16

Condos for Sale in 19966

Section Image
  • 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

    $5,000 SELLER CREDIT if a contract settles before 6/1/2026!! 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

    Valerie Ellenberger Compass

    33571 Windswept Dr Unit 9101, Millsboro, DE 19966
  • 33579 Windswept Dr Unit 8205, Millsboro, DE 19966
    33579 Windswept Dr Unit 8205, Millsboro, DE 19966
    33579 Windswept Dr Unit 8205, Millsboro, DE 19966
    /47

    $299,000

    • 2 Beds
    • 2 Baths
    • 1,397 Sq Ft

    33579 Windswept Dr Unit 8205, Millsboro, DE 19966

    Beautifully upgraded and freshly painted 2-bedroom condo featuring durable hardwood laminate floors, a modern kitchen with granite countertops and stainless-steel appliances, a cozy gas fireplace with built-in cabinetry, and elegant crown molding. Both bedrooms are master suites with private ensuite baths, offering comfort and privacy. Enjoy convenient living and a serene, screened porch

    Judith Dourgarian Northrop Realty

    33579 Windswept Dr Unit 8205, 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

    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 kitchen and bathrooms plus a neutral color palette. The kitchen features a

    TIFFINI ANDERSON Jack Lingo - Rehoboth

    33584 Windswept Dr Unit 5401, Millsboro, DE 19966
  • 33570 Windswept Dr Unit 3305, Millsboro, DE 19966
    33570 Windswept Dr Unit 3305, Millsboro, DE 19966
    33570 Windswept Dr Unit 3305, Millsboro, DE 19966
    /16

    $345,000

    Open Sat 10AM - 12PM Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,326 Sq Ft

    33570 Windswept Dr Unit 3305, Millsboro, DE 19966

    Breathtaking views and true resort‐style living await in this stunning penthouse‐level 2‐bedroom, 2‐bath condo in the highly sought‐after Peninsula on the Indian River Bay. Overlooking the natural beauty of Rehoboth Bay, this residence offers a lifestyle unlike any other at the Delaware beaches—where everyday living feels like a retreat. The condo is tastefully decorated and designed for both

    Michele Petrillo Long & Foster Real Estate, Inc.

    33570 Windswept Dr Unit 3305, 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

    $329,000

    $19K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    33585 Windswept Dr Unit 7303, Millsboro, DE 19966

    JUST REDUCED...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
  • 5202 Caitlins Way, Millsboro, DE 19966
    5202 Caitlins Way, Millsboro, DE 19966
    5202 Caitlins Way, Millsboro, DE 19966
    /38

    $235,000

    Open Sun 1PM - 3PM
    • 2 Beds
    • 2 Baths
    • 1,022 Sq Ft

    5202 Caitlins Way, Millsboro, DE 19966

    Welcome to 5202 Caitlins Way, a beautifully situated second-floor condominium in a desirable elevator building, perfectly positioned along the edge of a tranquil pond. Offering a comfortable layout and peaceful surroundings, this inviting residence combines low-maintenance living with relaxing water views and bright, open living spaces. Inside, the spacious kitchen is designed for both

    Phillip Knight Northrop Realty

    5202 Caitlins Way, Millsboro, DE 19966
  • 4306 Caitlins Way Unit 4306, Millsboro, DE 19966
    4306 Caitlins Way Unit 4306, Millsboro, DE 19966
    4306 Caitlins Way Unit 4306, Millsboro, DE 19966
    /24

    $240,000

    $10K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    4306 Caitlins Way Unit 4306, Millsboro, DE 19966

    This one will not last long! Located in the Villages at Millwood is where you will find this beautifully refreshed 3 bedroom, 2 bathroom condo located in a desirable elevator building. Step inside and discover the open floor plan designed for everyday living. The living and dining areas flow seamlessly to the kitchen with large island and new stainless steel appliances. The primary suite offers a

    SHERRY MITCHELL INDIAN RIVER LAND CO

    4306 Caitlins Way Unit 4306, Millsboro, DE 19966
  • 33564 Windswept Dr Unit 2102, Millsboro, DE 19966
    33564 Windswept Dr Unit 2102, Millsboro, DE 19966
    33564 Windswept Dr Unit 2102, Millsboro, DE 19966
    /67

    $449,000

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

    33564 Windswept Dr Unit 2102, Millsboro, DE 19966

    Presenting 33564 Windswept Drive, an exceptional first floor condominium nestled in the prestigious community of 'The Peninsula on the Indian River Bay'. This impeccably maintained residence boasts a spacious and inviting layout, featuring three bedrooms each with their own dedicated bathroom. Every inch of this property exudes sophistication and charm - from the elegant living space, filled with

    John Rishko Patterson-Schwartz-Rehoboth

    33564 Windswept Dr Unit 2102, Millsboro, DE 19966
  • 3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    3202 Caitlins Way, Millsboro, DE 19966
    /19

    $229,000

    • 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 and sliding glass doors leading to the screened porch and deck. The Villages at Millwood is ideally located near Millsboro's shopping, dining, and everyday conveniences. Just a short drive away, enjoy the Delaware

    Tina Moore The Real Estate Market

    3202 Caitlins Way, Millsboro, DE 19966
  • 1306 Caitlins Way, Millsboro, DE 19966
    1306 Caitlins Way, Millsboro, DE 19966
    1306 Caitlins Way, Millsboro, DE 19966
    /17

    $265,000

    • 3 Beds
    • 2 Baths
    • 1,488 Sq Ft

    1306 Caitlins Way, Millsboro, DE 19966

    Welcome to Villages at Millwood! This 3-bedroom, 2-bath condo offers an open-concept layout with fresh paint and new carpet throughout. The living area features sliding doors leading to a screened porch and open balcony, perfect for relaxing or enjoying outdoor space. The community offers a clubhouse and outdoor pool, and the location is convenient to shopping, schools, and a short distance to

    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 well-appointed

    MARIAN CAMPO Iron Valley Real Estate at The Beach

    5106 Caitlins Way, Millsboro, DE 19966
  • 5205 Caitlins Way, Millsboro, DE 19966
    5205 Caitlins Way, Millsboro, DE 19966
    5205 Caitlins Way, Millsboro, DE 19966
    /30

    $239,900

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft

    5205 Caitlins Way, Millsboro, DE 19966

    Welcome to 5205 Caitlins Way, 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

    Amanda Sweigert Keller Williams Realty Delmarva

    5205 Caitlins Way, 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
    /34

    $412,500

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

    33580 Windswept Dr Unit 4307, Millsboro, DE 19966

    Resort-style living at its finest in this quiet, top-floor end unit — one of the most unique and rarely available residences in Windswept at The Peninsula. This exceptional “Bonita” model is part of a highly limited collection — only 13 Bonita units were ever built in Windswept. They are the largest floor plans of their kind and the only end units of this size. Even more rare, only four

    Michael McKee Long & Foster Real Estate, Inc.

    33580 Windswept Dr Unit 4307, 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

    $425,000

    • 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

    $265,000

    $10K 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
Delaware Sussex County Millsboro 19966

Condos for Sale in 19966

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group