlessly, creating an atmosphere that feels both elevated and inviting. The heart of the home is a beautifully positioned kitchen that seamlessly connects to the main living areas, making it ideal for entertaining, gathering, and everyday life. Whether hosting friends or enjoying a quiet night in, this home delivers the versatility today’s buyers demand. Generously sized living spaces and bedrooms provide comfort, privacy, and flexibility, while the overall layout offers a sense of ease and functionality that appeals to a broad range of buyers — from families to professionals to those simply looking to upgrade their lifestyle. Step outside and experience your own private Florida escape — a backyard setting that invites relaxation, weekend gatherings, and year-round enjoyment. It’s the kind of outdoor space that sells the lifestyle just as much as the home itself. Perfectly positioned in a highly desirable Maitland location, this property offers unbeatable convenience to top-rated dining, shopping, entertainment, and major highways — putting everything Central Florida has to offer right at your fingertips. This is not just another listing — it’s a high-impact, high-demand opportunity that shows beautifully, lives effortlessly, and is primed to sell quickly. Homes with this combination of appeal, location, and lifestyle don’t sit… they move. Bring your buyers with confidence — this is the one they’ve been waiting for.

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Anthony Scaraggi (516-749-6675)

Remarks: More photos to come soon! Welcome to 200 Spartan Dr, a beautifully updated 3/2 (with bonus room and large laundry room) pool home in the heart of Maitland. The interior has been thoughtfully opened up by removing walls between the living area and kitchen, creating a much more spacious and modern feel, and a large island was added to make the kitchen the center of the home. The home also features a bonus room offering great flexibility for a home office, workout space, or hobby room. Outside, enjoy a private pool and backyard space perfect for relaxing or entertaining. Conveniently located near shopping, dining, parks, and major roadways, this home offers comfort, functionality, and a great Maitland location. Roof, HVAC, and Water heater from 2018.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Nick Mandiola (407-453-0190)