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20299 Fleming Cir Unit 82, Rehoboth Beach

Welcome to 20299 Fleming Circle, one of the most desirable homes in the Keys of Marsh Harbor — perfectly located to enjoy everything Rehoboth Beach has to offer. From beautiful beaches and the iconic boardwalk to outstanding restaurants, premier outlet shopping, and brand-new nearby shopping, dining, and gym facilities just a short walk away — plus the Park & Ride with convenient beach service — the location truly can’t be beat. This beautifully maintained and updated home is perfectly situated on a quiet cul-de-sac and boasts arguably the best setting in the community, backing directly to the community’s only pond with serene water views and a fountain. Enjoy the scenery and abundant wildlife from the spacious, maintenance-free deck. Offering just over 2,400 square feet, this home features a bright, open, and flowing floor plan beginning with a tiled foyer, generous living and dining rooms, and a large kitchen with Corian countertops, double sink, breakfast bar, and a cozy sitting area with a gas fireplace. The spacious primary suite features a tray ceiling, plush carpeting, and a walk-in closet. The tiled primary bath includes double sinks, an additional vanity, soaking tub, separate toilet area, and linen closet. Three additional carpeted bedrooms are privately set apart from the primary suite and share a full tiled hall bath. A tiled powder room is conveniently located near the large laundry room with tile flooring, which also provides access to the conditioned crawl space. Additional highlights include: Two-car garage with automatic openers Sun-filled tiled sunroom Engineered hardwood floors throughout main living areas Maintenance-free deck overlooking the pond and fountains — perfect for relaxing and enjoying nature Major renovations and upgrades include: 2019: Kitchen appliance upgrades and conversion to gas cooking 2020: New carpeting in bedrooms and ceiling fans 2022: New siding, dining room chandelier, garage lamps, tankless water heater, new fireplace, and new air conditioner 2023: Primary bath renovation, fourth bedroom addition, and new glass door system to deck 2024: New furnace 2025: Interior ceilings and trim painted, new landscaped beds installed Keys of Marsh Harbor is a maintenance-free community, including lawn care, irrigation, siding (brand new on this home), and roofing. Residents also enjoy a saltwater pool and tennis courts for summer fun. Nothing to do but move right in and start enjoying this exceptional home in one of Rehoboth Beach’s most convenient and desirable communities. Whether you’re looking for a primary residence, vacation escape, or investment opportunity, this property fits the bill. Short-term rentals allowed.

4 Beds ⋅ 3 Baths

Welcome to 20299 Fleming Circle, one of the most desirable homes in the Keys of Marsh Harbor — perfectly located to enjoy everything Rehoboth Beach has to offer. From beautiful beaches and the iconic boardwalk to outstanding restaurants, premier outlet shopping, and brand-new nearby shopping, dining, and gym facilities just a short walk away — plus the Park & Ride with convenient beach service — the location truly can’t be beat. This beautifully maintained and updated home is perfectly situated on a quiet cul-de-sac and boasts arguably the best setting in the community, backing directly to the community’s only pond with serene water views and a fountain. Enjoy the scenery and abundant wildlife from the spacious, maintenance-free deck. Offering just over 2,400 square feet, this home features a bright, open, and flowing floor plan beginning with a tiled foyer, generous living and dining rooms, and a large kitchen with Corian countertops, double sink, breakfast bar, and a cozy sitting area with a gas fireplace. The spacious primary suite features a tray ceiling, plush carpeting, and a walk-in closet. The tiled primary bath includes double sinks, an additional vanity, soaking tub, separate toilet area, and linen closet. Three additional carpeted bedrooms are privately set apart from the primary suite and share a full tiled hall bath. A tiled powder room is conveniently located near the large laundry room with tile flooring, which also provides access to the conditioned crawl space. Additional highlights include: Two-car garage with automatic openers Sun-filled tiled sunroom Engineered hardwood floors throughout main living areas Maintenance-free deck overlooking the pond and fountains — perfect for relaxing and enjoying nature Major renovations and upgrades include: 2019: Kitchen appliance upgrades and conversion to gas cooking 2020: New carpeting in bedrooms and ceiling fans 2022: New siding, dining room chandelier, garage lamps, tankless water heater, new fireplace, and new air conditioner 2023: Primary bath renovation, fourth bedroom addition, and new glass door system to deck 2024: New furnace 2025: Interior ceilings and trim painted, new landscaped beds installed Keys of Marsh Harbor is a maintenance-free community, including lawn care, irrigation, siding (brand new on this home), and roofing. Residents also enjoy a saltwater pool and tennis courts for summer fun. Nothing to do but move right in and start enjoying this exceptional home in one of Rehoboth Beach’s most convenient and desirable communities. Whether you’re looking for a primary residence, vacation escape, or investment opportunity, this property fits the bill. Short-term rentals allowed.

