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$845,000
5 Beds ⋅ 3 Baths ⋅ Lake Helen SubDv. ⋅ 32744 Zip Code
Welcome to your own slice of small-town paradise in the heart of charming Lake Helen. Perfectly positioned on an oversized corner lot with breathtaking views of Lake Helen, this one-of-a-kind home offers an incredible opportunity for multigenerational living, growing families, or anyone seeking room to spread out while enjoying the relaxed Florida lifestyle. All with no HOA! Originally designed as a 2-bedroom, 2-bath home, this spacious residence has been thoughtfully expanded to 4 bedrooms, 3 bathrooms, and an impressive 3,566 square feet of living space, plus a versatile upstairs loft with a closet that can easily serve as a fifth bedroom, guest suite, home office, or playroom. One of the home's standout features is its two private primary suites, each complete with walk-in closets and en-suite bathrooms, making it ideal for extended family, guests, or flexible living arrangements. Inside, you'll find an inviting open-concept layout where the kitchen and great room flow seamlessly together around a cozy wood-burning fireplace. A separate dining room, dedicated office or flex space, and expansive living areas provide endless possibilities for everyday living and entertaining. Large picture windows frame stunning views of Lake Helen, filling the home with natural light and creating a peaceful backdrop throughout the day. Recent updates provide peace of mind, including a new roof (2022), two new air conditioning systems (2024), new dishwasher and stove (2024), seamless gutters (2022), and solar panels installed in 2025 for improved energy efficiency. Tile flooring runs throughout the home, and outside you'll enjoy a fully vinyl-fenced backyard featuring a new 24-foot above-ground pool, extended driveway with room for your boat or RV, and no HOA restrictions. BRAND NEW COUNTERTOPS being installed pictures will be updated! Just across the street, embrace true lake life. Spend your mornings fishing, kayaking, canoeing, or simply enjoying the beautiful waterfront views. You'll also enjoy front-row access to Lake Helen's beautifully restored pavilion, completed through the Legacy Project, with an exciting second phase already underway that will include a brand-new public dock. Whether you're watching community events, taking evening strolls around the lake, or enjoying the friendly atmosphere that makes Lake Helen so special, this location offers a lifestyle that's difficult to replicate. If you've been searching for generous square footage, flexible living spaces, lake views, and the warmth of one of Central Florida's most beloved small towns, this exceptional home is ready to welcome you.

212 Pleasant Street, Lake Helen
$325,000
3 Beds ⋅ 2 Baths ⋅ Mc Gill Rep SubDv. ⋅ 32744 Zip Code
Under contract-accepting backup offers. This is it—your own slice of paradise! Welcome to 390 High Street in Lake Helen, Florida. This charming 3-bedroom, 2-bath farmhouse is picture-perfect, with abundant natural light, an updated kitchen, soaring ceilings, and a spacious deck overlooking the pond—ideal for entertaining. Sitting on nearly 1/3 of an acre with no HOA, there’s plenty of room to bring your toys. Need extra storage? A shed is included on the property. USDA offers 100% financing for qualified buyers. The roof was replaced in 2016, and a survey is available. Zoned for Deland High School—go Bulldogs!

