Refine Search
Sort by
$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

$200,000
2 Beds 1 Baths Lake Helen Blk 17 &W 1/2 Blk 18 SubDv. 32744 Zip Code
Discover timeless charm and exceptional potential with this 1935 cottage located at 130 W Pennsylvania Avenue in Lake Helen. Situated within the Downtown Commercial District (DCD) and part of the city's Historic Gateway corridor, the property offers unique flexibility with the potential for short-term rental use, live-work opportunities, or the thoughtful restoration of a classic Florida cottage. The main home features 2 bedrooms and 1 full bath, showcasing original pine wood floors, a metal roof with classic gable architecture, and a welcoming front porch reflective of its era. While the home is ready for updates and improvements, its character and setting provide a wonderful canvas for those looking to restore and personalize a charming piece of Central Florida history. Beyond the main residence, a detached 24 × 12 shed with electricity and air conditioning provides flexible space that could serve as a workshop, studio, hobby room, creative workspace, or private office. An additional structure on the property offers space for storage or potential use as an animal enclosure. Set on a generous 72 × 146 lot, the property provides ample outdoor space for gardening, animals, expansion, or outdoor enjoyment. Mature trees and peaceful surroundings add to the quiet charm that makes Lake Helen so special. Offered as-is and priced to sell, this property presents an appealing opportunity for investors, renovation buyers, or those seeking a flexible property with income potential in a unique small-town setting. Located in the charming city of Lake Helen, often referred to as the “Gem of Florida,” the area is known for its historic homes, tree-lined streets, and relaxed small-town atmosphere. Nearby are City Hall, Blake Park, the Lake Helen Equestrian Center, and local shops, while Lake Helen itself offers a public boat launch and fishing for largemouth bass, bluegill, and crappie. Whether you envision restoring a classic cottage, creating a rental opportunity, or establishing a live-work retreat, this property offers the chance to enjoy the character and charm that make Lake Helen such a special place to call home. DISCLAIMER Property is located within the Lake Helen Historic Gateway corridor and is zoned DCD (Downtown Commercial District). Short-term rentals with a minimum 30-day rental period may be permitted; however, buyers are advised to verify all zoning regulations, rental restrictions, and permitted uses directly with the City of Lake Helen. All room sizes, measurements, and property details are approximate and should be independently verified by the buyer.

130 W Pennsylvania, Lake Helen

$289,000
3 Beds 2 Baths Lake Helen Blks 51 & 60 Blakewood Resub SubDv. 32744 Zip Code
LAKE HELEN - Located on a generous .26-acre fully fenced lot, this well-maintained 3-bedroom, 2-bathroom home offers 1,524 square feet of living space which includes a 300 sq ft FL room under air, creating flexible space for everyday living. The home has seen extensive recent upgrades, including a new roof (2020), A/C system (2025), water heater (2025), septic tank and drain field (2025), and electrical panel (2025)—providing peace of mind for the next owner. Outdoor functionality is a standout feature. The property includes a 20x20 steel shop with garage door and power (2022), ideal for storage, projects, or a workshop setup, along with a 10x20 concrete pad with overhang and cooking area (2023), perfect for outdoor gatherings. Built in 1978, this home blends solid construction with modern system updates, offering a rare combination of usable outdoor space and significant improvements already completed. There is one flooring throughout which is laminate. All new interior and exterior paint. All bedrooms are spacious with closet storage. The primary bathroom has a beautiful tiled, dual head walk-in shower. Your laundry room is inside the home. Located seconds away from I4, 15 minutes from award-winning Downtown DeLand, shopping, dining, and Stetson University. Within 25 miles to numerous East Coast beaches, and 30 minutes to Orlando. Call today for your private showing. **MLS Info is intended to be correct but is not guaranteed and all information must be verified by buyers.**

