Homes for Sale Near Southwestern Middle in Deland - 68 homes

Remarks: Under contract-accepting backup offers. Multifamily Living is a real possibility here and you don't even have to worry about utility bills! Set on a private 2.41-acre lot in Glenwood , unincorporated DeLand, 2053 Bond Rd is the kind of property that gives you room to breathe—zoned for horses, high and dry. With 5 bedrooms, 4 full bathrooms, and 3,092 sq ft under air, the layout is especially well-suited for multigenerational living, featuring both a spacious primary suite and a second suite-style bedroom with its own full bath and large closet. Inside, the home feels open and welcoming with vaulted ceilings in the generous living spaces, and French doors that lead to an enclosed porch—ideal for morning coffee, game nights, or a quiet spot to unwind. The kitchen is the heart of the home, freshly remodeled with quartz countertops, a farmhouse sink, a center island, and updated appliances, offering a clean, modern look and great flow for everyday living and entertaining. The primary suite includes a large walk-in closet and a thoughtfully designed handicap-accessible bath with a tiled shower, tiled floor, and glass block window. Throughout the home you will find laminate flooring, full closets, and ceiling fans—simple, practical touches that make a difference. And if that was not enough, the property also shines on the Outside: a long driveway, fresh front landscaping, and a sidewalk wrapping the home to a backyard offering privacy. Car enthusiasts and hobbyists will be in heaven with the detached 1,764 sq ft 4+ car garage featuring a drive-thru door—perfect for vehicles, a workshop, equipment, or toys. The roof was replaced in September 2019, and the home is covered by a termite bond for added peace of mind. If you want acreage, privacy, and a home that supports big living—without sacrificing comfort—this one checks the boxes.

Listing is courtesy of: BEE REALTY CORP (386-279-7522)

Listing Agent: Bee Powell (386-490-0915)

Remarks: Under contract-accepting backup offers. Welcome to Glenwood, one of DeLand's Rural Communities. Located just minutes from Ponce De Leon Springs State Park, Lake Woodruff Wildlife Refuge, and the Spring to Spring biking / walking trail. This property features three acres of quiet country living with ample space for RVs, boats, workshops, or all your outdoor hobbies. This property offers the freedom and flexibility that’s hard to find. Inside, you’ll find two comfortable, well-sized bedrooms The original bathroom has been remodeled, offering a fresh, updated feel with modern finishes. A versatile interior flex room presents an excellent opportunity to create a separate living space or transform it into a spacious primary suite. The fully equipped kitchen with granite countertops, gas range is ready for everyday living and entertaining, and the inside laundry adds functionality and ease. An oversized screened porch extends your living space outdoors, creating the perfect setting for morning coffee, evening relaxation, and front-row views of deer grazing peacefully through the yard. Enjoy the privacy of country living while still having room to grow, gather, and make it your own. If horses are your hobby, the twin sister private roads, Manor Way and Twin Oaks Drive offer a deeded Bridal Path around the community. Very deep lot, 200x660. Enjoy the slower pace of life here, but only 45 minutes to the World's Most Famous Beach, Daytona Beach, one hour from Orlando, and the Florida Attractions.

Listing is courtesy of: ADAMS, CAMERON & CO., REALTORS (386-738-1920)

Listing Agent: Mary Ann Brawner (386-804-2800)

Remarks: If these walls could talk, they’d have over a century of stories to tell. Tucked into Downtown DeLand behind a charming little white picket fence, this 1910 home carries that rare kind of character you just can’t recreate. Three full floors, five bedrooms, and three bathrooms give you the space, while the soul of the home does the rest. Step inside and you’re welcomed into the living room, with an electric fireplace. Just off to the right, the only bedroom on the first floor offers flexibility for guests, an office, or a tucked-away retreat. To the left, a full bath conveniently located outside the kitchen. Simple, functional, and right where you need it. The kitchen has its own story to tell, with a hidden-away laundry room just off to the side, complete with built-in shelving and access to the rear porch and patio, perfect for slipping outside with your morning coffee or winding down at the end of the day. Back through the heart of the home, the dining area connects it all and leads you upstairs to the second floor. Here you’ll find four more bedrooms, a centrally located full bath, and a second laundry area, because homes like this were built for real living & convenience. And then there’s the third floor. Unfinished, but far from forgotten. With a full bathroom already in place, this space is full of possibility, a studio, retreat, extra living space or loft. This isn’t just another house. It’s a piece of DeLand’s history waiting for someone who appreciates the character, the quiet corners, and the feeling that you’re part of something that’s been standing strong for generations. It's a place where past & present meet, and where the next chapter is waiting to be told.

