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$685,000
4 Beds ⋅ 3 Baths ⋅ Lake Helen SubDv. ⋅ 32744 Zip Code
**Nestled on 2.3 beautiful acres in the “Gem of Florida, " Lake Helen, this unique property offers a spacious main home and separate guest cottage, providing flexibility for multi-generational living, guests, or potential rental opportunities. The main residence features 3 bedrooms, 2 bathrooms, a 2 car garage, and a relaxing back patio overlooking the expansive yard. The GUEST COTTAGE includes 1 bedroom, 1 bathroom, a FULL kitchen, and split system air conditioning, creating a comfortable and private living space. The property is equipped with city water, plus a separate well for irrigation, helping maintain the lush grounds. Additional features include a workshop with a 30 amp hook up, covered carport for RV, BOAT and other toys. Recent updates include Main house Roof 2021, GUEST Cottage roof 2024 and Water Heater 2026 for added peace of mind. Enjoy the privacy and space of country-style living and ability to spread out while remaining close to local amenities, shopping, dining, and major roadways (I-4). This versatile property offers endless possibilities in the very heart of Lake Helen, Florida. It is truly one of a KIND. AUDIO VISUAL on the property!!

267 N Orange Avenue, Lake Helen
$557,000
3 Beds ⋅ 4 Baths ⋅ Map/Lk Helen SubDv. ⋅ 32744 Zip Code
Welcome to 289 Garden Street in Lake Helen. Situated on a 0.40-acre lot, this 3BR/2.5BA home offers nearly 2,400 square feet of living space, over 3,300 square feet under roof, a two-car garage under air, and an in-ground heated pool. Located just outside the historic district with no HOA, the property provides a quiet residential setting with convenient access to DeLand and Interstate 4. This Mediterranean-inspired concrete block home features a metal roof, circular driveway, and a secondary side-entry drive to the garage with additional parking space for a boat or RV. A large front veranda overlooks mature landscaping and creates a welcoming entrance. Inside, the home features tile and hardwood flooring throughout, along with a functional layout that includes a foyer, half bath, office or den with custom built-ins, family room with propane fireplace, dining room, spacious kitchen, and laundry room with second-floor laundry chute. French doors open to a covered lanai and a fully fenced backyard with an expansive pool deck and rock waterfall feature. The second floor includes three bedrooms, highlighted by a spacious primary suite with dual ensuite baths, soaking tub, separate shower, and walk-in closet. An additional full bath serves the secondary bedrooms. Recent improvements include updated landscaping and sprinkler system, pool heater, and fencing, built-in home office, garage floor coating, and a split HVAC system in the garage. This property offers a balance of indoor functionality, outdoor living, and long-term durability in one of Central Florida’s historic established residential communities.

289 Garden Street, Lake Helen
$265,000
3 Beds ⋅ 1 Baths ⋅ Jennings Lake Helen SubDv. ⋅ 32744 Zip Code
Welcome to charming Lake Helen — known as the “Gem of Florida” — where small-town charm, community connection, and peaceful living come together. Nestled beneath mature trees on a quiet street, this beautifully updated block home offers the perfect opportunity to enjoy one of Central Florida’s most beloved hidden gems. Inside, you’ll find a move-in ready home featuring updated windows, roof, HVAC, electrical, water heater, and a renovated kitchen designed for everyday comfort and convenience. The flexible floor plan offers space for a home office, playroom, or guest area, while the fully fenced backyard creates the perfect setting for relaxing evenings, pets, gardening, or entertaining around the firepit. Beyond the home itself, Lake Helen offers a lifestyle buyers are searching for — golf cart-friendly streets, community events, scenic parks, lakes, and a welcoming hometown atmosphere that’s hard to find today. Enjoy local favorites like Lil’ Lake Helen Cafe and Roma’s Pizza, spend weekends exploring nearby parks and lakes, or take advantage of the area’s beloved equestrian community and riding facilities. Conveniently located near DeLand, I-4, Orlando, and the beaches, this home offers the perfect blend of peaceful small-town living with easy access to everything Central Florida has to offer. Don’t miss your opportunity to own an affordable piece of Lake Helen charm. USDA Eligible property!