444 W Main Street, Lake Helen

$176,000
2 Beds 2 Baths Lake Helen Blks 01-03 Inc Jeffery SubDv. 32744 Zip Code
Country Charm Meets Central Florida Convenience – Estate Sale in Lake Helen! If you’ve been dreaming of a little house with big potential, tucked away where the crickets sing louder than the traffic — this might just be your lucky find! This 2-bedroom, 1.5-bath home is part of an estate sale and is being sold as-is, offering a wonderful opportunity for anyone with a vision, a toolbox, and a bit of country flair. Located off the beaten path in the peaceful town of Lake Helen, this property sits in a growing area that still holds tight to its small-town charm. It’s quiet enough to feel like you’re miles away from it all, yet close enough to everything — just a short drive to the beaches, the theme parks, and all the major roadways that make Florida living so easy. Inside, you’ll find cozy living spaces waiting for your personal touch. Outside, there’s room to breathe, relax, and maybe even start that little garden or chicken coop you’ve always talked about. With a bit of love and elbow grease, this gem could shine brighter than a jar of fireflies on a summer night. So come on out and see what Lake Helen is known for — a slower pace, friendly neighbors, and a home that’s just waiting for someone to bring it back to life. Don’t miss your chance to make this sweet spot your own! More photos to come.

227 Elvira Street, Lake Helen

$259,000
3 Beds 2 Baths Lake Helen Blks 134-135 Palm Villa Resub SubDv. 32744 Zip Code
Welcome to this inviting 3-bedroom, 2-bath home located in the heart of Lake Helen, Florida. Inside, you’ll find beautiful cedar tongue-and-groove ceilings, tile flooring, and a charming kitchen featuring granite countertops and wood cabinetry. Step through the French doors to enjoy a screened-in, heated, in-ground pool and hot tub, ideal for relaxing or entertaining. The large vinyl fenced backyard includes a shed, fire pit and firewood box. Providing privacy and plenty of room to play or garden. Conveniently located near I-4 for easy access to shopping, dining, and nearby attractions, this home combines Florida charm and everyday function. This home is move-in ready and won't last long! This is a must see! *Updated metal roof, New heat pump/central air. New Hot water heater! Room dimensions and square footage are approximate and should be verified by the buyer.

450 Palm Avenue, Lake Helen

$335,000
3 Beds 2 Baths Triple S Unit 02 SubDv. 32744 Zip Code
One or more photo(s) has been virtually staged. Price improvement! Charming Home with Spacious Layout and Modern Amenities. Upon entering this meticulously maintained home, you will be immediately impressed by the open floor plan and elegant tray ceilings that create a bright and airy atmosphere. The kitchen is a true standout, featuring a large granite island with ample space for bar seating, sleek cabinetry, and a stylish decorative backsplash. Just off the kitchen, you will find a generously sized pantry and convenient laundry area for added functionality. The primary suite offers a tranquil retreat with a spacious layout and a walk-in closet. The master bathroom is a true highlight, boasting dual vanities and an expansive walk-in shower, providing a spa-like experience at home. Two well-sized guest bedrooms and a modern guest bath complete the home’s thoughtful design. This home has been freshly painted on the exterior and is in excellent condition, showcasing careful maintenance throughout. The private backyard and covered patio can be an ideal space for outdoor relaxation and entertainment, perfect for your grill and patio furniture. Conveniently located near I-4, this home offers a quick commute while maintaining a serene and private feel.