Listing is courtesy of: BEE REALTY CORP (386-279-7522)

Listing Agent: Bee Powell (386-490-0915)

Remarks: Spacious 3-Bedroom, 2-Bath Home on Over Half an Acre! This beautiful 1,900 sq. ft. home, built in 1997, sits on an expansive 24,394 sq. ft. lot offering plenty of room to relax, entertain, or expand. Inside, you’ll find a bright and open layout with generous living spaces, a well-appointed kitchen, and comfortable bedrooms. The primary suite features an en-suite bath for added privacy. Enjoy the outdoors with ample yard space — perfect for a pool, garden, or RV/boat parking. Conveniently located near schools, shopping, and major roadways, this home offers the perfect blend of comfort and space. NEW GENERATOR

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Nicholas Feinsod (407-607-7485)

Remarks: One or more photo(s) has been virtually staged. This beautiful new construction offers 1,784 sq. ft. of modern living with 3 spacious bedrooms, 2 stylish bathrooms, and a 2-car garage. The open floor plan features a sleek kitchen with brand new appliances, high ceilings, large backyard, and an inviting island, perfect for entertaining. This property is located approximately 2 miles away from Stetson University. Enjoy the peace of mind with hurricane impact windows and a thoughtfully designed master suite with an en-suite bath and walk-in closet. Situated in a growing community close to schools, parks, and stunning beaches, this home is a must-see! Schedule your private tour today!

Listing is courtesy of: KAY & CO REALTY INC (407-559-7333)

Listing Agent: Cherelle Registre (305-930-3635)

Remarks: Tucked away in the quiet charm of Glenwood—a peaceful hideaway known for its natural beauty and bird sanctuary charm—this 3-bedroom, 2-bath block home offers the perfect blend of quiet living and convenient access. Just 15 minutes from Historic Downtown DeLand, you’ll be close to delightful local shops, cozy cafés, and weekend strolls under the oaks. And when you’re ready for adventure, the shores of Daytona and New Smyrna Beach or the energy of Orlando are just a short drive away. Inside, the inviting eat-in kitchen features warm custom wood cabinetry, a stainless steel sink, dishwasher, range and microwave—ready for home-cooked meals and family gatherings. The adjacent laundry room includes washer and dryer hook-ups and added space for storage and ease. The primary bedroom serves as a peaceful retreat, complete with a skylight that bathes the ensuite in soft, natural light. For year-round comfort, the home Out back, you'll find a spacious, fenced yard—perfect for pets, playtime, or hosting weekend barbecues. The 2-car garage offers generous space for is equipped with a mini-split A/C for efficient climate control. Also offers room for vehicles, bikes, boats, or hobbies of your choosing. This lovingly maintained home is priced with value in mind—motivated sellers are ready to welcome you home. Come see the charm and comfort for yourself! Fan in Great Room does not convey.

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (386-222-3608)

Listing Agent: Linda Lee (386-383-3877)