390 N High Street, Lake Helen
$615,000
3 Beds ⋅ 2 Baths ⋅ Troy SubDv. ⋅ 32744 Zip Code
BEAUTIFUL AND UNIQUE CUSTOM HOME ON 1/3 ACRE LOT IN HEART OF LAKE HELEN. FANTASTIC LOCATION. NO HOA HERE. THIS 3 BEDROOM 2 BATH GEM BOASTS A SPLIT PLAN WITH 2 PRIMARY SUITES AND A THIRD BONUS ROOM CAN ALSO BE A 3RD BEDROOM. DESIGNED FOR COMFORT AND FLEXIBILITY. THE FIRST PRIMARY SUITE OFFERS A LARGE, SPACIOUS BATHROOM WITH SOAKING TUB, SEPARATE SHOWER, WATER CLOSET, AND TWO WALK IN CLOSETS. THE SECOND PRIMARY SUITE INCLUDES A PRIVATE BATH WITH A TUB SHOWER COMBO, IDEAL FOR GUESTS OR MULTIGNERATIONAL LIVING. VAULTED CEILINGS AND AN OPEN FLOOR PLAN AND SKYLIGHTS CREATE A BRIGHT, AIRY FEEL THROUGHOUT THE MAIN LIVING AREAS. THE KITCHEN SHOWCASES CUSTOM WOOD CABINETRY AND GRANITE COUNTERTOPS. CUSTOM FEATURES CAN BE FOUND THROUGHOUT THE HOME, ADDING CHARACTERR AND THOUGHTFUL DESIGN ELEMENTS AT EVERY TURN. ADDITIONAL INTERIOR HIGHLIGHTS INCLUDE A SMALL OFFICE, INDOOR LAUNDRY ROOM AND ABUNDANT STORAGE. ENJOY TRUE INDOOR-OUTDOOR LIVING WITH EXPANSIVE SCREENED WRAP AROUND BACK PORCHES. THE HOMES SLIDING DOORS FOLD INO THE WALL OPENING THE HOME TO ADDITIONAL LIVING SPACE DURING THE COOLER MONTHS. THE FRONT OF THE HOME FEATURES INVITING COVERED PORCHES OVERLOOKING A CHARMING COURTYARD, PERFECT FOR RELAXING OR ENTERTANING.

250 Garden Street, Lake Helen
$275,000
2 Beds ⋅ 2 Baths ⋅ Lake Helen Blks 132-133 146-147 Harlan Oaks SubDv. ⋅ 32744 Zip Code
This move-in ready 2 bedroom, 2 bath house is located in a quiet neighborhood in the “Gem” of Florida, Lake Helen. The home features a large living room, galley kitchen, dining area, with cathedral ceiling and a large sunroom facing the backyard. The exterior offers an approximate 20’ x 30’ detached garage, an RV port, a shed and is partially fenced.

461 Austin Street, Lake Helen
$714,000
4 Beds ⋅ 4 Baths ⋅ Jennings Lake Helen SubDv. ⋅ 32744 Zip Code
One or more photo(s) has been virtually staged. Pre-Construction. To be built. The "Summit House" — A Custom 4BR/2.5 BA Estate with Private In-Law Wing. Experience the ultimate "Whole Living" sanctuary in the heart of historic Lake Helen. This 2026 custom build represents a rare opportunity for multi-generational living. Spanning 2,391 square feet of living area and 3,336 total square feet under roof, this residence is designed for luxury, wellness, and durability. The Main Residence: The sun-drenched open floor plan is the heart of the home, featuring soaring 9'-4" ceilings throughout. The grand living and kitchen area is anchored by a stunning fireplace and elevated by custom exposed wood beams that span the ceiling, adding architecturally significant character and warmth. The gourmet kitchen is a chef's dream, featuring a massive island and premium gas appliances. The Private In-Law Suite: A standout feature of this estate is the fully integrated 552 sq. ft. In-Law Suite. Boasting its own private side entry porch, living area, full bathroom, and bedroom, this wing is ideal for aging parents, a high-end home office, or a long-term guest retreat. Mechanical Excellence & Future Potential: Tankless Gas Performance: Enjoy endless hot water with dual independent tankless gas water heaters serving the main residence and in-law suite separately. Pool-Ready Courtyard: The central courtyard has been intentionally designed to accommodate a future pool installation, offering the perfect foundation for your private backyard oasis.“PRE-CONSTRUCTION BONUS: Listed price of $714,000 INCLUDES a custom, in-ground courtyard pool and premium hardscape package to be completed by the builder! Want the home but don't need a pool? Builder is offering a direct $52,000 credit/deduction for buyers who prefer the estate without the pool package, bringing the purchase price down to an incredibly competitive $662,000. Don't miss this rare new construction opportunity featuring a fully integrated 552 sq. ft. private in-law/multi-generational suite under roof, Outdoor Living: Relax on the 212 sq. ft. front porch with wood flooring or the spacious screened-in rear porch. Energy & Safety: Outfitted with 2 high-efficiency Heat pump systems. Located minutes from Ivy Hawn Charter School this home offers the peace of the "Gem of Florida" with the modern performance of an expert custom build. No HOA and no compromises.

