Milton, DE 55+ active adult communities & homes for sale - Page 4

287 homes near Milton

Sort by:

Relevance

3 rating (5 reviews)

Heritage Creek

$400Ks - $500Ks

Heritage Creek, Milton, DE

New and Resale | Age-targeted | Built 2008 - present | 400 homes

3.3 rating (3 reviews)

Windstone

$400Ks

Windstone, Milton, DE

Resale Only | Age-targeted | Built 2017 - 2022 | 260 homes

5 rating (2 reviews)

Heritage Shores

$300Ks - $500Ks

Heritage Shores, Bridgeville, DE

New and Resale | 55+ age-restricted | Built 2004 - present | 1,816 homes

5 rating (3 reviews)

Four Seasons at Smithvill...

$400Ks - $500Ks

Four Seasons at Smithvill..., Galloway, NJ

Resale Only | 55+ age-restricted | Built 1998 - 2006 | 1,215 homes

5 rating (2 reviews)

Noble's Pond

$300Ks - $500Ks

Noble's Pond, Dover, DE

New and Resale | 55+ age-restricted | Built 2007 - present | 800 homes

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Holiday City at Monroe

$200Ks - $400Ks

Holiday City at Monroe, Williamstown, NJ

Resale Only | 55+ age-restricted | Built 1989 - 2007 | 682 homes

The Oaks of Weymouth

$100Ks - $200Ks

The Oaks of Weymouth, Mays Landing, NJ

Resale Only | 55+ age-restricted | Built 1984 - 2022 | 625 homes

5 rating (2 reviews)

Four Seasons at Millville

$300Ks

Four Seasons at Millville, Millville, NJ

New and Resale | 55+ age-restricted | Built 2008 - present | 610 homes

The Ponds at Bayberry

$500Ks - $600Ks

The Ponds at Bayberry, Middletown, DE

New and Resale | 55+ age-restricted | Built 2015 - present | 572 homes

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

2.8 rating (4 reviews)

The Villages at Red Mill ...

$400Ks - $600Ks

The Villages at Red Mill ..., Lewes, DE

New and Resale | Age-targeted | Built 2009 - present | 520 homes

5 rating (2 reviews)

The Parke at Ocean Pines

$200Ks - $300Ks

The Parke at Ocean Pines, Ocean Pines, MD

Resale Only | 55+ age-restricted | Built 2001 - 2005 | 503 homes

Roesville

$300Ks

Roesville, Felton, DE

Resale Only | 55+ age-restricted | Built 2008 - 2014 | 470 homes

2.5 rating (2 reviews)

The Fairways at Mays Land...

$100Ks - $200Ks

The Fairways at Mays Land..., Mays Landing, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2005 | 465 homes

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Independence

$100Ks - $700Ks

Independence, Millsboro, DE

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 455 homes

Chesapeake

$400Ks - $500Ks

Chesapeake, Easton, MD

Resale Only | 55+ age-restricted | Built 2002 - 2011 | 452 homes

The Village Grande at Cam...

$400Ks - $500Ks

The Village Grande at Cam..., Glassboro, NJ

Resale Only | 55+ age-restricted | Built 2008 - present | 450 homes

5 rating (1 reviews)

Bishop's Landing

$500Ks

Bishop's Landing, Millville, DE

New and Resale | Age-targeted | Built 2013 - present | 449 homes

5 rating (1 reviews)

Four Seasons at Weatherby

$400Ks

Four Seasons at Weatherby, Woolwich, NJ

Resale Only | 55+ age-restricted | Built 2005 - 2013 | 428 homes

Parke Place

$200Ks

Parke Place, Sewell, NJ

Resale Only | 55+ age-restricted | Built 1999 - 2003 | 406 homes

Four Seasons at Hatteras ...

$400Ks - $500Ks

Four Seasons at Hatteras ..., Magnolia, DE

New Construction | 55+ age-restricted | Built 2023 - present | 400 homes

The Village Grande at Eng...