20299 Fleming Cir Unit 82, Rehoboth Beach

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: RE/MAX Realty Group Rehoboth.

20389 Mallory Square Cir, Rehoboth Beach

$735,000

BACK ON MARKET and priced to sell!!!! Great opportunity to own a beach home that is literally walking, biking distance to beaches, bike trails, shopping and route 1. Also, ideal for the smart investor. Community allows seasonal rentals and long-term rentals. “5BR Beach Home | Just minutes from the beach | Walk to Dining | Rental Income Opportunity” Welcome to Keys of Marsh Harbor, where coastal convenience meets exceptional investment potential. This spacious 5-bedroom, 4-bath home is located within walking distance to popular restaurants and shopping and just minutes from the beach, making it an ideal coastal retreat, full-time residence, or high-demand vacation rental. With five generously sized bedrooms, including two private en-suite retreats, the home offers plenty of space for family, guests, and vacation renters. The open main living area flows seamlessly from the bright family and dining space into a large, well-appointed kitchen, creating the perfect gathering space after a day at the beach. Step outside to the screened porch, an inviting place to enjoy morning coffee, evening cocktails, or relaxing coastal breezes. One of the biggest advantages of owning in Keys of Marsh Harbor is the maintenance-free lifestyle. The association takes care of exterior maintenance—including roofing, siding, and landscaping—so you can spend more time enjoying the community’s pool and tennis courts, nearby beaches, restaurants, and shopping. With five bedrooms in a prime beach-area location, this home offers an incredible rental income opportunity with strong appeal for seasonal vacation renters as well as long-term tenants. Whether you're searching for a coastal getaway, full-time residence, or a smart investment property, this home delivers the perfect combination of space, location, amenities, and income potential just minutes from the Delaware beaches. Easy to show!

5 Beds ⋅ 4 Baths

BACK ON MARKET and priced to sell!!!! Great opportunity to own a beach home that is literally walking, biking distance to beaches, bike trails, shopping and route 1. Also, ideal for the smart investor. Community allows seasonal rentals and long-term rentals. “5BR Beach Home | Just minutes from the beach | Walk to Dining | Rental Income Opportunity” Welcome to Keys of Marsh Harbor, where coastal convenience meets exceptional investment potential. This spacious 5-bedroom, 4-bath home is located within walking distance to popular restaurants and shopping and just minutes from the beach, making it an ideal coastal retreat, full-time residence, or high-demand vacation rental. With five generously sized bedrooms, including two private en-suite retreats, the home offers plenty of space for family, guests, and vacation renters. The open main living area flows seamlessly from the bright family and dining space into a large, well-appointed kitchen, creating the perfect gathering space after a day at the beach. Step outside to the screened porch, an inviting place to enjoy morning coffee, evening cocktails, or relaxing coastal breezes. One of the biggest advantages of owning in Keys of Marsh Harbor is the maintenance-free lifestyle. The association takes care of exterior maintenance—including roofing, siding, and landscaping—so you can spend more time enjoying the community’s pool and tennis courts, nearby beaches, restaurants, and shopping. With five bedrooms in a prime beach-area location, this home offers an incredible rental income opportunity with strong appeal for seasonal vacation renters as well as long-term tenants. Whether you're searching for a coastal getaway, full-time residence, or a smart investment property, this home delivers the perfect combination of space, location, amenities, and income potential just minutes from the Delaware beaches. Easy to show!

20389 Mallory Square Cir, Rehoboth Beach

Listing courtesy of Iron Valley Real Estate at The Beach. Contact:

Selling Office: RE/MAX Realty Group Rehoboth.