Remarks: MULTIPLE OFFER SITUATION!!! SELLER SAYS SUBMIT HIGHEST AND BEST OFFER 3/25 BY 8 PM!!!Glenwood – A unique property with so much potential: 1.25 acres with 2 homes and 3 outbuildings on the property. The main home is 1,566 sq. ft. of living area; 3 bedrooms, 2 baths, and an attached two car garage. Interior was recently painted, kitchen cabinets have been stripped, sanded and painted. Fresh landscaping complements the mature trees and flowering bushes throughout the property. Oak floors; terracotta tiles in the Florida room and glazed tiles in the kitchen and dining room. The second home, lovingly called “the cottage” has 2 bedrooms and 2 baths in approximately 1,000 sq. ft. of living area. There is newly installed carpet with tiles in the kitchen and dining area. Seller has applied for a permit on a new septic tank and drain field for the cottage which should be completed prior to closing. The larger outbuilding, on a poured slab, has electric, water and A/C, and has been used as a woodworking shop; the two sheds offer loads of storage. The properties are under one legal description but has two address of 1976 Carr Street (cottage) and 3335 Grand Avenue. Think of the possibilities; live in the main house and rent out the cottage; live in the main house with extended family in the cottage; or rent both houses out for a potential income of $3,500 - $4,000. With all of the flexibility and possibilities this property will not last long. Now is the time! Call today!

Listing is courtesy of: GLORY INTL. REAL ESTATE CO (386-775-7778)

Listing Agent: Louis Castriota (386-469-9036)

Remarks: Adorable house with tons of potential just minutes from Stetson University and charming downtown DeLand! This three bedroom two bath home puts you right where you want to be—close to shops, dining, and all the local favorites without sacrificing neighborhood feel. Inside, you’ll find a layout that makes sense. A formal dining room and a bonus office/den that’s perfect for working from home and a kitchen/ family room combo. The one-car garage keeps your car out of the Florida sun, or gives you extra storage for all those “I’ll use this someday” items. Out back, a screened-in porch lets you enjoy the outdoors without becoming a buffet for mosquitos. It could use some updates, but whether you’re a first-time home buyer ready to build equity or an investor eyeing a strong rental near Stetson University, this home checks the boxes that actually matter: location, layout, and long-term potential. Come see it before someone else with vision and a Pinterest board beats you to it!

Listing is courtesy of: TOWN AND COUNTRY REALTY (386-734-8890)

Listing Agent: Jane Grose (386-801-2034)

Remarks: Under contract-accepting backup offers. Immaculate Pool Home | 3BR + Office | 3-Car Garage | Prime Location | Block Built Welcome to this beautiful one-owner home where pride of ownership truly shines! Meticulously maintained and move-in ready, this spotless residence offers the perfect combination of comfort, space, and style. Featuring 3 bedrooms, 2 baths PLUS a private office with French doors, this home is designed with a desirable split bedroom floor plan for added privacy. You’ll love the formal dining room and the spacious family room that opens seamlessly to the kitchen and dinette area—perfect for everyday living and entertaining. The kitchen is a standout with granite countertops, ample cabinetry, large Breakfast bar, and a layout that keeps you connected to the heart of the home. Dinette offers upper and lower built in cabinets. Step outside to your own private oasis—a huge screened-in lanai with pavers surrounding a sparkling in-ground saltwater pool with waterfall and lifetime pebble finish. Privacy Shade for the covered entertaining area. Planter accents! This is Florida living at its finest, ideal for relaxing or hosting gatherings year-round. The primary suite offers a peaceful retreat with dual closets, an en-suite bath featuring dual sinks, a whirlpool tub, private W/C, and a walk-in shower. Situated on a generous 1/3-acre lot in an established community, this home also features: a 3-car garage with built-in cabinets, floor coating, & 2 openers; natural gas connected; On-demand gas hot water heater & gas heating; two linen closets for extra storage; Gutters and beautifully maintained landscaping. Location, location, location! Conveniently located less than 2 miles to Advent hospital, about 3 miles to Publix, and close to shopping, dining, and everyday amenities. Less than 3 miles to charming Downtown DeLand and Stetson University. This home truly has it all—don’t miss your opportunity to own this exceptional property. Schedule your private showing today!

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Terry Bailey (386-801-9300)

Remarks: INCOME-PRODUCING QUADRUPLEX NEAR STETSON & DOWNTOWN DELAND! An investor’s opportunity awaits with this income-producing quadruplex in a prime DeLand location. Offering reliable rental income, key system updates, and strong long-term demand, this property is ideal for house-hackers, portfolio investors, or anyone entering the investment market.Major improvements have already been handled, including a new roof (2018) and newer A/C systems (2015) — allowing you to focus on income, not repairs. Three of the four units are currently rented, providing immediate cash flow with additional upside potential. Demand in this area stays consistently strong thanks to its unbeatable proximity to: Stetson University, Downtown DeLand's restaurants, boutiques, breweries, and nightlife, convenient access to major roads and commuting routes. High rental demand, dependable location, and low-maintenance updates combine to create the kind of investment that works for you from day one. This income-generating gem is ready for its next owner.