360 N Summit Avenue, Lake Helen
$320,000
3 Beds ⋅ 2 Baths ⋅ Norris Lake Helen SubDv. ⋅ 32744 Zip Code
Data Entry only - 3 bedroom, 2 bathroom in lovely Lake Helen.

416 Norris Lane, Lake Helen
$604,000
3 Beds ⋅ 3 Baths ⋅ 32744 Zip Code
PRICE IMPROVEMENT! Beautiful 11 acre property situated in Lake Helen. Looking to homestead? This is the property for you. Two story home with 3 bedrooms 2.5 bathrooms with over 1,900 sq ft of living space. Recently painted throughout and new HVAC units. Large green house, carports, and appears to be mostly barbed wire fenced. This is a Fannie Mae Homepath property.

2840 Ranch Road, Lake Helen
$900,000
4 Beds ⋅ 4 Baths ⋅ Lake Helen Blk 102 SubDv. ⋅ 32744 Zip Code
Welcome to this beautifully updated estate on 2.5 serene acres in the heart of Lake Helen. Built in 2000 and thoughtfully renovated, this 2,845 sq. ft. home blends modern updates with country charm. Offering 4 bedrooms, 2.5 baths, and a private office, it’s designed to suit both everyday living and entertaining. An oversized 2-car garage provides ample space for vehicles, storage, or hobbies. Inside, you’ll love the brand-new flooring and kitchen, along with peace of mind from recent upgrades including a new A/C and water heater (2024) and a new roof (2017). City water service adds convenience, while an automatic generator powered by a 500-gallon propane tank ensures comfort in any season. Step outside and enjoy your own resort-style retreat. The screened patio, overlooking the pool (resurfaced in 2019) is the centerpiece, complemented by an outdoor kitchen and cozy fireplace, perfect for gatherings with family and friends. A major highlight of this property is the 2,700 sq. ft. detached building, offering endless opportunities for Boat/RV storage, workshops, or business use. It also includes a 500 sq. ft. apartment, ideal for in-laws, guests, or potential rental income. For those desiring even more room to expand, an adjacent 2-acre parcel is available with the purchase. Conveniently located near I-4 with easy access to Orlando, Daytona, and surrounding areas, this estate offers the best of both worlds—privacy and space, with city conveniences just minutes away. Don’t miss your chance, please call to schedule a private showing!

591 Lake Pearl Drive, Lake Helen
$650,000
4 Beds ⋅ 4 Baths ⋅ Edgewood Estates SubDv. ⋅ 32744 Zip Code
Welcome to this brand-new construction home located in the charming town of Lake Helen, known as the ''Gem of Florida.'' Situated on a .49-acre corner lot, this 4 bedroom, 4 bathroom residence blends modern luxury with timeless design. From the moment you arrive, the large tiled front porch with cedar-paneled ceiling sets the tone for the quality and craftsmanship found throughout. Inside, vaulted ceilings and upgraded Acoustic LVP flooring flow seamlessly through the open layout, while recessed lighting and modern fixtures highlight the elegant finishes. The chef's kitchen features stainless steel appliances, a pot filler above the cooktop, brushed gold cabinet accents, and an expansive island, all opening to the living area with sliding accordion glass doors that bring the outdoors in. The primary suite is a true retreat, complete with tray ceilings, a spacious 10x11 walk-in closet, and a luxurious bathroom offering a double vanity, resort-style shower, and free-standing tub, all accented with elegant brushed gold hardware. Additional bedrooms and bathrooms are thoughtfully designed to provide comfort and privacy, while a large office space filled with natural light creates the perfect setting for working from home. Designed for both everyday living and entertaining, this home includes two AC units, a three-car garage, and a cedar-paneled back porch. It is also pre-wired for a home speaker system and future pool installation, giving you flexibility to enhance your lifestyle. Every detail has been carefully considered, from the brushed gold accents to the modern light fixtures, ensuring a home that is both sophisticated and functional. Lake Helen's unique character shines through with its small-town charm, quaint shops, and peaceful atmosphere, making this property the perfect opportunity to own a truly prestigious home in one of Florida's most special communities.