20234 Whitehead Cir Unit 100, Rehoboth Beach

$700,000

Discover your ultimate beach retreat, just moments from the vibrant Rehoboth Beach Boardwalk! This updated single-level home combines modern elegance with coastal charm, perfect for relaxation and making memories. The sleek kitchen features stainless steel appliances, Granite and Quartz countertops, and ample cabinetry. Hardwood floors flow through the open-concept living area, complemented by stylish built-ins. The all season sunroom, with heated tile floors and new pocket doors, offers a light-filled sanctuary for morning coffee or serene evenings. The primary suite includes private sunroom access, while thoughtful upgrades like a conditioned crawlspace, new HVAC system (2024) with propane backup, tankless water heater, and whole-house water filtration enhance functionality. Recent updates include Renewal by Andersen windows (2024) and Pella windows and sliding doors (2023) in the sunroom for comfort and energy efficiency. Step outside to a private outdoor haven featuring a paved patio, a deck with a retractable awning, and a 2-car garage. This low-maintenance condo community provides access to a pool, tennis courts, and is within walking distance to shopping and dining. With its close proximity to Rehoboth Beach and all its attractions, this home offers excellent Rental and Investment potential. Experience a lifestyle where every day feels like a getaway! Some rooms are virtually staged.

3 Beds ⋅ 2 Baths

Discover your ultimate beach retreat, just moments from the vibrant Rehoboth Beach Boardwalk! This updated single-level home combines modern elegance with coastal charm, perfect for relaxation and making memories. The sleek kitchen features stainless steel appliances, Granite and Quartz countertops, and ample cabinetry. Hardwood floors flow through the open-concept living area, complemented by stylish built-ins. The all season sunroom, with heated tile floors and new pocket doors, offers a light-filled sanctuary for morning coffee or serene evenings. The primary suite includes private sunroom access, while thoughtful upgrades like a conditioned crawlspace, new HVAC system (2024) with propane backup, tankless water heater, and whole-house water filtration enhance functionality. Recent updates include Renewal by Andersen windows (2024) and Pella windows and sliding doors (2023) in the sunroom for comfort and energy efficiency. Step outside to a private outdoor haven featuring a paved patio, a deck with a retractable awning, and a 2-car garage. This low-maintenance condo community provides access to a pool, tennis courts, and is within walking distance to shopping and dining. With its close proximity to Rehoboth Beach and all its attractions, this home offers excellent Rental and Investment potential. Experience a lifestyle where every day feels like a getaway! Some rooms are virtually staged.

20234 Whitehead Cir Unit 100, Rehoboth Beach

Listing courtesy of Compass. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

20240 Whitehead Cir Unit 99, Rehoboth Beach

$675,000

Discover the perfect blend of comfort, convenience, and investment potential in this beautifully updated four-bedroom, two-bath home in the Keys of Marsh Harbor. The thoughtfully updated interior features a sleek kitchen renovation completed in 2021, showcasing new cabinetry, quartz countertops, stainless steel appliances, and luxury vinyl plank flooring that extends throughout the main living areas. The open-concept design seamlessly connects the kitchen to the dining area and inviting family room, where a cozy fireplace creates the perfect gathering space. The spacious primary suite offers a private retreat with a large walk-in closet and an ensuite bath featuring a soaking tub and separate walk-in shower. Two guest bedrooms at the front of the home share a full bath, while a versatile fourth bedroom with French doors off the living area provides the perfect space for a home office, gym, study, or guest room. Enjoy outdoor living on the screened porch overlooking the backyard, and take advantage of the attached two-car garage for added convenience. Additional updates include a new air conditioning unit and siding (2020), and a new furnace, tankless hot water heater, and sump pump (2024-2025). The crawl space, accessible from inside the home, offers exceptional storage space. Residents of Keys of Marsh Harbor enjoy community amenities including a swimming pool and tennis courts. With weekly rentals permitted (see community regulations), this property also presents an outstanding opportunity for investors seeking rental income in one of Rehoboth Beach's most sought-after locations. The HOA dues cover most of the home's exterior, including the roof, siding, and lawn maintenance! Ideally located less than two miles from the Rehoboth Beach Boardwalk, this single-level home offers easy coastal living with restaurants, shopping, fitness centers, and entertainment just minutes away. Take a short stroll across the street to Fresh Market, Planet Fitness, Blue Coast Seafood, and Thompson Island Brewery! Whether you're looking for a primary residence, vacation getaway, or investment property, this move-in-ready home offers the best of coastal Delaware living.

