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Rhinebeck, NY

Rhinebeck, nestled in the heart of Dutchess County along the eastern banks of the Hudson River, is a quintessential historic town known for its colonial-era roots and timeless charm. Its bustling downtown area, adorned with boutique shops, gourmet restaurants, and quaint cafes, serves as a magnet for both locals and visitors. The town is also home to the Dutchess County Fairgrounds, which hosts numerous events throughout the year, including the renowned Dutchess County Fair. The real estate in Rhinebeck offers a harmonious blend of historic estates, modern homes, and scenic properties, making it a prime choice for those seeking a blend of history, culture, and natural beauty.

View The Market Report
77 UPPER HOOK RD, Rhinebeck, NY 12572
Open 5/24 1PM-2:30PM
49

$1,625,000

3 Beds 2 Baths 2,700 SqFt

77 UPPER HOOK RD, Rhinebeck, NY 12572

Listed by Atelier WM LLC

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
929 Centre RD, Rhinebeck, NY 12580
Open 5/24 11AM-1PM
42

$695,000

4 Beds 2 Baths 1,492 SqFt

929 Centre RD, Rhinebeck, NY 12580

Listed by Corcoran Country Living

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
440 Milan Hollow RD, Rhinebeck, NY 12572
New
34

$1,400,000

4 Beds 3 Baths 3,224 SqFt

440 Milan Hollow RD, Rhinebeck, NY 12572

Listed by Houlihan Lawrence Inc.

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
565 Route 308, Rhinebeck, NY 12572
New
26

$1,975,000

5 Beds 3 Baths 3,140 SqFt

565 Route 308, Rhinebeck, NY 12572

Listed by Rouse + Co Real Estate LLC

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
52 Pells RD, Rhinebeck, NY 12572
New
28

$3,850,000

7 Beds 7 Baths 6,089 SqFt

52 Pells RD, Rhinebeck, NY 12572

Listed by Four Seasons Sothebys Intl

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
400 Round Lake RD #Apt A, Rhinebeck, NY 12572
New
11

$2,000

1 Bed 1 Bath 1,000 SqFt

400 Round Lake RD #Apt A, Rhinebeck, NY 12572

Listed by BHHS Hudson Valley Properties

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
1-18 Willow WAY #7, Rhinebeck, NY 12572
Active
19

$2,895

2 Beds 2 Baths 28,505 SqFt

1-18 Willow WAY #7, Rhinebeck, NY 12572

Listed by BHHS Hudson Valley Properties

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
334 Lake DR, Rhinebeck, NY 12572
Active
31

$1,195,000

3 Beds 3 Baths 2,900 SqFt

334 Lake DR, Rhinebeck, NY 12572

Listed by BHHS Hudson Valley Properties

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
6 Woods RD, Rhinebeck, NY 12572
Coming Soon
9

$349,000

2 Beds 1 Baths 968 SqFt

6 Woods RD, Rhinebeck, NY 12572

Listed by Keller Williams NY Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
74 Lamoree RD, Rhinebeck, NY 12572
Active
23

$2,500

2 Beds 1 Baths 900 SqFt

74 Lamoree RD, Rhinebeck, NY 12572

Listed by BHHS Hudson Valley Properties

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
304 Ivy TRL, Rhinebeck, NY 12572
Active
24

$585,000

1 Bed 2 Bath 1,183 SqFt

304 Ivy TRL, Rhinebeck, NY 12572

Listed by Corcoran Country Living

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
44 Lorraine DR, Rhinebeck, NY 12572
Active
34

$1,150,000

3 Beds 2 Baths 1,723 SqFt

44 Lorraine DR, Rhinebeck, NY 12572

Listed by Compass Greater NY, LLC

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
11 Haggerty Hill RD, Rhinebeck, NY 12572
Active
49

$2,400,000

3 Beds 3 Baths 3,723 SqFt

11 Haggerty Hill RD, Rhinebeck, NY 12572

Listed by eXp Realty

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
20 Manor RD, Rhinebeck, NY 12572
Price Dropped by $35K
30

$790,000

3 Beds 3 Baths 2,175 SqFt

20 Manor RD, Rhinebeck, NY 12572

Listed by Corcoran Country Living

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
292 Mountain View RD, Rhinebeck, NY 12572
Active
30

$1,250,000

2 Beds 2 Baths 1,750 SqFt

292 Mountain View RD, Rhinebeck, NY 12572

Listed by LeGrand Real Estate, Inc.

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
1-18 Willow Way #5, Rhinebeck, NY 12572
Active
24

$2,625

2 Beds 1 Baths 1,300 SqFt

1-18 Willow Way #5, Rhinebeck, NY 12572

Listed by BHHS Hudson Valley Properties

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
155 Wey RD, Rhinebeck, NY 12572
Active
28

$815,000

1 Bed 1 Bath 1,225 SqFt

155 Wey RD, Rhinebeck, NY 12572

Listed by Upstate Down

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
420 Rhinecliff RD, Rhinebeck, NY 12572
Active
35

$790,000

5 Beds 3 Baths 2,906 SqFt

420 Rhinecliff RD, Rhinebeck, NY 12572

Listed by Four Seasons Sothebys Intl

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
420 Rhinecliff RD, Rhinebeck, NY 12572
Active
36

$790,000

5 Beds 3 Baths

420 Rhinecliff RD, Rhinebeck, NY 12572

Listed by Four Seasons Sothebys Intl

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
12 S Parsonage ST, Rhinebeck, NY 12572
Active
49

$730,000

5 Beds 4 Baths

12 S Parsonage ST, Rhinebeck, NY 12572

Listed by Century 21 Alliance Realty Grp

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
18 Fourth AVE, Rhinebeck, NY 12572
Active
24

$560,000

2 Beds 1 Baths 884 SqFt

18 Fourth AVE, Rhinebeck, NY 12572

Listed by Rouse + Co Real Estate LLC

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
34 Appletree DR, Rhinebeck, NY 12572
Pending
47

$459,000

4 Beds 3 Baths 1,693 SqFt

34 Appletree DR, Rhinebeck, NY 12572

Listed by Houlihan Lawrence Inc.

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
36 Pilgrims Progress RD, Rhinebeck, NY 12572
Active
36

$20,000

3 Beds 4 Baths 3,478 SqFt

36 Pilgrims Progress RD, Rhinebeck, NY 12572

Listed by Corcoran Country Living

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
21 Peacock RD, Rhinebeck, NY 12572
Pending
43

$1,195,000

3 Beds 3 Baths 3,162 SqFt

21 Peacock RD, Rhinebeck, NY 12572

Listed by Houlihan Lawrence Inc.

OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS
OneKey MLS/ Hudson Gateway (HGAR)/ Long Island MLS (MLSLI)/ Mid Hudson MLS

All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@MLSGrid.com. The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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Equal Housing Opportunity

© 2026 Anais O’Connor, REALTOR® | LIC #10401336489 | Compass - All rights reserved | Privacy Policy | DMCA Policy | Powered by Blok.

Anais O’Connor is a real estate agent affiliated with COMPASS, a licensed real estate broker and abides by all applicable Equal Housing Opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Some or all of the listings may not belong to the firm whose website is being visited. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the “DMCA”) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to anais.oconnor@compass.com. “The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

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