$400Ks

The Village Grande at Eng..., Egg Harbor Township, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 397 homes

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

5 rating (1 reviews)

Symphony Village

$500Ks

Symphony Village, Centreville, MD

Resale Only | 55+ age-restricted | Built 2003 - 2016 | 395 homes

4 rating (1 reviews)

Mystic Shores

$100Ks - $300Ks

Mystic Shores, Little Egg Harbor, NJ

Resale Only | 55+ age-restricted | Built 1975 - 1994 | 365 homes

5 rating (1 reviews)

Springmill

$300Ks - $400Ks

Springmill, Middletown, DE

Resale Only | 55+ age-restricted | Built 2000 - 2007 | 362 homes

Venue at Winchelsea

$300Ks - $500Ks

Venue at Winchelsea, Middletown, DE

New Construction | 55+ age-restricted | Built 2024 - present | 336 homes

Champions' Club

$300Ks - $400Ks

Champions' Club, Magnolia, DE

Resale Only | 55+ age-restricted | Built 2007 - 2022 | 326 homes

4 rating (54 reviews)

Cranberry Creek

$300Ks - $400Ks

Cranberry Creek, Little Egg Harbor, NJ

Resale Only | 55+ age-restricted | Built 2003 - 2010 | 325 homes

3 rating (2 reviews)

Spring Arbor

$400Ks

Spring Arbor, Middletown, DE

Resale Only | 55+ age-restricted | Built 2007 - 2018 | 317 homes

Four Seasons at Silver Ma...

$500Ks

Four Seasons at Silver Ma..., Middletown, DE

Resale Only | 55+ age-restricted | Built 2011 - 2017 | 299 homes

The Village Grande at Lit...

$300Ks - $400Ks

The Village Grande at Lit..., Egg Harbor Township, NJ

Resale Only | 55+ age-restricted | Built 2002 - 2006 | 299 homes

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Four Seasons at Baymont F...

$500Ks - $600Ks

Four Seasons at Baymont F..., Middletown, DE

New Construction | Age-targeted | Built 2019 - present | 288 homes

Forest Landing at Bethany...

$400Ks - $500Ks

Forest Landing at Bethany..., Frankford, DE

New and Resale | Age-targeted | Built 2012 - present | 280 homes

Four Seasons at Belle Ter...

$600Ks - $700Ks

Four Seasons at Belle Ter..., Lewes, DE

New Construction | 55+ age-restricted | Built 2019 - present | 269 homes

Auburn Meadows

$400Ks

Auburn Meadows, Smyrna, DE

New Construction | 55+ age-restricted | Built 2022 - present | 262 homes

Coves at Ocean Club

$400Ks

Coves at Ocean Club, Egg Harbor Township, NJ

New Construction | 55+ age-restricted | Built 2024 - present | 258 homes

Bay Crossing

$400Ks - $700Ks

Bay Crossing, Lewes, DE

Resale Only | 55+ age-restricted | Built 2005 - 2016 | 256 homes

Traditions at Whitehall

$400Ks - $600Ks

Traditions at Whitehall, Middletown, DE

New Construction | 55+ age-restricted | Built 2019 - present | 250 homes

Longacre Village

$200Ks - $300Ks

Longacre Village, Dover, DE

Resale Only | 55+ age-restricted | Built 2006 - 2016 | 250 homes

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Woods Landing

$400Ks

Woods Landing, Mays Landing, NJ

Resale Only | 55+ age-restricted | Built 2006 - 2022 | 249 homes

5 rating (2 reviews)

