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Condos for Sale in 19966

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  • 2303 Caitlins Way, Millsboro, DE 19966
    2303 Caitlins Way, Millsboro, DE 19966
    2303 Caitlins Way, Millsboro, DE 19966
    /29

    $220,000

    $7K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 730 Sq Ft

    2303 Caitlins Way, Millsboro, DE 19966

    Welcome to this charming 2-bedroom, 2-bathroom condo in the desirable Villages at Millwood community of Millsboro, Delaware. This well-designed home features an open floor plan that creates a spacious and inviting atmosphere, perfect for everyday living and entertaining. The light-filled kitchen opens seamlessly to the living area, where luxury vinyl plank flooring adds both style and durability.

    Agent Photo

    Dustin Oldfather

    Compass

    2303 Caitlins Way, Millsboro, DE 19966
  • 33585 Windswept Dr Unit 7204, Millsboro, DE 19966
    33585 Windswept Dr Unit 7204, Millsboro, DE 19966
    33585 Windswept Dr Unit 7204, Millsboro, DE 19966
    /94

    $585,000

    • 3 Beds
    • 2 Baths
    • 1,980 Sq Ft

    33585 Windswept Dr Unit 7204, Millsboro, DE 19966

    Discover a residence where timeless craftsmanship meets effortless coastal luxury in Delaware's premier gated resort community, The Peninsula on the Indian River Bay. Thoughtfully transformed through an extensive 2024 renovation, this exceptional condominium offers a level of design, quality, and attention to detail rarely found in today's market.From the moment you enter, custom finishes,

    Agent Photo

    Lisa Nemeth

    Northrop Realty

    33585 Windswept Dr Unit 7204, Millsboro, DE 19966
  • 33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
    /73

    $340,000

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966

    Best value three bedroom condominium in the Peninsula. Welcome to Windswept Drive, Unit 9101! Perfectly positioned along the 6th fairway of the Jack Nicklaus Signature golf course, this residence enjoys a peaceful, private backdrop of golf, ponds and woods, with glimpses stretching toward the Indian River Bay. A pergola-covered patio extends the living space outdoors and invites quiet mornings or

    Valerie Ellenberger Compass

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
  • 33584 Windswept Dr Unit 5302, Millsboro, DE 19966
    33584 Windswept Dr Unit 5302, Millsboro, DE 19966
    33584 Windswept Dr Unit 5302, Millsboro, DE 19966
    /63

    $286,900

    $13K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,326 Sq Ft

    33584 Windswept Dr Unit 5302, Millsboro, DE 19966

    Welcome to 33584 Windswept Drive, Unit 5302, a beautifully appointed two-bedroom condominium in The Peninsula, offering a peaceful setting and a thoughtfully designed, open-concept layout. Enjoy lush, wooded views throughout the summer months, followed by scenic golf course views as the leaves fall.The home has been enhanced with numerous updates over the years, including freshly painted

    Liz Grace Northrop Realty

    33584 Windswept Dr Unit 5302, Millsboro, DE 19966
  • 27270 18th Blvd Unit 13303, Millsboro, DE 19966
    27270 18th Blvd Unit 13303, Millsboro, DE 19966
    27270 18th Blvd Unit 13303, Millsboro, DE 19966
    /63

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 1,106 Sq Ft

    27270 18th Blvd Unit 13303, Millsboro, DE 19966

    Welcome to 27270 18th Boulevard, a top-floor, three-bedroom, two-and-a-half-bath condominium in The Peninsula, where refined coastal living and exceptional resort-style amenities come together in one of the area’s premier communities.Enjoy serene views overlooking a peaceful pond, creating a picturesque and relaxing backdrop for everyday living. Inside, the residence offers three spacious

    TONI SCHROCK Northrop Realty

    27270 18th Blvd Unit 13303, Millsboro, DE 19966
  • 3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    /19

    $220,000

    $9K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 729 Sq Ft

    3202 Caitlins Way, Millsboro, DE 19966

    Welcome to the Villages of Millwood, where you'll find this cozy 2-BR, 2-BA Condo. Recent improvements include new laminate flooring and new water heater. Extras include appliances including washer and dryer. Sliding glass doors leading to the screened porch and deck for relaxation on these summer evenings. The Villages at Millwood is ideally located near Millsboro's shopping, dining, and