559 Virginia Drive, 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

$315,000
4 Beds 2 Baths Lake Helen Blks 50 & 61 Blakewood Resub SubDv. 32744 Zip Code
PRICE ADJUSTMENT ON THEIS DESIRABLE LAKE HELEN 4 BEDROOM 2 BATH HOME. BEAUTIFULLY RENOVATED! THIS LOVELY HOME IS IN USDA FINANCE AREA. THIS HOME FEATURES GRANITE COUNTERTOPS, CUSTOM CABINETRY, AND STAINLESS-STEEL APPLIANCES. OPEN FLOOR PLAN, 4TH BEDROOM IS SPACIOUS AND CAN SERVE AS A BONUS ROOM. INDOOR LAUNDRY ROOM COMPLETE WITH NEW WASHER AND DRYER. ENJOY THE BEAUTIFUL CAREFREE LUXURY VINYL PLANK FLOORING THROUGH OUT! THERE IS EVEN A CONCRETE SLAB IN THE BACK YARD, FOR A SHED, WORKSHOP OR STORAGE BUILDING IS DESIRED! COME ENJOY A QUAINT LIFESTYLE IN THIS WILDLIFE ABUNDANT NEIGHBORHOOD WHERE WALKING, BIKING, GOLF CARTS AND HORSES ARE THE NORM. LAKE HELEN HAS ITS OWN PD, LIBRARY, POST OFFICE, TENNIS AND PICKLE BALL COURTS, HORSE ARENA, PARKS, LAKES SCHOOLS AND LOTS MORE! EASY I-4 ACCESS AND ONLY 19 MILES FROM EAST COAST BEACH!

266 N High Street, Lake Helen

$230,000
4 Beds 2 Baths Groveland SubDv. 32744 Zip Code
BRAND NEW ROOF!! WOW! Check out this spectacular FOUR BEDROOM one and a half bathroom home nestled in heart of Lake Helen. Step inside and be greeted by the sleek and modern tile flooring that flows seamlessly throughout the entire home, making cleaning a breeze and giving a fresh, polished look to every room. The abundance of natural light pouring in through brand new windows not only illuminates the space but also contributes to an energy-efficient environment, ensuring a pleasantly low electric bill. BRAND NEW DOUBLE PANE WINDOWS!! The thoughtfully designed layout encompasses 1 full bathroom and 1 half bathroom, providing optimal functionality for both privacy and shared use. Each of the 4 bedrooms is equipped with ceiling fans to create a comfortable atmosphere and a restful retreat. The heart of the home showcases a vast living and dining area that invites a multitude of design possibilities. Whether you envision cozy gatherings with loved ones or an expansive entertainment space, this area caters to your lifestyle needs. One of the standout features of this property is the massive fenced backyard that stretches beyond your imagination. Ideal for outdoor enthusiasts, pet owners, and anyone seeking their own personal oasis, this space provides ample room for relaxation, play, gardening, and more. Located in the charming community of Lake Helen, this rental offers a serene escape while still being within reach of modern amenities and conveniences. Take advantage of nearby parks, local shops, and eateries, ensuring you have everything you need just a stone's throw away. Don't miss out on the opportunity to expand or start your investment portfolio! Schedule your exclusive tour, TODAY!

422 S Euclid Avenue, 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

$253,000
2 Beds 1 Baths Lake Helen Blks 50 & 61 Blakewood Resub SubDv. 32744 Zip Code
One or more photo(s) has been virtually staged. Welcome to this cozy home in the serene neighborhood of Lake Helen. Step inside to discover a spacious living room, bathed in warmth from the beautiful wood floors. The room's expansive layout invites you to create memorable moments with family and friends. The heart of the home is the eat-in kitchen, recently revitalized with fresh paint. It's equipped with newer, modern stainless steel appliances that are all less than two years old and a tasteful tile backsplash rounds out this lovely space. This kitchen is not just for cooking; it's a space to gather and make memories. Adjacent to the kitchen lies a massive family room. This space is a true gem, featuring a gorgeous wood ceiling that adds character and charm. It's large enough to accommodate a dining table, couch, and armchairs, making it a versatile multipurpose area for your daily activities. A unique feature of this home is the Florida room, accessible from the family room. Here, you'll find your washer and dryer, but that's not all. Bathed in natural light, it provides a tranquil view of the backyard and serves as a passageway to outdoor bliss. The home offers two bedrooms and a full bath. One bedroom ingeniously includes a Murphy bed system, optimizing space and functionality. The bathroom is not just stylish with its pedestal sink, but also practical, featuring a walk-in shower that is handicap accessible. For those who love to tinker or entertain, the detached two-car garage is a dream come true. Equipped with A/C and built-in speakers, it's an ideal space for casual gatherings or would make a fantastic workshop. The conveniences continue outside with an outdoor shop sink near the garage and a large shed equipped with electrical hookups. Whether for storage or hobby projects, these amenities add significant value to the property. Finally, the fenced backyard is a sanctuary of its own. This home features roof that is only a year and a half old along with a NEW A/C. Beautifully landscaped, it's the perfect retreat for relaxation or entertainment. This home is not just a dwelling; it offers comfort, versatility, and charm in the beautiful setting of Lake Helen. Welcome home!