624 W New York Avenue, Lake Helen
$650,000
3 Beds ⋅ 2 Baths ⋅ Hill Blks 90 & 91 Lake Helen SubDv. ⋅ 32744 Zip Code
Assumable mortgage is available for this stunning residence in a highly desirable, well-established neighborhood, offering luxury upgrades, accessibility, and resort-style outdoor living. This magnificent 3 bedrooms, 2 baths, 3,500 sq ft residence sits on an extra-large, fully fenced lot with everything thoughtfully designed on one level for easy, comfortable living. Recent upgrades include a new roof installed last year, new central air conditioning, a new gas tankless hot water heater completed in 2025. The interior shines with real wood floors throughout, crown molding, upgraded baseboards, and extra-wide doors with smooth wood-to-tile transitions—designed for comfortable accessibility and barrier-free movement for persons with disabilities. The grand master suite features a spacious walk-in closet (newly customized in 2025) and a luxurious master bath with an upgraded shower package, including a large frameless open glass shower and premium finishes. Additional living spaces include a formal living area with fireplace, formal dining area, spacious family room, casual dining nook, and wet bar. The custom kitchen offers an open concept with timeless cherry wood cabinetry matched throughout the home, abundant storage, contrasting dark granite countertops on the bar and island, a large standalone island, and a breakfast area that overlooks the backyard. Step outside to your private resort-style oasis: a huge sparkling pool surrounded by an expansive paved deck—perfect for entertaining and enjoying Florida's long, sunny months. Perfection, value, and location all in one—this sought-after area is poised for growth with schools, shopping, dining, and much more nearby. Schedule your private showing today!

746 W Washington Avenue W, Lake Helen
$125,000
2 Beds ⋅ 2 Baths ⋅ Stevens Lot 1 SubDv. ⋅ 32744 Zip Code
*CASH ONLY- INVESTORS WELCOME & ENCOURAGED* This delightful 2-story residence, built in 1945, perfectly blends vintage charm with local history. Nestled on just under a half-acre of lush, mature landscaping, this property boasts well-established trees that provide a serene, shaded retreat. Step inside to discover beautiful wood floors that add warmth and character throughout the home. The spacious layout offers plenty of room for relaxation and entertainment, with ample natural light streaming in from above. Located just a stone's throw away from Cassadaga, you'll enjoy the convenience of nearby amenities while savoring the tranquility of Lake Helen. Plus, this home is not in a flood zone, giving you peace of mind. Don’t miss the opportunity to own this unique gem in a picturesque setting. Schedule your showing today and experience the charm of this lovely Lake Helen home!

210 Colby Lane, Lake Helen
$555,000
3 Beds ⋅ 2 Baths ⋅ 32744 Zip Code
LAKE HELEN: VERY MOTIVATED SELLER! Nestled on over four acres of serene hilltop in Lake Helen, this exceptional INGROUND POOL home offers complete privacy at the end of a peaceful dead-end street. Surrounded by majestic oak trees, the property features an screened in..inground pool and spa area incorporating a Gazebo complete with ceiling fans and lights, all you need is a cold drink and you've got a true haven of relaxation. Recent upgrades include a newer air conditioner installed in 2023, a roof replaced in 2017, an owned water treatment system and a newer well by Evan’s Well Drilling. Multiple detached structures enhance the property's versatility, including spaces for a barn, hay storage, workshop, horse stall and a caretaker’s cabin equipped with loft space and a mini kitchen. Inside, the home boasts a formal dining room, large family room and breathtaking views of the pasture from the great room. Additionally, the property has an agricultural exemption that—with the proper paperwork—can be transferred to the next owner. This rare opportunity beautifully blends comfort, functionality and natural beauty into one remarkable package.