    Tina Moore The Real Estate Market

    3202 Caitlins Way, Millsboro, DE 19966
  • 33571 Windswept Dr Unit 9302, Millsboro, DE 19966
    33571 Windswept Dr Unit 9302, Millsboro, DE 19966
    33571 Windswept Dr Unit 9302, Millsboro, DE 19966
    /104

    $490,000

    $5K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,823 Sq Ft

    33571 Windswept Dr Unit 9302, Millsboro, DE 19966

    NEW PRICE!! Welcome to 33571 Windswept Drive #9302, a beautifully appointed third-floor condominium in The Peninsula, offering 3 bedrooms, 3 full bathrooms, and spectacular views of the 6th hole fairway, tranquil ponds, and the Indian River Bay beyond. This spacious residence combines comfort, convenience, and coastal elegance within one of Delaware's premier gated resort communities. Step inside

    Brian Barrows Monument Sotheby's International Realty

    33571 Windswept Dr Unit 9302, Millsboro, DE 19966
  • 33559 Windswept Dr Unit 11102, Millsboro, DE 19966
    33559 Windswept Dr Unit 11102, Millsboro, DE 19966
    33559 Windswept Dr Unit 11102, Millsboro, DE 19966
    /85

    $434,900

    Open Sat 10AM - 12PM $5K PRICE INCREASE
    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft

    33559 Windswept Dr Unit 11102, Millsboro, DE 19966

    Welcome to Windswept at The Peninsula, where resort-style living meets comfort, convenience, and coastal charm. This beautifully maintained, turnkey ground-floor condominium is ideally situated within the sought-after Windswept neighborhood, just a short stroll from The Peninsula's world-class amenities. Enjoy easy access to the clubhouse, indoor and outdoor pools, fitness center, spa, tennis

    Ian Blyth 360 PROPERTY SOLUTIONS

    33559 Windswept Dr Unit 11102, Millsboro, DE 19966
  • 5202 Caitlins Way, Millsboro, DE 19966
    5202 Caitlins Way, Millsboro, DE 19966
    5202 Caitlins Way, Millsboro, DE 19966
    /4

    $224,900

    Coming Soon Sep 19
    • 2 Beds
    • 2 Baths
    • 1,022 Sq Ft

    5202 Caitlins Way, Millsboro, DE 19966

    Professional Photos and Remarks Coming Soon

    Adam monico Coldwell Banker Realty

    5202 Caitlins Way, Millsboro, DE 19966
  • 1306 Caitlins Way, Millsboro, DE 19966
    1306 Caitlins Way, Millsboro, DE 19966
    1306 Caitlins Way, Millsboro, DE 19966
    /17

    $249,900

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    1306 Caitlins Way, Millsboro, DE 19966

    Welcome to Villages at Millwood! This well-maintained 3-bedroom, 2-bath condo features an open-concept floor plan with fresh paint and new carpet throughout. The bright and spacious living area offers sliding doors leading to a screened porch and open balcony—perfect for relaxing or enjoying the outdoors. The community amenities include a clubhouse and outdoor pool, and the convenient location

    Susan Mills JACK LINGO MILLSBORO

    1306 Caitlins Way, Millsboro, DE 19966
  • 5106 Caitlins Way, Millsboro, DE 19966
    5106 Caitlins Way, Millsboro, DE 19966
    5106 Caitlins Way, Millsboro, DE 19966
    /33

    $275,000

    $5K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    5106 Caitlins Way, Millsboro, DE 19966

    Charming 3-Bedroom Condo in Villages at Millwood – Millsboro, DEWelcome to easy living in the heart of Millsboro! This beautifully maintained 3-bedroom, 2-bath first-floor condo is located in the desirable Villages at Millwood—a vibrant community known for its comfort, convenience, and charm.Step inside to find a spacious open-concept layout with plenty of natural light, a

    MARIAN CAMPO Iron Valley Real Estate at The Beach

    5106 Caitlins Way, Millsboro, DE 19966
  • 33579 Windswept Dr Unit 8204, Millsboro, DE 19966
    33579 Windswept Dr Unit 8204, Millsboro, DE 19966
    33579 Windswept Dr Unit 8204, Millsboro, DE 19966
    /86

    $495,000

    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft

    33579 Windswept Dr Unit 8204, Millsboro, DE 19966

    Opportunity knocks with this premium corner unit featuring fantastic views of the 6th fairway. The Marco model is seldom available with three bedrooms, two baths, and two screened balconies. The HVAC was replaced in 2017, along with the kitchen's stainless steel appliances. Newer luxury vinyl plank flooring spans the common areas, with carpeted bedrooms and a tile kitchen. The spacious open floor