4 Beds ⋅ 2 Baths

Discover the perfect blend of comfort, convenience, and investment potential in this beautifully updated four-bedroom, two-bath home in the Keys of Marsh Harbor. The thoughtfully updated interior features a sleek kitchen renovation completed in 2021, showcasing new cabinetry, quartz countertops, stainless steel appliances, and luxury vinyl plank flooring that extends throughout the main living areas. The open-concept design seamlessly connects the kitchen to the dining area and inviting family room, where a cozy fireplace creates the perfect gathering space. The spacious primary suite offers a private retreat with a large walk-in closet and an ensuite bath featuring a soaking tub and separate walk-in shower. Two guest bedrooms at the front of the home share a full bath, while a versatile fourth bedroom with French doors off the living area provides the perfect space for a home office, gym, study, or guest room. Enjoy outdoor living on the screened porch overlooking the backyard, and take advantage of the attached two-car garage for added convenience. Additional updates include a new air conditioning unit and siding (2020), and a new furnace, tankless hot water heater, and sump pump (2024-2025). The crawl space, accessible from inside the home, offers exceptional storage space. Residents of Keys of Marsh Harbor enjoy community amenities including a swimming pool and tennis courts. With weekly rentals permitted (see community regulations), this property also presents an outstanding opportunity for investors seeking rental income in one of Rehoboth Beach's most sought-after locations. The HOA dues cover most of the home's exterior, including the roof, siding, and lawn maintenance! Ideally located less than two miles from the Rehoboth Beach Boardwalk, this single-level home offers easy coastal living with restaurants, shopping, fitness centers, and entertainment just minutes away. Take a short stroll across the street to Fresh Market, Planet Fitness, Blue Coast Seafood, and Thompson Island Brewery! Whether you're looking for a primary residence, vacation getaway, or investment property, this move-in-ready home offers the best of coastal Delaware living.

20240 Whitehead Cir Unit 99, Rehoboth Beach

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: RE/MAX Realty Group Rehoboth.

$620,000

Welcome to the Keys of Marsh Harbor, a beautifully maintained community featuring a pool and tennis court. This is the lowest priced 4BR townhouse available in Rehoboth/Dewey—a great value for personal use or investment. 20291 Flagler Court is a 4 bedroom, 3.5 home with an open loft area perfect for an office or den being sold furnished as seen. The open living space has a cozy gas fireplace and glass sliding doors that open to a screened porch and outdoor patio ideal for grilling and dining al fresco. On the main level, the primary bedroom is complete with an ensuite bath. The half bath for guests is off the kitchen. Upstairs find three additional bedrooms, one with an ensuite bath, along with another bath and the loft that serves as a great flex space. An attached garage can store bikes, beach chairs and a car (includes electric for a car charger). Many owners ride their bikes to the beach and town or walk to the DelDOT Park and Ride bus stop to catch easy, hassle-free transportation to downtown Rehoboth Beach. You are also walking distance to Fresh Market, popular restaurants and Planet Fitness gym. In recent years community replaced roof & siding on all units; updated irrigation system, pool, pool house and tennis courts Whether seeking a serene beach retreat or an investment opportunity, seize the chance to make this coastal gem your own. Don’t delay its a great time to live at the beach

4 Beds ⋅ 4 Baths

Welcome to the Keys of Marsh Harbor, a beautifully maintained community featuring a pool and tennis court. This is the lowest priced 4BR townhouse available in Rehoboth/Dewey—a great value for personal use or investment. 20291 Flagler Court is a 4 bedroom, 3.5 home with an open loft area perfect for an office or den being sold furnished as seen. The open living space has a cozy gas fireplace and glass sliding doors that open to a screened porch and outdoor patio ideal for grilling and dining al fresco. On the main level, the primary bedroom is complete with an ensuite bath. The half bath for guests is off the kitchen. Upstairs find three additional bedrooms, one with an ensuite bath, along with another bath and the loft that serves as a great flex space. An attached garage can store bikes, beach chairs and a car (includes electric for a car charger). Many owners ride their bikes to the beach and town or walk to the DelDOT Park and Ride bus stop to catch easy, hassle-free transportation to downtown Rehoboth Beach. You are also walking distance to Fresh Market, popular restaurants and Planet Fitness gym. In recent years community replaced roof & siding on all units; updated irrigation system, pool, pool house and tennis courts Whether seeking a serene beach retreat or an investment opportunity, seize the chance to make this coastal gem your own. Don’t delay its a great time to live at the beach

20291 Flagler Ct, Rehoboth Beach

Listing courtesy of Jack Lingo - Rehoboth. Contact:

Selling Office: American Premier Realty, LLC.