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

Listing Agent: Mark Ramey (407-496-1766)

Remarks: Under contract-accepting backup offers. Step into a piece of DeLand history—where timeless charm meets modern comfort—at this beautifully preserved 1914 home nestled in the heart of the historic district. From the moment you arrive at 426 N Clara Ave, you can almost feel the stories this home holds. Picture mornings on the porch with a cup of coffee, shaded by mature trees, and evenings spent strolling just blocks away to the vibrant shops, restaurants, and events of Downtown DeLand—or a quick walk to Stetson University’s picturesque campus. Inside, the home welcomes you with original hardwood floors and stunning built-ins, rich with character you simply can’t recreate. Natural light pours through the windows, highlighting the perfect blend of historic craftsmanship and thoughtful modern updates. The updated kitchen is both warm and functional, featuring butcher block countertops, stainless steel appliances, and new wood flooring, creating a space that’s equally suited for quiet mornings or hosting friends and family. Upstairs, the bedrooms provide a cozy retreat, complete with the convenience of second-floor laundry. The remodeled bathrooms bring a touch of luxury to everyday living—especially the upstairs bath with its classic clawfoot tub, perfect for unwinding at the end of the day. And just when you think you’ve seen it all, the finished third-floor attic awaits—equipped with its own mini-split system. Whether you envision a private guest suite, creative studio, or inspiring home office, this versatile space adapts to your lifestyle. Sitting on a rare double lot, this property offers incredible future potential. With room to add an ADU (Accessory Dwelling Unit), you have the possible opportunity to create additional income, a guest house, or multi-generational living—something increasingly hard to find in this sought-after location. (City approval required) This is more than just a home—it’s a lifestyle. A place where history, walkability, and opportunity come together in one truly special property. Don’t miss your chance to own a piece of DeLand’s past—while building your future. Roof and new gutters (2024), Exterior Paint (2025), Master Bath remodel (2025), Mini split added to attic (2025), 2 AC Units (2023), Floors refinished (2023), Crawlspace enclosed (2018) Electric Vehicle Outdoor Outlet (2025)

Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)

Listing Agent: Lisa Bertin Queena (407-952-4468)

Remarks: Under contract-accepting backup offers. Tucked along the shores of Lake Beresford, this inviting DeLand home offers a rare waterfront setting with an approximately 8-foot-deep canal, providing easy and reliable access for boating out to the St. Johns River. With no HOA and just over 3000 square feet of living space, this property delivers both freedom and functionality in a scenic setting. Inside, the home features refreshed interior paint (2026), laminate flooring (2021), plantation shutters, and a central vacuum system for added convenience. The kitchen, bathroom, and laundry room have been thoughtfully updated, creating a clean and comfortable feel while maintaining the home’s original charm. A Florida room with newly finished stained concrete floors (2026) adds a versatile space filled with natural light—ideal for relaxing or entertaining. Character details shine throughout, including tongue-and-groove porch ceilings and stylish shiplap accents that bring warmth and texture to the home’s design. Outdoors, a newly added paver fire pit (2026) creates a welcoming gathering space, while the chain link fenced yard (2026) adds both function and flexibility. RV and generator hookups provide additional practicality for a variety of lifestyles. For water enthusiasts, the boathouse with a belt driven lift with aluminum cradle (2023) makes lake access effortless. Additional updates include exterior paint (2022) and a roof replacement (2022), offering peace of mind for years to come. This property is a rare opportunity to enjoy laid-back lakeside living with modern touches in one of DeLand’s most scenic settings.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Elvira Hanna (386-785-7735)