Spring Meadow

$300Ks - $400Ks

Spring Meadow, Smyrna, DE

Resale Only | 55+ age-restricted | Built 2006 - 2014 | 246 homes

1 2...3

The Parke at Ocean Pines

11425 MANKLIN CREEK RD UNIT 2, OCEAN PIN..., Ocean Pines, MD 21811

$280,000

$274,900

3 beds

2 baths

1,181 sq ft

Condo

11427 MANKLIN CREEK RD UNIT 2, OCEAN PIN...

Community: The Parke at Ocean Pines

Symphony Village

807 HARMONY WAY, CENTREVILLE, MD, 21617, Centreville, MD 21617

$595,000

4 beds

3 baths

2,804 sq ft

807 HARMONY WAY, CENTREVILLE, MD, 21617

Community: Symphony Village

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Symphony Village

714 HARMONY WAY # 714, CENTREVILLE, MD, ..., Centreville, MD 21617

$559,900

4 beds

3 baths

2,804 sq ft

714 HARMONY WAY # 714, CENTREVILLE, MD, ...

Community: Symphony Village

SummersGate

1178 KESTREL WAY, SALISBURY, MD, 21804, Salisbury, MD 21804

$459,500

4 beds

3 baths

3,000 sq ft

1178 KESTREL WAY, SALISBURY, MD, 21804

Community: SummersGate

Chesapeake

7459 TIMOTHYS WAY, EASTON, MD, 21601, Easton, MD 21601

$524,000

3 beds

3 baths

3,052 sq ft

7459 TIMOTHYS WAY, EASTON, MD, 21601

Community: Chesapeake

Chesapeake

7389 KAREN AVE, EASTON, MD, 21601, Easton, MD 21601

$499,000

3 beds

3 baths

3,052 sq ft

7389 KAREN AVE, EASTON, MD, 21601

Community: Chesapeake

Chesapeake

29653 LYONS DR, EASTON, MD, 21601, Easton, MD 21601

$429,900

2 beds

2 baths

1,878 sq ft

29653 LYONS DR, EASTON, MD, 21601

Community: Chesapeake

The Parke at Ocean Pines

11 HATTERAS ST, OCEAN PINES, MD, 21811, Ocean Pines, MD 21811

$327,500

2 beds

2 baths

1,195 sq ft

11 HATTERAS ST, OCEAN PINES, MD, 21811

Community: The Parke at Ocean Pines

Chesapeake

29638 JANETS WAY, EASTON, MD, 21601, Easton, MD 21601

$525,000

3 beds

3 baths

2,342 sq ft

29638 JANETS WAY, EASTON, MD, 21601

Community: Chesapeake

Chesapeake

29805 DUSTIN AVE, EASTON, MD, 21601, Easton, MD 21601

$495,000

2 beds

2 baths

1,878 sq ft

29805 DUSTIN AVE, EASTON, MD, 21601

Community: Chesapeake

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

The Parke at Ocean Pines

11421 MANKLIN CREEK RD UNIT 4, BERLIN, M..., Berlin, MD 21811

$299,900

3 beds

2 baths

1,181 sq ft

Condo

11421 MANKLIN CREEK RD UNIT 4, BERLIN, M...

Community: The Parke at Ocean Pines

Parks Edge at Bayberry

3032 BARBER LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$699,000

3 beds

2 baths

3032 BARBER LN, MIDDLETOWN, DE, 19709

Community: Parks Edge at Bayberry

Riverbend

216 HERON CIR, NEW CASTLE, DE, 19720, New Castle, DE 19720

$514,888

3 beds

2 baths

2,390 sq ft

216 HERON CIR, NEW CASTLE, DE, 19720

Community: Riverbend

Bay Crossing

34953 COMPASS CV, LEWES, DE, 19958, Lewes, DE 19958

$725,000

4 beds

4 baths

4,061 sq ft

34953 COMPASS CV, LEWES, DE, 19958

Community: Bay Crossing

New The Village of Cinderberry

14 MULBERRY ST, GEORGETOWN, DE, 19947, Georgetown, DE 19947

$345,000

2 beds

2 baths

1,591 sq ft

14 MULBERRY ST, GEORGETOWN, DE, 19947

Community: The Village of Cinderberry

New Four Seasons at Hatteras Hills

58 WANCHESE DR, MAGNOLIA, DE, 19962, Magnolia, DE 19962

$569,900

4 beds

2 baths

2,344 sq ft

58 WANCHESE DR, MAGNOLIA, DE, 19962

Community: Four Seasons at Hatteras Hills

Four Seasons at Baymont Farms

505 CHERRY BARK RD, MIDDLETOWN, DE, 1970..., Middletown, DE 19709

$565,000

4 beds

3 baths

2,650 sq ft

505 CHERRY BARK RD, MIDDLETOWN, DE, 1970...

Community: Four Seasons at Baymont Farms

Auburn Meadows

303 VIRDIN DR, SMYRNA, DE, 19977, Smyrna, DE 19977

$459,000

2 beds

2 baths

2,176 sq ft

303 VIRDIN DR, SMYRNA, DE, 19977

Community: Auburn Meadows

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Four Seasons at Belle Terre

21160 CONTI ST, LEWES, DE, 19958, Lewes, DE 19958

$759,900

5 beds

3 baths

3,630 sq ft

21160 CONTI ST, LEWES, DE, 19958

Community: Four Seasons at Belle Terre

The Ponds at Bayberry

5338 NEWMAN LN, MIDDLETOWN, DE, 19709, Middletown, DE 19709

$639,000

3 beds

2 baths

1,925 sq ft

5338 NEWMAN LN, MIDDLETOWN, DE, 19709

Community: The Ponds at Bayberry

New Bay Crossing

35224 SEAPORT LOOP, LEWES, DE, 19958, Lewes, DE 19958

$670,000

2 beds

4 baths

2,972 sq ft

35224 SEAPORT LOOP, LEWES, DE, 19958

Community: Bay Crossing