800 Sand Crane Lane, Lake Helen
$444,990
3 Beds ⋅ 2 Baths ⋅ Lake Helen SubDv. ⋅ 32744 Zip Code
Price to Sell! Remodeled Lake Helen Retreat on 1.33 Acres – Now Only $444,990! Discover your own private paradise in this completely remodeled home sitting on a rare 1.33-acre lot in beautiful, peaceful Lake Helen — with NO HOA! Step inside to enjoy natural light-filled spaces and a modern open layout. The updated kitchen is a dream for any cook, featuring: stainless steel appliances, Sleek modern cabinets & Plenty of countertop space for prep and entertaining with 3 spacious bedrooms and 2 fully renovated bathrooms, comfort and privacy are effortless. Stylish tile flooring flows throughout the entire home — beautiful and easy to maintain. Outside, the expansive backyard offers endless potential: Garden, build, host, or just relax under the trees, Detached shed/storage building included, Brand new garage doors & Oversized driveway for multiple vehicles or even a boat or RV. Solar panels are already installed — enjoy big savings on your electric bill! Best of all: NO HOA means freedom to live your way, with no restrictions or fees. Just minutes from I-4, Deltona, Cassadaga, Sanford, and everything Central Florida has. Move- In Ready. Don’t miss this rare gem with space, privacy, and upgrades. Schedule your private showing today — this one won’t last.

237 Church Street, Lake Helen
$330,000
3 Beds ⋅ 2 Baths ⋅ Lake Helen Blk 102 SubDv. ⋅ 32744 Zip Code
2+ acres on Lake Macy. House is solid but needs updating. Property sold as is. Super lot that has 160' on Lake Macy. This lot is perfect for someone who wants space but needs to have shopping close by or be at I-4 in 8 minutes. Make it your own with your own updates. Open floor plan with fireplace. Check this home out.

695 Macy Avenue, Lake Helen
$729,000
5 Beds ⋅ 3 Baths ⋅ Memorial SubDv. ⋅ 32744 Zip Code
Enchanting Countryside Retreat in Lake Helen! Discover the timeless elegance of “the house on the hill," a stunning 5-bedroom, 3-bath residence nestled on a serene 7.94-acre estate in picturesque Lake Helen. This unique home invites you to step back to a simpler, more peaceful time without sacrificing contemporary comforts. Inside, the kitchen, is equipped with granite countertops and leads into a living area adorned with rich hardwood floors, creating a warm, inviting atmosphere, a fireplace is perfect for those chilly evenings in the family room. Recent upgrades include a new roof installed in 2020. Outdoors, the property is a haven for relaxation and entertainment. A fully enclosed veranda offers privacy and ample space for family gatherings or large parties within the expansive screened enclosure, which provides a weather-proof setting for any event. The home has a wraparound porch that overlooks pastoral views, is ideal for enjoying a tranquil morning cup of coffee. This property stands as a testament to originality in a world of uniformity. Avoid the cookie-cutter and choose a home with character and charm—choose "The house on the hill.”

455 W Kicklighter Road, Lake Helen
$895,000
6 Beds ⋅ 3 Baths ⋅ 32744 Zip Code
JUST WHAT YOU HAVE BEEN WAITING FOR!! EVERYTHING IN ONE PACKAGE!! Main house, Guest house, Horse Stalls, oversized garage for ALL YOUR TOYS!! All this on 5.14 acres in beautiful LAKE HELEN. No HOA in the country! This property is fenced in completely. The Main house is a 4br/2bath/2car garage with an inground pool. The guest house (mother-in-law suite) or potential rental is a 2BR/ 1Bath /20x30 2 car garage is a 1200 SQ unit. Bring the horses and enjoy the 36x48 horse barn with stalls that open to the paddock area. Bring your four wheelers, side by sides, or extra cars / trucks for this oversized 30x40 three car garage. This metal garage has three 10x10 roll up doors and is insulated with foam. The garage also has a covered storage area off the back of the building with 100amp power and water. Covered storage area for RV and or BOAT. The buildings are connected with graded asphalt millings for driveway through the property. New title and Quartz countertops in 2022. New air handler 2022. Each home with its own septic tank passed inspection and pumped one year ago. Two wells for easy irrigation. AMAZING LOCATION - 30 MINUTES TO SANDY BEACHES AND 40 MINUTES FROM ORLANDO.