Remarks: Tastefully remodeled, country-style home in the city for your family or turnkey cashflow positive investment for your portfolio, you choose! 3/2 features contemporary finishes w/ traditional touches, large master suite, an open floorplan throughout complete w/ a warm/inviting dining area. The spacious back patio includes a traditional brick BBQ & partial view of the expansive near 10,000sqft lot! Right-side studio is a great rental for any young professional/student. Tap into the seemingly endless supply of potential tenants from nationally renowned Stetson Law University (just over a mile away) & central location to historic downtown Deland area (coffee shops & restaurants just across the street). Gross rent for both sides is cashflow positive at a 10+ cap rate ($31,000 - $34,000yrly). Click "virtual tour 2" for prop website. Owner owns adjacent lot & is open to sell. Own the entire corner! Government backed rent-to-own program elegible! >Click "VIRTUAL TOUR 1" FOR VIDEO< Call now to see before the summer rush!!

Listing is courtesy of: TOWER TEAM REALTY, LLC (786-233-4959)

Listing Agent: Brandon Ford (305-305-0105)

Remarks: Is there a 3-bed home in DeLand under $400K with a pool, office space, and modern upgrades. This 3-bedroom, 2-bath home in Mallory Square offers 1,679 square feet, built in 2019, featuring a newly installed screened pool, a dedicated bonus room used as an office, and a 2 car garage. Welcome to 112 Big Pine Key Blvd in the desirable Mallory Square community of DeLand, FL. This well-maintained home delivers the perfect balance of functionality and lifestyle. Inside, the open-concept layout connects the living, dining, and kitchen areas, creating an inviting space for both daily living and entertaining. A standout feature is the bonus room currently used as a home office, ideal for remote work, study space, or a flexible-use room that adapts to your needs. The primary suite offers a private retreat with a well-appointed bathroom and generous closet space. Two additional bedrooms provide comfortable accommodations for guests or household members. Built in 2019, the home benefits from newer construction and modern efficiencies. Step outside to enjoy the newly installed pool with a full screen enclosure, designed for year-round Florida enjoyment with added comfort and reduced maintenance. Located in Mallory Square, this home offers convenient access to historic downtown DeLand, parks, shopping, and dining. If you're searching for a move-in ready home with flexible space and outdoor living, this property delivers.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Tawanda Purdie Llc (352-346-3721)

Remarks: Fantastic opportunity to own a two-story duplex in the heart of DeLand! This well-located property features two spacious units - one offering 2 bedrooms and 1.5 bathrooms, and the other a 3-bedroom, 1.5-bathroom layout. Both units include their own laundry spaces and private back patio areas, perfect for added comfort and convenience. With one unit vacant and one occupied, this duplex offers flexibility for investors or owner-occupants alike. Enjoy unbeatable walkability to downtown DeLand, Stetson University, and nearby county and city buildings, along with dining, shopping, and entertainment just steps away. A prime location, versatile layout, and strong potential make this duplex a standout opportunity you don’t want to miss! (All info to be verified by buyer)

Listing is courtesy of: GREENE REALTY OF FLORIDA LLC (386-734-2200)

Listing Agent: Hailey Graham (386-405-8016)

Remarks: Under contract-accepting backup offers. Welcome to this lovingly-maintained, one-owner 4 bedroom, 2 bath brick home with a 2-car garage, located in the desirable neighborhood of Fern Garden Estates, known for larger lots. The home offers a great split floor plan with comfortable living spaces and a layout designed for everyday living. Pride of ownership is evident throughout, with added features including a new refrigerator and central vacuum system. Enjoy outdoor living with a large screened rear porch, and a brick paver planter area that could easily be converted into a charming firepit. With the home's classic, straightforward design, it provides an excellent foundation for personalization. Conveniently located near shopping, with easy access to I-4, and just minutes from historic downtown DeLand, this home combines comfort, location, and long-term value.