    Paul Maltaghati Monument Sotheby's International Realty

    33579 Windswept Dr Unit 8204, Millsboro, DE 19966
  • 5205 Caitlins Way, Millsboro, DE 19966
    5205 Caitlins Way, Millsboro, DE 19966
    5205 Caitlins Way, Millsboro, DE 19966
    /30

    $229,999

    $10K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    5205 Caitlins Way, Millsboro, DE 19966

    Motivated to sell! Located in the desirable Villages at Millwood in Millsboro—where comfort, convenience, and coastal charm come together. This beautifully maintained 2-bedroom, 2 full bath home offers effortless, move-in-ready living with an inviting open floor plan designed for both relaxation and entertaining. The spacious primary suite features a walk-in closet, while the main living areas

    Amanda Sweigert Keller Williams Realty Delmarva

    5205 Caitlins Way, Millsboro, DE 19966
  • 33570 Windswept Dr Unit 3307, Millsboro, DE 19966
    33570 Windswept Dr Unit 3307, Millsboro, DE 19966
    33570 Windswept Dr Unit 3307, Millsboro, DE 19966
    /86

    $428,800

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    33570 Windswept Dr Unit 3307, Millsboro, DE 19966

    Take the elevator to the top floor to this triple mint condo. Fully furnished - turnkey. This end unit is flooded with light. The prime location offers fantastic golf and water views. Walk to the world class amenities of the Peninsula. This 3br/2bth 1,860 sf condo features nine-foot ceilings with crown molding, recessed lights, and ceiling fans. Impeccably maintained. New HVAC in 2023. The

    Paul Maltaghati Monument Sotheby's International Realty

    33570 Windswept Dr Unit 3307, Millsboro, DE 19966
  • 2204 Caitlins Way Unit 2204, Millsboro, DE 19966
    2204 Caitlins Way Unit 2204, Millsboro, DE 19966
    2204 Caitlins Way Unit 2204, Millsboro, DE 19966
    /30

    $235,000

    • 2 Beds
    • 2 Baths
    • 714 Sq Ft

    2204 Caitlins Way Unit 2204, Millsboro, DE 19966

    Welcome to this charming 2-bedroom, 2 full-bathroom second-floor unit in the Villages at Millwood. Featuring a screened-in porch, this home offers the perfect spot to enjoy your morning coffee or unwind at the end of the day.Residents enjoy access to the community pool and the convenience of being just minutes from local restaurants, shopping, and Route 113. With Delaware's beaches, golf

    Rachel Cooper Berkshire Hathaway HomeServices PenFed Realty

    2204 Caitlins Way Unit 2204, Millsboro, DE 19966
  • 33584 Windswept Dr Unit 5401, Millsboro, DE 19966
    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
    /16

    $359,000

    • 3 Beds
    • 2 Baths
    • 1,894 Sq Ft

    33584 Windswept Dr Unit 5401, Millsboro, DE 19966

    SPECIAL INCENTIVE UNTIL END OF AUGUST: SELLER WILL ACCEPT $325,000 , AS IS .This top floor, corner unit condo is situated in the amenity-rich community of The Peninsula on the Indian River Bay. It has three bedrooms, two full baths, an open floor plan, 9-foot ceilings, built-in bookcases flanking a gas fireplace, LVP flooring throughout the living areas, carpeting in the bedrooms, tile in the

    Shirley Kalvinsky Jack Lingo - Rehoboth

    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
  • 33580 Windswept Dr Unit 4207, Millsboro, DE 19966
    33580 Windswept Dr Unit 4207, Millsboro, DE 19966
    33580 Windswept Dr Unit 4207, Millsboro, DE 19966
    /49

    $399,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,865 Sq Ft

    33580 Windswept Dr Unit 4207, Millsboro, DE 19966

    Welcome to 33580 Windswept, unit 4207, a beautifully appointed three-bedroom, two-bath condo in the sought-after Peninsula community. With an unbeatable location you will enjoy being close to the clubhouse, pools, golf course, tennis courts, bay, and more, this home places you at the center of an active, amenity-filled lifestyle while offering stylish, stress free, low-maintenance living. The

    Jim Lattanzi Northrop Realty

    33580 Windswept Dr Unit 4207, Millsboro, DE 19966
  • 5306 Caitlins Way, Millsboro, DE 19966
    5306 Caitlins Way, Millsboro, DE 19966
    5306 Caitlins Way, Millsboro, DE 19966
    /27