$580,000

Welcome to 20252 Simonton Court, a beautifully maintained and fully furnished townhome located in the sought-after Rehoboth Beach community of the Keys of Marsh Harbor. (Remaining pictures to be entered no later than end of day on 10/11/2025) This 3-bedroom, 2.5-bath property with a 1-car garage offers 1,626 sq. ft. of coastal charm and turnkey convenience. Whether you're looking for a personal beach retreat or a proven income producing property, this home delivers both — with an outstanding rental history spanning 2023, 2024, and 2025 (Rental Income information available in the attached documents). The location is unbeatable — enjoy extreme close proximity to everything Rehoboth has to offer including Jungle Jim’s Water Park, the Park & Ride, Wawa, BlueCoast Restaurant, Thompsons Island Restaurant, Fresh Market, Downtown Rehoboth including the Boardwalk and Beaches, along with so much more — all just minutes away from the property's front door. Inside, the first floor features an open layout with stylish luxury vinyl plank and ceramic-style flooring, a cozy and impressive propane fireplace as the focal point, a dedicated dining area, and a bright kitchen with granite countertops and ample cabinetry. A charming 3-season room and rear patio extend your living space into the light of the outdoors — ideal for morning coffee, evening cocktails, nights of relaxation, or extra space for all of your desired hosted gatherings. All three bedrooms and both full baths are located upstairs, offering privacy and separation from the downstairs main living areas & dedicated dining area off of the expansive kitchen space. This home is sold furnished and accessorized, with a few minor exclusions, making it an easy, move-in-ready option for anyone looking for the ease of coming home into an already well decorated and accompanied space. You'll also love the unbeatable proximity to all of the wonderful community amenities — just steps from the pool and tennis/Sport court. Whether you're chasing beach days, rental income, or a relaxing year-round lifestyle here at the Delaware beaches, 20252 Simonton Court offers the best of coastal living with comfort, style, and location that truly delivers. Opportunities like this don’t come often — schedule your tour today and start making memories (or income!) all right here in our beautiful area of Coastal Delaware!

3 Beds ⋅ 3 Baths

Welcome to 20252 Simonton Court, a beautifully maintained and fully furnished townhome located in the sought-after Rehoboth Beach community of the Keys of Marsh Harbor. (Remaining pictures to be entered no later than end of day on 10/11/2025) This 3-bedroom, 2.5-bath property with a 1-car garage offers 1,626 sq. ft. of coastal charm and turnkey convenience. Whether you're looking for a personal beach retreat or a proven income producing property, this home delivers both — with an outstanding rental history spanning 2023, 2024, and 2025 (Rental Income information available in the attached documents). The location is unbeatable — enjoy extreme close proximity to everything Rehoboth has to offer including Jungle Jim’s Water Park, the Park & Ride, Wawa, BlueCoast Restaurant, Thompsons Island Restaurant, Fresh Market, Downtown Rehoboth including the Boardwalk and Beaches, along with so much more — all just minutes away from the property's front door. Inside, the first floor features an open layout with stylish luxury vinyl plank and ceramic-style flooring, a cozy and impressive propane fireplace as the focal point, a dedicated dining area, and a bright kitchen with granite countertops and ample cabinetry. A charming 3-season room and rear patio extend your living space into the light of the outdoors — ideal for morning coffee, evening cocktails, nights of relaxation, or extra space for all of your desired hosted gatherings. All three bedrooms and both full baths are located upstairs, offering privacy and separation from the downstairs main living areas & dedicated dining area off of the expansive kitchen space. This home is sold furnished and accessorized, with a few minor exclusions, making it an easy, move-in-ready option for anyone looking for the ease of coming home into an already well decorated and accompanied space. You'll also love the unbeatable proximity to all of the wonderful community amenities — just steps from the pool and tennis/Sport court. Whether you're chasing beach days, rental income, or a relaxing year-round lifestyle here at the Delaware beaches, 20252 Simonton Court offers the best of coastal living with comfort, style, and location that truly delivers. Opportunities like this don’t come often — schedule your tour today and start making memories (or income!) all right here in our beautiful area of Coastal Delaware!

20252 Simonton Ct, Rehoboth Beach

Listing courtesy of Keller Williams Realty. Contact:

Selling Office: Jack Lingo - Rehoboth.