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Hannah Hoffmann (386-956-0411)

Remarks: Tucked away on 0.97 ACRES off the main road on a private road, this property offers the perfect opportunity to build the workshop you have been dreaming of or the ADU (Accessory Dwelling Unit). With NO HOA, you will have the freedom to bring your Work Trucks, RV, boat, or other recreational vehicles. This one owner home has been meticulously maintained and is located 10 minutes from charming downtown DeLand, while providing privacy, peace and quiet in a country setting with city conveniences. USDA ELIGIBLE AVAILABLE! This 3-bedroom, 2-bathroom home features an open floor plan with both a spacious living room and separate family room area, offering flexibility for everyday living and entertaining. The kitchen overlooks the main living space and flows seamlessly through sliding glass doors to the fully fenced, expansive backyard, ideal for backyard barbeques and outdoor enjoyment. An exterior shed provides additional storage space. Major updates include: Hardie Board siding added (2008) Roof (2013) AC system (2014) with annual service, Drainfield replaced (2017) Water heater (2018) Well serviced (2025) Exterior paint (2024) Newer Sliding glass doors with Blinds between the double pane glass. Transferable termite bond, Windows have pre-cut storm boards. Septic Cleaned 2026 Living in DeLand means being part of a vibrant, welcoming community with a rich history and culture. Join the Friday and Saturday night activities, browse unique shops, enjoy locally owned restaurants, and take in the bustling farmers' market. Blue Springs State Park, De Leon Springs, and Gemini Springs, Lake Beresford Park and Hontoon Island State Park are nearby, offering endless opportunities for hiking, kayaking, and bike trails. Easy access to I-4, connecting you to Orlando, Daytona Beach, and the recently added SunRail to DeLand’s Amtrak station.

Listing is courtesy of: LANE REALTY SERVICES, LLC (386-747-5054)

Listing Agent: Pam Dean (386-747-5054)

Remarks: Under contract-accepting backup offers. Tucked away in the highly sought-after Mallory Square community, this beautifully updated 3-bedroom, 2-bath home offers nearly 2,000 square feet of stylish, move-in ready living. From the remodeled kitchen to the spa-like primary suite, every detail has been thoughtfully upgraded. Inside, you’ll find upgraded flooring and a flexible layout with two versatile flex spaces—perfect for a home office, media room, playroom, or additional living or dining space. The fully remodeled kitchen features seamless countertops, upgraded appliances, and expanded cabinetry and counter space, creating a functional and inviting space for everyday living and entertaining. The primary suite is a true retreat, complete with a beautifully renovated bathroom and soaking tub designed for relaxation. Additional upgrades and features include a fully fenced backyard for added privacy, an epoxy-coated garage floor with a transferable lifetime warranty, a new roof in 2020, and solar panels designed to help significantly reduce monthly electric costs. Conveniently located near downtown DeLand, shopping, dining, and major roadways for an easy commute, this impeccably maintained home offers the perfect blend of comfort, flexibility, and location.

Listing is courtesy of: KGV REALTY GROUP (407-474-0844)

Listing Agent: Megan Gooding (407-616-6734)

Remarks: Move-in Ready and Priced to Sell! Beautiful 3 bedroom, 2 bathroom home with brand new flooring and painted walls- ready for its new owners! Great starter home for a small family or for someone looking to downsize. Nestled on a quiet street with a HUGE backyard surrounded by beautiful trees. Conveniently located close to downtown Deland and minutes from I-4. Windows, A/C, electrical were all updated in 2018. Come take a look!

Listing is courtesy of: COLDWELL BANKER COAST REALTY (386-490-4240)

Listing Agent: Rochelle Colangelo (386-679-6567)

Remarks: Under contract-accepting backup offers. Honey Stop The Car! Look at that huge Garage in the back! Concrete Block style home with New Roof 2020, updated fixtures, new baseboards and more. Located in the Heart of Deland just minutes from Historic Downtown and Stetson University. This home also has New Laminate Flooring throughout most of the home and owners have left enough new laminate to finish off the rest of the home. Home is freshly painted outside and most inside. The huge Family room boasts a Gas Fireplace as well as access to screened covered porch. The back yard is large enough for a pool and has a 20x32 Garage-Workshop that may be used as a man cave or she shed. Close to I-4 for easy access to Orlando attractions or the beaches. Come and enjoy this turn key property today!

Listing is courtesy of: COLDWELL BANKER PREMIER (386-445-5880)

Listing Agent: Anne Leon (386-214-1292)