292 W Delaware Avenue, Lake Helen
$440,000
2 Beds ⋅ 2 Baths ⋅ Baker & Peltons Rep SubDv. ⋅ 32744 Zip Code
One or more photo(s) has been virtually staged. Welcome to the Lake House, a rare lakefront gem nestled in the beautiful and quaint town of Lake Helen — a peaceful place to call home. This charming property offers a true retreat with clear, spring-fed Lake Helen, perfect for canoeing, kayaking, swimming, and fishing. Lake Helen Park also known as Royal Park, offers a bandstand, boat launch, fishing areas, picnic areas and walking/hiking trails. Nearly every room in the home provides a stunning view of the lake, and the expansive 20x40 ft back deck is the perfect place to relax and enjoy breathtaking sunsets each evening. Situated on a spacious 0.63-acre lot, this home features 2 bedrooms, 2 bathrooms, and 1,950 heated square feet, all wrapped in a cozy cabin-style feel with rich wood accents throughout. The primary bedroom boasts vaulted ceilings, a large walk-in closet, and sliding doors that open directly to the back deck — complete with an electric hookup ready for your future hot tub. The primary bathroom has been beautifully remodeled with a large walk-in shower, and the family room features a warm and inviting fireplace. This home has seen thoughtful updates, including a new metal roof in 2023, concrete siding added in 2024, a new hot water heater in 2025, and new insulated windows and doors for improved energy efficiency. The attached 1,000-square-foot garage offers plenty of space for two cars plus a large workshop with built-in cabinets — ideal for hobbies, a studio, or even band practice. There’s even a rare root cellar perfect for storing canned goods or wine. Located just minutes from the local farmers market and beloved city park, this property offers not just a home but a lifestyle. It’s a rare opportunity to own a true lakefront home on Lake Helen, where charm, nature, and comfort come together in one unforgettable setting.

160 Rose Avenue, 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
$700,000
3 Beds ⋅ 4 Baths ⋅ Lake Helen SubDv. ⋅ 32744 Zip Code
Many possibilities

140 E Michigan Avenue, Lake Helen
$279,900
2 Beds ⋅ 1 Baths ⋅ Lake Helen Blk 16 SubDv. ⋅ 32744 Zip Code
Own a piece of history. Charming 1940 Cottage in the Historical District of Lake Helen. Come in and step back in time. 2BR 1BA Viking Gas Range for the Gourmet Chef. Many upgrades in 2018. New Roof, new bathroom, insulated windows, 2 mini-split AC/Heat units for energy efficiency. If you’re looking for charm and not a cookie cutter house, this could be it.