190 Running Deer Trail, Lake Helen
$648,000
3 Beds ⋅ 3 Baths ⋅ Woods Of Lake Helen SubDv. ⋅ 32744 Zip Code
Under Construction. This beautiful custom floorplan features open-concept design with split bedrooms and separate Study/Den with french doors. Spacious Family Rm overlooks rear covered porch, and Tile flooring is featured throughout the main living areas. Kitchen features 42” upgraded cabinetry with crown molding, quartz countertops, stainless appliances, pendant lights over large island, and beautiful Tile backsplash. Expansive Primary suite includes 2 walk-in closets, and Primary bath offers dual adult-height vanities. The Woods of Lake Helen is located in the historic district in Volusia County and offers vintage style home plans including large front and back porches, and side entry garages. Come tour this unique community where you can ride golf carts, bikes, and horses through town. Close to shopping and restaurants and conveniently located near major thoroughfares.

427 W Main Street, Lake Helen
$529,990
3 Beds ⋅ 2 Baths ⋅ Woods Of Lake Helen SubDv. ⋅ 32744 Zip Code
Under Construction. This beautiful new home is located in the Woods of Lake Helen - known as " The Hidden Gem" of Florida! Lots of windows allow for plenty of natural light in this open concept plan. Kitchen includes upgraded 42" cabinetry with crown molding, stainless appliances, tile backsplash, and walk-in pantry. Spacious Primary Suite features large walk-in closet with dual adult-height vanities in Primary Bath. Expansive Great Room accommodates both dining and entertaining. The historic district in Volusia County offers exclusive vintage style home plans including front and back porches, and side entry garages allowing you to live in an old-world Florida style with all the advantages of living in a brand new home. Come tour this unique community where you can ride golf carts, bikes, and horses through town. Shopping nearby and easy access to major highways.

375 W Main Street, Lake Helen
$548,990
3 Beds ⋅ 3 Baths ⋅ Woods Of Lake Helen SubDv. ⋅ 32744 Zip Code
Under Construction. Beautiful new home located in the Woods of Lake Helen - known as " The Hidden Gem" of Florida! This open concept plan features large Gourmet Kitchen with stainless built-in ovens and cooktop, tile backsplash, and large walk-in pantry. Spacious Primary Suite features 2 walk-in closets with split vanities in Primary Bath. Great Room opens to rear covered porch, perfect for entertaining. The historic district in Volusia County offers exclusive vintage style home plans including huge front and back porches, and side entry garages allowing you to live in an old-world Florida style with all the advantages of living in a brand new home. Come tour this unique community where you can ride golf carts, bikes, and horses through town. Shopping nearby and easy access to major highways.

327 W Main Street, Lake Helen
$670,000
5 Beds ⋅ 4 Baths ⋅ Lake Helen Blk 102 SubDv. ⋅ 32744 Zip Code
True MULTIGENERATIONAL home sitting pretty on a 0.72 ACRE LOT that backs up to a conservation area in quaint community of Lake Helen. 2 homes in one. 5 Bedrooms, 4 Baths contemporary Masterpiece. OVER 3,400 Sq Ft. home with an amazing Floor plan offering 2 Living rooms, 2 dining rooms, one for each side of the home. As you step into the entryway there is a spacious Living room and formal dining room with beautiful hardwood floors. The Kitchen is every cooks dream and the heart of the home. Kitchen and dining area is done in Travertine tile. There are 3 bedrooms and two full baths on this side of the home. You can step out from the kitchen to a Vinyl Fenced courtyard, perfect for your fur babies or playground area. As you walk through the kitchen into the 2nd area, it is perfect for In-laws to have their own space or Great room for entertaining from the Lanai and pool area. Great room has a wood burning fireplace to cozy up on the couch during the cooler months. Offers 2 bedrooms and 2 full bathrooms, dining room space or exercise room. You can step through to the 18 x 19 covered lanai area and relax and enjoy the brand new salt water pool and spa. You will be able to enjoy this year round since it is solar heated. . Home has two interior Laundry/Utility Rooms. With an oversized 23 x 33 Side-Entry garage with workshop area or storage area. Garage has pull down access to a large floored storage area. Exterior storage shed conveys. Minutes to I-4 easy access. 30 min drive to the Beaches and 40 min drive to Orlando. Brand new roof and solar was installed this year and has two Tesla Battery backup units that will run the entire home, except pool in any power outage. 2 Hot water heaters for each side of the home. Panel Box was updated when new solar system was installed.

838 N Summit Avenue, Lake Helen