Bay Crossing

34944 COMPASS CV, LEWES, DE, 19958, Lewes, DE 19958

$649,900

3 beds

3 baths

2,400 sq ft

34944 COMPASS CV, LEWES, DE, 19958

Community: Bay Crossing

New Traditions at Whitehall

314 CHAROLAIS ST ASHTON, MIDDLETOWN, DE,..., Middletown, DE 19709

$456,000

2 beds

3 baths

1,794 sq ft

314 CHAROLAIS ST ASHTON, MIDDLETOWN, DE,...

Community: Traditions at Whitehall

New Traditions at Whitehall

204 BALDY LN ALRICH, MIDDLETOWN, DE, 197..., Middletown, DE 19709

$425,000

2 beds

3 baths

1,794 sq ft

204 BALDY LN ALRICH, MIDDLETOWN, DE, 197...

Community: Traditions at Whitehall

New Traditions at Whitehall

204 BALDY LN ANNANDALE, MIDDLETOWN, DE, ..., Middletown, DE 19709

$425,000

2 beds

3 baths

1,794 sq ft

204 BALDY LN ANNANDALE, MIDDLETOWN, DE, ...

Community: Traditions at Whitehall

New Windstone

29645 RIVERSTONE DR, MILTON, DE, 19968, Milton, DE 19968

$475,000

3 beds

2 baths

1,730 sq ft

29645 RIVERSTONE DR, MILTON, DE, 19968

Community: Windstone

Heritage Shores

$464,900

3 beds

2 baths

1,576 sq ft

338 HERITAGE SHORES CIR, BRIDGEVILLE, DE...

393 SCRANTON LN, OCEAN VIEW, DE, 19970

Community: Silver Woods

Four Seasons at Belle Terre

21227 DAUPHINE ST, LEWES, DE, 19958, Lewes, DE 19958

$659,900

3 beds

2 baths

2,002 sq ft

21227 DAUPHINE ST, LEWES, DE, 19958

Community: Four Seasons at Belle Terre

Want to learn more about 55+ communities in Milton? 55places can help!

Questions? Call us: (302) 329-3970

Independence

29432 ANDREW JACKSON DR, MILLSBORO, DE, ..., Millsboro, DE 19966

$715,000

3 beds

2 baths

2,900 sq ft

29432 ANDREW JACKSON DR, MILLSBORO, DE, ...

Community: Independence

Independence

29688 PATRICK HENRY CIR, MILLSBORO, DE, ..., Millsboro, DE 19966

$649,900

3 beds

2 baths

2,156 sq ft

29688 PATRICK HENRY CIR, MILLSBORO, DE, ...

Community: Independence

1 2 3 4 5 6 7…8

Frequently Asked Questions

What size 55+ communities are there in Milton?

In Milton, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Milton?

The smallest 55+ communities in Milton has 260 homes, the largest has 400 homes, and the average communities consists of 330 homes.

Are there new 55+ homes available in Milton?

Yes, there is new 55+ home available in Milton. The most recent communities started in Milton include Windstone, Heritage Creek. There is also 1 communities in Milton that offers new construction homes, including Heritage Creek.

Are there gated 55+ communities in Milton?

Yes, there is gated 55+ communities in Milton. Approximately 50.0% of 55+ communities in the area are gated. For instance, Windstone is a gated communities with 260 homes.

How long do listings in 55+ communities in Milton typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Milton stay on the market for around 394 days. The average price of homes for sale in these communities is approximately $487,905, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Heritage Creek average around $490,116, while homes in Windstone average around $485,694.

Want more information about active adult communities around Milton?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

Want to learn more about 55+ communities in Milton?

Call us: (302) 329-3970

287 homes

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2026 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Jan 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

Milton, DE 55+ active adult communities & homes for sale - Page 4

82 communities near Milton

287 homes near Milton

3 beds

2 baths

1,181 sq ft

Condo

3 beds

3 baths

2,074 sq ft

3 beds

3 baths

3,052 sq ft

3 beds

2 baths

1,181 sq ft

Condo

4 beds

3 baths

2,804 sq ft

4 beds

3 baths

2,804 sq ft

4 beds

3 baths

3,000 sq ft

3 beds

3 baths

3,052 sq ft

3 beds

3 baths

3,052 sq ft

2 beds

2 baths

1,878 sq ft

2 beds

2 baths

1,195 sq ft

3 beds

3 baths

2,342 sq ft

2 beds

2 baths

1,878 sq ft

3 beds

2 baths

1,181 sq ft

Condo

3 beds

2 baths

3 beds

2 baths

2,390 sq ft

4 beds

4 baths

4,061 sq ft

2 beds

2 baths

1,591 sq ft

4 beds

2 baths

2,344 sq ft

4 beds

3 baths

2,650 sq ft

2 beds

2 baths

2,176 sq ft

5 beds

3 baths

3,630 sq ft

3 beds

2 baths

1,925 sq ft

2 beds

4 baths

2,972 sq ft

3 beds

3 baths

2,400 sq ft