171 W Pennsylvania Avenue, Lake Helen
$350,000
3 Beds ⋅ 2 Baths ⋅ Baker & Peltons Sub SubDv. ⋅ 32744 Zip Code
One or more photo(s) has been virtually staged. AMAZING PRICE REDUCTION FROM THESE MOTIVATED SELLERS! EXCELLENT OPPORTUNITY TO LIVE IN DESIRABLE LAKE HELEN! BEAUTIFUL AND UPDATED. 3/2 POOL HOME LOCATED ON A QUIET CORNER LOT, IT HAS A FULLY FENCED BACK YARD WITH WIDE GATE FOR RV ENTRY. THERE IS A LARGE PARTIALLY COVERED SCREENED IN BACK PORCH FOR YOUR MORING COFFEE AND AFTERNOON BARBECUES, THEN ENJOY COOLING OFF IN THE NEWER ABOVE GROUD POOL FOR SOME SUMMERTIME FUN! INSIDE THERE ARE 3 LARGE BEDROOMS AND 2 FULL BATHROOMS. THI IS A SPLIT PLAN LAYOUT, AND BEAUTIFULLY UPDATED WITH NEWER FLOORING, BASE BOARDS, CROWN MOLDINGS, AND MUCH MORE. YOU WILL ENJOY THE SPACIOUS LIVING ROOM WITH HIGH CEILINGS AND A BEAUTIFUL WOOD BURNING FIREPLACE WITH ITS CUSTOM STONE HEARTH. THERE IS A WIDER GATE ACCESS FOR VEHICLE ACCESS TO BACK YARD OR STORAGE OF BOAT AND THERE IS A NICE BLOCK WORKSHOP WITH ELECTRIC FOR STORAGE OR SHOP PURPOSES. THE ROOF IS ONLY 8 YEARS OLD! FANTASTIC LOCATION WITH QUICK ACCESS TO I-4 AND HWY 44, WHICH WILL LEAD YOU DIRECTLY TO THE BEAUTIFUL NEW SMYRNA BEACH! LAKE HEKEN IS A BEDROOM COMMUNITY IN HIGH DEMAND DUE TO THE QUAINTNESS OF THE CITY AND THE AMENITIES IT PROVIDES: GOLF CARTS ARE ALLOWED, THERE IS ABUNDANT WILDLIFE, OUR OWN POST OFFICE, LIBRARY, FIRE STATION, POLICE DEPARTMENT, EQUESTRIAN CENTER, TENNIS COURTS, SHUFFLEBOARD COURT, PARKS, HORSES, LAKES, GREAT SCHOOLS AND MUCH MORE! THIS LOVELY HOME IS NOT IN AN HOA.

296 N Orange Avenue, Lake Helen
$390,000
4 Beds ⋅ 3 Baths ⋅ Lake Helen Blk 102 SubDv. ⋅ 32744 Zip Code
If you know Lake Helen then you know what a gem it is to find a 4 bedroom, 2.5 bathroom, 2 car garage, block home on over 1/2 an acre in this location! Being extremely close to I-4 for commuting to pretty much anywhere, this small town has a historic charm and is also close to New Smyrna Beach, Deland and Daytona Beach! The home features a split plan with a formal dining room, formal living room, formal family room and a bonus room off of the master bedroom! The kitchen is the center of the home so you still have a somewhat open feeling even though you do have a more formal layout. The interior laundry with a half bath is a great size allowing for storage. All new engineered hardwood flooring was done last year, a new roof was installed in 2023 and the AC was replaced in 2021! The yard is fully fenced and also features a large detached workshop/shed. Realtors please see realtor remarks.

431 Tiffany Lane, Lake Helen
$167,500
2 Beds ⋅ 1 Baths ⋅ Lake Helen Blk 24 SubDv. ⋅ 32744 Zip Code
Heart of Lake Helen Home Back on Market. Buyer loss and Now Your Gain. Charming home located across the street of Lake Helen's central park. Farmer's market on Saturdays. Children's playground and community activities. Home needs TLC, but has so much potential with wood floors and gorgeous wood ceilings in living/dining room. Interior has been painted. Yard is spacious to plant flowers, food garden, and a pool. Horse lovers can board their horses and enjoy riding, training, playing with their horses at Lake Helen Equestrian Center. The center is walking distance. Equestrian offers outdoor rodeo arena, spacious stalls, and practice areas, and much more. The shed, pool, and tent in back belong to the tenants. Easy access to I-4, shopping, delicious food, parks, and more. Plenty of room for a pool. Seller is Florida licensed real estate agent.