377 W New York Avenue, Lake Helen

$203,440
3 Beds 1 Baths Groveland SubDv. 32744 Zip Code
Wonderful location for this Handyman Special!! Lake Helen is known as "the Gem of Florida" located 2 miles to Interstate 4, just 20 miles to East Coast beaches, a 10-minutes' drive to award winning Downtown Deland, and 30-minutes' drive to Orlando. This BLOCK home offers a screened-in front porch, 3 good sized bedrooms each with a closet, 1-bathroom, indoor laundry, living room, study/den, and a back porch. Situated on approx. 0.20-acre corner lot with a fully fenced back yard and storage shed. Updates include NEW roof in 2022, windows were updated in 2009, the storage shed in the backyard has hurricane straps. Call for your private showing today. **MLS Info is intended to be correct but is not guaranteed and all information must be verified by buyers.**

442 S Euclid Avenue, Lake Helen

$260,000
3 Beds 2 Baths Lake Helen Blks 134-135 Palm Villa Resub SubDv. 32744 Zip Code
One or more photo(s) has been virtually staged. Recent price improvement! Ready to make the move to quaint Lake Helen? This ranch style, block home features 3-bedrooms and 1 1/2-bathrooms and is nestled on 1/4 acre with a fully fenced backyard. Located on a quiet street off the main roads and no HOA! The mature landscaping and oaks offer plenty of privacy to relax on the back patio or the 12'x10' screened back porch. The kitchen features wood cabinetry and Corian countertops and is open to the living room and dining room, great for entertaining guests. All bedrooms have closets, and both guest bedrooms have newer carpet. The HVAC was replaced in 2020. Roof was replaced in 2009. Seller had the septic pumped in 2020 as well as new windows in 2009! Lake Helen is known as "the Gem of Florida" is minutes from I-4, just a 30-minute drive to Orlando, 25 miles to East Coast beaches, and minutes from award-winning Downtown Deland. Call today for your private showing. **MLS Info is intended to be correct but is not guaranteed and all information must be verified by buyers.**

425 Clough Avenue, Lake Helen

$212,000
3 Beds 2 Baths Memorial SubDv. 32744 Zip Code
Charming Home is one of a kind... 3 Story Home Antique Home built in 1940 in the renowned Spiritual Community of Cassadage. Another room with 1/2 bath is ideal to operate your own business. There is also a separate entrance and customers would not have to go inside the home. Main Floor: Foyer, Living room with decorative electric Fireplace, Master bedroom with adjacent room that could be used as a nursery, or study, office, or Large second closet. The second bedroom includes the full Bath. This room could be used as media room, bedroom, or office. The third floor is finished attic offers grand suite. This area could be sub-divided to create two bedrooms, or one bedroom with living area, or man-cave, game/play room or combination. Yours to create! Downstairs features large room with 1/2 Bath, Hookups for Washer & Dryer. This area is ideal to operate a business from home. Plus 1 Car garage, and abundance of storage under the home. Home shaded among mature vegetation and a huge but rare “Monkey Tree”. An easy walk to Cassadaga Hotel/Restuarant, Post Office, Museum, etc. under House. Lake Helen is comprised of many parks some with boat ramps, others with playgrounds, and BBQ grills, and picnic tables. Colby Park that's a short stroll away has all these amenities. Easy access to I-4. 60 miles from Disney, 50 miles from famous Daytona Beach and other beaches.

1050 Marion Street, Lake Helen