    $253,000

    $22K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    5306 Caitlins Way, Millsboro, DE 19966

    Welcome to living in the Villages at Millwood! This building includes an elevator to take you to this beautiful 3-bedroom, 2-bath third-floor unit. It offers a bright and open layout designed for both comfort and convenience. Step inside to find an open-concept kitchen and living room, perfect for everyday living and entertaining. The kitchen features a center island with bar seating, providing

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    5306 Caitlins Way, Millsboro, DE 19966
  • 33585 Windswept Dr Unit 7303, Millsboro, DE 19966
    33585 Windswept Dr Unit 7303, Millsboro, DE 19966
    33585 Windswept Dr Unit 7303, Millsboro, DE 19966
    /49

    $321,000

    $27K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    33585 Windswept Dr Unit 7303, Millsboro, DE 19966

    PRICE IMPROVEMENT...Welcome to 33585 Windswept Drive #7303 in the highly sought-after Peninsula community of Millsboro. This beautifully appointed Sanibel model by Schell Brothers offers coastal elegance, golf course views, and resort-style living just minutes from the Indian River Bay. Located on the second level with elevator access this 2 bedroom, 2 bath condominium offers approximately 1,325

    Chrisy Tingle Keller Williams Realty

    33585 Windswept Dr Unit 7303, Millsboro, DE 19966
  • 33580 Windswept Dr Unit 4202, Millsboro, DE 19966
    33580 Windswept Dr Unit 4202, Millsboro, DE 19966
    33580 Windswept Dr Unit 4202, Millsboro, DE 19966
    /67

    $315,000

    • 2 Beds
    • 2 Baths
    • 1,323 Sq Ft

    33580 Windswept Dr Unit 4202, Millsboro, DE 19966

    Fully furnished - Turnkey. Welcome to Windswept Condominiums in The Peninsula, Coastal Delaware’s premier private gated country club community, where luxury living meets a resort-style lifestyle. 800 acres located on the Indian River Bay with private sandy beaches. Ideally positioned just steps from the Clubhouse, this home provides effortless access to world-class amenities, dining, and social

    Paul Maltaghati Monument Sotheby's International Realty

    33580 Windswept Dr Unit 4202, Millsboro, DE 19966
  • 32768 Oak Orchard Rd Unit 101, Millsboro, DE 19966
    32768 Oak Orchard Rd Unit 101, Millsboro, DE 19966
    32768 Oak Orchard Rd Unit 101, Millsboro, DE 19966
    /16

    $999,999

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,539 Sq Ft

    32768 Oak Orchard Rd Unit 101, Millsboro, DE 19966

    A rare opportunity to own new construction directly on the Indian River Bay, Bayside Oak Estates is an exclusive collection of just six waterfront condominium residences in Millsboro, Delaware, now under construction and available for pre-sale.Designed for those who value an elevated coastal lifestyle, each residence includes a designated oversized boat slip, offering exceptional access

    Henry Jaffe Monument Sotheby's International Realty

    32768 Oak Orchard Rd Unit 101, Millsboro, DE 19966
  • 32768 Oak Orchard Rd Unit 102, Millsboro, DE 19966
    32768 Oak Orchard Rd Unit 102, Millsboro, DE 19966
    32768 Oak Orchard Rd Unit 102, Millsboro, DE 19966
    /16

    $1,200,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,599 Sq Ft

    32768 Oak Orchard Rd Unit 102, Millsboro, DE 19966

    A rare opportunity to own new construction directly on the Indian River Bay, Bayside Oak Estates is an exclusive collection of just six waterfront condominium residences in Millsboro, Delaware, now under construction and available for pre-sale.Designed for those who value an elevated coastal lifestyle, each residence includes a designated oversized boat slip, offering exceptional access

    Henry Jaffe Monument Sotheby's International Realty

    32768 Oak Orchard Rd Unit 102, Millsboro, DE 19966
  • 33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
    /76

    $412,500

    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966

    Welcome to Windswept Condominiums in The Peninsula, Coastal Delaware’s premier private gated country club community, where luxury living meets a resort-style lifestyle. 800 acres located on the Indian River Bay with private sandy beaches This fully furnished and generously sized three-bedroom residence offers an exceptional setting overlooking the first fairway of the renowned Jack Nicklaus

    Paul Maltaghati Monument Sotheby's International Realty

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966
Delaware Sussex County Millsboro

Condos for Sale in 19966

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