150 E Washington Avenue, Lake Helen
$389,000
4 Beds ⋅ 3 Baths ⋅ Yourlando SubDv. ⋅ 32744 Zip Code
Country living in the city! This wonderful home has been remodeled and ready for it's new owners! As you enter, you'll find brand new LVP floors throughout along with new light fixtures, ceiling fans and blinds! The kitchen has been updated and has brand new granite counters! There's plenty of cabinet space with built-in pantry with slide out drawers and stainless steel appliances! The spacious family room has high ceilings and french doors leading to the large lanai. Once outside you'll find a 24 x 16 shed with french doors and electricity. There's an additional small shed as well. The split bedroom floor plan is attractive for those wanting privacy. The large spacious master bedroom has a large walk in closet and a master bathroom with shower, tub and dual sink vanity and private entrance to the lanai. The additional 2 bedrooms have large closets and are next to the updated bathroom with new vanity! There's also a 399 sf in-law studio/bonus room/4th bedroom through the utility room! It has a large closet and an updated half bath. As a bonus, it also has a private entrance! There's also formal living and dining areas as well. The large carport is perfect for your boat or camper! Additional upgrades in this home include: new HVAC 2023, new Hot Water Heater 2023, new Roof 2022. All of this on .34 of an acre! Conveniently located near schools, medical, I-4, restaurants and shopping! Schedule your showing today!

1070 Matanzas Street, Lake Helen
$505,000
3 Beds ⋅ 2 Baths ⋅ Edgewood Estates SubDv. ⋅ 32744 Zip Code
In Historical Lake Helen, this 3 bedroom 2 bath 2 car garage sits on a nicely landscaped .52 acre corner lot with covered front porch. ;Water: City

260 S Euclid Avenue, Lake Helen
$750,000
4 Beds ⋅ 3 Baths ⋅ Westside SubDv. ⋅ 32744 Zip Code
One or more photo(s) has been virtually staged. Standing proudly in succession among other equally admirable estates, this strikingly beautiful home reflects the character of the historic City of Lake Helen, the gem of Florida, known for its old Florida charm, graced with Victorian architecture of yesteryear and now the current rage of newly built, high-end homes. The MAIN HOUSE (1568 sf) - CUSTOM-BUILT by a local builder for his private residence, the quality and craftsmanship exceed the norm with CEMENT BLOCK POURED with CONCRETE, high-quality stucco, and real stone. Soaring VAULTED CEILINGS, CROWN MOLDING, PLANTATION SHUTTERS, a SKYLIGHT, CUSTOM MILLWORK and CABINETRY, all crafted to create a home with elegance, inviting cottage charm, warm character and simple sophistication! Two sets of FRENCH DOORS open to a COVERED and SCREENED LANAI with a SALT WATER, SELF-CLEANING, HEATED POOL surrounded only by flora and fauna creating a private escape to a world all its own. The GUEST HOUSE (308 sf) - Complete with its own front porch and private garage, the efficiency suite, with a fully functional kitchen, bath, and large walk-in closet, could easily be expanded by incorporating what is presently a storage room as the entire area is 840 sf under roof. The METAL BUILDING - New as of 2023 measuring 40’x40’ and 16’ at center height, it is equipped with 200 amp electrical, has a 6” concrete slab with 3400 pcf and an epoxy finishing, one door measuring 12’x12’ and another 12’x20’, and will convey with a self-standing air conditioning unit. The LAND and POND - Arising from a setting that is truly storybook worthy, a picturesque TWO ACRE SPRING-FED POND filled with brim and bass naturally borders the north end of the FIVE FENCED ACRES with CODED GATE ENTRY. The property also boasts additional fenced cross-sections, one for gardening and another for animals. A large chicken coop with water and electricity is positioned at the rear of the property near a back-entry double gate. Water heaters-2023. Roof-2017. A fire hydrant is just outside the front gate on the other side of the road.

1102 Mckenzie Road, Lake Helen