Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (167 Rentals) Page 3 of 4

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2 Bedroom Apartments

10 Winchester Plz

10 Winchester PlzWinchester, MA 01890

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1 Bedroom Apartments

507-509 Main St

507-509 Main StStoneham, MA 02180

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2 Bedroom Apartments

40 Elmwood Ave

40 Elmwood AveWinchester, MA 01890

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1 to 3 Bedroom Apartments

39 Chestnut St

39 Chestnut StStoneham, MA 02180

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Studio Apartments

29 Orange St

29 Orange StWoburn, MA 01801

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Studio Apartments

Foxcroft

71 Montvale AveStoneham, MA 02180

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1 Bedroom Apartments

Fifteen Dix Street

15 Dix StWinchester, MA 01890

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1 Bedroom Apartments

Noonan Glen

75 Hemingway StWinchester, MA 01890

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Studio Apartments

3 Warren St

3 Warren StStoneham, MA 02180

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1 Bedroom Apartments

426 Main St

426 Main StStoneham, MA 02180

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2 Bedroom Apartments

395 Main St

395 Main StStoneham, MA 02180

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Studio Apartments

50 Franklin St

50 Franklin StStoneham, MA 02180

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Studio Apartments

William Griffin Fuller House

73-75 Franklin StStoneham, MA 02180

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Studio Apartments

Emerson 61 Square

61 Wright StStoneham, MA 02180

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Studio Apartments

56-64 Fowle St

56-64 Fowle StWoburn, MA 01801

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1 Bedroom Apartments

72 Wright St

72 Wright StStoneham, MA 02180

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Studio Apartments

Park Place

1 Albert DrWoburn, MA 01801

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2 Bedroom Apartments

Village Estates

201 Main StWoburn, MA 01801

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Studio Apartments

Amasa Farrier House

55 Central StStoneham, MA 02180

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1 to 3 Bedroom Apartments

4-6 MT Pleasant St

4-6 MT Pleasant StWoburn, MA 01801

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1 to 4 Bedroom Apartments

61 Warren Ave R

61 Warren Ave RWoburn, MA 01801

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Studio Apartments

Prospect Estates

35 Prospect StWoburn, MA 01801

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1 to 2 Bedroom Apartments

13 Pomeworth St

13 Pomeworth StStoneham, MA 02180

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Studio Apartments

42 Pleasant St

42 Pleasant StStoneham, MA 02180

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Studio Apartments

27 Montvale Ave

27 Montvale AveWoburn, MA 01801

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1 Bedroom Apartments

114 Central St

114 Central StStoneham, MA 02180

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Studio Apartments

Salem Place Condominiums

295 Salem StWoburn, MA 01801

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Studio Apartments

14 Walnut St

14 Walnut StWoburn, MA 01801

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2 Bedroom Apartments

177 Franklin St

177 Franklin StStoneham, MA 02180

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2 Bedroom Apartments

Franklin Condo

179 Franklin StStoneham, MA 02180

Utilities Included

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1 Bedroom Apartments

4 Montvale Ave

4 Montvale AveWoburn, MA 01801

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1 to 4 Bedroom Apartments

43 Salem St

43 Salem StWoburn, MA 01801

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1 Bedroom Apartments

9-11 Salem St

9-11 Salem StWoburn, MA 01801

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1 to 2 Bedroom Apartments

11 N Warren Ave

11 N Warren AveWoburn, MA 01801

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2 Bedroom Apartments

Continental Court Condominiums

74 Beach StWoburn, MA 01801

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Studio Apartments

6R Salem St

6R Salem StWoburn, MA 01801

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Studio Apartments

Ambassador Manor

25-31 Arlington RdWoburn, MA 01801

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Studio Apartments

Monterosa East

289 Elm StMedford, MA 02155

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Studio to 1 Bedroom Apartments

57 Pleasant St

57 Pleasant StWoburn, MA 01801

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Studio Apartments

1 N Warren St

1 N Warren StWoburn, MA 01801

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1 to 3 Bedroom Apartments

1 Warren St

1 Warren StWoburn, MA 01801

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1 to 2 Bedroom Apartments

33 Center St

33 Center StWoburn, MA 01801

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Studio Apartments

59 Winn St

59 Winn StWoburn, MA 01801

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Studio Apartments

85 Pleasant St

85 Pleasant StWoburn, MA 01801

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Studio Apartments

26 Franklin St

26 Franklin StWoburn, MA 01801

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Studio Apartments

79-81 Winn St

79-81 Winn StWoburn, MA 01801

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1 Bedroom Apartments

627 Main St

627 Main StWoburn, MA 01801

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Studio Apartments

628 Main St

628 Main StWoburn, MA 01801

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Studio Apartments

632 Main St

632 Main StWoburn, MA 01801

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Studio Apartments

Bradford Condominiums

80 N Warren StWoburn, MA 01801

Showing Results 101-150, Page 3 of 4

Winchester Highlands, Winchester, MA Local Guide

Apartments for rent in Winchester Highlands, MA

How much does it cost to rent an apartment in Winchester Highlands?

Bedroom	Average Price	Cheapest Price	Highest Price
Winchester Highlands Studio Apartments	$2,506	$1,950	$2,964
Winchester Highlands 1 Bedroom Apartments	$2,947	$1,750	$4,070
Winchester Highlands 2 Bedroom Apartments	$3,559	$2,375	$5,354
Winchester Highlands 3 Bedroom Apartments	$4,890	$3,200	$7,312
Winchester Highlands 4 Bedroom Apartments	$3,900	$3,700	$4,100

How much does it cost to rent a home in Winchester Highlands?

Bedroom	Average Price	Cheapest Price	Highest Price
2 Bedroom Homes	$2,740	$1,000	$3,500
3 Bedroom Homes	$3,800	$2,900	$5,500
4 Bedroom Homes	$4,333	$3,500	$5,500
5 Bedroom Homes	$10,450	$4,850	$10,000+
6 Bedroom Homes	$7,500	$7,500	$7,500

Browse Apartments in this Neighborhood

There are currently 167 rentals with your search options within a 2 mile radius of the Winchester Highlands Neighborhood of Winchester, MA.

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Frequently Asked Questions about Winchester Highlands

What is the current pricing and availability for apartments for rent in the Winchester Highlands area of Winchester, MA?

As of today, September 21, 2026, there are currently 167 available Winchester Highlands apartments priced from $1,750 to $12,539, with an average monthly rent of $3,426.

How much are Studio apartments in Winchester Highlands?

There are currently 38 Studio Apartments in Winchester Highlands with rent ranges from $1,950 to $2,964 with an average price of $2,506.

What is the current price range for One Bedroom Winchester Highlands Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winchester Highlands ranges from $1,750 to $4,070 with an average monthly rent of $2,947.

What does renting a Two Bedroom Apartment in Winchester Highlands cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester Highlands range from $2,375 to $5,354. Today's average rental price for Two Bedrooms here is $3,559.

How expensive are Winchester Highlands Three Bedroom Apartments?

There are currently 16 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $3,200 to $7,312 - averaging $4,890 for the location.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.